Faculty of
Science
2009 school of Chemistry
research report
CONTENTS
04
05
07
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52
54
56
59
Advice to Postgraduate Candidates
Message from the Head of School
Profiles
Publications
Research Income Statement
Benefactors and Donations
Staff and Student Achievements
Student Prizes and Scholarships
List of Staff and Students
Graduates of 2009
2009 Chemistry Research Report
4
advice to postgraduate candidates
T
he University of Sydney’s School of Chemistry is one of the largest chemistry departments in
Australia with a strong record of achievement and an international research reputation. There
are typically around 100 postgraduate students undertaking research towards doctorate and masters
degrees.
The School offers postgraduate programs in all areas of contemporary chemistry leading to the following
degrees:
iMaster of Science (MSc)
ii
Doctor of Philosophy (PhD)
iii
Graduate Diploma in Science (equivalent to 4th year of a BSc degree)
The School welcomes expressions of interest from both Australian and international students to
undertake a postgraduate degree in Chemistry.
All information on how to apply for candidature, scholarships, research projects in the School of
Chemistry and other information for both Australian and international students may be found at:
http://sydney.edu.au/science/chemistry/study/postgraduate.html
Contact
School of Chemistry
The University of Sydney NSW 2006 Australia
T: +61 2 9351 4504
F: +61 2 9351 3329
E: [email protected]
http://sydney.edu.au/science/chemistry
5
2009 Chemistry Research Report
welcome
from the head of school
Professor Gregory G Warr
Head of School
T +61 2 9351 4504
F +61 2 9351 3329
E [email protected]
W http://sydney.edu.au/science/chemistry/research/warr.html
2
009 marked 50 years of occupancy of the “new” School of
Chemistry building, although it wasn’t officially opened until
June 1960. Although a mature discipline in the world and
within the University of Sydney, chemistry continues to expand its
boundaries and interdisciplinary reach through new collaborations
and new research directions. Many of our staff are engaged in
biomedical research, developing new drug leads, diagnostic tools
and targeted therapy-delivery systems, involving collaborations with
the faculties of Medicine and Pharmacy, as well as with industrial
partners in Australia and internationally. Our work encompasses
many new materials, from solid state energy-storage materials,
molecularly patterned surfaces and nanostructured particles to
photovoltaic and photonic devices. The theoretical chemistry group
has a proud tradition in the School and remains strong, working both
in collaboration with experimentalists while also boldly looking where
experiments cannot yet see.
To paraphrase the vice-chancellor in the 2010 Green Paper, in
chemistry we eschew the artificial distinction between fundamental
and applied research. The spectrum is a continuum, and all colours
and shades can yield interesting problems to be solved, and important
breakthroughs in understanding.
In 2009 the School maintained its strong publication record,
producing two books, 11 book chapters, 234 research papers and 56
refereed conference papers. Our research outputs continue to be
focused on highly-ranked, international journals. Staff and students
also presented their research at too many national and international
conferences to keep track of, supported by external and internal
travel grants. I thank our alumni/ae and donors for their support,
particularly of postgraduate scholarships and travel grants.
Despite some turnover and departures of senior members of the
School, recently-appointed staff already contribute to our very high
level of competitive research grant success. In 2009, members of
the School held 32 Discovery Grants, 8 Fellowships and 5 Linkage
Grants from the Australian Research Council, totaling (with other
grants) $10.6M in competitive research funding. Our research
receives national and international recognition including NSW Young
Tall Poppy Awards to both A/Professor Sébastien Perrier and
Dr Timothy Schmidt; the 2009 David Sangster Polymer Science
and Technology Award and the 2009 Rennie Memorial Medal to
A/Professor Perrier; and the H G Smith Medal to Professor Jeff
Reimers.
The School’s diverse research infrastructure is supported by
dedicated, high-level professional and technical expertise in the form
of NMR Spectroscopy, Mass Spectrometry, Vibrational and Optical
Spectroscopy, X-ray Crystallography, Chromatographic Separations,
and High-Performance Computing facilities, as well as mechanical
and electronic workshops. Numerous other facilities within research
groups further enhance our research capacity. School members also
make extensive use major national and international research facilities
including the Australian Synchrotron, the Opal research reactor, the
Australian National Beamline in Japan, and the UK’s RutherfordAppleton Laboratory.
Together, these opportunities markedly
enhance the quality of research training we provide, and keep our
research activities internationally competitive at the highest level.
In addition to the 122 postgraduate research students in the
School in 2009, there were 32 honours students undertaking yearlong, research-intensive training, as well as numerous undergraduate
scholars completing Talented Student Program research projects or
summer research scholarships. Our postgraduate profile is changing,
with the School of Chemistry increasingly acting as a magnet for
postgraduate students from elsewhere in Australia and overseas.
This growing population complements our busy schedule of seminar
speakers, guest lecturers and visiting scientific collaborators, helping
create the exciting research environment in which we are privileged
to work.
Professor Greg Warr
Head of School
2009 Chemistry Research Report
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7
2009 Chemistry Research Report
Associate Professor Adam Bridgeman
Room 222
School of Chemistry, F11
T +61 2 9351 2731
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/bridgeman.html
computational inorganic chemistry and education
Computational Study of Polyoxometalates
Polyoxometalates are a huge and structurally
diverse class of compounds with remarkable
but poorly understood chemical and
physical properties. They are prototypical of
the highly praised nanomaterials, displaying
a versatility that raises interest in various
domains of catalysis, magnetism, medical
biology and functional materials. Their
diversity, size and complexity make rational
design of functional nanomaterials a real
challenge.
We have published the first studies of
their vibrational spectra and fundamental
studies of their electronic structure. With
ARC funding, we are currently developing
a global framework for predicting their
structures and spectroscopic properties.
This approach uses genetic algorithms to
process, locate and analyze the very many
minimum energy structures that are possible
for these large and highly flexible clusters.
This is enabling us to probe the interactions
of these clusters with biomolecules and
identify the structural and chemical basis
of their medicinal properties. Figure 1
shows the Keggin anion which is build from
edge and corner sharing octahedra. The
octahedral are slightly distorted, leading to
low basicity on the surface and complex
interactions with organic and bioorganic
counter ions.
The Electronic Structure of Transition
Metal and High Temperature Molecules
We use density functional theory
to model the structures, energetics
and spectroscopy of transition metal
complexes. For example, we have recently
developed a method for calculating the
polarized ligand-field spectrum of transition
metal complexes with applications in
bioinorganic and organometallic chemistry.
This model allows us to accurately model
the vibrational fine structure, band shape
and intensity of linearly and circularized
spectra of known molecules and to predict
these features in the spectra of active sites
in metalloenyzmes. Figure 2 shows the
variation in the 1A2g  1A1g band in [PtCl4]2with temperature, modelled using density
functional calculations which include spinorbit coupling.
Chemical Education
We are involved in a number of University
and nationally funded projects designed
to enhance chemical education and the
student experience. These include the ALTC
funded projects in active learning in science
and language difficulties in first year science
education. We were recently awarded
University funding for projects developing
generic attributes and the scientific
method in first year science courses and a
Vice Chancellor Award for Support of the
Student Experience for the development of
software to deliver rapid and personalized
feedback.
Figure 1
Figure 2
8
2009 Chemistry Research Report
Professor John Canning
Interdisciplinary Photonics Laboratories/School of Chemistry
Madsen Building, F09
T +61 2 9351 1934
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/canning.html
interdisciplinary
photonics
The Interdisciplinary Photonics
Laboratories carries out research
in all aspects of photonics,
particularly those in novel material
systems and applications. Through
our extensive collaborations, both
national and international, we
maintain strong interdisciplinary
activities in all areas. A number of
highlights were reported in 2009,
some of which we mention below.
Self-Assembled Photonics
Ongoing work has reproduced the original
demonstration of porphyrin molecular wires
and slabs in Denmark, in Sydney by PhD
student George Huyang. With Brant Gibson
from Melbourne University, focussed ion
beam (FIB) milling of these structures
was demonstrated. Detailed reports on
this work were produced in 2009. These
self-assembled technologies have been
extended to SiO2 and TiO2 nanoparticles
both in the bulk form and are being used to
enhance chemical sensors in waveguides.
Noticeably, UNSW Summer student Danijel
Boskovic and Chemistry student Masood
Naqshbandi have demonstrated impressive
results.
Laser Processing of Materials
In 2009 we have worked in several areas
using a suite of lasers both here and
elsewhere. At a materials level, work
with our colleagues at the Universite de
Paris Sud 11 we showed that 2-photon
absorption in Er-Al doped glasses resulted
in densification changes which explained
the refractive index changes utilised to
make gratings in non-photosensitive glass.
The effect of higher order multiphoton
absorption processes within wet and dry
silica were also studied using femtosecond
lasers. Results were exploited to
demonstrate periodic refractive index
change within large diameter glass fibres
with a cladding of air holes. These pure silica
air-clad optical fibres offer great potential in
fibre lasers but also in meeting the needs
of the next generation optical telescopes
with large numerical apertures – in 2009 we
reported the first evaluation of such fibres.
In yet another novel material system, we
demonstrated in collaboration with Adelaide
University high quality laser cleaving of
polymer PMMA and TOPAS terahertz fibres
of record high air fraction.
Applying Periodic Structures
Whether it is by laser processing or by
utilising advanced CMOS facilities in
Denmark, the fabrication of periodic
gratings is of interest in a number of
applications. With colleagues from the
Attosecond Science Facility at Griffith
University we have combined chirped fibre
gratings and the high coherence retained
in supercontinuum generated light within
an optical fibre to produce a mode-locked
pulse source at any arbitrary wavelength.
Our work on ultrahigh stable temperature
gratings, the tour de force of thermal
processing of glass, has progressed with
the recent demonstration that regeneration
retains nanoscale resolution of features
within a seed structure inscribed by UV
laser. This permits complex profiles to
be produced for ultra high temperature
environments. Together with colleagues in
Denmark, we reported on large polarisation
conversion using the dispersion within a
silicon photonic crystal waveguide. The
narrow polarisation conversion has potential
applications in biosensing on a chip.
New Optical Fibre Fabrication Facility
In a close collaboration with colleagues at
the University of New South Wales, we are
establishing a new optical fibre fabrication
facility for specialty fibres. In 2009 we have
installed a new modified chemical vapour
deposition (MCVD) lathe system. Funding
for a new optical fibre draw tower was
obtained and this will be purchased in 2010.
International Relations
Roberson Oliveira from Federal university
of Technology continues our ongoing
collaborations with Brazil by spending
one year of his PhD at iPL on a CAPES
scholarship. We also hosted Daniele Tosi
from Milan Polytechnic, Italy an Endeavour
Research Fellow. In 2009 we hosted the 1st
Australia-China Joint Workshop on Optical
Fibre Sensors for Industrial Applications,
(ed. G. D. Peng & J. Canning) at UNSW.
2009 saw the launch of Sydney
University’s WORLD magazine which
reported on iPL’s European activities
in sensing.
Prof. John Canning
Dr. Mattias Aslund
Dr. Kevin Cook
Dr. Andrew Michie
Dr. Albert Canagasabey (UNSW)
Mr. Michael Stevenson
Mr. George Huyang
Mr. Masood Naqshbandi
Mr. Danijel Boskovic
Mr. Jack Orford
Mr. Roberson Oliveiro
Prof. Alexandre Pohl
Prof. Max Crossley
Dr. Jeff Reimers
Dr. Hank de Bruyn
Dr. Chiara Neto
Prof. Gang-Ding Peng (UNSW)
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2009 Chemistry Research Report
Dr Ronald J Clarke
Room 358
School of Chemistry, F11
T +61 2 9351 4406
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/clarke.html
biophysical chemistry of membranes
Mechanism of the Na+,K+-ATPase (PilotelleBunner, Matthews, Kuchel, Cornelius1, Apell2,
Sebban3)
The Na+,K+-ATPase, which is found in the
plasma membrane of all animal cells, utilizes
the free energy derived from ATP hydrolysis
for the transport of Na+ ions out of and K+
ions into the cell. The concentration gradients
of Na+ and K+ thus generated across the
cell membrane have numerous important
physiological functions, e.g. maintenance
of the resting potential in nerve cells, cell
volume regulation and nutrient reabsorption
in the kidney. The aim of this project is to
determine the kinetics and thermodynamics
of the individual reaction steps of the
enzyme’s complex reaction cycle and
thus obtain a deeper understanding of
the mechanism of ion pumping and how
it is coupled to ATP hydrolysis. Major
tools involved in these investigations are
stopped-flow fluorescence spectroscopy,
which allows conformational changes and
charge translocation steps of the enzyme
to be resolved on the millisecond timescale,
and isothermal titration calorimetry, which
can resolve the heat released in individual
reaction steps.
Recently we discovered that the
Na+,K+-ATPase occurs in the membrane in
dimeric form. This allows the enzyme to
have two gears of ion pumping depending
on the ATP concentration. The proteinprotein interactions within a dimer also
increase the enzyme’s ATP affinity and
allow it to function more efficiently at low
oxygen levels.
Based on a comparison of kinetic and
thermodynamic measurements of Mg2+
binding to the enzyme we were able to
demonstrate that Mg2+, which is an essential
cofactor required for phosphorylation, is
bound indirectly to the enzyme via ATP.
Molecular Origin of the Membrane Dipole
Potential (Starke-Peterkovic)
The membrane dipole potential is an electrical
potential of several hundred millivolts
situated within phospholipid membranes. It
has been postulated to play an important role
in controlling the kinetics of ion transport
processes in biological membranes (ion
channels and pumps). Its origin is, however,
still unclear. According to one hypothesis it
may be due to orientated water molecules
on the surface of the membrane. Dipolar
groups from the lipids themselves could
however also be contributing. The aim of
this project is to investigate each of these
hypotheses using spectroscopic methods
specifically developed for the quantification
of the dipole potential.
Using fluorescence spectroscopy with
the voltage-sensitive fluorescent probe di8-ANEPPS, we have found that the dipole
potential can be modified by changing the
degree of saturation of the membrane
lipids and by the incorporation of either
charged or dipolar hydrophobic species
(e.g. cholesterol) into the membrane. In
recent studies we showed that one of the
carbonyl groups linking the lipid headgroup
to the hydrocarbon chains plays a critical
role in determining the magnitude of the
dipole potential.
Voltage-Sensitive Fluorescent Membrane
Probes (Pham)
The kinetics of ion transfer across lipid
membranes can be conveniently studied
using voltage-sensitive dyes, such as RH421
and di-8-ANEPPS. So far these dyes have
been particularly successful in resolving the
mechanisms of the biologically important
ion-transporting membrane protein, the
Na+,K+-ATPase. The current dyes do,
however, suffer from the problem of
photochemical instability. We are presently
investigating the mechanisms of the dyes’
photochemical reactions in order to devise
a synthetic strategy of increasing their
stability.
1
2
3
University of Aarhus, Denmark
Unversity of Constance, Germany
Laboratoire de Chimie-Physique, Universite
Orsay, France
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2009 Chemistry Research Report
Professor Maxwell J Crossley, FAA
Room 514
School of Chemistry, F11
T +61 2 9351 2751
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/crossley.html
device were further developed and further
work was undertaken on design and
synthesis of these advanced materials. New
porphyrin chemistry was developed which
allowed synthesis of tetrakis-porphyrin
Tröger’s base helices.
synthesis of
functional organic
molecules
Researchers from the Crossley
and Schmidt Groups have come up
with an ingenious low-cost device
to harvest low energy photons
that are currently unused by solar
cells – utilising the process of
photochemical upconversion.
Efficient Photochemical Up-Conversion
by Triplet-Triplet Annihilation (Auckett,
Cheng, Khoury, Clady, Tayebjee, EkinsDaukes*, Schmidt)
Ring annulation of the pyrrolic rings
of porphyrins leads to very interesting
compounds that behave as π-expanded
systems. We previously synthesised
tetrakis(quinoxalino)porphyrins, porphyrins
that are expanded in four directions; for
example, Pd(II) tetrakisquinoxalinoporphyrin
2 from the porphyrin 1 by three different
routes (Scheme 1).
Upconversion is the process whereby a
stream of light of a given photon energy is
converted into one of a higher energy. Very
efficient red to yellow light upconversion by
triplet-triplet annihilation is achieved using
the palladium π-expanded porphyrins as
sensitizer molecules and rubrene as the
emitter molecule. We have also achieved
red to green, red to blue, and green to blue
upconversion using other emitters. We have
Scheme 1
demonstrated TTA efficiencies estimated
at 25%, far in excess of the statistical
11.1% limit of singlet formation. A series of
novel porphyrin sensitiser molecules were
prepared and their use as sensitisers is
under investigation
Porphyrins in Structured Optical Fibres
(Martelli*, Canning, Stocks, Huyang,
Naqshbandi, Boskovic)
Compounds that form highly ordered
monolayers on the interior of optical fibres
were synthesized and studied. A new acid
sensor was developed and meso-structured
silica and titania particle were constructed.
New Advanced Materials (Hammershoj,
Khoury, Larsen, Stocks, Webb, A. Sum,
Reimers)
The design and synthesis of new advanced
materials based on metalloporphyrins
was continued. A novel approach to rigid
extended aromatic systems has been further
developed to include the synthesis of novel
polymers with the potential to behave as
electrical conductors and semi-conductors.
Studies in the areas of molecular switching
devices and novel molecular circuitry were
continued. New ideas for the development
of a non-volatile molecular-scale memory
Crossley Group photo: from left – Jimmy Lee, George Huyang, Tony Khoury, Dianne
Fisher, Max Crossley, Anthony Sum, Fargol Taba, Grace Simpkins and Max Sum
Synthesis and Photophysics of Models for
the Photosynthetic Reaction Centre (Lee,
Reimers, Hutchison*, Ghiggino*, Fukuzumi*,
Ohkubo*, Wu*)
Tris-and tetrakis-porphyrin chemical mimics
of the chromophore arrangement of the
photosynthetic reaction centre (PRC)
have been further studied. The kinetic and
thermodynamic properties of the synthetic
PRC’s were investigated using ultrafast and
ESR spectroscopy and electrochemistry.
New Donor-Acceptor systems for charge
separation were constructed and studied.
More elaborate models that incorporate
an additional C-60 acceptor unit were
designed and synthesised. These are the
closest mimics of the natural systems to be
developed anywhere.
Porphyrins on Surfaces (Elemans*, Khoury,
Chin, Reimers, Martelli*, Canning, Huyang)
Tetra-alkyl porphyrins were shown to form
well-ordered monolayers on HOPG surfaces
and to form microrods on silicon and wormlike structures on silica.
Porphyrin
Analogues
as
Gingivitis
Inhibitors (Yap, Simpkins, Collyer*, Hunter*,
A. Sum)
The black-pigment, Gram-negative bacterium
Porphyromonas gingivalis is an important
etiological agent the adult periodontal disease
Gingivitis: an inflammatory process affecting
supporting tissues surrounding the teeth.
This anaerobic bacterium has been reported
to display an absolute requirement for either
hemin or hemoglobin as growth factors. A
series of porphyrin-antibiotic and porphyrinamino acid-antibiotic conjugates and analogues
contaning biotin were prepared and used to
further define requirements for recognition by
HA2 receptors of the gingipains and to explore
transport and in-cell processing.
Steroid Bioconjugates (Taba, M. Sum)
Porphyrin-steroid and porphyrin-sugar
conjugates were synthesised and found
to permeate A549 (human lung cancer)
cells. Bioaccumulation was followed by
confocal microscopy. Various water-soluble
porphyrin-estradiol adducts were prepared
for cell recognition studies.
11
2009 Chemistry Research Report
Dr Adrian V George*
Room 224
School of Chemistry, F11
T +61 2 9351 6055
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/george.html
synthesis, analysis
and education
Our current research covers two
areas. In one we are interested
in developing analytical methods
sensitive enough to detect doping
in competitive sport and to identify
the origin of illegal drug seizures.
In the second we examine the
processes by which students
learn chemistry to determine the
most effective methods to present
information.
Detection of Steroid Use in Sport (Brooker,
Cawley)
Improved High-Performance Liquid Chromatography - Tandem Mass Spectrometry
(LC-MS/MS) methodology for the quantification and confirmation of synthetic
glucocorticosteroid (GCs) abuse in sport
has been developed and validated. Utilizing stable isotopically labeled processed
internal standards, the method was used
to assess excretion studies from permitted
(topical/local) and prohibited (systemic)
modes of therapeutic synthetic GC administration. Results from four forms of topical/local administration (dermal, inhalation,
nasal spray, heel injection) of the synthetic
GC triamcinolone acetonide (TA) showed
that all TA excretion was completed within 24 hours, except for the injection study
where detection was confirmed for up to
four days post-administration. Results from
an oral (systemic) administration of triamcinolone (T) showed that the maximum
urinary concentration was greater than
3 mg/mL, or more than 100 times the World
Anti-doping Agency (WADA) specified
(laboratory) minimum required performance
limit.
Adrenosterone is an endogenous
steroid hormone that has been promoted
as a dietary supplement capable of reducing
body fat and increasing muscle mass. It
has been proposed that adrenosterone
may function as a specific inhibitor of the
11b-hydroxysteroid dehydrogenase type
1 enzyme (11b-HSD1) that is primarily
responsible for re-activation of cortisol
from cortisone. The urinary metabolism
of adrenosterone was investigated by gas
chromatography-mass spectrometry (GCMS) and gas chromatography-combustionisotope ratio mass spectrometry (GC-CIRMS). The exogenous origin of the most
abundant adrenosterone metabolites was
confirmed by GC-C-IRMS analysis with
reference to urinary steroids from separate
metabolic pathways. To develop anti-doping
screening and confirmation criteria, GCMS and GC-C-IRMS data from a reference
population consisting of urine samples from
85 elite athlete volunteers was collated for
comparison. As the analytical techniques
used in this study are available to World
Anti-doping Agency (WADA) accredited
laboratories worldwide, the proposed criteria
may be able to be efficiently implemented
for the doping control of adrenosterone.
Profiling of Synthetic Illicit Drugs
(Salouros)
Trace impurities in clandestine manufactured drugs are the result of a number of
reasons. They can be due to impurities being present in the precursors, solvents and/
or reagents which can be carried over into
the final product unchanged or they can
react and be transformed into other prod-
ucts. Impurities can also be generated as
by-products in the drug manufacturing process. Finally the conditions of storage, such
as exposure to light and heat, as well as cutting agents introduced may affect the drug
and/or impurities, thus introducing new
impurities. Research is being undertaken to
link the impurity profile in a reaction with
method and conditions of synthesis. This
will enable a ‘finger print’ of a synthetic approach to be established and, ultimately,
provide a method to determine the origin of
batches of seized drugs. More recently isotope ratio mass spectrometry has been applied to the profiling of methylamphetamine
synthesis and is able to provide valuable information on the origin of the ephedrine or
pseudoephedrine precursors.
Education in Chemistry (Schmid, Yeung)
The connection between a person’s learning style (eg whether they prefer to learn
in group situations or ‘go it alone’) and they
way they interact with different leaning situations has been investigated. In particular
whether the personalization of text (where
the material is presented in a conversational
style) results in different learning outcomes
compared to a more traditional impersonalized presentation.
* Excellence in Teaching Award
12
2009 Chemistry Research Report
Professor Trevor W Hambley
Room 412a
School of Chemistry, F11
T +61 2 9351 2830
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/hambley.html
medicinal inorganic chemistry
Monitoring
the
Penetration
and
Effectiveness of Anticancer Drugs in Solid
Tumours (Byrce, Kim, Klein, Yamamoto,
Zhang)
A limiting factor in the effectiveness of
current anti-cancer treatments is the inability
of the drug to penetrate throughout the
entire tumour at a concentration sufficient
to kill all cells, particularly those in hypoxic
regions. The aim of this project is to develop
a 3 and 4-dimensional cellular models of solid
tumours for use as model systems to study
anti-cancer drug penetration and the effect
of those drugs on cell status and viability.
Tumour spheroids are a unique cellular
system that allows the study of cancer
within a 3-dimensional environment and
they possess many tumour characteristics,
including the development of necrotic cores.
We successfully developed 4-dimensional
cellular models of solid tumours using
transfected DLD-1 colon carcinoma cells by
transfecting them with genes that turned
on the expression of a photoconvertible
green fluorescent when the cell was under
conditions of hypoxic stress and cell status
reporting fluorescent proteins (Fucci
constructs). We were able to show that
the cells in regions more 70 µm from the
spheroid surface were indeed hypoxic. Using
cobalt complexes that released fluorescent
groups we showed that activation occurred
preferentially in the hypoxic regions (Fig. 1).
Thus, we are now able to monitor the fate
of hypoxia selective complexes in real in
Figure 1: Fluorescence image for a spheroid
of DLD-1 cells transfected with HRE-EosFP
following treatment with [Co(C343)2(cyclam)]
ClO4 and cell migration.
time while simultaneously monitoring the
state and response of the cells to the drug
treatment.
Tuning the Chemistry of Platinum(IV)
and Cobalt(III) Complexes for Anticancer
Applications (Bonnitcha, Gui, Klein, Norman,
Yamamoto, Zhang)
Platinum(IV) complexes are more inert than
their platinum(II) analogues and therefore
have the potential to be less toxic while
cobalt(III) complexes are able to carry toxic
agents in a pacified form. The preparation
of charged complexes designed to establish
whether it was possible to manipulate the
uptake in different regions of solid tumours
with lower pH was continued. It was found
that the reduction potentials and pKa values
of the cobalt complexes, critical determinants
of their biological behaviour and tumour
selectivity, could be tuned over a wide range
using subtle variation of the carrier ligand.
This has allowed us develop complexes with
the desired properties without compromising
their stability and establishes that the
tripyridyl ligand framework we have used in
the development of most of these complexes
can be employed to produce delivery agents
with carefully optimised properties. Studies of
cellular and spheroid uptake were undertaken
for a range of cobalt complexes and showed
selective activation in the hypoxic regions of
spheroids.
We developed new methods for
functionalising
platinum(IV)
complexes
which will enable us to produce a wider range
of complexes than are currently accessible,
again with carefully optimised reduction
potentials and, where relevant, pKa values.
The attachment of peptides to the axial sites
of platinum(IV) complexes was achieved.
Selective Targeting of Solid Tumours using
Cobalt Complexes (Kim, Yamamoto)
The goal of our work is to develop new
agents that selectively target solid tumours
by taking advantage of the physiological
differences between tumours and healthy
tissues. The specific aims of this project are to
develop new cobalt-based hypoxia-selective
agents and to modify such agents to achieve
the desired level of targeting. In order to do
this, we are developing new methods for
determining the fate of the hypoxia-selective
agents in solid tumours and in models of this
environment. The rational development of
hypoxia-selective agents has been hampered
by a lack of knowledge of where and when
the agent is reduced and the cytotoxic ligand
released. We continued our investigations of
cobalt complexes with hydroxamate ligands
attached that become fluorescent on release.
Work on developing cobalt complexes with
a range of physical and chemical properties
was continued with a series of complexes
with different of charges prepared. Work was
continued on the use of the fluorescence
based methods to report on the release of
ligands in cancer cell spheroids and confirmed
that the penetration and distribution of the
compounds could be tracked.
Targeting of Metastatic Tumours using
MMP Binding Agents (Di Marco, Doan,
Green, Kassiou)
Almost all compounds used in the treatment
of cancer cause serious side effects because
they lack selectivity for tumours. However,
the rapidly increasing knowledge and
understanding of the differences between the
chemistry and biochemistry of tumours and
healthy tissues means that it is now possible
to envisage drugs that act selectively on
tumours. Our work is aimed at developing new
agents that selectively target solid tumours
by taking advantage of these differences.
An important difference that has emerged
relatively recently is the overexpression
of matrix metalloproteinases (MMPs) in
metastasising tumours. The synthesis of a
range of novel MMP binding agents with the
ability to carry therapeutic and/or imaging
radionuclides was continued in the context
of two sub-projects: (i) Tc and Re labelling
for SPECT imaging studies and radiotherapy
and (ii) F and I labelling for PET and SPECT
imaging studies respectively. Radiolabelling
of HcHIP-LPED with technetium-99m was
carried out with high efficiency (>70%) and
yielded a highly pure product which was
suitable for use in animals studies. Work
continued on fluorine-18 labelling and new
strategies for achieving high level labelling
were developed.
New ligands were developed with
quinoline donor groups and these were
shown to generate fluorescent complexes on
coordination to tricarbonylrhenium(I).
13
2009 Chemistry Research Report
Associate Professor Brian S Hawkett
Room 350
School of Chemistry, F11
T +61 2 9351 6973
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/hawkett.html
polymer colloids
Our research is aimed at
gaining an understanding of
the factors governing the
formation and stabilisation
of
colloidal
dispersions
so that we can use this
understanding
to
solve
scientific problems that are
of interest to our industry
collaborators.
RAFT in Disperse Phase Systems (Warr,
Nguyen, Hall, Pham, Aziz, Dastoor, Such,
Ali, Heuts, van Herk)
Controlled radical polymerization allows
a control of polymer and nanoparticle
architecture that was previously only dreamt
of. Reversible addition fragmentation chain
transfer (RAFT) is the most versatile of
the currently available controlled radical
processes. In this broad based project with
DuluxGroup Australia we exploit this new
capability in our research to design and
synthesize polymer particles and composite
nanoparticles with particular emphasis
on applications in surface coatings.
Achievements in this project include the
coating of individual unaggregated pigment
particles with polymer to achieve improved
pigment efficiency and thus reduce the
amount required in a coating. Coating
particles in this way has been a “Holy
Grail” of the coatings industry for many
decades. Pigment efficiency has been
still further improved by encapsulating
individual pigment particles within hollow
polymer particles, thus halving the amount
of TiO2 needed to achieve a given opacity.
Also in this project, in collaboration with
the University of Newcastle we have been
preparing latexes containing photoactive
polymers in a step towards generating
water based light harvesting coatings. In
yet another aspect of the project we have
discovered a new approach to making Janus
particles that enables their preparation both
economically and on a large scale.
Polymer Stabilisation of Superparamagnetic Nanoparticles for Biomedical Applications (Hambley, Warr, Jain, Pan, Pham,
Bryce, Tanudji, Jones)
In this project, in collaboration with Sirtex
Medical Limited, we are using short
chain amphiphilic macro-RAFT agent
surfactants as anchored steric stabilisers
for
superparamagnetic
nanoparticles.
One objective in this project is to prepare
microbeads (about 35 microns in diameter)
that contain a high concentration (about
109/bead)
of
individually
stabilised
magnetic nanoparticles that can be used
for the hyperthermia treatment of liver
cancer. The beads are of just the right size
to lodge in the tumor when injected into the
hepatic artery. The patient is then put in an
oscillating magnetic field of appropriate
field strength and frequency, causing the
0.30 mm
TiO2 particles encapsulated by
polymer
0.1 mm
Gibbsite clay particles encapsulated
by polymer
beads to heat up and destroy the tumor,
with little collateral damage to other tissue.
Stabilisation and Rheological Control of
Concentrated Inverse Emulsions (Warr,
Priyananda, Fitzgerald, Gore)
In this collaboration with Dyno Nobel
Asia Pacific we are gaining a fundamental
understanding of the factors governing the
formation and behaviour of gas bubbles
in concentrated inverse emulsions. This
understanding has allowed us to devise
cost effective approaches to stabilise
gas bubbles in the continuous phase of
explosive emulsions. In a separate part of
this project we have been investigating the
various factors that impact on the rheology
and yield stress of concentrated inverse
emulsions and ways of controlling them.
0.5 mm
TiO2 particles inside hollow polymer
particles
50 nm
Anisotropic nanoparticles
14
2009 Chemistry Research Report
Dr Toby Hudson
Room 456
School of Chemistry, F11
T +61 2 9351 7648
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/hudson.html
Theoretical
materials chemistry
Modern computational tools
allow us to examine structural
phenomena in simplified models
of condensed matter from
a perspective that allows us
to examine precise atomistic
detail, often in systems where
experiment is unable to probe
the appropriate time scales,
length scales, or unable to
achieve the required control
over the conditions or purity.
Dense Packing (Kummerfeld, Marshall,
Harrowell)
Hard sphere packing models have been
widely used to understand the structure
of intermetallics and metallic glasses. The
packing density of colloidal structures is also
known to determine the thermodynamic
outcome in self-assembled systems such as
opals. Interest has also picked up again in
recent times because packing is one way to
control the architecture of self-assembled
Figure 1. An optimally dense packed
structure, based on the NaZn13 structure
type. Inside each snub cube is a large
sphere.
nanostructures. Despite this, no systematic
search has ever been made to find the
densest structure for even something as
simple as spheres of two sizes. We have
approached the structural search problem
in two ways. Firstly we have used the entire
Inorganic Crystal Structure Database as
starting points and representation classes
for computer optimization, and secondly
starting from categories of structures with
interesting geometric motifs. These two
approaches have identified a number of
densely packed structures that are not seen
in atomic systems, as well as significantly
improving the best known binary packing
for systems over large ranges of size
ratio. The outcomes of this work include:
an explanation for the observed size ratio
of silica spheres in some precious opals;
an argument that even after considering
electronic effects in alloys with the NaZn13
structure type, the detailed structure is
still principally determined by the solution
to a sphere packing problem; and, the
first demonstrations of structures better
than segregated close-packed lattices for
all binary combinations with small sphere
sizes of up to 65% of the size of the large
spheres.
The approach used here, a combination
of data mining and Monte Carlo simulated
annealing, is a powerful tool for structural
searches. Future projects will apply this
method to the design of materials with
a range of geometric and functional
properties.
Amorphous Network Relaxation (Andrews,
Harrowell, Poole†)
In contrast to crystals, where relaxation and
diffusion mechanisms are dominated by the
motion of discrete well-defined defects,
amorphous materials often evolve using
collective and unpredictable mechanisms.
Unfortunately we cannot probe these
complex events easily with experiment,
because in glasses all we can usually get
are averages and distributions. Computer
modelling on the other hand has the ability
to probe atomic and topological information
directly.
We have developed a systematic series
of topology-altering mechanisms, which can
be applied to any network. It can be used to
categorize observed topological changes,
or as a broad set of trial moves that can be
used in Monte Carlo (MC) simulations. We
Figure 2. A low energy configuration
of the continuous random network.
showed that a previously known and widely
used mechanism (the WWW mechanism) is
optimal for both energetic minimization and
structural sampling at low temperatures
where relaxation is slowest. We are now
using a generalization of this methodology
to study rearrangement mechanisms in
supercooled water.
Further investigation has focused on
stress relaxation in these networks. Stress
relaxation is related to the viscosity of a
material, and therefore is a key player in the
transition from liquid to glassy behaviour.
We have shown that the WWW mechanism,
irrespective of where it occurs in these
networks causes a characteristic but not
yet predictable change in both the structure
and stress. Furthermore, we find that local
stresses have a role in selecting the likely
sites for rearrangement events.
These insights will be built upon to
establish a full model of stress relaxation in
the linear response regime from what we
know about the elementary mechanisms in
these equilibrium simulations. This will help
the understanding of viscosity in amorphous
materials to catch up with that of creep
in crystalline materials, where models
have superseded the phenomenological
classification methods.
Co-worker not associated
University of Sydney.
†
with
the
15
2009 Chemistry Research Report
Dr Luke Hunter
Room 516
School of Chemistry, F11
T +61 2 9114 1190
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/hunter.html
organofluorine chemistry
Our research focuses on the element
fluorine, and on what happens when
this extreme element is incorporated
into organic molecules. A particular
interest concerns the ways in which
fluorine atoms affect molecular
conformation. Understanding the
conformational outcomes of fluorine
substitution allows us to design shapecontrolled molecules such as bioactive
peptides for applications in medicine
and biotechnology.
The highly polarised C–F bond participates
in various stereoelectronic interactions
with neighbouring functional groups, and
these interactions favour certain molecular
conformations. For example, C–F bonds
prefer to align antiparallel (180°) to
adjacent C=O bonds but gauche (60°) to
adjacent C–N or C–F bonds. According
to these rules, organofluorine compounds
can be “programmed” to adopt unique
conformations including linear, bent and
helical shapes (Figure 1).
As an application of this concept, we
are synthesising unnatural g- or d-amino
acids containing several vicinal fluorines. We
use the techniques of X-ray crystallography
and NMR spectrometry to show that
these novel amino acids adopt different
conformations depending on the fluorine
stereochemistry. As such, they can be used
as building blocks for incorporation into
shape-controlled peptides.
One example of this is our planned
research on RGD peptides. The tripeptide
sequence RGD (arginine-glycine-aspartate)
is commonly found in extracellular proteins,
where it is recognised by cell-surface
receptors called integrins. The integrins
are involved in many important biological
processes, and there is worldwide interest in
targeting specific integrins for the treatment
of various diseases including cancer and
osteoporosis. Crucially, in Nature the integrin
selectivity is determined by the shape of the
RGD motif, and this is where fluorination
chemistry can play a role. We are synthesising
a library of fluorinated RGD peptides that
have subtly different shapes and should
therefore exhibit different integrin-binding
selectivities. We will be collaborating with
GSK (England) to investigate the selectivity
and pharmaceutical potential of these
fluorinated peptides.
Figure 1: Selective fluorination chemistry
can produce helical (top) and zigzag
(bottom) molecular shapes.
16
2009 Chemistry Research Report
Professor Katrina A Jolliffe
Room 515
School of Chemistry, F11
T +61 2 9351 2297
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/jolliffe.html
organic synthesis
and supramolecular
chemistry
Our research focuses on using
and developing the tools of
organic synthesis for the
development of molecules with
a particular function. Specific
targets
include
molecules
capable of recognizing and
sensing other molecules, and
new antifungal drugs with a
novel mode of action.
Cyclic Peptide Based Anion Receptors
(Butler, Dungan, Young)
The selective recognition and sensing
of biologically important anions under
physiological conditions is of intense current
interest to both chemists and biologists.
Anions such as pyrophosphate (P 2O74-,
PPi) play important roles in bioenergetic
and metabolic processes and the ability
to selectively sense such anions has
applications in biomedicine. Backbone
modified cyclic peptides are ideal scaffolds
for the construction of molecular anion
receptors and we are currently investigating
the synthesis and application of a range
of such receptors. We have exploited the
preorganisation of the Lissoclinum class
of backbone rigidified cyclic peptides to
prepare a number of anion receptors and
have also investigated receptors with a
diketopiperazine scaffold. These bear side
chains with either hydrogen bonding or
metal ion binding sites for anions and in
some cases show selective binding for
pyrophosphate ions.
Exploiting Reversible Turn-Inducers for
the Efficient Cyclisation of Small Peptides
(Cochrane, Fairweather, Wong)
Naturally occurring cyclic peptides exhibit
a wide range of biological activities and
are often more resistant to enzymatic
hydrolysis than their linear counterparts.
Additionally, the restricted conformational
flexibility of cyclic peptides allows them
to present functional groups in a spatially
well-defined manner and is of use in the
study and mimicry of protein folding.
However, the currently available methods
for the head-to-tail cyclisation of linear
peptides are often slow and low-yielding.
We recently developed a new method for
the efficient head-to-tail synthesis of small
cyclic peptides and examined its use in a
model system. We have now extended this
methodology to the synthesis of novel cyclic
peptides incorporating from 4-9 amino acids
and have applied it in the synthesis of the
antitumour cyclic peptide Axinellin A and
in the synthesis of the core of LI-F04a, a
cyclic depsipeptide with antifungal activity.
We have also expanded our methodology to
synthesise all-L cyclic tetrapeptides in good
yield.
Design and Synthesis of Antifungal Agents
with Novel Modes of Action (Cochrane,
Koda, Yoon, Sorrell*, Djordjevic*)
Pathogenic fungi are increasingly implicated
as a cause of serious and potentially fatal
disease, especially in immunocompromised
hosts. Current therapies are limited in
safety and/or efficacy and resistant fungi
are an emerging problem. The primary aim
of this project is to design and synthesise
novel antifungal agents with activity against
key fungal pathogens and favourable
pharmacokinetic and safety profiles.
We have synthesised several classes of
antifungal compounds with novel structures
and assessed their haemolytic activity and
cytotoxicity as initial indicators of safety.
We have commenced work on determining
the mode of action of these compounds,
which appears to be different to those of
currently used antifungal agents. Our best
compounds have activity comparable to
the gold standard of antifungal drugs,
Amphotericin B and exhibit low toxicity
towards mammalian cells. These compounds
are promising lead sturctures for the
development of new antifungal agents.
17
2009 Chemistry Research Report
Dr Meredith Jordan
Room 241
School of Chemistry, F11
T +61 2 9351 4420
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/jordan.html
intermolecular
interactions
Theoretical and computational
methods are used to study
molecular interactions and
quantum effects in chemistry.
Potential Energy Surfaces (Collins (ANU),
Gordon (Iowa))
Molecular potential energy surfaces
(PES) describe how the energy of a
molecule changes as its atoms move.
We have developed new interpolation
techniques for constructing PES based
on ab initio quantum chemical calculations
and have coupled these with iteration
methods capable of growing a PES until
the calculation of a given quantity has
converged. Research into growing PES as
efficiently as possible is ongoing and we
are currently extending our Grow computer
package to enable calculations on nonmetallic crystalline materials.
Hydrogen Storage Materials (Kolmann)
Electronic structure calculations have
been used to develop reduced-dimensional
PESs for model systems that mimic H2
adsorption in the Lithium-doped metalloorganic framework material (MOF-5).
Grow has been combined with quantum
diffusion Monte Carlo (QDMC) simulations
to predict vibrationally averaged (ground
state) structures of adsorbed H2. This
has demonstrated that the H2 molecule
is delocalised over the organic fragment.
We are currently developing path integral
Monte Carlo techniques to investigate
Above: Equillibrium structures for one, two
and three adsorbed H2 molecules
Above: Minimum energy structures and HOMOs for 4 possible s binding ligands
how the quantum nature of such systems
changes with temperature.
Reaction Dynamics (Kable, Heazlewood)
In collaboration with experiment, the photodissociation dynamics of acetaldehyde,
CH3CHO, on both the S 0 and T1 electronic
PES has been studied. This has confirmed
the presence of a newly discovered “roaming” reaction mechanism and we have
shown that this mechanism dominates
photodissociation on S 0. Our studies have
also pinned down various experimental
parameters for the acetaldehyde PES.
Ongoing experiments, electronic structure
calculations and kinetic modelling further
explore the nature of the CH3CHO PES and
of “non-conventional” reaction dynamics.
Computational Drug Design (Kassiou,
Banister)
Sigma receptors (s1 and s2 subtypes) exert
a neuromodulatory effect in the central
nervous system. Indeed they were originally
proposed as an opioid receptor subtype.
Experimentally, trishomocubane-derived
hemiaminals can be used to develop highly
selective s ligands. In order to understand
the selectivity of aza- and oxo-bridged
ligands computational studies have
investigated their gas phase geometries,
charge distribution and the nature of the
highest occupied and lowest unoccupied
ligand molecular orbitals (HOMOs and
LUMOs).
These calculations indicate that s
binding affinity is largest for ligands where
there is significant HOMO character along
the alkyl bridge between the hemiaminal
and the fluorobenzene group, suggesting
electrons are donated from this orbital into
the LUMO of the receptor site. HOMO
density on the aromatic ring (ie in the p
orbitals) reduces affinity for the s-receptor.
Above: Schematic of acetaldehyde
photodissociation
18
2009 Chemistry Research Report
Professor Scott Kable
Room 311
School of Chemistry, F11
T +61 2 9351 2756
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/kable.html
laser spectroscopy and photochemistry
Laser spectroscopy provides a window
into molecular structure and chemical
reactivity. We utilize the sensitivity and
discrimination of a variety of methods to
find and characterize new molecules, and
to discover new chemical mechanisms.
Experimental research is conducted in the
Laser Spectroscopy Laboratory.
A New Chemical Reaction Mechanism
[Jordan, Maccarone, Rowling, Heazlewood,
Osborn (Sandia), Bowman (Emory)]
Chemical reactions are usually understood
in terms of a specific reaction mechanism.
The transition state (TS) is the lowest
energy structure that connects reactants
and products. In conventional kinetics,
most of the reaction flux passes near
the TS. In 2005, a new chemical reaction
mechanism was published that seems
to violate our normal understanding of
reaction mechanisms [Townsend et al.,
Science, 2005] In this mechanism unusual
chemical products emerge involving groups
on different parts of the original molecule. In
2006, we published the second account of
this mechanism,[Houston and Kable, PNAS,
2006] and have gone on to show that the
mechanism is much more complicated
and ubiquitous than first envisioned.
[Heazlewood et al., PNAS, 2008] In 2009,
we demonstrated that up to 10% of
CD3CHO reactants undergo H/D isotope
exchange before dissociation, leading to
10% DCO product yield.
Spectroscopy and Structure of Radicals
[Schmidt, Nauta, Richmond, Gibson, Reid
(Marquette), Dawes (Sandia)]
Free radicals are elusive to study because
of their inherent reactivity. Our interest
in isolated free radicals is driven by their
importance as intermediates in combustion
and atmospheric processes and in their
presence in the interstellar medium. Using
our new two-dimensional fluorescence
technique (J Phys Chem A, 2006) we
identified a number of organic free radicals
for the first time, including phenylpropargyl
[Reilly et al., J Chem Phys, 2009],
vinylpropargyl [Reilly et al., JACS, 2009] and
indanyl [Troy et al., J Phys Chem A, 2009].
This work has been done in collaboration
with Dr Schmidt and more details can be
found on his page.
In 2009 we also continued to explore the
highest valence states of small halogenated
carbenes. These states are the lowest
linear form of the carbene, and have very
different electronic structure to the lower
lying states. [Dawes et al., J Phys Chem
Lett, 2010]
1.
to provide professional development
of science academics by expanding
their understanding of learning in the
laboratory environment;
2. to build a community of practice by
providing mentoring, workshops and
activity at conferences;
3. to build a shared database of
experiments; and
4. to conduct research into learning and
teaching in the laboratory.
Recently, ASELL is collaborating with
the Australian Council of Deans of Science
to evaluate the student experience across
whole laboratory programs in chemistry,
physics and biology across many Australian
universities. As part of this investigation,
we are exploring how to build a sustainable
mechanism to embed this evaluation as
standard institutional practice.
2009 Laser Spectroscopy Group photo and
collaborators at group retreat
Chemistry Education [Barrie, Sharma,
Buntine (Curtin), Burke de Silva (Flinders),
Lim (Deakin), Pyke (Adelaide)]
The Advancing Science by Enhancing
Learning in the Laboratory (ASELL) project
is a successful Australian initiative contributing to improvements in undergraduate
laboratory curricula nationwide. The project
has four goals:
Schematic and experimental spectra showing the formation of HCO (>38660 cm−1) and DCO (<38660 cm−1). DCO is only produced
on the ground state of acetaldehyde. Up to 10% of the reactant undergoes intramolecular isotope exchange before dissociating.
19
2009 Chemistry Research Report
Associate Professor Michael Kassiou
Brain and Mind Research Institute/School of Chemistry, F11
Room 516
T +61 2 9351 2745
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/kassiou.html
drug discovery/
medicinal chemistry
Immunomodulation in the Treatment and
Diagnosis of CNS Disease (Reynolds,
Hanani)
The recognition that microglial activation
is closely linked to the pathophysiology
of brain disease has made the Translator
Protein (18 kDa) TSPO, formally known as
the peripheral benzodiazepine receptor,
an important therapeutic and diagnostic
target. We investigated the structure
activity profile of molecular probes based
on pyrazolopyrimidines and determined
parameters required for maintaining
high binding affinity based an existing
pharmacophore model. We have further
refined this model by investigating the
effects on nitrogen substitution within the
heterocyclic scaffold. Although this is not
considered in the pharmacophore model it
has great impact on binding affinity of these
molecules.
Chemistry and Biology of Nicotinic
Receptors (Paine)
Nicotinic acetylcholine receptors (nAChRs)
belong to the family of ligand-gated
ion channels which are regulated by
acetylcholine, one of the major excitatory
transmitters in the nervous system. These
receptors play an important role in complex
Figure 1
brain functions, including cognitive
processing; and they are also thought to
be involved in the pathogenesis of several
brain disorders, such as Alzheimer’s
disease, Parkinson’s disease, Tourette’s
syndrome, schizophrenia, depression, and
attention deficit/hyperactivity disorder. It
is known that neuronal nAChRs contain
between 2 and 5 distinct binding sites,
depending on the subtype (Figure 1). The
two major nAChR subtypes are known
in the brain corresponding to a7 and
a4b2. We have developed strategies in
which the following small molecules can
be used to target individual or multiple
sites simultaneously leading to drugs with
potentially diverse therapeutic properties. Purinergic P2X7 Receptor in Depression
(Gunosewoyo, Cheung)
Over the last two decades there has
been increasing evidence of a strong
relationship between depression and
immunological dysfunction in depressed
patients. Excessive secretion of cytokines,
such as interleukin-1b (IL-1b), and tumour
necrosis factor-a (TNF-a) is increasingly
recognised as a potential cause of
depression. The purinergic P2X7 receptor
modulates the maturation and release of
cytokines such as IL-1b in macrophages and
microglia and is involved in inflammatory
and neurodegenerative mechanisms. This
suggests that the P2X7R could play a role
in the pathophysiology of depression and
that blockade of the P2X7R might result in
antidepressant-like properties.
To date, only a few classes
of drug-like molecules are known
to interact with the P2X7R.
We have developed a library of
small polycyclic scaffolds with
varying polycyclic hydrocarbon
and aromatic segments, which
are currently the subject of
pharmacological studies in order
to evaluate their antidepressant
potential.
Chemistry of Sigma Receptors
(Banister, Moussa)
Ligands which bind with high
affinity at sigma receptors have
been shown to modulate and
interfere with several neurotransmitters
and have potent activities in animal
models suggestive of antipsychotic,
cognitive enhancing, neuroprotective, and
antidepressant activities. We have recently
reported the synthesis and binding a novel
series of trishomocubanes of the type 4-az
ahexacyclo[5.4.1.02,6.0 3,10.0 5,9.0 8,11]dodecane
which display high affinity for sigma-2 and
sigma-1 receptor subtypes respectively.
These molecules have also been shown
to modulate cocaine induced behaviours.
These lead compounds provide the basis
for further refinement of the binding and
functional activity of this class.
Arylalkyl 4-benzyl piperazines have only
recently been reported as ligands for sigma
receptors. Targeting sigma-receptors with
arylalkyl piperazines should help in defining
a pharmacophore and establishing a SAR of
arylalkyl piperazines for sigma-receptors.
The Kassiou group
20
2009 Chemistry Research Report
Professor Brendan Kennedy
Room 458
School of Chemistry, F11
T +61 2 9351 2742
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/kennedy.html
solid state and
materials chemistry
Our current research strives
to understand the importance
of local instabilities on the
structures and properties of
metal oxides. The motivation
for this work is to discover new
physical and chemical properties
and to provide fundamental
understanding to allow for
the development of improved
materials for applications in
areas such as electronics and
energy generation Specifically
we are interested in the effects
of chemical substitutions on
structural phase transitions,
using variable temperature high
resolution powder diffraction
methods.
Perovskites
2009 saw two significant achievements in
our ongoing studies of the phase transitions
in perovskites. Firstly we established the
characteristic length scale for strain fields
around impurity cations in the system Pr 1LaxAlO 3 to be around 16 Å through a series
x
of variable temperature high resolution
neutron powder diffraction studies,
focussing on the first order Imma-C2/c
phase transition. Secondly we revealed
the presence of electron transfer between
Mn and Ru in the series CaRu1-xMnxO 3
through details structural (synchrotron
X-ray and neutron diffraction) and X-ray
absorption spectral studies. The presence
of Mn 3+-Ru5+ redox pairs in these oxides is
remarkable given that in both end member
oxides, CaRuO 3 and CaMnO 3, the transition
metal is present in the +4 oxidation state.
Coupling of Jahn-Teller and Tilting
Distortions in Manganese Oxides
Colossal magnetoresistive materials (i.e.
materials which show changes in electrical
resistance on placing in a magnetic field)
find applications in a variety of magnetic
storage media e.g. computer hard drives.
Here we are using a broad range of
synthesis and characterisation methods
(including neutron and synchrotron X-ray
diffraction) to understand how tilting of
the corner sharing octahedra influences
long range orbital ordering associated
with the Jahn-Teller active Mn3+ cation.
Neutron diffraction studies of the pair of
oxides (Sr0.8Ce0.2)(Mn1-yCoy)O3 (y = 0 and
0.2) show they are iso-structural in space
group I4/mcm at room temperature, and
have almost identical tilts around the c-axis.
The Mn(Co)O6 octahedron is elongated in
the undoped sample due to the cooperative
Jahn-Teller (JT) effect, but it is essentially
regular in the Co doped sample due to
the absence of JT-active Mn3+ ions. Both
compounds undergo a continuous phase
transition at around 400 ° C to a cubic
structure, with no indication of a distinct
transition in (Sr 0.8Ce0.2) MnO3 from the
removal of the static JT distortion.
Group Members &
Collaborators
•
•
•
•
•
•
•
•
•
•
Dr Qingdi Zhou
Dr Rene Macquart
Jimmy Ting
Richard Clements
Teck-Yee Tan
Labib Ali Awin
Gordon Thorgood
Michael Carpenter
(Cambridge)
Chris Howard
(Newcastle)
Zhaoming Zhang
(ANSTO)
21
2009 Chemistry Research Report
Professor Cameron Kepert
Room 308
School of Chemistry, F11
T +61 2 9351 5741
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/kepert.html
molecular framework materials
Nanoporous
Molecular
Frameworks
(Southon, Price, Li, Keene, Iremonger,
Duyker, Chen, Chadbourne, Barkhordarian)
A range of new framework materials that
display reversible guest sorption is being
investigated. Characterisation of the dynamic
host-guest structures of these phases
was explored using two new experimental
techniques developed in our lab, the first
involving the in-situ measurement of single
crystal X-ray diffraction data during gas
and vapour sorption/desorption, and the
second involving the measurement of diffuse
X-ray scattering to provide differential pair
distribution functions (PDFs). Following
our design and construction of purposebuilt capillary flow cells, the up-take of a
number of small molecular sorptives into a
range of different nanoporous phases has
been explored. Gas and vapour sorption
measurements and in-situ powder X-ray
diffraction investigations have further
enhanced our kinetic, thermodynamic and
structural understandings of the sorption
chemistry of these phases.
Thermal Expansion (Duyker, Wu, Chen,
Cameron, Chadbourne, Mullaney, Goux,
Phillips, Lock, Halder, Chapman, Goodwin,
Peterson, Kearley)
Materials that shrink upon warming
(negative thermal expansion; NTE) or that
are temperature invariant (zero thermal
expansion; ZTE) are of considerable
fundamental interest due to their rarity
and have diverse potential applications in
thermal compensation. We have recently
uncovered two very broad families of such
materials: metal-cyanide frameworks and
metal-organic frameworks. For the cyanide
phases, we attribute the unprecedented
NTE to two different modes of transverse
motion of the linear cyanide bridge. For
the metal-organic framework systems,
both soft transverse phonons and,
uniquely, local molecular vibrations are
responsible for the anomalous expansion
properties. Investigations of Cu3(btc)2 (btc
= 1,3,5-benzenetricarboxylate) uncovered
a highly complex NTE mechanism involving
both ‘trampoline’-type ligand modes and
local dynamic distortion of a dinuclear metal
complex (see figure).
Hydrogen Storage (Iremonger, Duyker,
Chen, Chadbourne, Barkhordarian, Southon,
Peterson)
The safe and efficient storage of hydrogen
gas represents a pivotal challenge in the
development of hydrogen as an alternative
energy carrier. Our recent report of a system
in which dihydrogen molecules bind directly
to bare metal surface sites has paved the way
to hybrid materials in which hydrogen gas can
be stored under non-extreme temperatures
and pressures. Extension of this approach
to other framework systems has established
the generality of this approach and led to
significant improvements in hydrogen binding
enthalpies.
Switching Nanoporous Materials (Price, Li,
Southon, Goux, Keene, Sciortino, Fellows,
Mullaney, Neville, Halder, Chapman, Murray,
Moubaraki, Toftlund, Steel, Létard)
Our incorporation of molecular electronic
switches into nanoporous frameworks and
discrete complexes is leading to materials and
molecules that have unique physicochemical
properties and potential applications
in molecular sensing and data storage.
Nanoporous Magnetic Frameworks (Keene,
Barkhordarian, Katsuda, Neville, Chapman,
Kurmoo)
As an extension of our efforts to incorporate
function
into
frameworks
we
are
synthesising porous materials that display
magnetic ordering. This work opens a new
route to explore the influence of structural
perturbation on magnetic properties.
Energy-Conversion Frameworks (Price,
Beves, Constable, Housecroft)
Exploratory synthetic efforts are being
extended to the incorporation of light-active
metalloligands into nanoporous frameworks
with the goal of generating materials capable
of photoactivation and, in future, solar energy
conversion.
Through the systematic variation of the
ligands and counter-ions we have developed
an extensive family of materials of this type,
allowing fine-tuning of guest-exchange (pore
size and shape) and switching (transition
temperature) properties; the latter includes
a novel two-step transition involving a
chess-board arrangement of switching sites
at internediate temperature (see figure). Of
particular note is the recent characterisation
of an array of Hofmann-type systems, which
display highly novel guest sorption properties
and hysteretic spin-crossover.
Oxygen-Binding Frameworks (Southon,
Price, Nielsen, McKenzie)
Biomimetic dinuclear metal centres capable
of binding oxygen gas are being investigated
with an interest in O2 sequestration and
sensing. Examples include a porous phase
that reversibly sorbs more than 99% of
atmospheric O2.
Porous Mineral Formulations (Yuan, Antill,
Green, Matthews, Anderson, Wells)
Nanotubular mineral phases are being
explored as host materials for the controlled
release delivery of bioactives.
Recent
progress has seen the successful control of
release properties through the modification
of surface chemistry.
22
2009 Chemistry Research Report
Professor Peter Lay
Room 307
School of Chemistry, F11
T +61 2 9351 4269
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/lay.html
bioinorganic
chemistry and
electrochemistry
Chemistry, Biochemistry and Cell Biology
of Chromium, Vanadium and Molybdenum
in Relation to Anti-Diabetics Effects
(Aitken, Carter, Finney*, Glover,* Hackett,
Harris,* Jalilehvand,* Kremer, Lai,* Levina,
Liang, McLeod, Nguyen, Pham, Pulte, Safitri,
Tarr, Tobin,* Vogt,* Whan*)
Empirical methods were employed to
determine the structures and speciation of
Cr, Mo and V complexes in biological fluids,
cells, and tissues using linear combinations of
XANES from model complexes that contain
biologically relevant ligand donor groups. This
was used to study the biotransformations
of anti-diabetic drugs and supplements in
gastrointestinal juices, blood and target cells.
We have also used X-ray absorption mapping
of protein gels of blood fractions or cell
lysates to determine the proteins to which
the Cr is bound and to examine the local
environment of Cr within the bands using
micro-XANES.
Further research has been conducted
on both a new Cr-bound protein in Crsupplement-treated blood serum, and
oxidation of Cr(III) dietary supplements to
carcinogenic Cr(VI) by biological oxidants. A
combination of X-ray and vibrational microbe
techniques have been used to provide
evidence that Cr(VI), Cr(V), and V(V),
inhibit phosphatase enzymes within target
adipocytes (fat cells), which is probably a
major cause of the anti-diabetic activities
of Cr(III) and V(IV) anti-diabetic drugs and
supplements. Further evidence has been
obtained for a natural role for V in control of
glucose metabolism.
Bioactive Ga and Ru Anti-Cancer Drugs
(Aitken, Finney,* Glover,* Hambley, Levina,
Lim, Liu, Katsifis,* Mitra, Nguyen, Vogt,*)
Research has been conducted on Ru
and Ga anti-cancer drugs using similar
methodologies as those described above to
study their biotransformations in biological
fluids and cells.
Ru anticancer drugs undergo substantial
aquation, hydrolysis and oligomerisation
processes under physiological conditions
and bind to various proteins and cells. The
differences in reactivities of different drugs
were explained by the kinetics of ligand-
exchange reactions with respects to whether
the drugs react primarily against extracellular
molecules (anti-metastatic effects) or
within the cell (cytotoxicity against primary
tumours). These studies are directed toward
an understanding of the efficacy mechanisms
of the drugs and in the design of new Ru
drugs. In particular, a range of assays on
adducts of Ru drugs with serum albumin
have shown that these adducts are highly
anti-metastatic. This is a very important
result since up to 95% of Ru is bound to
serum albumin on intravenous administration
of certain drugs currently in phase 2 clinical
trials and these adducts have been previously
considered as inactive side-products.
Similarly, Ga drugs are pro-drugs and
differences in their biotransformations are
important in understanding their efficacies
and safety. The speciation of different
Ga pro-drugs in blood, gastric juices and
cells was examined using X-ray absorption
spectroscopy and radioisotopes.
As described for the Cr complexes, newly
developed X-ray microprobe studies of
protein gels were also used to further
understand the speciation of these drugs in
biological fluids and cells.
XAS Studies of Isolated and Intracellular
Heme Proteins
(Aitken, Almaraz,* Antao,* Austin,* Ball,*
Carter, Cheng,* Farmer,* Giles,* Harris,*
Hunt,* Irwin, Jalilehvand,* Levina, Rayner*,
Richardson,*
Richter-Addo,*
Stocker*,
Whitnall,* Witting*, Yi*)
Raman and XAFS studies were conducted
on various isolated heme proteins and
those within cells and tissues. The research
involved: heme degradation in the hearts
of mice models of Friedrich’s ataxia; the
neuroprotective effects of neuroglobin during
strokes; the effect of induction of heme
oxygenase-1 on mammalian cells in relation to
its role in a variety of essential functions; the
structures of indoleamine 2,3-dioxygnease-2
that has recently been isolated from kidneys
and is involved in blood pressure control,
and HNO, RNO and nitrite adducts of heme
proteins. All of these studies have produced
important new results on the functions and
structures of heme proteins of relevance to a
range of biological processes and diseases.
Metal Anti-inflammatories
(Bonin, Hambley, Kaur)
Cu and Zn complexes of acemetacin (a
NSAID) have higher efficacy and lower
toxicity than the parent drug in rat models
of inflammation in humans.
Disease Diagnosis and Differentiation in
Cells and Tissues
(Aitken, Ali, Antao,* Armstrong, Barnard,*
Carter, Chan,* Cohen,* Cooper,* de
Jonge,* Double,* Edwards,* El-Assaad,*
Giles,* Gottlieb,* Grau*, Hackett, Hunt,*
Jalilehvand,* Lee, Levina, McQuillan,*
Paterson,* Siegele,* Sorrell*, Tobin,* Vogt,*
Witting*)
Vibrational spectroscopic diagnostics for
various diseases including cerebral malaria,
bacterial meningitis, viral meningitis, graftversus-host disease and Parkinsons disease
were investigated. Strong correlations were
observed between these diagnostics and
standard pathology diagnostics and, in
some cases, the vibrational spectroscopic
techniques had the potential to enable
disease diagnosis prior to any clinical effects.
Such early diagnosis has considerable
potential in improving the health outcomes
and the University has filed a PCT patent on
the technology. Vibrational spectroscopic
techniques were also used to identify and
differentiate pathogenic microorganisms,
such as different species of clinically
important Aspergillus fungal pathogens.
Vibrational spectroscopic mapping and
imaging were used, together with protoninduced X-ray emission (PIXE) and
synchrotron X-ray microprobe techniques,
to understand the biochemistry of various
diseases, such as cerebral malaria and
meningitis, that affect the brain.
These
microprobe
spectroscopic
techniques were also used to understand the
effects of metals and biochemical changes in
Parkinsons disease, the formation of arterial
plaques, breast cancer, and strokes, and for
new diagnostics for Alzhemiers disease and
treatments for cancer.
Identification of Ancient and Extant
Microbes
(Aitken, Carter, de Jonge,* Edwards,*
Emry,* Marshall,* Paterson,* Vogt*)
X-ray microprobe techniques were used
to identify ancient microbial fossils and to
compare them with the signatures of extant
extremophiles in research that is aimed at
understanding more about the origins of
life on Earth and as part of a program to
investigate whether life exists on Mars.
23
2009 Chemistry Research Report
Dr Chris Ling
Room 455
School of Chemistry, F11
T +61 2 9351 4780
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/ling.html
Materials Chemistry;
neutron & x-ray
scattering science
The most important underlying
principle in materials chemistry
is that of “structure-property
relations” – the idea that we
can relate the crystal structure
of a material to its chemical
composition on the one hand,
and to its physical properties
on the other. A detailed
understanding of structure
provides a link through which we
can use chemistry to manipulate
and optimise the properties of
functional materials.
The goal of our research is the discovery,
characterisation and optimisation of
functional solid-state materials. Structural
characterisation plays a central role, and
we make particularly heavy use of neutron,
synchrotron X-ray and electron diffraction
as well as complementary techniques such
as spectroscopy and electron microscopy.
Structural information is used to guide
exploratory synthetic studies and to
interpret the results of physical property
measurements.
Solid-State Ionic Conductors (Avdeev,
Kharton, Johnson)
Solid-state ionic conductors are the
performance-limiting
components
of
emerging energy technologies such as solidoxide fuel cells and lithium-ion batteries.
The materials currently used are quite
simple – they have small unit cells with high
symmetries, which are partially disordered
at ionic conducting temperatures. Examples
include yttria-stabilised zirconias in fuel-cell
membranes and lithium cobaltates in battery
cathodes. Some more complex materials
show better performance under ideal
conditions, but they are too unstable for
practical applications. A major impediment
to improving their performance and stability
is a lack of detailed understanding of the
atomic-scale mechanisms responsible for
their properties.
In 2009 we discovered and characterised
a number of new complex solid-state ionic
conductors, and made substantial progress
towards understanding how they work
on an atomistic level. This includes a new
series of mixed oxide ionic, protonic and
electronic conductors Ba4(Nb,Ta)2O9.xH2O.
Both the Nb and Ta compounds undergo
reconstructive phase transitions at ~1200
°C from a common low-temperature phase
to completely different high-temperature
phases. The quenched high-temperature
form of Ba4Nb2O9 is particularly interesting
as it hydrated stoichiometrically (x =
1/3), giving rise to 2D layers built of NbO4
tetrahedra and discrete OH groups that
allow fast ion conduction.
We are now beginning to expand the
scope of our studies from structure to
dynamics, using a combination of ab initio
(density functional theory) molecular
dynamics calculations and inelastic/
quasielastic neutron scattering experiments
to gain insight into ionic conduction
mechanisms. This is a particularly powerful
approach in systems where we can grow
large (cm-scale) single crystals for the
experimental component using our floatingzone image furnace.
Frustrated and Low-Dimensional Magnets
(Avdeev)
Frustrated magnetism arises when strong
interactions exist between unpaired
electrons of neighbouring ions (usually
transition metals), but the geometry of the
crystal lattice precludes co-operative longrange magnetic order. The archetypal case
is of antiferromagnetic (AFM) interactions
on a 2D triangular lattice; when spins are
constrained to be collinear, those on two
neighbouring vertices of a triangle can be
opposite, but the spin on the third vertex
cannot be opposite to both of them.
Such systems have no unique ground
state, but rather, a macroscopic number
of degenerate ground states. They are
of more than just theoretical interest: the
suppression of long-range spin order is
one of the key ingredients in complex (and
desirable) magnetic properties such as
superconductivity and multiferroicity.
We have been focusing on oxides of
platinum-group metals, which have very
flexible oxidation states, and the unique ability
to form stable 4+, 5+ and 6+ valent cations
with unpaired d electrons. This allows them
to be substituted for non-magnetic cations
such as Ti4+, Nb5+ or W6+ in structure types
with interesting frustrated topologies. New
compounds studied in 2009 include BiRe2O6
(Re 4.5+ substituted for both Nb5+ and Ti4+
in the SbNbTiO6 structure) and Ba3BiIr2O9
(Ir4.5+ in the 6H-type perovskite structure).
Both compounds contain hexagonally
distributed arrays of M4.5+O6 octahedra
which dimerise in different ways, resulting
in strong M–M interactions in addition to
conventional M–O–M superexchange,
and giving rise to anomalous magnetic and
electronic behaviour at low temperatures.
24
2009 Chemistry Research Report
Professor Thomas Maschmeyer
Room 303
School of Chemistry, F11
T +61 2 9351 2581
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/maschmeyer.html
advanced catalysis for sustainability
Sustainable Chemistry and Processes
The world is standing at the technological
threshold of a revolution that is driven by
the need for truly sustainable (industrial)
processes, both in the production of
chemicals as well as in the generation of
power.
At current rates of resource usage, a
world population operating with Australian
standards of living would require between
4 – 6 planets. Clearly, this is untenable and,
from a chemical viewpoint, the inherent
challenges can only be met by devising
strategies for increased use of renewable
resources,
waste
reduction,
energy
optimisation and process intensification
as outlined in the 12 principles of “Green
Chemistry”.
Our group aims to tackle these issues
and enhance sustainability by generating
and using new fundamental insights on the
molecular and nanoscopic level to develop
feasible leads for the design of new catalytic
chemical routes and processes.
Renewable Chemicals and Fuels
We model the processing of carbohydrates,
lignins and lignocellulosic biomass in stateof-the-art continuous flow reactors (in
a joint effort with Prof. Brian Haynes at
Chemical
Engineering).
Sophisticated
physical techniques are used to identify
reaction products and obtain reaction
kinetics. Design and synthesis of model
compounds also play a significant part of
the projects. Some of the questions we
want to answer are:
• Can we influence carbohydrate
decomposition pathways in water
such that the onset of decarboxylation
(the main pathway for biomass
de-oxygenation) can be clearly
delineated?
• What are the linkages in lignin that are
most susceptible to hydrolysis in supercritical water? Can we predict whether
certain biomass feedstocks are better
or worse suited to hydrothermal
upgrading?
• Is it possible to achieve hydrogen
transfer
and
subsequent
deoxygenation via in-situ generated
formates?
Aqueous Phase Reforming
Recently, Dumesic reported a most unusual
observation – the generation of alkanes
from sugar in water. The micro-kinetics of
this extremely complex reaction system
are increasingly well understood. However,
the catalysts used function well only in
the absence of sulphur. Imparting sulphur
resistance while maintaining catalytic
performance is the key target of this project.
Our main approach is via the synthesis of
multimetallic nanoparticles in which various
catalytic properties can be tuned. Success
would allow ordinary cellulosic materials
to be turned into alkanes in water in one
step. Activities in this area involve inorganic
synthesis and characterisation as well as
catalytic testing and sophisticated analyses
by gas chromatographic and mass-spec
techniques.
Ionic Liquids as Novel Synthesis Media
Ionic liquids are experiencing boom-times
– why? Increasingly it is becoming clear
that this most versatile group of liquids has
very special properties that are most likely
rooted deeply in their ‘saltiness’, i.e. their
large degree of organisation, even in the
liquid state.
Projects in this area involve the
synthesis and characterisation of ionic
liquids as well as the evaluation of chemical
selectivity that can be imparted by them
onto various chemical conversions. Some of
the questions we are trying to answer are:
• Can we delineate a relationship
between
observed
changes
in
reactivity and presumed structural
features of ionic liquids?
• What are the key structural features
that have the most impact?
• Can we design ionic liquid systems for
particular conversions?
Photocatalysis: Hydrogen from Water
Although this reaction has been proven
to work – it is still as long way from being
effective enough to be useful. Here, we
aim to prepare new materials, based on the
band-gap engineering of self-assembled
nanostructures to provide better catalysts
for this reaction. Our focus lies on dispersed,
TiO2-stabilised
exotic
multicomponent
nanoparticles and coupling these to
reducing ‘sacrificial’ solutions that enhance
the thermodynamics of the system. Such
solutions can be readily found in the
environment where they often present
problems. Our approach yields hydrogen
from water using sunlight and as a ‘spinoff’ improves the water quality by oxidising
smelly and toxic species such as sulphides.
Professor Thomas Maschmeyer
Room 303, +61 2 9351 2581
[email protected]
www.acs.chem.usyd.edu.au
Thomas Maschmeyer was born in
Hamburg in 1966. He completed his
PhD at the University of Sydney and
then moved to the UK for research
appointments
in
London
and
Cambridge. After his positions as
Professor, Head of Department, and
Vice-Chairman at the Delft Institute
of Chemical Technology, he returned
to Australia as ARC Federation
Fellow in late 2003 and was recently
awarded a Professorial ARC Future
Fellowship. He is also cofounder
and one of the directors of Ignite
Energy Resources Ltd, a low carbon
footprint energy and fuels company.
He serves on the editorial boards
of five international journals, is
President of the Catalysis Society
of Australia as well as advisor and
consultant to many governmental
bodies and companies. He received
the 2007 Le Févre Prize of the
Australian Academy of Sciences
for outstanding basic research in
chemistry by scientists under 40.
25
2009 Chemistry Research Report
Associate Professor Tony Masters
Room 459
School of Chemistry, F11
T +61 2 9351 3743
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/masters.html
organometallic
chemistry and
catalysis
If we are unable to hand to our children,
and to their children, the means to
at least as good a lifestyle as that we
now enjoy, we have failed miserably as
a civilisation. This challenge becomes
more acute as we approach the resource
and energy limits of our planet.
To even approach a sustainable
existence, such that the ecosphere exists
in a steady state able to support our
current lifestyle, a 4- to 10-fold increase
in the resource efficiency of existing
production processes is necessary. In
the longer term, this will involve the
development of a suite of novel industrial
chemical transformations, such as those
envisaged in the biorefinery. However,
in the short term, small absolute
improvements to existing large-scale
processes can have maximum impact.
Our research embraces both short
and long term approaches involving,
for example: fundamental studies
of workhorse reactions, such as
catalytic hydrogenations; as well as the
development of improved catalysts for
existing process, such as hydrocarbon
oxidations.
In applied studies, we
collaborate with local industry to
develop an Australian manufacturing
capability for novel ionic liquid reagents.
Representative projects are described
below.
Hydrocarbon Oxidation Catalysts
One of the most fundamental industrial
petroleum-based operations is the catalytic
selective oxidation of hydrocarbons to
produce materials such as epoxides, ketones,
aldehydes, alcohols, acids, and derivatives of
these molecules. These account for some
25% of industry’s monomer and chemical
intermediate production, annually generating
in excess of $50 billion of business – roughly
equally across America, Europe and Asia. As
a consequence, oxidation catalysts rank
second only to polymerisation catalysts in
industrial usage. We have developed novel
hydrocarbon oxidation catalysts, capable
of delivering significant gains in resource
efficiency.
Catalytic Properties of Silica Surfaces
Within the high technology world of
advanced materials, one simple stoichiometry
reigns supreme – SiO2. Silica dominates
the field of catalysis, as supports, shapeselective catalysts; Lewis and Brønsted
acids; crystalline, amorphous, structured
amorphous, microporous, mesoporous and
macroporous solids; or, “simply” as surfaces.
Silica occupies an equally dominant position
in electronic and optical devices. Silica is
conventionally presumed to be an “inert”
catalyst support, however, we have shown
the silica surface, once thermally activated,
to be an excellent catalyst for the production
of high quality polymers. Our work has
also focused on the understanding of this
effect by examining the reaction chemistry
of silsesquioxanes – molecular models of
fragments of the silica surface.
The silsesquioxane, [(C7H11)6Si6O9]
Nanotherapeutics
The delivery and release of drugs specifically
to the disease site remains one of the great
challenges of modern chemotherapies.
Many drugs suffer from a lack of specificity,
resulting in a systemic distribution of the
drug to both healthy and diseased cells
with consequent deleterious side effects.
We are attempting to solve this problem by
using nanoparticles as generic drug delivery
platforms, able to convey a drug to a disease
site, releasing the drug only when within that
site. Nanoparticles are particles small enough
to enter cells, and chemical functional groups
capable of binding chemotherapeutic agents
are readily attached to their surfaces.
A multiply functionalised nanoparticle,
incorporating a disease seeking agent,
a biocompatibility coating, a disease
seeking agent and a releasable drug.
Catalytic Cascade Reactions with Dynamic
Kinetic Resolution
Performing two sequential reactions which
use otherwise incompatible catalysts in the
same reactor would provide significant savings
of energy, infrastructure, environmental
footprint and reduce wastes. We have
combined an enzyme and a solid acid catalyst
(which would normally deactivate the
enzyme) to effect the efficient synthesis of an
optically active pharmaceutical intermediate
in the same reactor. The solid acid is isolated
from the enzyme by encapsulating it in a
membrane, permeable to the reagents and
products but not to the catalysts.
Other projects include novel catalysts for
remediation of non-potable water supplies,
the development of new, high surface area
solids as catalysts and catalyst supports,
catalysts formed by molecular imprinting,
and sulfur-tolerant reforming catalysts.
Confocal microscope image of a solid
acid catalyst encapsulated within a
semi-permeable membrane.
26
2009 Chemistry Research Report
Dr Chris McErlean
Room 518a
School of Chemistry, F11
T +61 2 9351 3970
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/mcerlean.html
synthetic organic chemistry
Advances in all aspects of
chemistry are reliant on our ability
to build new molecular entities in
a timely, efficient, economically
sustainable and environmentally
benign manner. Our research group
is addressing this challenge by
investigating new reactions and
applying known reactions in novel
settings to access molecules that
display biological promise.
Intramolecular Stetter Reaction to Access
Polycyclic Ethers (Goldys)
Polycyclic ethers are a class of natural
products isolated from the marine algae
responsible for ‘red-tide’ events. Some
of these structurally imposing molecules
have been identified as causative agents
in mass outbreaks of seafood poisoning,
but other members of the class,(such as
protoceratinII) display beneficial properties.
To date, however, the potent anti-tumour,
anti-fungal, and anti-cystic fibrosis activity
of polycyclic ethers has been poorly studied
due to difficulties in isolating or building the
desired molecules.
We have recently disclosed our solution
to this problem which involves the use
of an intramolecular Stetter reaction to
rapidly generate arrays of polycyclic ethers
in a stereocontrolled fashion. Efforts are
underway to generate a library of analogues
in order to elucidate the structural features
responsible for the biological activities of
this class of compounds.
Enantiocontrolled Access to Oxygenated
Tetrahydrofurans (Nesbitt)
Tetrahydrofuran rings that have an oxygen
atom attached at the 3-position are a
commonly encountered structural motif;
they are present in natural products from the
terrestrial and marine environments (such
as kumausallene) as well as being present
in some pharmaceuticals. Frustratingly,
the synthesis of these units appears to be
treated on a case-by-case basis.
We have uncovered a general route
to this unit using a palladium-mediated
carbonylation strategy. This new approach
can deliver any diastereomer of the
3-oxygenated tetrahydrofuran unit, and
either enantiomer in as little as four steps.
Work has commenced to highlight this new
strategy by the total synthesis of certain
compounds.
Ligands for Novel Transformations
(Recsei)
The class of binol derived ligands occupies a
privileged position in the arena of synthetic
organic chemistry. Of particular importance
in this respect is the subset of ligands based
on the 3,3´-disubstitued binol scaffold.
With an appropriate choice of sterically
demanding substituent at these flanking
positions, impressive levels of enantioand diastereocontrol have been realised
over a wide range of transformations. We
are interested in utilising 3,3´-dipyridyl
substituted binol ligands for organocatalytic
applications. As such we have devised
a rapid, 3-step synthesis based on the
microwave assisted Suzuki coupling of
trifluoroboronates. Using this approach,
we have synthesised a series of ligands in
overall yields ranging from 53 – 100%. This
library of ligands will be utilised in a series of
organocatalysed transformations.
N-Acyl Pyrroles (Phippen)
The a,b-unsaturated N-acyl pyrrole unit
offers many opportunities in the arena
of synthetic organic chemistry. We are
conducting syntheses that exploit the high
electrophilicity of the alkene, the activated
nature of the acyl unit and which utilise
the masked aldehyde group inherent in the
structure.
27
2009 Chemistry Research Report
Dr Chiara Neto
Room 349
School of Chemistry, F11
T +61 2 9351 2752
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/neto.html
liquid/solid & nano
interfaces
Our research focuses on
understanding the properties
of solid/liquid interfaces, with
the aim to design biocompatible
patterned surfaces for biomedical
applications,
engineer
new
functional materials, and produce
more efficient microfluidic and
water capture devices. We
investigate fundamental physicochemical mechanisms that have
the potential to lead to new
technological applications.
Biocompatible Surfaces Through MicroPatterning (Telford, Gamble, Meagher, Lim)
The ability to control protein and cell
positioning on a microscopic scale is crucial
in many biomedical applications. We achieved
micro- and nano-patterning of proteins and
cells, using self-assembly principles, such
as the dewetting of unstable polymer films,
followed by selective adsorption of proteins. In
collaboration with the Centenary Institute, the
micropatterning method is being investigated
as a means to improve the biocompatibility of
stents.
Nanopatterns in Block Copolymer Films
(Sriprom, Lim, Perrier, James, Sahin)
Thin films of block copolymers can be used
to produce templates for large area patterned
surfaces
for
various
nanofabrication
applications, such as high-density magnetic
recording devices. We investigated the
evolution of the morphology of di-block
copolymer thin films with techniques such
as tapping mode atomic force microscopy
(AFM), and neutron and x-ray reflectivity, and
ascertained the factors affecting their regular
nanostructure.
Functional Surfaces (Joseph, SamuelThambiah, Sahin, Thickett, Harris)
We developed two new methods to produce
robust magnetic superhydrophobic surfaces,
which have self-cleaning ability, anti-fouling
and drag-reducing ability. Our approach
exploits self-assembly principles, such as
electrochemical deposition through a template
and coating with multiply-crystallised stearic
acid. We are investigating the ability of
producing new water capture devices based
on engineered nanostructured surfaces
that mimic Nature’s examples, such as the
Stenocara Namib desert beetle.
Microfluidics (Zhu, Attard)
A huge hydrodynamic resistance slows down
liquid flow in microscopic capillaries and our
recent discovery of the occurrence of liquid
slip at the solid surface promises to solve
this problem, fundamental for more efficient
microfluidic devices. We investigated the
effect of surface structure, compliance and
texturing, using colloid probe AFM.
Contact Electrification (Lee, Harrowell)
Contact electrification is exploited in many
industrial processes such as xerography and
drug delivery, but its mechanism, especially
in polymers, remains unknown. Even the
nature of the charge carriers involved remains
ACHIEVEMENTS
•
Our research on
superhydrophobic nickel
nanocarpets was highlighted
on ABC Science Online: http://
www.abc.net.au/science/
articles/2009/11/16/2741961.
htm
•
Dr Neto’s research was
awarded this year an ARC
Discovery project, an ARC
LIEF project, an ARC Linkage
project, a ISAT Linkages Fund
travel grant (New Zealand),
and a Seeding Grant from the
University of Sydney Institute
for Sustainable Solutions.
•
Dr Neto was invited to
present seminars at various
symposia, including at the
National Measurements
Institute Workshop on SPM,
the NZ Nano and Microfluidics
Workshop (Wellington), and
at the ANZ First Microfluidics
Meeting (Monash Uni).
a source of controversy. We investigated
proposed theories regarding the mechanism of
contact electrification by observing the effect
of surface history on the charge transfer.
The Neto group
28
2009 Chemistry Research Report
Dr Richard Payne
Room 545
School of Chemistry, F11
T +61 2 9351 5877
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/payne.html
organic synthesis, drug discovery and chemical biology
Inhibition of Iron Sequestration Pathways
as Tuberculosis Drug Leads (ManosTurvey, Bulloch, Lott, Baker, Britton)
Mycobacterium tuberculosis, the etiological
agent of tuberculosis (TB), is a devastating
human pathogen, responsible for enormous
morbidity and mortality. Every second a
new person is infected with M. tuberculosis,
resulting in close to 2 million deaths from
TB annually. The emergence of multi-drug
resistant (MDR) and extensively drug
resistant (XDR) strains of M. tuberculosis
threaten to overcome current drug
regimens. TB therapeutics with novel
modes of action are therefore urgently
needed. Iron is known to be essential for
the survival, replication and virulence of
Mycobacteria and, as such, prevention
of iron assimilation in M. tuberculosis
represents a promising new strategy
for drug development. Mycobacteria
utilise small molecule siderophores, called
mycobactins, to acquire iron from their host
during the infection process. Inhibition of
the pathways responsible for mycobactin
biosynthesis represents a novel approach
for the development of new TB drug
leads. We have designed and synthesised a
number of potent inhibitors against the first
committed step in mycobactin biosynthesis
which now serve as lead compounds for
the synthesis of a second generation library
of inhibitors against this novel drug target.
Design and Synthesis of Type II
Dehydroquinase Inhibitors as Broad
Spectrum Antiinfectives (Tran, Xue,
Payne)
New drugs with novel modes of action are
desperately needed to overcome infections
which are resistant to currently prescribed
antibacterials. We are targeting key steps
in the shikimate pathway, a biosynthetic
route used by plants, bacteria, fungi and
parasites to generate essential secondary
metabolites, including the aromatic amino
acids. Since the pathway does not occur in
mammals, constituent enzymes represent
exciting targets for the development of
herbicides, antibacterials, fungicides and
antimalarial drugs.
Development of New Methods for the
Rapid Construction of Therapeutic
Glycopeptides (Conroy, Hsieh, Taleski)
Glycosylation is a common modification
of proteins, with over fifty percent of all
human proteins containing covalently bound
sugars. These sugars play an important role
in a variety of biological recognition events,
including cell adhesion, cell differentiation
and cell growth. There are currently a
number of glycoprotein drugs on the market
for the treatment of a variety of diseases.
Glycoprotein drugs are commonly sold as
complex mixtures and are thus are difficult to
study. As such, methods to enable the total
synthesis of homogeneous glycopeptide and
glycoprotein drugs would be of significant
interest to the pharmaceutical industry and
has been the focus of intense research in
our laboratory. We have recently developed
a number of new methods for the synthesis
of homogeneous glycopeptides. These
methodologies are currently being employed
in the total synthesis of glycopeptides and
glycoproteins of therapeutic interest.
Synthesis of Glycopeptide Cancer Vaccine
Candidates (Wilkinson, Malins, Chun)
In cancer cells there is a significant
increase in the expression of a number
of glycoproteins, which is combined with
incomplete assembly of oligosaccharides
which are covalently linked to the side chains
of amino acids. This aberrant glycosylation
results in the exposure of additional
peptide epitopes, which therefore become
accessible to the immune system. We
have utilised solid phase peptide synthesis
(SPPS) along with cutting edge ligation
techniques to produce multiantigenic
cancer-associated glycopeptides. These
are currently being assessed for their ability
to generate tumour-selective immunostimulating antigens in mouse models.
Payne Research Group 2009
29
Associate Professor Sébastien Perrier
Room 351
School of Chemistry, F11
T +61 2 9351 3366 | F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/perrier.html
http://sydney.edu.au/kcpc/
molecular
engineering
Our research focuses on the synthesis of
macromolecules with highly controlled and
pre-determinable structures. We exploit
supramolecular interactions to organise
these molecules into nanostructured materials, for applications in pharmacology
(e.g. drug delivery), biology (e.g. antimicrobial materials, synthetic proteins), nanotechnology (e.g. components for optoelectronic applications), material scence
(e.g. rheology modifiers) or chemistry (polymerization catalysts, processes, etc.).
Polymer Synthesis (Brown, Gray-Weale,
Hawkett*, Hornby*, Jitchum*, Kakwere*,
Koh*, Konkolewicz*, Ladmiral*, Motherwell,
Siaw*, Tom*, West*)
Two of the key polymerization techniques
used in our group are reversible addition
fragmentation chain transfer (RAFT)
polymerization and transition metal mediated
living radical polymerization (TMMLRP),
which are radical processes that allow the
synthesis of complex polymeric architectures
in a simple manner. In 2009, we pursued
our efforts in understanding the principles
underpinning the mechanism of RAFT
polymerization, and described the structure
of the intermediates of reactions, and final
polymer products. We also established a
new technique of TMMLRP catalysed by
copper (0) powder that proceeds at room
temperature. This system is an excellent
candidate for industrial applications.
An important section of our research
focuses on the design of new macromolecular
architectures via radical polymerization.
For instance, we have designed miktoarm star copolymers (star polymers which
arms are made of different polymers) by
combining RAFT polymerization to ring
opening polymerization. We also exploited
the versatility of thiol-yne chemistry to build
hyperbranched polymers in a very simple, yet
very effective manner.
Polymer
Self-Assembly
(Chapman*,
Kakwere*, Lim*, Neto*, Samuel-Thanbiah*,
Sriprom*, Suchao-In*, Suwabun, Tanushan*)
The use of the self-assembly of polymeric
structures to design materials at the
nanoscale is one of our main fields of interest.
In 2009, we developed new polymers that
A star copolymer
can self-assemble into nanoparticles in
solution. The polymers can be designed
such as variation in the solution environment
triggers the self-assembly into well-defined
structures. For instance, we demonstrated
that variation in the pH of an aqueous
solution enable the production of either
polymeric micelles or polymeric vesicles.
We also applied this approach to engineer
nanoparticles from the self-assembly of
block copolymers in aqueous solution, and
used the versatility of thiol-ene coupling to
functionalise the surface of these new soft
nanoparticles. We also pursued our studies
on the self-assembly of block copolymers in
thin films, and demonstrated the effect of
molecular weight distribution on the control
of morphologies. In order to design more
complex nanostructures, we combined
polymers to peptides, and exploited the selforganisation of the peptide segment to form
a variety of nanoobjects (nanocapsules,
nanotubes and nanorods).
An artistic representation of a
‘soft’ nanoparticle
Hybrid Synthetic / Natural Materials
(Chapman*, Kakwere*, Moraes*, Semsarilar*,
Zhao)
Combining polymer synthesis to natural
polymers enables the design of new
materials, which combine the functionality
and properties of both natural and synthetic
polymers. In 2009, we pursued our work on
the use of radical polymerization to control
the growth of functional polymeric chains
attached to peptides sequences and design
functional nanoobjects. We also developed
further our pioneering work on conjugation
of synthetic polymers to silica (partly in
collaboration with the team of Prof Zhao from
Soochow University, China) and cellulose, to
produce functional and sustainable materials.
Our review on cellulose grafting
made the cover of Chem Soc Rev.1
1. Roy, D; Semsarilar, M; Guthrie, JT;
Perrier, S. Chem. Soc. Rev. 2009, 38
2046-2064.
2009 saw the award of many prizes
and distinctions to the group: A/Prof
Perrier received the David Sangster
Polymer Science and Technology
Award (RACI), the Rennie Memorial
Medal (RACI) and the Young Tall
Poppy Science Award. Dominik
Konkolewicz received the C. G. and
R. J. W. Le Fèvre Student Lecture
Award (USyd Chemical Society), Rob
Chapman received the Treloar Prize
for Best Poster Presentation at the
31st Austalasian Polymer Symposium
and Jessica Tom received the 2009
CRC for Polymers Prize for Best
Thesis.
30
2009 Chemistry Research Report
Professor Leo Radom
Room 309
School of Chemistry, F11
T +61 2 9351 2733
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/radom.html
computational
quantum chemistry
Chemistry is traditionally an
experimental science. However,
recent advances in computer
technology and the development
of highly efficient computer
algorithms have opened the
way for a viable alternative
approach
to
chemistry:
chemistry by computer. We use
such computer calculations,
based on the laws of quantum
mechanics, to determine the
structures of molecules and to
help understand how molecules
react with one another.
Enzyme-Catalysed Reactions (Sandala,
Bucher, Durbeej¶, Kovacevic§, Baric§,
Smith§)
Vitamin B12 is one of nature’s essential
vitamins. We have used ab initio quantum
chemistry calculations to try to understand
how coenzyme B12 facilitates certain
reactions. We have proposed mechanisms
involving partial-proton-transfer (donation
or acceptance) provided by enzymatic
hydrogen bonding. Supporting evidence for
our proposals has come from site-directed
mutagenesis experiments. In recent work,
we have found that the orientation of a
sugar moiety can strongly influence the
activation of coenzyme B12-dependent
enzymes.
Fundamentals of Free Radical Chemistry
(Menon, Graham, Taylor, Sandala, Chan,
O’Reilly, Coote‡, Henry†)
Radicals are ubiquitous in chemistry, biology,
and polymer science. Because they are
reactive species, they are often difficult to
study experimentally and therefore theory
has a potentially useful role to play in their
characterisation. However, there are also
challenges for theory, and the development
of new theoretical procedures for treating
open-shell systems is an important area of
research. We have formulated and tested a
restricted-open-shell variant of the doublehybrid density functional theory procedure
ROB2-PLYP.
It shows very promising
performance.
Peptide Radical Chemistry (Taylor, Ivanic,
Bacskay, Wood, Chan, O’Reilly, Easton‡,
Davies‡, O’Hair‡)
An understanding of the oxidation of proteins
by free radicals is of great importance
because of its implication in a number
of human disorders such as Alzheimer’s
disease, atherosclerosis, and diabetes, as
well as aging. We have been using highlevel quantum chemistry calculations to
address the problem. Specifically, we have
been examining the abstraction of hydrogen
by chlorine atom in small amino acids and
related model systems.
HOCl-Mediated Damage to Proteins
(O’Reilly, Pattison‡, Davies‡)
Activated white blood cells secrete the
enzyme myeloperoxidase, which catalyzes
the reaction of H2O2 with Cl– and Br–
to produce HOCl and HOBr. HOCl has
important antibacterioral properties but
excessive or misplaced production of HOCl
has been implicated in several diseases,
including atherosclerosis, inflammatory
diseases and some cancers. Both HOCl and
HOBr are able to induce N-halogenation of a
number of biologically important molecules.
We have been investigating the factors that
influence the structures and stabilities of
the resulting N-halo derivatives, and are
attempting to understand the mechanism
of their formation.
Hydrogenation and Hydrogenolysis (Chan,
Zhong)
We are using theory to try to design
systems in which metal-free hydrogenation
and hydrogenolysis reactions can occur
with low energy requirements. As part
of such studies, we have designed a new
class of zeolites that show the potential to
transform carbon dioxide to methanol at a
low energy cost. We have also identified
catalysts that can potentially convert toxic
polychlorinated hydrocarbons to benign
compounds.
31
2009 Chemistry Research Report
Professor Jeffrey Reimers
Room 546
School of Chemistry, F11
T +61 2 9351 4417
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/reimers.html
molecular
electronics,
photosynthesis
Our work concerns the development of
theoretical and computational methods for the prediction and interpretation of the properties of large molecular systems.
Quantum-mechanical
treatments of electronic and nuclear
structure lead to predictions of spectroscopic properties, charge and exciton transport properties, steady-state
conductivity, and coherence/decoherence effects.
Figure 2
Photosynthesis and Photovoltaics (Hush,
Lee, Crossley)
The conversion of optical to chemical energy
by plants is central to most forms of life on
this planet. A priori computational methods
were developed for predicting the rates of
photochemical processes involving charge
separation and subsequent recombination
in molecules designed for applications in
organic photovoltaics. These were used
to identify the nature of fundamental
processes in ferrocene-porphyrin-fullerene
solar-energy conversion molecules. New
materials for use in semiconductor dye
solar cells were designed and tested. See
figure 1.
perform other logic tasks. It provides in
principle ways of scaling electrical devices
beyond the limits of CMOS and other existing computer technologies. Our work
in 2009 focused on the nature of thiol interfaces of molecules to gold surfaces and
gold nanoparticles, showing how the basic
conductivity and structural properties could
be chemically controlled. In addition, the effect of head-group hybridization of nitrogen
linkages to gold were determined, as well as
the structure of some norbornadiene-based
building blocks for molecular circuitry above
silicon surfaces. Finally, some novel porphyrin interfaces to silica photonic wires were
investigated, revealing novel spectroscopic
properties controlled by the unusual nature
of silica surfaces inside the holes of optical
fibres. See figure 2.
Molecular Electronics (Chin, Wohlthat,
Wang, Hush, Crossley, Canning)
Molecular electronics involves understanding the properties of single molecules used
as wires to transport electrical current or
optical energy, to store information, or to
Underpinning Fundamental Science (Cai,
McKemmish, Hush, Lindoy)
Fundamental research is performed in areas
such as molecular conduction and control,
solvation, quantum chemistry, and quantum
mechanics in order to determine effective
Figure 1
Figure 3
means for dealing with both simple and
complex chemical systems.
These led
to an understanding of how conductivity
can be controlled by chemical means. In
2009, research underpinning our ability
to model complex interactions to gold
was performed on some large crystalline
silver complexes that display a range of
covalent, ionic, and pi-stacking interactions.
Modelling such detailed experimental
information is essential to the validation of
our computational methods. In addition,
fundamental
research
underpinning
our ability to understand coherent and
incoherent molecular processes was
applied to the origin of intelligence. The
common belief that neural networks are
solely responsible for intelligence has
been questioned and alternate quantumcomputing models proposed.
We
thoroughly investigated the possibility
of Bose-Einstein-like condensation in
biological media (see figure 3), as well as
the dynamics of microtubules, the biological
component assumed responsible for
biological quantum computation.
32
2009 Chemistry Research Report
Associate Professor Louis M. Rendina
Room 518
School of Chemistry, F11
T +61 2 9351 4781
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/rendina.html
bioinorganic and
medicinal chemistry
Our research group has a strong
interest in the development of new
agents for an exciting experimental
cancer treatment known as Neutron
Capture Therapy (NCT), one of the
few groups in the world to be involved
in this area of research. To date, we
have discovered several new classes of
DNA- and tumour-targeted compounds
and we are currently exploring their
potential as NCT agents. Our research
is funded by organizations including
the Australian Research Council, Cure
Cancer Foundation of Australia and The
National Breast Cancer Foundation.
Pt-B Complexes as New Agents for BNCT
(Ching, Clarke, Collins†, Hosseini, Rutledge)
Boron neutron capture therapy (BNCT) is
an experimental cancer treatment which
makes use of two key components that can
be manipulated independently. One of the
components is the non-radioactive 10B isotope which possesses a large, effective neutron capture cross-section (3838 barns).
It has the unusual capacity to capture
low-energy thermal neutrons (the second
component) and undergo a fission process
that results in the formation of high linear
energy transfer (LET) particles (4He2+ and
7 3+
Li ) and approximately 2.4 MeV of energy.
Due to the short path lengths of 4He2+ and
7 3+
Li ions (9 and 5 µm, respectively), these
nuclei are confined only to the tumour cell
in which they originated. We are particularly interested in developing new DNA- and
mitochondrial-targeting agents for BNCT,
with several new classes of boronated compounds developed to date.
Boron-rich platinum(ii) complexes of the
type [PtL2(phen)](NO3)2 and [PtL(trpy)]
(NO3)2 (where phen = 1,10-phenanthroline,
trpy
=
2,2’:6’,2”-terpyridine,
L
=
1-(1,X-dicarba-closo-dodecaboranyl)-4pyridylmethanol; X = 2, 7, and 12) have been
prepared and fully characterised. Their
interaction with b-cyclodextrin (b-CD)
results in the formation of stable, watersoluble host-guest complexes in which each
carborane moiety is encapsulated by the
cyclic sugar. The complexes possess a strong
affinity for DNA despite the presence of the
bulky carborane-b-CD groups. The chiral
N-donor ligands have now been successfully
resolved and the enantiomerically-pure
complexes have also been prepared. We
also have explored the preparation of DNA
metallointercalators possessing simple
boronic acid derivatives, e.g. [Pt(trpy)L]
(NO3)n (L = 3- or 4-pyridineboronic acid,
n = 2; HL = 4-mercaptophenylboronic acid,
n = 1) and [{Pt(trpy)}2(m-pzB)](NO3)3
(HpzB = 4-pyrazoleboronic acid). Sugar
binding experiments revealed that selected
compounds can bind avidly to D-fructose,
D-ribose, D-sorbitol and D-mannitol in
aqueous solution (pH 7.4) with Keq > 103 M-1
in all cases. The thermodynamic parameters
of these reactions were determined using
the ITC technique.
Preliminary DNAbinding experiments with calf-thymus DNA
showed potent DNA binding for selected
complexes and the strength of binding did
not appear to be affected by the presence
of D-fructose.
Tumour-Targeted Boronated Phosphonium
Salts as a New Class of Agents for BNCT
(Ioppolo, Issa, Kassiou, Morrison, Rutledge,
Witting†)
Arylphosphonium
salts
represent
a
promising class of delocalised lipophilic
cations (DLCs) for use in tumour targeting
and imaging. It is known that the tumour
selectivity and retention of these species
in animal models is at least one order of
magnitude greater than for clinical agents
currently used in BNCT. The incorporation
of boron into DLCs would potentially result
in the selective delivery of this nucleus
to the tumour site, notably by exploiting
the key differences in the mitochondrial
membrane potential between cancerous and
healthy cells. We have recently prepared a
number of boronated arylphosphonium salts
containing either a carborane or boronic acid
moiety. Both types of compounds exhibited
excellent uptake into human glioma (T98G)
cells in vitro but the boron-rich carborane
derivatives have the capacity to deliver a
much greater number of boron atoms into
these cells.
We have recently prepared
some PEG analogues of these carborane
derivatives which can be radiolabelled with
18
F and used to monitor their uptake and
biodistribution in tumour-bearing animals
by PET imaging. These compounds are the
subject of an international PCT application
which recently entered National Phase
assessment (US and EU).
Gadolinium Agents for Neutron Capture
Therapy (Crossley, Harris†, Morrison,
Wang)
Gadolinium neutron capture therapy
(GdNCT) is a relatively unexplored binary
therapy which utilises the non-radioactive
157
Gd isotope (natural abundance = 15.7%) in
a highly-effective thermal neutron capture
reaction to destroy tumour cells. 157Gd
possesses the largest effective nuclear
capture cross-section of all the naturallyoccurring elements (2.55 x 105 barns), a
figure which is approximately 66 times
greater than that of the 10B nucleus which is
used in BNCT. In contrast to the 10B isotope,
157
Gd does not undergo a fission reaction
but instead gives the products of internal
conversion and accompanying Auger and
Coster-Kronig (ACK) electron emission. The
extremely limited range of ACK electrons
means that the Gd must be localised in close
proximity to critical cellular components
such as the cell nuclei or mitochondria if the
neutron capture reaction is to be exploited
effectively. Treatment of A549 human lung
carcinoma cells with a novel Pt-Gd complex
resulted in the selective aggregation of
the intact agent within the cell nuclei, as
determined by synchrotron XRF imaging
(Fig. 1). This work represents the first
example of Gd delivery to a tumour cell
nucleus by a platinum(II) complex. We also
have initiated a study of mitochondriallytargeted compounds containing Gd3+ based
upon the arylphosphonium salts described
above.
Figure 1
Collaborators from University College,
UNSW, The University of Adelaide, and
School of Medical Sciences, The University
of Sydney.
†
33
2009 Chemistry Research Report
Dr Peter Rutledge
Room 547
School of Chemistry, F11
T +61 2 9351 5020
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/rutledge.html
bio-inspired
synthesis and
chemical biology
Our research combines organic synthesis and bio-organic
chemistry to develop new drugs
and sensors for biomedical applications, biologically-inspired
catalysts for important synthetic transformations, and chemical solutions to environmental
problems.
Hydrocarbon Oxidation
The selective oxidation of simple
hydrocarbons to functionalised products
(e.g. alcohols, and epoxides) is an important
goal in synthesis, but can be difficult to
achieve under mild, environmentally benign
conditions. Nature uses iron-based enzymes
to catalyse hydroxylation at primary,
secondary and tertiary C–H positions,
alkene epoxidation and even dihydroxylation
of aromatics. These enzymes use molecular
oxygen, the ultimate green oxidant,
with water the only by-product. We are
developing bio-inspired small-molecule ironbased complexes to oxidise hydrocarbon
substrates, and have recently observed
iron-promoted alkene dihydroxylation and
allylic oxidation reactions. (For recent
progress, see Org. Biomol. Chem., 8 1666
(2010).) In a parallel approach, we are
using non-heme iron(II) enzymes from
Mycobacteria in a biocatalytic approach
to alkene epoxidation, in collaboration with
Dr Nick Coleman (School of Molecular and
Microbial Bioscience).
Nitrile Hydration
The conversion of nitriles to primary amides
is another reaction that is difficult to achieve
under mild conditions while also being
of considerable synthetic interest. Nitrile
hydratases execute this transformation in
nature, making them interesting targets for
biocatalytic and bio-inspired approaches to
nitrile hydration. The nitrile hydratase active
site contains cobalt(III) or iron(III) bound by
two amide nitrogens and three differentially
oxidised sulfur atoms. We have devised
a series of peptide and peptido-mimetic
systems to mimic nitrile hydratase structure
and function and recently characterised
these systems using XAFS, in collaboration
with Professor Peter Lay and Dr Jade Aitkin.
Mercury Binding
Building on natural strategies for mercury
binding and sequestration, we have
designed a series of sulfur-rich ferrocenoyl
peptides as new agents for mercury binding,
and used electrochemistry and NMR to
monitor their interactions with metal ions.
These compounds respond more strongly to
mercury than to other thiophilic metals such
as cadmium and lead. (For recent examples
see Tetrahedron 2010, doi: 10.1016/j.
tet.2010.05.070.)
New Directions
2009 saw the launch of new projects in
medicinal chemistry, biocatalysis, sensing,
and
antibiotic
synthesis,
extending
existing collaborations with A/Prof Louis
Rendina (Chemistry) and Dr Nick Coleman
(Microbiology), and establishing new links
with Dr Matthew Todd and Dr Richard
Payne (Chemistry). Stay tuned for further
developments in these areas in 2010.
With the last of our Irish émigrés Vicky
Dungan and Cillian Byrne completing in
2008, a number of new researchers joined
the group in 2009. The photograph below
shows the group in May 2009, left to right:
Tim Sheedy, Yu Heng Lau, Kaitlin Beare,
Rowan Nieuwenhuizen (Leiden), Samantha
Cheung, Peter Rutledge and Joseph Wong.
Günther Thiele (Marburg) was with us until
March 2009, while David Porter joined us in
July for Honours 2009/2010.
In September 2009, Peter and his
research group were profiled in
Chemistry World, the international
chemistry magazine published by
the Royal Society of Chemistry in
the UK. The piece was written by
Karen Harries-Rees, a freelance
science writer based in Melbourne,
following an interview with Peter
in May 2009. This was the first
time that the monthly Profile
segment in Chemistry World has
featured a chemist based outside
of Europe or the USA. To read
more, see http://www.rsc.org/
chemistryworld/ Issues/2009/
September/ScienceinSydney.asp.
34
2009 Chemistry Research Report
Dr Siegbert Schmid
Room 223
School of Chemistry, F11
T +61 2 9351 4196
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/schmid.html
inorganic solid state chemistry and chemistry education research
Research in our group focuses on
two major areas. Projects in Inorganic
Solid State Chemistry are in general
geared towards developing novel and
improved materials for use in a range
of technological applications. Chemistry
Education research projects are designed
to improve our understanding of how
we best support student learning.
Formation and Structural Phase Transitions
of Modulated Fresnoite Ba2xSr 2‑2xTiSi2O8
Compounds (Allen)
The fresnoite, A2BM2O8 (A = Ba, Sr; B = Ti, M
= Si, Ge), family of modulated structures has
been shown to exhibit excellent piezoelectric
properties. Therefore it is one of several
possible alternatives to replace PZT and
other lead‑based electroceramic materials.
Variable-temperature X-ray powder
diffraction data have been collected
recently on the powder diffraction beamline
at the Australian Synchrotron for a detailed
investigation of the structural chemistry
of members of the fresnoite-based solid
solution Ba2‑2xSr2xTiSi2O8 (0 ≤ x ≤ 1). Use
of a modulated structure approach to
the refinement of the structural model
against powder diffraction data using
Jana2006 allows us to properly understand
the structure-property relationships and
the changes in modulation parameters
as substitutions are made across a solid
solution series.
Results will be reported on the changes
in cell parameters across the Ba2xSr2-2xTiSi2O8
series, including temperature-dependent
results providing further evidence of
a phase transition which removes the
modulation from the Ba2TiSi2O8 structure
at 433 K (Figure 1).
Investigation into the Design of e-Learning
Modules (Yeung, George, King†)
Student populations in higher education
are diverse. A range of tools and teaching
materials are used to develop students’
understanding
in
different
domains.
Information and Communications Technology
has been increasingly incorporated into
teaching activities in higher education. In
support of this best practice for design of
multimedia instructional materials and for
establishing effective e-learning environments
has been investigated. A number of studies
have shown that animations and pictures when
used together with text and presented in a
concurrent way can enhance learning. Recent
studies have suggested that interactivity may
enhance learning by allowing students to be
more active learners while using technology
during the learning process. However, there
is limited empirical evidence to fully support
this idea.
We have developed an online chemistry
module with three different versions,
designed to determine the most effective
way for enhancing student learning and
addressing misconceptions students may
have. The present study investigates
students’ performance associated with using
these different versions of the module. One
version incorporates the use of still pictures,
one version uses animations and simulations,
and the third version uses animations and
simulations together with interactivity. We
have been able to show that no one of the
three versions is superior in all cases, but
rather it depends on the exact nature of the
learning required whether students benefit
more from interactive, animated or e-book
type material.
Defect Perovskites and Li ion Batteries
(Brant, Kuhn†)
Compounds that can reversibly intercalate
lithium have the potential to be used as
Figure 1: The change
in cell parameter a
as the temperature
of Ba2TiSi2O8 is
increased from 125 K
to 1223 K, indicating
a phase transition at
433 K. Data were
collected using the
low-temperature and
high temperature
attachments
on the powder
diffraction beamline
at the Australian
Synchrotron.
cathodes in rechargeable lithium ion batteries.
Two characteristics, the availability of
interstitial or defect sites for the incorporation
of lithium and the presence of reducible
cations are found in some defect perovskites.
We have previously synthesised a number of
defect perovskites, which might be useful
as host materials for Li intercalation, and
investigated their structures using X-ray and
neutron powder diffraction. After careful
characterisation of the structures for the
Li free samples, these exact samples were
then chemically intercalated with Li (via the
butyl-lithium route). Subsequently neutron
diffraction patterns were collected for two
of these samples at RT. It was found that
only subtle changes were detectable in the
neutron diffraction patterns.
In this project the electrochemical
intercalation of Li was investigated and
in-situ X-ray powder diffraction patterns
were recorded during the Li-intercalation
process for some samples. We have been
able to show that Li-intercalation is possible
and best for samples with large vacancy
concentrations. In-situ X-ray diffraction
showed that the cell dimensions of the
investigated samples increased slightly on
Li-intercalation, while on de-intercalation
they returned to the original value.
†
Collaborators from outside the School of
Chemistry
35
2009 Chemistry Research Report
Dr Timothy Schmidt
Room 457
School of Chemistry, F11
T +61 2 9351 2781
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/schmidt.html
probing molecules with lasers: astronomy and solar energy
My research group uses lasers to interrogate
molecules, a field known as molecular
spectroscopy. Studying the interaction
between light and matter is a fundamental
pursuit which can be applied to very different
fields of research. We study exotic molecules
in simulated astrophysical environments in
order to discern the precise wavelengths
absorbed by isolated molecules. The goal is
to learn more about interstellar chemistry
by matching laboratory measurements with
astronomical ones. In another laboratory,
my group studies the consequences of
light absorption, tracking the degradation
of energy on the femtosecond time-scale.
These studies are aimed squarely at solving
the biggest problem facing our species –
harnessing solar energy.
Molecules in Space
Entwined with the problems associated with
understanding the origin of life itself is the
understanding of the formation of prebiotic
complex organic molecules in space. There
is mounting evidence of the presence of
polycyclic aromatic hydrocarbon material
(fuzed benzene rings) in space. Yet, to date
not a single chemical species of this nature
has been identified. Remote identification of
specific molecules in space requires the close
collaboration of molecular spectroscopists
(found in chemistry departments) and
astronomers (found on top of mountains).
One chance to identify new molecules
in space is by observing the resultant visible
spectrum after white light has passed through
diffuse interstellar clouds. Such experiments
date from the 1920s and have resulted in
the cataloguing of over 300 so-called diffuse
interstellar bands (DIBs). The absorbers
responsible for the DIBs are widely held to
be gas-phase molecules yet not a single DIB
carrier has so-far been indentified in over 80
years!
My research group is undertaking
a comprehensive research program to
solve this problem; creating and studying
potentially interstellar molecules never seen
before. We have now created a plethora of
new hydrocarbon species in the laboratory.
Among the latest discovered are a group of
aromatic hydrocarbon radicals which pose a
tantalizing match to the emission spectrum of
the Red Rectangle, a nearby protoplanetary
nebula. The experiments are far from over,
and promise to yield dozens of new spectra,
further increasing the understanding of
chemistry of exotic, radical molecules
while potentially solving the oldest riddle in
molecular spectroscopy and astronomy –
the identity of the carriers of the DIBs.
Making Light Work Harder
All solar energy devices with a single
energy threshold suffer from an inability
to harvest more than about 30% of the
energy available from the sun. This limit,
first derived by Shockley and Queisser for
photovoltaic cells, is due to the inability to
make use of that part of the solar spectrum
with photon energies below the threshold;
and, particularly in solar cells, the energy
of an electron-hole pair in excess of the
threshold is degraded back to the bandgap
within picoseconds. The Shockley-Queisser
limit imposes a ceiling on the efficiency
and thus cost-effectiveness of all singlethreshold photovoltaic technologies.
One way to address these losses is
with upconversion (joining two low energy
photons together) to make more energetic
radiation. Implementation of upconversion
for solar cells boosts the efficiency ceiling
to 48%. Achieving this in a cost-effective
manner thus represents a reduction of solar
energy costs of approximately one-third.
Molecules may store energy from low
energy photons for a short amount of time
(hundreds of microseconds) in so-called
triplet states, from which fluorescence is
forbidden. When triplet molecules encounter
one-another, the combined energy may be
transferred to a single molecule, which may
then radiate the energy as fluorescence. In
so doing, red light can be converted to blue!
(see figure for world record upconversion
by 1eV) This does not violate the laws
of thermodynamics - two red photons
are required to create one blue photon.
Nevertheless, this process can potentially
harvest unused energy from a solar cell,
and radiate this back in a usable form,
boosting the efficiency. The mechanism
that Schmidt’s group employ, triplet-triplet
annihilation, was long thought to have an
upper efficiency limit of 11%. By employing
ingenious experiments, in 2009 Schmidt
demonstrated that, experimentally, more
than 30% of low energy photons could
be harvested for upconversion. Recent
(unpublished)
time-resolved
analysis
of the data shows that for the model
system employed, the limit is >60%. These
discoveries are game-changing, and should
see photochemical upconversion employed
for the improvement solar cell efficiencies in
the future.
Global Climate and Energy Project: The Hot
Carrier Solar Cell
Our group contribute to a large consortium
working on implementation of a “hot carrier”
solar cell, widely touted as the ultimate PV
converter. Along with UNSW, and laboratories
in Madrid and Paris, the consortium seeks
to break 50% energy conversion eventually
using only silicon. Our role in the project is
to time-resolve the cooling of electrons in
semiconductors on the sub-picosecond
time-scale – one millionth of one millionth
of a second. We do this using lasers: one
pulse serving to excite the sample with the
timing of a second laser pulse serving as a
“shutter”. Scanning the delay between the
pulses reveals ultrafast dynamics which guide
the choice of materials for more efficient
solar cells. A comparison of GaAs and InP
has revealed the key effect that a phononic
band gap may help to keep electrons hot for
longer.
36
2009 Chemistry Research Report
Dr Matthew Todd
Room 517
School of Chemistry, F11
T +61 2 9351 2180
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/todd.html
organic synthesis
and chemical biology
Our lab motto is: To make the
right molecule in the right place at
the right time. While figuring out
what this means, my students try
to make molecules in new ways,
observe their interactions with
biomolecules, and think up new
ways to monitor organic reactions
as they happen
New Organic Reactions
Synthesis is the most enabling part of
Chemistry, which is itself the most central of
sciences. To discover new ways to construct
molecules is the lifeblood of our discipline.
We have recently discovered a new carboncarbon bond forming reaction that operates
under extremely mild conditions and is
complete in a few minutes. The products
of this reaction can easily be converted to
chiral diamines (1), of immense importance in
medicine and catalysis. We have also recently
discovered a way of making such molecules
asymmetrically, which provides access to a
whole range of diamines that have never
previously existed. Finding and synthesising
catalysts for such unprecedented reactions
is one of the most exciting new areas in the
group.
Bio-Responsive Molecules
My group pioneered a new kind of
coordination compound that changes its
shape in a defined way when it binds to
a biological molecule. The central metal
atom of these complexes is coordinated
by a “scorpion” ligand that is removed
upon binding, and the metal acts as a
sensor of this event. We are working with
Peter Rutledge’s group to try to adapt this
important idea for various medical areas,
since such selective responses to biological
molecules embody the original concept of
magic bullet drugs. We have successfully
attached a range of small molecule ligands
to these new metal complexes, and are now
evaluating their fundamental behaviour in
biological media, and were recently awarded
a grant to develop the idea into a sensor for
breast cancer.
Neglected Tropical Diseases
With the World Health Organisation we
are addressing the chemical biology of the
neglected tropical disease schistosomiasis
(Bilharzia). This terrible parasitic infection
is one of the world’s most burdensome
infections, with hundreds of millions of
people worldwide currently suffering
its effects. We are in a very dangerous
situation: one drug called praziquantel
(PZQ) is being given to millions, yet there
are no back-up drugs available for when
resistance emerges. We are working to
discover the mechanism of action of PZQ,
synthesise a small number of new analogs
that are likely to be effective, and, crucially,
synthesise the active enantiomer of PZQ
for a low price on a ton scale. This latter
project, funded through an ARC Linkage
grant, is essential for postponing the
development of resistance to the drug in
the short term, and while the drug itself
is simple, synthesising only the active
enantiomer under a very significant price
constraint is a serious challenge.
Open Science
Science is conducted through a process
of pre-publication peer review originating
from papers submitted by groups often
working in isolation and in competition with
PROFILE:
Mat’s student Althea Tsang discovered a new reaction during her
Honours year, and published this discovery before she started her PhD.
Althea was awarded a prize from
the RACI Western Sydney section
for her Honours thesis, a Lamberton Scholarship for her PhD studies
from the School of Chemistry, and a
highly competitive DAAD scholarship
to spend 6 months in the laboratory
of Professor Stephen Hashmi at the
University of Heidelberg in Germany.
She is now working with Mat to elucidate a detailed mechanistic picture
of her reaction for her PhD.
one another. Beginning with our project on
PZQ, above, we are piloting the world’s first
government-funded open science project
in Chemistry. By placing all synthetic data
and ideas on the web as they are created,
and by inviting anyone in the world to
become an active collaborator, we are
hoping to show the solution to a scientific
problem by exploitation of the “Wisdom of
the Crowd.” Besides a fundamental shift
in the psychology of how we do science,
such a project requires the development
of new tools for massively-distributed
collaborations over the web. For a recent
feature article on this project in Nature, see
http://bit.ly/cyWmbV.
37
2009 Chemistry Research Report
Professor Gregory Warr
Room 310
School of Chemistry, F11
T +61 2 9351 2106
F +61 2 9351 3329
E [email protected]
http://sydney.edu.au/science/chemistry/research/warr.html
Surfactant-Templated Biominerals (Liu,
FitzGerald)
Surfactants have been used for well
over a decade to template silicates, with
the surfactant’s self-assembly structure
dictating the pore size, shape and
connectivity. We are using this idea to
template amorphous carbonate and other
biologically-significant minerals.
Using
the Australian Synchrotron to rapidly
scan structure, we found that cationic
surfactants with carbonate, phosphate
and oxalate counterions exhibit some rare
lyotropic liquid crystals which depend on the
hydrolysis state of the system, and hence
on pH. Unlike most cationic surfactants
these are sensitive to temperature.
soft condensed
matter and
interfaces
Our research is aimed at
understanding
the
behaviour
of amphiphiles in bulk phases
(solutions, liquid crystals, complex
fluids), in colloidal systems
(emulsions, foams, dispersions),
and at interfaces. We pursue a
wide range of projects examining
structure and dynamics using
techniques
including
neutron
and X-ray scattering (SANS
and SAXS), optical microscopy,
rheology and calorimetry, and
interfacial structure by neutron
and X-ray reflectometry, atomic
force microscopy, and surface
force
measurements.
By
combining these techniques we
are discovering new structures
formed
when
surface-active
molecules adsorb at interfaces
or when complex fluids abut an
interface, and use this to design
new nanostructured materials.
Structure and Self-Assembly in Ionic
Liquids (Zhang, Churton, Atkin,* Hayes,*
Rutland* Wakeham,* Nelson*)
Our recent work has focused on the
structure in protic room-temperature ionic
liquids understanding how the structure
and H-bonding between cations and anions
affects the structure of the ionic liquid,
and its properties as a solvent for complex
fluids. Wide-angle neutron scattering has
revealed a locally bicontinuous structure
in alkylammonium ILs which is almost
completely absent when the cation
structure is changed slightly. This has a
very strong effect on surfactant solubility
and amphiphilicity. Our previous work on
layering at solid-liquid interfaces was been
expanded to air/IL interfaces, including
adsorbed layers. We’ve also examined how
changing the anion has a strong effect on
ionic liquid structure, and amphiphilic solute
self-assembly.
Polymerisable Surfactant Nanostructures
(Baptista, Chatjaroenporn, FitzGerald,
Baker)
We have shown that the textbook picture
of spherical micelles being permanently
fixed into globular nanoparticles by
polymerization
into
is
completely
inaccurate. Instead, UV-initiation creates
a population of elongated polymer +
monomer mixed structures. These remain
in dynamic equilibrium with the changing
solution composition throughout the
reaction, during which they assemble into a
new equilibrium globular structure.
We have refined the synthesis
of our new, base-catalysed reactive
alkylpyridinium surfmers, including a facile
microwave methodology. The rate and
distribution of dimer and oligomer species
is very sensitive to the positioning of the
reactive group, and this in turn affects selfassembly structures.
38
2009 Chemistry Research Report
Books
1.
Comba, P; Hambley, TW and Martin, B. Molecular modeling
of inorganic compounds. Third Edition (completely revised and
enlarged edition), ISBN: 978-3-527-31799-8, 326 pages, WileyVCH Verlag GmbH & Co, 2009.
2.
Ridley, DD. Information retrieval: SciFinder. Publisher: John
Wiley & Sons Ltd, ISBN 978-0-470-71245-0 (pbk). 2nd Edition,
214 pages, 2009.
8.
Schmid, S; Yeung, A; George, AV and King, MM. Designing
effective e-learning environments - should we use still pictures,
animations or interactivity?. Book chapter in: Chemistry
Education in the ICT Age. (Collection of of selected papers
presented at the 20th International Conference on Chemical
Education (ICCE) held in Mauritius, 3-8 August, 2008. Editors:
Minu Gupta-Bhowon, Sabina Jhaumeer-Laulloo, Henri Li Kam
Wah and Ponnadurai Ramasami. ISBN: 978-1-4020-9731-7,
235-247, 2009.
9.
Ward, AJ; Masters, AF and Maschmeyer, T. Transition metal
single site catalysts - from homogeneous to immobilized
systems. Book chapter in: Modern Surface Organometallic
Chemistry. ISBN: 978-3-527-31972-5. Editors: Jean-Marie
Basset, Rinaldo Psaro, Dominique Roberto and Renato Ugo.
Chapter 5, 167-237, 2009.
Book chapters
1.
Aquino, C and Maschmeyer, T. A new family of mesoporous
oxides-synthesis, characterisation and applications of TUD-1.
Book chapter in: Ordered Porous Solids: Recent Advances and
Prospects. Editors: Valentin Valtchev, Svetlana Mintova and
Michael Tsapatsis. Published by Elsevier, First Edition, (ISBN:
978-0-444-53189-6), Volume 1, pp. 3-30, 2009.
2.
Atkin, R and Warr, GG. Bulk and interfacial nanostructure in
protic room temperature ionic liquids. Book chapter in Ionic
Liquids: From Knowledge to Application. ACS Symposium
Series, Volume 1030, Chapter 22, ISBN: 978-08412-69972,
Editors: Plechkova, NV; Rogers, RD and Seddon, KR, American
Chemical Society, Washington, pp. 317-333, 2009.
3.
4.
George, AV; Read, JR; Barrie, SC; Bucat, RB; Buntine, MA;
Crisp, GT; Jamie, IM and Kable, SH. What makes a good
laboratory learning exercise? Student feedback from the
ACELL project. Book chapter in: Chemistry Education in the
ICT Age. (Collection of of selected papers presented at the 20th
International Conference on Chemical Education (ICCE) held in
Mauritius, 3-8 August, 2008. Editors: Minu Gupta-Bhowon,
Sabina Jhaumeer-Laulloo, Henri Li Kam Wah and Ponnadurai
Ramasami. ISBN: 978-1-4020-9731-7, 363-376, 2009.
Jitchum, V; Kakwere, H; Ladmiral and Perrier, S. RAFT
polymerization, a versatile tool for the production of functional
soft nanoparticles. Book chapter in: Controlled/Living Radical
Polymerization: Progress in RAFT, DT, NMP & OMRP. ACS
Symposium Series 1024, ISBN: 978-0-8412-6996-5, Editor:
Krzysztof Matyjaszewski, 279-292, 2009.
5.
O’Brien, RW; Beattie, JK and Hunter, RJ.
Particle
characterization using electro-acoustic spectroscopy. Book
chapter in: Highlights in Colloid Science. Editors: Professor
Dimo Platikanov and Professor Dotchi Exerowa. Published by
Wiley-VCH Verlag GMBH & Co, (ISBN: 978-3-527-32037-0),
Volume 1, pp. 55-77, 2009.
6.
Levina, A; Codd, R and Lay, PA. Chromium in cancer and
dietary supplements. Book chapter in: High Resolution EPR.
Application to Metalloenzymes and Metals in Medicine. Volume
28, ISBN: 978-0-387-84855-6, Editors: Graeme Hanson and
Lawrence Berliner, Published by Springer, 666 pages, 551-579
2009.
7.
Schmid, S; Yeung, A and Read, JR. Students’ learning styles and
academic performance. Book chapter in: Chemistry Education
in the ICT Age. (Collection of of selected papers presented
at the 20th International Conference on Chemical Education
(ICCE) held in Mauritius, 3-8 August, 2008. Editors: Minu
Gupta-Bhowon, Sabina Jhaumeer-Laulloo, Henri Li Kam Wah
and Ponnadurai Ramasami. ISBN: 978-1-4020-9731-7, 249262, 2009.
10. Yeung, A; Schmid, S; George, AV and King, MM. Using the
personalization hypothesis to design e-learning environment.
Book chapter in: Chemistry Education in the ICT Age.
(Collection of of selected papers presented at the 20th
International Conference on Chemical Education (ICCE) held in
Mauritius, 3-8 August, 2008. Editors: Minu Gupta-Bhowon,
Sabina Jhaumeer-Laulloo, Henri Li Kam Wah and Ponnadurai
Ramasami. ISBN: 978-1-4020-9731-7, 287-299, 2009.
11.
Zhang, J; Whan, R and Hambley, T. Chemical biology of platinum
anticancer drugs. Book chapter in: Wiley Encyclopedia of
Chemical Biology. Edited by Tadhg P. Begley, (ISBN: 978-0470-47019-0), Volume 3, 721-730, 2009.
Dr Julia James, Honorary Associate Professor
within the School of Chemistry, emerging after
water sampling from Koonalda Cave, Nullarbor
Plain, SA.
39
2009 Chemistry Research Report
Journal publications
1.
2.
3.
4.
Ahmad, NM; Charleux, B; Farcet, C; Ferguson, CJ; Gaynor,
SG; Hawkett, BS; Heatley, F; Klumperman, B; Konkolewicz, D;
Lovell, PA; Matyjaszewski, K and Venkatesh, R. Chain transfer
to polymer and branching in controlled radical polymerizations
of n-butyl acrylate. Macromol. Rapid Commun., 30 (23), 20022021, 2009.
Ali, SI; Heuts, JPA; Hawkett, BS and van Herk, AM. Polymer
encapsulated gibbsite nanoparticles: Efficient preparation of
anisotropic composite latex particles by RAFT-based starved
feed emulsion polymerization. Langmuir, 25 (18), 10523-10533,
2009.
Allen, OR; Dalgarno, SJ; Field, LD; Jensen, P and Willis, AC.
Insertion of CO2 into the Ru–C bonds of cis- and transRu(dmpe)2Me2 (dmpe = Me2PCH2CH2PMe2). Organometallics,
28 (8), 2385-2390, 2009.
Altarawneh, M; Carrizo, D; Ziolkowski, A; Kennedy, EM;
Dlugogorski, BZ and Mackie, JC. Pyrolysis of permethrin and
formation of precursors of polychlorinated dibenzo-p-dioxins
and dibenzofurans (PCDD/F) under non-oxidative conditions.
Chemosphere, 74 (11), 1435-1443, 2009.
5.
Altarawneh, M; Dlugogorski, BZ; Kennedy, EM and Mackie,
JC. Mechanisms for formation, chlorination, dechlorination
and destruction of polychlorinated dibenzo-p-dioxins and
dibenzofurans (PCDD/Fs). Progress in Energy and Combustion
Science, 35 (3), 245-274, 2009.
6.
Anand, R; Hamdy, MS; Parton, R; Maschmeyer, T; Jansen, JC;
Cläser, R; Kapteijn, F and Hanefeld, U. Metal-TUD-1 catalyzed
aerobic oxidation of cyclohexane: A comparative study. Aust. J.
Chem., 62 (4), 360-365, 2009.
7.
Antonioli, B; Büchner, B; Clegg, JK; Gloe, K; Gloe, K; Götzke, L;
Heine, A; Jäger, A; Jolliffe, KA; Kataeva; O; Kataev; V; Klingeler,
R; Krause, T; Lindoy, LF; Popa, A; Seichter, W and Wenzel,
M. Interaction of an extended series of N-substituted di(2picolyl)amine derivatives with copper(II). Synthetic, structural,
magnetic, and solution studies. Dalton Transactions, 47954805, 2009.
8.
Åslund, ML and Canning, C. Air-clad fibres for astronomical
instrumentation: Focal-ratio degradation. Exp. Astron., 24 (13), 1-7, 2009.
9.
Atkin, R; De Fina, L-M; Kiederling, U and Warr, GG. Structure
and self assembly of Pluronic amphiphiles in ethylammonium
nitrate and at the silica surface. J. Phys., Chem. B, 113 (36),
12201-12213, 2009.
10. Attard, P. The second entropy: A general theory for nonequilibrium thermodynamics and statistical mechanics. Physical
Chemistry: Annual Reports on the Progress of Chemistry,
Section C, 105, 63-165, 2009.
11.
Attard, P. Statistical mechanical theory for non-equilibrium
systems. IX. Stochastic molecular dynamics. Journal of
Chemical Physics, 130 (19), 194113 (10pp), 2009.
12. Attard, P. Statistical mechanical theory for nonequilibrium
systems. X. Nonequilibrium phase transitions. Journal of
Chemical Physics, 131 (118), 184509 (10pp), 2009.
13. Attard, P. Nonequilibrium Monte Carlo simulation for a driven
Brownian particle. Physical Review E, 80 (4), 041126 (7pp),
2009.
14. Auckett, JE; Chen, YY; Khoury, T; Clady, RGCR; Ekins-Daukes,
NJ; Crossley, MJ and Schmidt, TW. Efficient up-conversion by
triplet-triplet annihilation. J. Phys.: Conf. Series, 185, 012002
(4pp), 2009.
15. Bar-Nes, G; Hall, R; Sharma, V; Gaborieau, M; Lucas, D;
Castignolles, P and Gilbert, RG. Controlled/living radical
polymerization of isoprene and butadiene in emulsion. European
Polymer Journal, 45 (11), 3149-3163, 2009.
16. Beattie, JK; Djerdjev, AM and Warr, GG. The surface of neat
water is basic. Faraday Discuss., 141 (1), 31-39, 2009.
17. Beattie: JK. Comment on: “Behaviour of hydroxide at the
water/vapor interface. [Chem.Phys. Lett. 474 (2009) 241]”.
Chemical Physics Letters, 481 (1-3), 17-18, 2009.
18. Bhuiyan, DHM; Mahon, AB; Jensen, P; Clegg, JK and Try, AC.
Synthesis of symmetric dinitro-functionalised Tröger’s base
analogues. Eur. J. Org. Chem., (5), 687-698, 2009.
19. Bhuiyan, DHM; Clegg, JK and Try, AC. Diethyl 6H, 12H5,
11-methanodibenzo-[b,f][1,5]diazocine-1,7-dicarboxylate.
Acta Crystallographica Section E: Structure Reports, E65,
o187-u2907, 2009.
20. Boyer, C; Bulmus, V; Davis, TP; Ladmiral, V; Liu, J and Perrier, S.
Bioapplications of RAFT polymerization, Chem. Rev., 109 (11),
5402-5436, 2009.
21. Brooker, L; Parr, MK; Cawley, A; Flenker, U; Howe, C;
Kazlauskas, R; Schanzer, W and George, A. Development of
criteria for the detection of adrenosterone administration by gas
chromatography-mass spectrometry and gas chromatographycombustion-isotope ratio mass spectrometry for doping control.
Drug Testing and Analysis, 1 (11-12), 2009.
22. Brotherhood, PR; Luck, IJ and Crossley, MJ. Complete
1
H and 119Sn NMR spectral assignment for an asymmetric
di[dihydroxotin(IV)] bis-porphyrin supramolecular host and its
corresponding tetraacetato complex. Magn. Reson. Chem., 47
(3), 257-262, 2009.
23. Brown, SL; Konkolewicz, D; Gray-Weale, A; Motherwell, WB
and Perrier, S. Searching for stars: Selective desulfurization
and fluorescence spectroscopy as new tools in the search for
cross termination side-products in RAFT polymerization. Aust.
J. Chem., 62 (11), 1533-1536, 2009.
24. Brown, CM; Liu, Y; Yildirim, T; Peterson, VK and Kepert, CJ.
Hydrogen adsorption in HKUST-1: A combined inelastic neutron
scattering and first-principles study. Nanotechnology, 20 (20),
204025 (11pp), 2009.
25. Bryce, NS; Zhang, JZ; Whan, RM; Yamamoto, N and Hambley,
TW. Accumulation of an anthraquinone and its platinum
complexes in cancer cell spheroids: The effect of charge on
drug distribution in solid tumour models. ChemComm., (19),
2673-2675, 2009.
26. Canning, J; Kristensen, M; Skivesen, N; Martelli, C; Têtu, A and
Frandsen, LH. Spectrally narrow polarisation conversion in a
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2009 Chemistry Research Report
Refereed conferences
1.
Altarawneh, M; Dlugogorski, BZ; Kennedy, EM and Mackie,
JC. Rate constants for hydrogen abstration reactions by the
hydroperoxyl radical from methanol, ethanol, acetaldehyde,
toluene and phenol. Proceedings of the Australian Combustion
Symposium, The University of Queensland, 4pp, 2-4 December,
2009.
2.
Åslund, M; Canning, J; Stevenson, M; Cook, K and Martelli,
C. Novel low-loss high-temperature stable strong fibre Bragg
gratings, International Conference on Advanced Materials
(ICAM), Rio de Janeiro, Brazil, 2009.
3.
Åslund, M; Canning, J; Stevenson, M and Cook, K. High
temperature regeneration of long period gratings. The 14th
OptoElectronics and Communications Conference (OECC),
Hong Kong, 2009.
4.
5.
6.
7.
8.
9.
Åslund, ML; Jovanovic, N; Jackson, SD; Canning, J; Marshall,
GD; Fuerbach, A; Withford, MJ and Cook, K. Photo-erasure
of type-II femtosecond laser written Bragg gratings employed
as high reflectors in moderate power Q-swtich fibre laser.
Conference on SPIE Europe Optics and Optoelectronics. ISBN:
9780819476302, Vol. 7356, Prague, Czech Republic, 22-23 April,
2009.
Auckett, JE; Cheng, YY; Khoury, T; Clady, RGCR; Ekins-Daukes,
NJ; Crossley, MJ and Schmidt, TS. Efficient up-conversion by
triplet-triplet annihilation. The 8th Asian International Seminar
on Atomic and Molecular Physics held at the University of
Western Australia, 24-28 November, 2008. Journal of Physics:
Conference Series, 185, 012037(4pp), 2009.
Bandyopadhyay, S; Canning, J; Biswas, P; Chakraborty, R and
Dasgupta, K. Regeneration of complex Bragg gratings. 20th
International Conference on Optical Fibre Sensors. Editor(s):
Julian Jones, Brian Culshaw, Wofgand Ecke, Jose Miguel LopezHiguera, Reinhardt Willsch. Proceedings of SPIE, Volume 7503,
750326(4pp), Edinburgh, UK, 5-9 October, 2009.
Damont, A; Camp, NV; Kuhnast, B; Hinnen, F; Boisgard, R;
Chauveau, F; Boutin, H; Probst, K; Clarke, J; Katsifis, A; Kassiou,
M; Tavitian, B and Dolle, F.
[18F]DPA-714, [18F]PBR111 and
[18F]FEDAA1106 as potent PBR PET-imaging candidates. 18th
International Symposium of Radiopharmaceutical Sciences,
Edmonton, Canada, 52 (S1) page S122, 12-17 July, 2009.
Canning, J; Fenton, J and Stevenson, M.
Ultra-strong
regenerated gratings.
The 14th OptoElectronics and
Communications Conference (OECC), Hong Kong, ISBN: 9781-4244-4103-7, 2009.
Canning, J. Structured fibres and gratings for sensors. Invited,
Asia-Pacific Conference on Photonics (ACP), Shanghai, China,
2009.
10. Canning, J. Sensing with structured fibres and gratings.
Invited, 20th International Conference on Optical Fibre Sensors.
Editor(s): Julian Jones, Brian Culshaw, Wofgand Ecke, Jose
Miguel Lopez-Higuera, Reinhardt Willsch. Proceedings of SPIE,
Volume 7503, 750326(4pp), Edinburgh, UK, 5-9 October, 2009.
11.
Canning, J; Gibson, BC; Huyang, G; Khoury; T, Sum, TJ; Neto, C
and Crossley, MJ. Processing waveguide photonic components
into self-assembled organic films. The 14th OptoElectronics and
Communications Conference (OECC), Hong Kong, ISBN: 9781-4244-4103-7, 2009.
12. Canning, J; Huyang, G; Gibson, BC; Neto, C; Khoury, T;
Martelli, C; Skivesen, N; Sum, TJ; Kristensen and Crossley, MJ.
Supramolecular porphyrin wires and post processing. The 14th
OptoElectronics and Communications Conference (OECC),
Hong Kong, ISBN: 978-1-4244-4103-7, 2009.
13. Canning, J; Stevenson, M; Groothoff, N; Cook, K; Åslund, M;
Ecke, W; Willsch, R; Bartelt, H; Kalinowski, H; Martelli, C; Braga, A
and Peng, GD. Optical fibre Bragg gratings for high-temperature
sensing. 20th International Conference on Optical Fibre Sensors.
Editor(s): Julian Jones, Brian Culshaw, Wofgand Ecke, Jose
Miguel Lopez-Higuera, Reinhardt Willsch. Proceedings of SPIE,
Volume 7503, 750326(4pp), Edinburgh, UK, 5-9 October, 2009.
14. Canning, J.
Emerging fibre component technologies for
sensors. Invited, The 14th OptoElectronics and Communications
Conference (OECC), Hong Kong, 2009.
15. Canning, J. Overview on gratings and optical fibers. Invited, 1st
International Workshop on Photonics for the Sensor Industries
(WPSI), Rio, Brazil, 2009.
16. Canning, J; Gibson, BC; Huyang, G; Khoury, T; Sum, T; Neto, C
and MJ Crossley. Ion beam engineering of photonic components
in organic supramolecular structures. Sir Mark Oliphant
Nanophotonics Down Under 2009 Devices and Applications
(SMONP2009), Melbourne, Australia, 2009.
17. Canning, J; Martelli, C; Gibson, BC and Huntington, ST. Towards
lower loss structured fibres - case study: Fractal fibres and ultralow bend loss. Sir Mark Oliphant Nanophotonics Down Under
2009 Devices and Applications (SMONP2009), Melbourne,
Australia, 2009.
18. Canning, J. Structured fibres and gratings for sensors. Invited,
International Conference on Optics and Photonics (ICOP).
Chandigarh, India, October 2009.
19. Canning, J; Bandyopadhyay, S; Stevenson, M; Biswas, P; Fenton,
J; Chakraborty, R and Åslund, ML. Thermal preparation of
highly stable glass periodic changes with nano-scale resolution
using a laser-inscribed hydrogen loaded seed template. IEEE
Photonics Society (formerly LEOS) Annual Meeting, Antalya,
Turkey, October, 2009.
20. Canning, J; Åslund, ML; Stevenson, M and Cook, K. Tailored
thermal stabilisation fo Type I gratings. IEEE Photonics Society
(formerly LEOS) Annual Meeting, Antalya, Turkey, October,
2009.
21. Canning, J; Gibson, B; Huyang, G; Khoury, T; Sum, T: Neto, C and
Crossley, M. Post-processing of self-assembled supramolecular
structures. Australian Conference on Optical Fibre Technology
(ACOFT), Adelaide, Australia, 29 November to 3 December,
2009.
22. Canning, J; Bandyopadhyay, S; Stevenson, M; Biswas, P;
Fenton, J and Åslund, M. Preservation of nanoscale resolution
after macro-scale thermal annealing and regeneration of Bragg
gratings in silica. Australian Conference on Optical Fibre
Technology (ACOFT), Adelaide, Australia, 29 November to 3
December, 2009.
23. Canning, J; Åslund, M; Stevenson, M and Cook, K. Tuning
the thermal stability of type I fibre Bragg gratings. Australian
Conference on Optical Fibre Technology (ACOFT), Adelaide,
Australia, 29 November to 3 December, 2009.
2009 Chemistry Research Report
48
24. Canning, J; Khoury, T; Jensen, P; Huyang, G; Sum, T; Chin, Y;
Reimers, J and Crossley, M. Alkyl chain control of the formation
of self-assembled monolayers, iridescent microrods and crystals
of alkylporphyrins of potential use in photonics. Australian
Conference on Optics Lasers and Spectroscopy (ACOLS),
Adelaide, Australia, 29 November to 3 December, 2009.
37. Cook, K; Canning, J; Poon, CK and Pohl, AAP. Tuneable ringDFB PCF laser for ultra-high resolution spectroscopy. 20th
International Conference on Optical Fibre Sensors. Editor(s):
Julian Jones, Brian Culshaw, Wofgand Ecke, Jose Miguel LopezHiguera, Reinhardt Willsch. Proceedings of SPIE, Volume 7503,
750326(4pp), Edinburgh, UK, 5-9 October, 2009.
25. Canning, J; Stevenson, M; Fenton, J; Åslund, M and
Bandyopadhyay, S.
Strong regenerated gratings.
20th
International Conference on Optical Fibre Sensors. Editor(s):
Julian Jones, Brian Culshaw, Wofgand Ecke, Jose Miguel LopezHiguera, Reinhardt Willsch. Proceedings of SPIE, Volume 7503,
750326(4pp), Edinburgh, UK, 5-9 October, 2009.
38. Dewhurst, C; Holdsworth, J; Canning, J; Åslund, M; Cook, K and
Stevenson, M. DFB fibre lasers for sensing, coherence issues
and packaging. Invited, 1st International Workshop on Photonics
for the Sensor Industries (WPSI), Rio, Brazil, 2009.
26. Carter, EA; Neo, R and Reade, W. Vibrational spectroscopic
studies of ivory from the ancient city of Pella (North Jordon).
Abstract from the Proceedings of the 5th International
Conference on the Application of Raman Spectroscopy in Art
and Archaeology, Editor: Juan Manuel Madariaga, p 150-151,
Bilbao, Spain, 14-18 September, 2009.
39. Dolle, F; Damont, A; Valette, H; Hinnen, F; Kuhanst, B; Saba, W;
Schollhorn-Peyronneau, M; Kozikowski, A; Bottlaender, M and
Kassiou, M. ZW-102 and ZW-104, two novel fluorine-18 labelled
radioligands for imaging nicotinic acetylcholine receptors with
PET. 18th International Symposium of Radiopharmaceutical
Sciences, Edmonton, Canada, 52 (S1), page S364, 12-17 July,
2009.
27. Carter, EA; Montgomery, J; Melton, ND; Hargreaves, MD;
Wilson, AS and Edwards, HGM. Gristhorpe man: A Raman
spectroscopic study of a Bronze Age warrior burial. Abstract
from the Proceedings of the 5th International Conference on
the Application of Raman Spectroscopy in Art and Archaeology,
Editor: Juan Manuel Madariaga, p 154, Bilbao, Spain, 14-18
September, 2009.
40. George, AV; Buntine, MA; Read, JR; Barrie, SC; Bucat, RB; Crisp,
GT and Jamie, IM and Kable, SH. What makes a good laboratory
learning exercise? Student feedback from the ACELL project.
Proceedings of the 20th International Conference on Chemical
Education, Mauritius, 2008. In: Chemistry Education in the ICT
Age, Editors: Gupta-Bhowon, M; Jhaumeer-Laulloo, S; Li Kam
Wah, H and Ramasami, P. Springer 2009, ISBN: 978-1-40209731-7 (Print), 978-1-4020-9732-4 (Online), 363-376, 2009.
28. Conibeer, G; Patterson, R; Aliberti, P; Huang, L; Guillemoles,
J-F; Konig, D; Shrestha, S; Clady, R; Tayebjee, M; Schmidt, TW
and Green, M. Hot carrier solar cell absorbers. Proceedings
from the 24th European Photovoltaic Solar Energy Conference,
Hamburg, Germany, 21-25 September, 2009.
41. Gibson, BC; Rollinson, C; Canning, J; Martelli, C and Huntington,
S. Fractal fibre: exposure and characterisation of nanoscale
features. Sir Mark Oliphant Nanophotonics Down Under 2009
Devices and Applications (SMONP2009), Melbourne, Australia,
2009.
29. Contos, AK and James, JM. Iron(III) bio-mineralization and its
significance in Odyssey Cave, Bungonia, New South Wales,
Australia. Proceedings of the 15th International Congress of
Speleology, Kerrville, Texas, USA, 19-26 July, 360-361, 2009.
42. Groothoff, N and Canning, J. Grating writing in pure silica fibres.
Invited, 1st International Workshop on Photonics for the Sensor
Industries (WPSI), Rio, Brazil, 2009.
30. Cook, K; Canning, J and Holdsworth, J. Acetylene line-width
measurement using a piezo-tuned, erbium-doped ring DFB-PCF
laser. The 14th OptoElectronics and Communications Conference
(OECC), Hong Kong, 2009.
31. Cook, K; Canning, J; Pohl, AAP; Holdsworth, J; Stevenson, M;
Bandyopadhyay, S and Groothoff, N. Bragg writing in photonic
crystal fibres. Proceedings of SPIE, “Photonic Crystal Fibres III”,
Editor: Kyriacos Kalli, Volume 7357, 73570H(pages 1-11), ISBN:
9780819476319, Prague, Czech Republic, 22-23 April, 2009.
32. Cook, K; Canning, J and Groothoff, N. Type IIa gratings in
photonic crystal fibers. Invited, 1st International Workshop on
Photonics for the Sensor Industries (WPSI), Rio, Brazil, 2009.
33. Cook, K; Poon, CK; Pohl, AA and Canning, J. Acetylene linewidth
measurement using a piezo-tuned, erbium-doped ring DFB-PCF
laser. IEEE Photonics Society (formerly LEOS) Annual Meeing,
Antalya, Turkey, October 2009.
34. Cook, K; Ducros, N; Fevrier, S; Åslund, M and Canning, J. Bragg
gratings in chalcogenide optical fibre written with a frequency
doubled Nd:YAG laser. IEEE Photonics Society (formerly LEOS)
Annual Meeing, Antalya, Turkey, October 2009.
35. Cook, K; Poon, CK; Pohl, AAP and Canning, J. Piezo-tuned
erbium-doped BFB-PCF laser for high-resolution spectroscopy.
Australian Conference on Optical Fibre Technology (ACOFT),
Adelaide, Australia, 29 November to 3 December, 2009.
36. Cook, K; Ducros, N; Février, S; Canning, J and Kar, AK. Inscription
of Bragg gratings in chalcogenide optical fibre using 532nm
radiation. Australian Conference on Optical Fibre Technology
(ACOFT), Adelaide, Australia, 29 November to 3 December,
2009.
43. Huyang, G; Åslund, M; Canning, J; Khoury, T; Crossly, MJ and
Martelli, C. Towards structured fibre based porphyrin sensors.
International Conference on Advanced Materials (ICAM), Rio de
Janeiro, Brazil, 2009.
44. James, JM; Martin, DJ; Tunnock, GM and Warild, AT. A cave
survey for research and tourist cave management. Proceedings
of the 15th International Congress of Speleology, Kerrville, Texas,
USA, 19-26 July, 1381- 1387, 2009.
45. James, JM and Spate, A. Sustainability in a karst – the
Bungonia Cavies, New South Wales, Australia. Conference on
the Sustainability of the Karst Environment-Dinaric Karst and
Other Karst Regions, Plitvice Lakes (Croatia). 23-26 September,
2009.
46. Jewart, CM; Chen, KP; Avdeev, I; Michie, A; Hambley, P and
Canning, J. Torsion of air-hole microstructured fibres under
large deflection. 20th International Conference on Optical Fibre
Sensors. Editor(s): Julian Jones, Brian Culshaw, Wofgand Ecke,
Jose Miguel Lopez-Higuera, Reinhardt Willsch. Proceedings of
SPIE, Volume 7503, 750326(4pp), Edinburgh, UK, 5-9 October,
2009.
47. Kennedy, S; Barnes, CM and James, JM. A cave survey project
for the Duke of Edinburgh’s Silver Award. Proceedings of the
15th International Congress of Speleology, Kerrville, Texas, USA,
19-26 July, 2006-2010, 2009.
48. Lancy, M; Groothoff, N; Guizard, S; Yang, W; Poumellec, B;
Kazansky, P and Canning, J. Femtosecond laser processing of
silica glasses with varying hydroxyl concentrations. Australian
Conference on Optics Lasers and Spectroscopy (ACOLS),
Adelaide, Australia, 29 November to 3 December, 2009.
49
49. Oliveira, RA; Marques, CAF; Noueira, RN; Canning, J and Pohl,
AAP. Fast acousto-optic add-drop based on fibre Bragg grating.
IEEE Photonics Society (formerly LEOS) Annual Meeting,
Antalya, Turkey, October, 2009.
50. Stevenson, M; Canning, J and Bandyopadhyay, S. Regenerated
gratings. Invited, 1st International Workshop on Photonics for
the Sensor Industries (WPSI), Rio, Brazil, 2009.
51. Reilly, NJ; Nakajima, M; Troy, TP; Kokkin, DL; Chalyavi, N; Duncan,
K; Nauta, K; Sharp, RG; Schmidt, TW and Kable, SH. Twodimensional fluorescence spectroscopy for the identification
of discharge intermediates. The 8th Asian International Seminar
on Atomic and Molecular Physics held at the University of
Western Australia, 24-28 November, 2008. Journal of Physics:
Conference Series, 185, 012037(4pp), 2009.
52. Schmid, S; Yeung, A; George, AV and King, MM. Proceedings
of the 20th International Conference on Chemical Education,
Mauritius, 2008. In: Chemistry Education in the ICT Age,
Editors: Gupta-Bhowon, M; Jhaumeer-Laulloo, S; Li Kam Wah,
H and Ramasami, P. Springer 2009, ISBN: 978-1-4020-9731-7
(Print), 978-1-4020-9732-4 (Online), 235-247, 2009.
53. Whitby, JL; Bellamy, KA and James, JM. Spelean history
revealed when naming features for a cave survey. Proceedings
of the 15th International Congress of Speleology, Kerrville, Texas,
USA, 19-26 July, 2048-2053, 2009.
54. Yeung, A; Schmid, SA; George, AV and King, M. Increasing
students’ interest and motivation through effective design on
online learning environments. In: Proceedings of the Motivating
Science Undergraduates: Ideas and Interventions. A. Hugman
(Ed.), ISBN: 978-1-74210-149-1, Sydney, NSW: UniServe Science,
132-138, 2009.
55. Yeung, A; Schmid, S; George, AV and King, MM. Using the
personalisation hypothesis to design E-learning environments.
Proceedings of the 20th International Conference on Chemical
Education, Mauritius, 2008. In: Chemistry Education in the ICT
Age, Editors: Gupta-Bhowon, M; Jhaumeer-Laulloo, S; Li Kam
Wah, H and Ramasami, P. Springer 2009, ISBN: 978-1-40209731-7 (Print), 978-1-4020-9732-4 (Online), 287-299, 2009.
2009 Chemistry Research Report
56. Zhang, F; Lidbury, B; Schulte, J; Bridgeman, A; Rodgers, J and
Yates, B. Embedding in-discipline language support for first
year students in the sciences: outcomes and future directions.
UniServe Science, The University of Sydney Conference
Proceedings: Motivating Science Undergraduates: Ideas
and interventions. ISBN: 9781742101491, pp139-145, Sydney,
Australia, 1-2 October, 2010.
2008
Books
2
Book Chapters
8
Journal Publications
186
Refereed Conference Publications
38
Conferences and other presentations attended
255
2009
Books
2
Book Chapters
11
Journal Publications
234
Refereed Conference Publications
56
Conferences and other presentations attended
272
50
2009 Chemistry Research Report
Research income statement
for the year ended 31 December 2009
Australian Competitive Research Grants − Commonwealth Schemes
ARC Discovery Projects
$4,623,256
ARC Linkage Projects
$1,637,120
ARC Linkage International Grants
$10,000
ARC Linkage − Infrastructure Equipment and Facilties (LIEF)
$350,000
ARC Fellowships
$1,104,122
National Health and Medical Research Grants (NH&MRC)/Project Grants
$352,485
Australian Institute of Nuclear Science and Engineering/ Awards
$94,990
National Breast Cancer Foundation/Novel Concept Awards
$106,124
TOTAL
$8,278,097
University of Sydney Grants
Seeding Grants from the USYD Sustainable Energy Research (SER) Grants Scheme
$104,590
Major Equipment Grants
$180,000
University of Sydney Bridging Support Grants
$165,000
DVC Research / Sustainable Energy Research Grants (SERG)
$120,550
University of Sydney Fellowships
$168,600
TOTAL
$738,740
TOTAL
$1,334,155
TOTAL
$235,403
TOTAL
$499,452
Other Public Sectors
Industrial and Other Grants
Bequests and Other Donations
TOTAL 2009 RESEARCH INCOME (not including Bequest or Donations)
$10,586,395
51
2009 Chemistry Research Report
Benefactors
Donations
The School of Chemistry would like to thank the following
benefactors for their generous contributions:-
The School of Chemistry would like to thank the following
people for their generous donations during 2009:-
Agnes Campbell Bequest
The Foundation for Inorganic Chemistry
Bruce Veness Chandler Bequest
Professor Archibald Liversidge Bequest
Alpha Chemicals (Australia) Pty Ltd
Scholfield Bequest
Mr Lance Cowled
RJW Le Fèvre Bequest
Mr Reid William Docherty
GG Blake Radio Research Bequest
Mr Kaled El Hassan
Janet Elspeth Crawford Bequest
Dr James Friend
Charles E Fawsitt Bequest
Mr Robbie Geyer
Edna Maude Goulston Bequest
Professor Peter Lay
Arthur Hollis Memorial Prize
Dr John Lambert-Smith
George Harris Scholarship
Lastek Pty Ltd
CH Wilson Prize
Emeritus Professor Len Lindoy
Dr Joan R Clark Research Scholarship
Mr Roberto Pavan
John A Lamberton Research Scholarship
Mr Thomas Savage
Surface Coating Association of Australia Scholarship
The Nell & Hermon Slade Trust
The Gritton Scholarships
Mr John Suster
Dr Alexander Boden
Jack Campbell Norrie
Harold Theodore Howard
Mrs Brightie Phillips
Dr Francis Lions
The Cornforth Foundation for Chemistry
Ms Carol Bae
Dr Roger Brown
Dr John Corrie
Mr Lance Cowled
Mrs M. Jean Porter
The Hush Trust
Dr Thomas Barlow
Dr James Friend
Dr Steven Hacobian
Mr Gregory Petfield
Dr John and Mrs Dorothy Lamberton
52
2009 Chemistry Research Report
2009 staff
& student
achievements
Physical Chemistry Chemical Physics has been highlighted
on ABC Science Online: http://www.abc.net.au/science/
articles/2009/11/16/2741961.htm
•
PhD students Mark Hackett, Dominik Konkolowicz and Stephen
Butler who have been awarded the 2009 Le Fèvre Lecturerships.
These Lectures were presented at the 648th meeting of the
Sydney University Chemical Society on Wednesday 18th
November 2009 in Le Fèvre Lecture Theatre 4.
•
Researchers from the Crossley and Schmidt Groups who have
come up with an ingenious low-cost device to harvest low
energy photons that are currently unused by solar cells. Their
research has been published in the latest issue of the journal
Physical Chemistry Chemical Physics: On the efficiency limit of
triplet–triplet annihilation for photochemical upconversion, Yuen
Yap Cheng, Tony Khoury, Raphaël G. C. R. Clady, Murad J. Y.
Tayebjee, N. J. Ekins-Daukes, Maxwell J. Crossley and Timothy
W. Schmidt, Phys. Chem. Chem. Phys., 2010 DOI: http://dx.doi.
org/10.1039/b913243k
•
Dr Tim Schmidt who has been selected the Coblentz Award
recipient for 2010. The Coblentz Award is presented annually to
an outstanding young molecular spectroscopist under the age
of 36. The Award is presented and the Coblentz Award Lecture
is delivered each June at the Ohio State University International
Symposium on Molecular Spectroscopy.
•
Ms Jenny Zhang, Postgraduate Teaching Fellow and PhD
candidate, who has been awarded the Australia-Israel Scientific
Exchange Foundation Postgraduate Fellowship for 2010.
Jenny will undertake research at the Department of Medicinal
Chemistry and Natural Products, School of Pharmacy, The
Hebrew University, Israel. Jenny has also received the following
2009 Grant-in-Aid Scholarships:- The William and Catherine
McIlrath Scholarship; R & M Bentwich Scholarship and the
Kenneth Firth Vickery Scholarship.
•
Mr Patryck Allen, Postgraduate Teaching Fellow and PhD
candidate, who received the Asian Crystallographic Association
Rising Star Award. This award selects students to present their
work in a special plenary session at the Joint Conference of the
Asian Crystallographic Association and Chinese Crystallographic
Society.
Further, Pat received a International Union of
Crystallography (IUCr) Travel Grant worth USD$800.
•
Mr Dominik Konkolewicz who received the C. G. and R. J. W. Le
Fèvre Student Lecture Award (USyd Chemical Society)/
•
The School has again performed exceptionally well in the
recently announced ARC Discovery Grant outcomes, with a
success rate of 44% which is almost double the overall national
success rate of 22.7%. We also had one successful Linkage
Project, equating to a 50% success rate (44.9% nationally). The
total funding awarded is $4.9 million.
•
Associate Professor Sébastien Perrier and Dr Tim Schmidt have
become the School’s latest Young Tall Poppy Science awardees.
These prestigious Awards aim to recognise the achievements
of Australia’s outstanding young scientific researchers and
communicators and are the initiative of the Australian Institute
of Policy and Science. Our previous Award holders include
Professor Cameron Kepert, Professor Thomas Maschmeyer,
Professor Kate Jolliffe and Dr Peter Rutledge.
•
Postdoctoral Fellow and PhD graduate, Dr Jack Clegg, who
has been awarded the University’s 2009 Convocation Medal.
This prestigious award is presented to an outstanding recent
graduate who has also contributed exceptionally to the life of
the University. This follows upon the award of the Medal to
Honours graduate Andrew McLeod in 2008.
•
PhD candidate Alexandra Manos-Turvey who was one of 25
nominees for the 2009 Convocation Medal.
The School congratulates the following people:
•
•
•
•
•
•
Dr Mat Todd and Dr Peter Rutledge, who, together with
Professor Rob Sutherland and Dr Alison Butt of the Garvan
Institute, have been awarded a National Breast Cancer
Foundation Novel Concept Award/Pilot Study grant for the
project “Target Activated Therapeutics: A New Strategy for
Monitoring and Treating Breast Cancer”. The Grant is valued at
$199,633 over 2 years.
Associate Professor Sébastien Perrier who has been awarded
the 2009 David Sangster Polymer Science and Technology
Award by the Royal Australian Chemical Institute. This award
recognises the outstanding achievements of Australian polymer
scientists in their early careers. Sébastien was awarded it
on the basis of outstanding original scientific and technical
contributions to the synthesis of complex polymer architectures
using controlled radical polymerisation techniques. This award
is named after David Sangster who for many years was an
Honorary Associate in the School.
Dr Vanessa de Souza who has been unanimously awarded the
Computational Physics Thesis Prize for 2008 from the Institute
of Physics. This prize is given for the PhD thesis (completed
in the UK or Ireland) that contributes most strongly to the
advancement of Computational Physics.
Professor Jeff Reimers who has been awarded the prestigious
H G Smith Memorial Award by the Royal Australian Chemical
Institute. The Medal is awarded annually to a researcher who,
in the opinion of the Board of the RACI, has contributed most
to the development of some branch of chemical science,
this contribution being judged by research work published or
accepted for publication during the ten years immediately
preceding the award.
Associate Professor Sébastien Perrier who has been awarded the
2009 Rennie Memorial Medal by the Royal Australian Chemical
Institute. The Rennie Memorial Medal is awarded annually to a
researcher with less than 8 years of professional experience
since completing their most recent relevant qualification of a
BSc, BSc (Hons), MSc or PhD, or the equivalent, who in the
opinion of the Board of the RACI, has contributed most towards
the development of some branch of chemical science. Such
contribution is judged by the research work published during
the ten (10) years immediately preceding the award.
Dr Peter Rutledge, who was awarded the “RACI NSW 2009
Citation” by the Royal Australian Chemical Institute for service
to RACI NSW and Chemistry in Schools through the Nyholm
Lectures.
•
Dr Peter Rutledge who was profiled in the September issue of
Chemistry World.
•
PhD student Cameron Weber on his award of a Dr Joan R Clark
Scholarship for 2009.
•
Dr Chiara Neto, whose recently published article On the
superhydrophobic properties of nickel nanocarpets in
53
•
2009 Chemistry Research Report
Professor Thomas Maschmeyer who has been awarded a
Future Fellowship for his project Sustainable Solar Hydrogen
Production from Waste Water. The role of the ARC Future
Fellowship scheme is to promote research in areas of critical
national importance by giving outstanding researchers incentives
to conduct their research in Australia. It aims to attract and
retain the best and brightest mid-career researchers. Project
Summary: The world energy demand, expected to triple by
2100, must be met from sustainable and non-polluting sources.
Sunlight is the largest available carbon-neutral energy source,
with enough energy striking the planet in one hour to satisfy our
current requirements for about a year. With the novel catalysts
designed in this project, we will use this energy to simultaneously
generate hydrogen and destroy organic pollutants by oxidation.
The hydrogen can then be used as a clean source of sustainable
energy and the water recycled. Our climate, proximity to major
economies of the future, and long commercial and research
experience in solar energy make Australia an ideal location for a
hydrogen production industry.
•
Dr Tim Schmidt on his award of the inaugural Physical Chemistry
Division Lectureship of the Royal Australian Chemical Institute.
Tim will be delivering a series of lectures across Australia.
•
Emeritus Professor Len Lindoy on his award of the 2009 Craig
Medal by the Australian Academy of Science. The David Craig
Medal recognises the outstanding contribution to chemical
research of Emeritus Professor David Craig, AC, FAA, FRS. Its
purpose is to recognise contributions of a high order to any
branch of chemistry by active researchers. The award is made
annually. This follows the award of the 2008 Medal to Professor
Leo Radom and the 2007 Medal to the late Professor Hans
Freeman.
•
Emeritus Professor Len Lindoy on his award by the Royal Society
of Chemistry UK of an RSC Centenary Lectureship and Medal
for 2009 - 2010 for his wide ranging and important contributions
to coordination chemistry, ligand design and supramolecular
chemistry.
•
PhD student, Nahid Chalyavi, on her award of an Endeavour
International Postgraduate Research Scholarship for 2008 2010 by the Australian Government.
•
PhD student Connie Liu, on her award of an AINSE top-up
scholarship.
•
PhD student, Sören Wohlthat, who received the poster prize
at the Australasian Molecular Modelling Association Conference
held at the Gold Coast in July.
•
PhD student, Andrew Telford, on his award of a University of
Sydney International Student Scholarship and a CSIRO Flagship
top-up scholarship for 2008 - 2010.
•
PhD student, Liz Fellows, who won the best poster prize at
CRYSTAL 26, the 26th Biennial Conference of the Society of
Crystallographers in Australia and New Zealand, in Barossa,
South Australia, in April 2009.
•
PhD student, Robert Chapman, who received the Treloar Prize
for Best Poster Presentation at the 31st Austalasian Polymer
Symposium.
•
Professor Leo Radom, who presented the 2009 Löwdin Lectures
at Uppsala University in Sweden.
•
PhD student and Postgraduate Fellow, Dominik Konkolewicz,
who was one of the 5 Australian research students who were
invited to attend the HOPE 2009 meeting in Hakone, Japan.
•
Dr Chiara Neto and her co-investigator Andrew Harris (Chemical
and Biomolecular Engineering) for their award of a Seeding Grant
from the University of Sydney Institute for Sustainable Solutions
on “Sustainable water for Australian cities.” -$104,590.
•
Recent PhD graduate, Dr Paul Saines, on his award of the AINSE
Gold Medal.
•
PhD student, Robert O’Reilly, who has been awarded the
2009 Postgraduate Research Prize for outstanding academic
achievement in chemistry.
•
PhD students, Elizabeth Fellows and Jess Chadbourne for
winning the student poster prizes at the Crystal-26 SCANZ
2009 conference.
•
PhD student, Althea Tsang, who was selected as one of the
two Highly Commended awardees of the 2009 Royal Australian
Chemical Institute’s Western Sydney Section Honours Prize.
Althea will give a talk on her Honours project at a presentation
ceremony at the University of Western Sydney.
•
Dr Toby Hudson and co-investigator, A/Prof. Michael Wheatland
(Physics, USyd) on their award of a SciFER grant. Titled:
Subject retention rates in physics and chemistry - $2 500.
•
Professor Cameron Kepert on his award of the 2009 Royal
Society of Chemistry Australasian Lectureship. This Lectureship
is awarded every two years by the RSC (UK) and allows the
recipient to give a series of research lectures at universities
across Australia and New Zealand.
•
PhD student, Nat Yamamoto, on her award of a DAAD
Scholarship by the German Government to spend 6 months
undertaking research at Ruhr-Universitaet Bochum.
•
Professor Scott Kable on his award of a 2009 Fulbright Senior
Scholarship to undertake research into ultra-fast photochemistry
at the University of Wisconsin.
54
2009 Chemistry Research Report
2009 Student prizes and scholarships
The School of Chemistry awards over $85 000 in Prizes and Scholarships each year to the best of its students. The following students were
awarded prizes or scholarships for academic achievements in 2009 based on their academic achievements in 2008. Scholarships are awarded
subject to the students satisfying conditions required for each of the individual scholarships.
Agnes Campbell Prize
Arthur Hollis Memorial Prize
Inglis Hudson Scholarship Major
Awarded to Honours and Postgraduate
students for excellence in research in organic
chemistry.
Awarded to the student gaining the
combined highest marks in both Semester 1
and Semester 2 Core Intermediate Chemistry
unit of study.
Awarded for proficiency in both Semester 1
and Semester 2 Senior Chemistry units of
study by a student proceeding to honours in
the area of Organic Chemistry.
Mr Derrick Roberts
Ms Jessica Tom
Australia-USA Foundation Prize
Inglis Hudson Scholarship
Mr Scott Lucas
Awarded for outstanding improvement in
Chemistry performance between junior and
intermediate Chemistry unit of study.
Ms Alexandra Manos-Turvey
Ms Tamara Simic
Awarded for proficiency in both Semester 1
and Semester 2 Senior Chemistry units of
study by a student proceeding to honours in
the area of Organic Chemistry.
Honours:
Mr Robert Cheung
Mr Trent Conroy
Ms Fiona Ky
Mr Robert Thompson
Ms Kamila Marzec
Ms Caroline Nesbitt
Charles E. Fawsitt
Mr Daniel Paraska
Ms Belinda Poon
Awarded for proficiency in both Semester 1
and a Semester 2 Junior Chemistry unit.
Mr Tze Han Sum
Ms Yizhou Huang
Mr Tze Jing Sum
Mr Deni Taleski
C.H. Wilson Prize
Ms Althea Tsang
Awarded to a student graduating in first
position with First Class Honours in the area
of Organic Chemistry.
Ms Michelle Wong
Ms Alexandra Manos-Turvey
Postgraduates:
Mr Samuel Banister
Ms Kaitlin Beare
Edna Maude Goulston Prize in Organic
Chemistry
Mr James Cochrane
Awarded annually to the Chemistry Honours
students gaining the highest mark in the
Organic coursework module, provided that
the student’s work is of sufficient merit.
Mr Hendra Gunosewoyo
Ms Michelle Wong
Mr Stephen Butler
Mr Hong Yue Vincent Ching
Mr George Huyang
Mr Sai Ho Lee
Frank E Dixon Scholarship
Ms Iman Moussa
Mr Shiva Prasad
Awarded for proficiency in both Semester 1
and Semester 2 Senior Chemistry units of
study by a student proceeding to Honours
in Chemistry.
Ms Helen Salouros
Ms Anh Thu Tran
Ms Taliesha Paine
Ms Grace Simpkins
Mr Danial Stocks
GS Caird Scholarship
Mr Tze Jing Sum
Three scholarships have been awarded for
proficiency in both Semester 1 and Semester
2 Senior Chemistry units of study by a student
proceeding to Honours in Chemistry.
Mr Muneer Syed Musthakahmed
Ms Fargol Taba
Mr James Webb
Mr Benjamin Yap
Mr Philip Young
Mr Yu Heng Lau
Ms Georgina Hutton
Mr Thomas Lee
Ms Samantha Cheung
Iredale Prize
Awarded for outstanding merit in both
a Semester 1 and a Semester 2 Core
Intermediate Chemistry unit of study.
Mr David Yoo
Ms Marina Cagnes
Janet Elspeth Crawford Prize in Chemistry
Awarded for the most proficient female
student who has completed Chemistry
Honours.
Ms Alexandra Manos-Turvey
Levey Scholarship No. 2
Awarded for proficiency in both Semester
1 and a Semester 2 Junior Chemistry unit
of study by a Science, Arts or Engineering
student who is proceeding to Intermediate
Chemistry.
Mr Aaron Tin Long Lun
Levey Scholarship No. 3
Awarded for proficiency in both Semester
1 and a Semester 2 Junior Chemistry unit
of study by a Science, Arts or Engineering
student who is proceeding to Intermediate
Chemistry.
Ms Yin Cao
55
RJW Le Fèvre – DAASN RAO Prize for
Physical Chemistry
Awarded for outstanding performance in
Physical Chemistry at the Senior Chemistry
level.
Mr Thomas Lee
Slade Prize
Awarded for proficiency in the practical
component of both a Semester 1 ands a
Semester 2 Intermediate Chemistry unit of
study.
Ms Goldie Lui
Walter Burfitt Scholarship No. 1
Awarded for proficiency in both Semester 1
and Semester 2 Senior Chemistry units of
study by a student proceeding to Honours
in Chemistry.
Mr Christopher Phippen
Prize and Scholarship winners
2009 Chemistry Research Report
56
2009 Chemistry Research Report
Staff and students
Head of School
WARR, Prof Greg
Deputy Head of School
KABLE, Prof Scott
Head of Research
JOLLIFFE, Prof Kate
Head of Teaching
BAKER, Dr Rob
1st Year Director
BRIDGEMAN, A/Prof Adam
2nd Year Coordinator
RUTLEDGE, Dr Peter
3rd Year Coordinator
RENDINA, A/Prof Lou
Honours
SCHMIDT, Dr Timothy (Coordinator)
TODD, Dr Mat (Deputy Coordinator)
Postgraduate Studies
HARROWELL, Prof Peter (Coordinator)
CLARKE, Dr Ron (Deputy Coordinator)
Academic Staff
BAKER, Dr Rob
BEATTIE, A/Prof James
BRIDGEMAN, A/Prof Adam
CLARKE, Dr Ron
CROSSLEY, Prof Max
GEORGE, Dr Adrian
HAMBLEY, Prof Trevor
HARROWELL, Prof Peter
HUDSON, Dr Toby
JOLLIFFE, Prof Kate
JORDAN, Dr Meredith
KABLE, Prof Scott
KASSIOU, A/Prof Michael
KENNEDY, A/Prof Brendan
KEPERT, Prof Cameron
LAY, Prof Peter
LING, Dr Christopher
MASCHMEYER, Prof Thomas
MASTERS, A/Prof Tony
McERLEAN, Dr. Christopher
NETO, Dr Chiara
PAYNE, Dr Richard
PERRIER, A/Prof Sebastien
RENDINA, A/Prof Lou
ROBINSON, Prof Robert
RUTLEDGE, Dr Peter
SCHMID, Dr Siggi
SCHMIDT, Dr Timothy
TODD, Dr Mat
WARR, Prof Greg
Academic Research Staff
AITKEN, Dr Jade
ASLUND, Dr Mattias
ATTARD, A/Prof Phil
BRYCE, Dr Nicole
CAI, Dr Zheng-Li
CANNING, Prof John
CHAN, Dr Bun
CLADY, Dr Raphael
CLEGG, Dr Jack
COOK, Dr Kevin
COURCOT, Dr Blandine
DE SOUZA, Dr Vanessa
DJERDJEV, Dr Alex
DUNGAN, Dr Vicky
FAIRWEATHER, Dr Kelly
FISHER, Dr Dianne
FITZGERALD, Dr Paul
HALL, Dr Ulrich
HAWKETT ,A/Prof Brian
HEINROTH, Dr Falk
HUNTER, Dr Luke
ISSA, Dr. Fatiah
JAIN, Dr Nirmesh
KEENE, Dr Tony
KHOURY, Dr Tony
KODA, Dr Yasuko
KOH, Ms Jia
LEONARD, Dr Sebastien
LEVINA, Dr Aviva
LI, Dr. Feng
MACCARONE, Dr Alan
NAUTA, Dr Klaas
NGUYEN, Dr Duc
NGUYEN, Mr Henry
O’BRIEN, Dr Richard
PAN, Mr Eh Hau
PATRA, Dr Swarna
PRICE, Dr David
PRIYANADA, Dr Pramith
RADOM, Prof Leo
READ, Mr Justin
REIMERS, Prof Jeff
REYNOLDS, Dr Aaron
SANDALA, Dr Greg
SAYYADI, Dr Nima
SOUTHON, Dr Peter
STEVENSON, Mr Michael
TAYLOR, Dr Mark
THICKETT, Dr Stuart
TURNER, Dr Peter
WANG, Dr Xin
WANG, Dr Yun
WARD, Dr Antony
WEN, Dr Ping
Wilkinson, Dr Brendan
YEUNG, Ms Alexandra
YUEN, Dr Alex
ZHANG, Dr Xiaoli
ZHOU, Dr Qingdi
Honorary Staff
ARMSTRONG, A/Prof Bob
ARONEY, Dr Manuel
BACSKAY, Dr George
BARNES, Dr Craig
BISHOP, Dr Michael
CAWLEY, Mr Adam
CODD, Dr Rachel
ECKERT, Dr Jim
FORAN, A/Prof Garry
HUNTER, A/Prof Bob
HUSH, E/Prof Noel
IRWIN, Dr Michael
JAMES, Dr Julia
LACEY, Dr Tony
LINDOY, E/Prof Len
MACKIE, A/Prof John
RADFORD, Dr Don
RICH, Dr Anne
SANDALA, Dr Greg
STERNHELL, Prof Sev
WEI, Dr Gang
WILLIAMS, Dr Alan
Administrative & Finance Staff
HURST, Dr Jeanette
LAZER, Dr Warren
MOERMAN, Ms Rachel
PATSALIDES, Mrs Sophie
PENWRIGHT, Mr Philip
PERERA, Mrs Shanthi
RAMESH, Mrs Nimmi
WOODS, Ms Anne
WOODS, Ms Kate
WU, Ms Lisa
XU, Ms Julie
Technical & Professional Staff
ARMSTRONG, Mr Jeff
ASHNA, Ms Marjan
BARASOAIN, Mr Fernando
CARTER, Dr Elizabeth
DE BRUYN, Dr Hank
DE COURCEY, Mr Eric
DELLIT, Mr Bruce
DU BOULAY, Dr Doug
DUCKWORTH, Mr John
FISHER, Dr Keith
GATFIELD, Mr Cliff
GOPAL, Mr Hitendra
JENSEN, Dr Paul
KAEGI, Mr Marcel
KENT, Mr John
LA, Mr Tuan
LEOW, Mr Richard
LOGGE, Mr Bernie
LUCK , Dr Ian
MACQUART, Dr Rene
OPRYSA, Mrs Anna
PICKER, Dr Kelvin
PISCICELLI, Mr Carlo
57
POPIOLKIEWICZ, Mr Jarek
SAINSBURY, Mr James
THANT, Ms Janette
THOMPSON, Ms Gemma
WAERN, Dr Jenny
ZYLMANS, Mr Jack
Research Assistants
BROTHERHOOD, Dr Peter
SHIRODKAR-ROBINSON, Dr B
Honours Students
BAPTISTA, Miss Natalie
BEINAT, Miss Corinne
BRANT, Mr. William
CHEUNG, Miss Samantha
HANANI, Mr Raphy
HUTTON, Miss Georgina
KERSHAW, Miss Holly
KIM, Mr Byung Juen
KOH, Mr Ming
KREMER, Ms Lauren
LAU, Mr Yu Heng
LEE, Mr Thomas
LIFA, Ms Tulip
LIM, Mr Say Kwang
LO, Mr Anthony
MACQUEEN, Mr Rowan
MULLANEY, Mr Ben
NGUYEN, Mr Tim
PHIPPEN, Mr Christopher
PORTER, Mr David
RECSEI, Mr Carl
SAMUEL-THAMBIAH, Mr Tanushan
SUN, Mr Victor
TARR, Miss Sally
THOMPSON, Mr Rob
TOM, Ms Jessica
TRAN, Mr Anh Thu Eve
TREVERROW, Mr Benjamin
WARD, Mr Jeremy
WONG, Mr Joseph
WORTHINGTON, Ms Katy
XUE, Miss Millie
Postgraduate Students
ABD AZIZ, Ms Azniwati
AMARASINGHE, Mrs Nilupa
ANAM, Mr Swapnil
AQUINO, Ms Cindy
AWIN, Mr Labib Ali
BANISTER, Mr Samuel
BARKHORDARIAN, Mr Arnold
BEARE, Ms Kaitlin
BROOKER, Mr Lance
BUTLER, Mr Stephen
CAMERON, Ms Lisa
CHAlLYAVI, Ms Nahid
CHAN, Mr Hoi-Ming
CHAPMAN, Mr Robert
CHATJAROENPORN, Miss Khwanrat
CHEN, Ms Chun
CHEN, Ms Hui Lin (Donna)
CHENG, Mr Yuen Yap
CHEUNG, Mr Robert
CHIN, Mr Yiing
CHING, Mr Vincent
CHUN, Ms Candy Ka Yin
2009 Chemistry Research Report
CLEMENTS, Mr Richard
COCHRANE, Mr James
CONROY, Mr Trent
COSTANZO, Mr Lorenzo
DOAN, Mr JOHN
DUYKER, Mr Samuel
GIBSON, Mr Bligh
GONG, Ms Nelly
GREEN, Mr Bradley
GUI, Mr Xiao
HALLIDAY, Ms Jill
HORNBY, Mr Ben
HOSSEINI, Mrs Simin Sadat
HSIEH, Mr Yves Shang-Yi
HUYANG, Mr George
IOPPOLO, Mr Joseph
KAKWERE, Mr Hamilton
KAUR, Mrs Ravinder
KAZA, Mrs Arati
KOLMANN, Mr Stephen
KY, Ms Fiona
LAU, Mr Vincent
LEE, Mr Jimmy
LEE, Mr Joonsup
LESIC, Ms Rebecca
LI, Ms Li
LIM, Ms Zhi Jun
LIU, Miss Mimi
LIU, Ms Connie
McALPINE, Ms Jeannette
MENON, Mrs Ambili
MORRISON, Mr Daniel
MOUSSA, Ms Iman Ahmed
NESBITT, Ms Caroline
NGUYEN, Ms Annie
O’REILLY, Mr Robert
PAINE, Miss Tallesha
PAKCHUNG, Ms Amalie
58
2009 Chemistry Research Report
PARK, Ms Soo-Jean
PHAM, Ms Thi Nahn Nquyen
PHUNG, Mr Peter
PRASAD, Mr Shiva
RICHMOND, Mr Craig
ROWLING, Mr Steven
SALOUROS, Ms Helen
SCIORTINO, Ms Natasha
SEMSARILAR, Ms Mona
SHEEDY, Mr Timothy
SIAUW, Ms Meiliana
SIMPKINS, Ms Grace
SRIPROM, Ms Wilasinee
SUM, Mr Anthony
SUM, Mr Max
SYED MUSTHAKAHMED, Mr Muneer
TABA, Ms Fargol
TALESKI, Mr Deni
TAN, Ms Teck Yee
TAYEBJEE, Mr. Marad
TELFORD, Mr Andrew
THIRUKKUMARAN, Mr T
THOROGOOD, Mr Gordan J
TING, Mr Jimmy
TSANG, Ms Althea
WEBB, Mr James
WEST, Mr Andrew
WOHLTHAT, Mr Soren
WONG, Ms Michelle Sik Ying
WU, Mr Yue
YAMAMOTO, Ms Natsuho
YAP, Mr Aaron
YAP, Mr Benjamin
YOON, Mr Dong Hee
YOUNG, Mr Philip
YOUSSEF, Mr Ali
YU, Mr Mingfeng
ZHU, Ms Liwen
Graduate Diploma
AMOS, Miss Nikki
NAQSHBANDI, Mr Masood Ahmad
SAHIN, Mr Ziya
Postgraduate Teaching Fellows
ALLEN, Mr Patryck
CHADBOURNE, Miss Jessica
DI MARCO, Ms Lina
FELLOWS, Ms Elizabeth
GUNOSEWOYO, Mr Hendra
HACKETT, Mr Mark
HEAZLEWOOD, Ms Brianna
KLEIN, Ms Alice
KONKOLEWICZ, Mr Dominik
MANOS-TURVEY, Miss Alexandra
MORAES, Mr John
NORMAN, Ms Julia
TROY, Mr Tyler Patrick
WEBER, Mr Cameron
ZHANG, Ms Jenny
Visitors
DE OLIVEIRA, Mr Roberson
GUILFOYLE, Ms Amy
HUTCHINGS, Ms Joanne
KHALD, Dr. Mohammed
KUSADA, Mr Kohei
MALINS, Miss Lara
MUNNIK Mr. Peter
MUNRO, Ms Kristie
NOSKE, Mr Raimund
RADZEY, Ms Hanna
SCHREPPEL, Ms Katja
SCHUEDEL, Mr Philipp
SOLOMON, Ms Gemma
TOURLE, Mr Sam
VINCENT, Ms Kim
VOGT, Professor Thomas
WYCZESANY, Mr Tomasz
Casuals/Volunteers
RIZVI, Mr Syed
ROWLANDS Dr W
SANGSTER, Mr David
SCHILTER, Mr David
SHARMA, Mr Neeraj
THIYAKESAN, Mr Kesan
TOSI, Mr DanieLle
59
2009 Chemistry Research Report
Graduates of 2009
Bachelor of Science (Honours)
The following students had their degrees awarded in 2009:-
Ms Corinne Beinat
The development of polycyclic NR2B antagonists for the treatment
of neurological disease
Supervisor: Associate Professor Michael Kassiou
Mr William Brant
Development of defect perovskites for use as cathode materials in
lithium ion batteries
Supervisor: Dr Siegbert Schmid
Ms Samantha Cheung*
Biocatalytic epoxidation of alkenes using mycobacterium sp. strain
NBB4
Supervisor: Dr Peter Rutledge
Mr Raphy Hanani
Design and synthesis of novel heterocyclic ligands for the translocator
protein (18 kDa)
Supervisor: Associate Professor Michael Kassiou
Ms Georgina Hutton*
Multifunctional Iron oxide nanoparticles: platforms for nanomedicine
Supervisor: Associate Professor Tony Masters
Mr Say Lim
Preferential protein adsorption on micro-phase separated blockcopolymer thin films
Supervisor: Dr Chiara Neto
Mr Anthony Lo*
Synthesis of biomimetics that bind and cleave DNA
Supervisor: Dr Mat Todd
Mr Benjamin Mullaney*
Nanoporous bimetallic frameworks: In search of tunable spin
crossover
Supervisor: Professor Cameron Kepert
Mr Timothy Nguyen*
The study of electronic structure and spectra of transition metal
complexes
Supervisor: Dr Adam Bridgeman
Mr Christopher Phippen
Toward the synthesis of polycyclic ethers
Supervisor: Dr Chris McErlean
Mr Carl Recsei
3,3´-disubstituted BINOL-derived phosphoramidites: Synthesis and
application
Supervisor: Dr Chris McErlean
Ms Holly Kershaw
Towards homogeneous molecular templating using ionic liquids
Supervisor: Professor Thomas Maschmeyer
Mr Jia Sun
New approaches to heterocyclic ring closure of THIQ derivatives
through C-H activiation
Supervisor: Dr Mat Todd
Mr Byung Kim**
Visualising the hypoxia selectivity of cobalt(III) prodrugs in tumour
spheroids
Supervisor: Professor Trevor Hambley
Ms Sally Tarr
Complementary fluorescence, IR and XRF spectroscopy of glucose
metabolism in adipocytes
Supervisor: Professor Peter Lay
Mr Ming Koh*
Synthesis of hyperbranched polymers by reversible additionfragmentation chain transfer (RAFT) polymerization
Supervisor: Associate Professor Sébastien Perrier
Mr Robert Thompson
Biomimetic and convergent approaches to the total synthesis of
microcin B17
Supervisors: Professor Kate Jolliffe and Dr Richard Payne
Ms Lauren Kremer*
Synthesis and characterisation of biopolymer vanadium complexes
as controlled release anti-diabetic agents
Supervisor: Professor Peter Lay
Ms Jessica Tom*
Investigation and optimisation of Cu(0)-mediated living radical
polymerisation of styrene
Supervisor: Associate Professor Sébastien Perrier
Mr Yu Heng Lau*
Tetraazamacrocyclic scorpionand complexes: Synthesis and study of
pendant coordination
Supervisors: Dr Mat Todd and Dr Peter Rutledge
Ms Anh Tran*
Design, synthesis and biological evaluation of type II dehydroquinase
inhibitors as tuberculosis drug leads
Supervisor: Dr Richard Payne
Mr Thomas Lee*
The origin of the contact electrification of insulators
Supervisor: Dr Chiara Neto
Mr Jeremy Ward
Controlling metal configuration in chiral-at-metal rhodium (III)
complexes via tripodal indenyl ligands
Supervisor: Dr Robert Baker
Ms Tulip Lifa
b-thioamino acid building blocks: A palladium(II)/palladium(IV) sp3
C-H activation strategy
Supervisors: Dr Chris McErlean and Professor Kate Jolliffe
Mr Joseph Wong*
Synthetic approaches to cyclobutanone analogues of b-Lactam
antibiotics
Supervisor: Dr Peter Rutledge
60
2009 Chemistry Research Report
Ms Katy Worthington*
Improving poison resistance of aqueous-phase reforming catalysts
Supervisor: Professor Thomas Maschmeyer
Dr Katie Cergol
Development of new organocatalysts for asymmetric synthesis and
solution conformations of marine natural product (−)-lasonolide A
Supervisor: Professor Katrina Jolliffe
*Bachelor of Science (Advanced) Honours
**Bachelor of Science (Molecular Biology & Genetics) Honours
Dr Xiaojuan Gong
Self-assembled drug lipid conjugates as chemotherapeutics and
cancer
Supervisor: Professor Gregory Warr
Dr Damian Kokkin
The spectroscopy of intersellar molecules towards the identification
of the diffuse intersellar bands
Supervisor: Dr Timothy Schmidt
Graduate Diploma in Science
The following students had their degrees awarded in 2009:Ms Nikki Amos
A nanoparticulate ruthenium oxide-silica catalyst for the oxidation
of cyclohexane
Supervisor: Associate Professor Tony Masters
Dr Joshua Peterson
Development of light-activated bioconjugates for bioelectronics
Supervisor: Associate Professor Louis Rendina
Dr Anne Pilotelle-Bunner
Lipid-protein and protein-protein interactions in the mechanisms of
photosynthetic reaction centre and the Na+,K+-ATPase.
Supervisor: Dr Ronald Clarke
Master of Science
The following students had their degrees awarded in 2009:-
Ms Sandra Ivanic
Thermodynamic and kinetic indications of radical stability
Supervisor: Professor Leo Radom
Ms Anna Safitri
Determination of chromium speciation in biological fluids
Supervisor: Professor Peter Lay
Mr Douglas Willoughby
Screening the IRRI mutant rice population for mutations that have
altered the structure of endosperm starch
Supervisor: Professor Greg Warr
Doctor of Philosophy
The following students had their degrees awarded in 2009:-
Dr Mohamed Ali
Characterization of fungal pathogens by vibrational spectroscopy
Supervisor: Professor Peter Lay
Dr David Bray
d-block metallo-supramolecular chemistry, from
studies to gold surface functionalisation
Supervisor: Professor Kate Jolliffe
Dr Cillian Byrne
Peptide based nitrile hydration:
active site
Supervisor: Dr Peter Rutledge
Dr Daniel Obando Gutierrez
Synthesis and antifungal activity of bispyridinium compounds
Supervisor: Professor Katrina Jolliffe
complexation
Mimics of the nitrile hydratase
Dr Neil Reilly
Fluorescence spectroscopy of jet-cooled hydrocarbon discharge
products
Supervisor: Professor Scott Kable
Dr David Schilter
Synthesis and DNA-binding of metallocyclic architectures
Supervisor: Associate Professor Louis Rendina
Dr Erin Sheridan
Targeting tumour cells with boronated cyclic peptides for boron
neutron capture therapy
Supervisor: Associate Professor Louis Rendina
Dr Tomasz Wyczesany
Asymmetric catalysis: Nonlinear effects and real-time polarimetry
Supervisor: Dr Matthew Todd
Faculty of Science
T +61 2 9351 3021
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http://sydney.edu.au/science/chemistry
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