Journal of Inorganic and General Chemistry
ARTICLE
www.zaac.wiley-vch.de
Zeitschrift für anorganische und allgemeine Chemie
DOI: 10.1002/zaac.201600120
Coordination Polymers with 2D 씮 3D Interdigitated Arrays Based on
5-(4-(1H-1,2,4-Triazol-1-yl)phenyl)-1H-tetrazole: Syntheses, Structures,
and Properties
Xi-Chi Wang,[a] Yu Chen,[a] Hao Yuan,[a] Qi Yang,[a] Xiao-Shan Zeng,[a] Hai-Jiang Qiu,[a]
and Dong-Rong Xiao*[a,b]
Keywords: Entangled network; Interdigitation; Double-bilayer; Copper; Rod-shaped SBU
Abstract. The interdigitated coordination networks [Cu(tyty)] (1) and
[Cu1.5(L1)(L2)(tyty)] (2) [Htyty = 5-(4-(1H-1,2,4-triazol-1-yl)phenyl)1H-tetrazole, HL1 = 2,3,4,5-tetrachlorobenzoic acid, HL2 = 2,3,4,5,6pentachlorobenzoic acid], were hydrothermally synthesized and further
characterized by single-crystal X-ray diffraction, powder X-ray diffraction, elemental analyses, IR and UV/Vis spectroscopy, and TG
analyses. Compound 1 consists of unique 2D double-bilayers, which
are interdigitated by adjacent 2D double-bilayers to yield a
2D 씮 3D interdigitated framework. Compound 1 is the first example
of a coordination polymer containing double-bilayer motifs. Compound 2 exhibits a new 2D 씮 3D interdigitated network, which is
assembled from sidearm-containing 2D layers that are formed by tyty
anions and rod-shaped secondary building units. The magnetic properties of 2 were also investigated.
Introduction
coordination modes and conformations. Among the N-donor
linkers, rigid N-donor ligands may possess a certain rigidity
and stability, which are more effective to reduce the uncertainty in the assembly process.[31]
Hitherto, a multitude of entangled coordination polymers
with different structural features, like interpenetration, polyrotaxane, polycatenane, polythreading etc., were documented.[32–34] Interdigitated networks, a special type of entangled
systems, can be disentangled without breaking links.[35] The
main feature of interdigitation is an extended array in which
individual motifs interweave each other in a gear-like (or
tongue-and-groove) fashion.[36] This feature may lead to a
change in structure and dimensionality and furthermore influence the resulting properties. Nevertheless, the combination of
interdigitation with other structural motifs of coordination
polymers, such as rod-shaped second building units (SBUs),
double-bilayer nets etc., still remains a challenge and is, in
some degree, limited at present.
With this background information, the coordination polymers [Cu(tyty)] (1) and [Cu1.5(L1)(L2)(tyty)] (2) were isolated
under similar hydrothermal conditions by using a rigid N-donor ligand, 5-(4-(1H-1,2,4-triazol-1-yl)phenyl)-1H-tetrazole
(Htyty) and carboxylate ligands. The details of their syntheses,
crystal structures, and properties are presented and discussed
in this paper.
In recent years, coordination polymers (CPs) have gained
reasonable attention because of their diverse structures, intriguing topologies, and tunable dimensionalities,[1–5] meanwhile
coordination polymers have emerged as a new platform for
various applications such as gas storage and separation,[6–9]
catalysis,[10–12] drug delivery,[13–15] sensors,[16–18] magnetism,[19–21] and optical properties.[22,23] With this trend, the rational design and synthesis of CPs has aroused as essential
issue, especially on molecular level. A number of parameters,
such as the reaction solvent system, pH, reactant concentration,
temperature, reaction time, organic carboxylates, and N-donor
ligands[24–28] partly account for the final structural and functional diversities. Among these factors, organic carboxylates
play a significant role in the design and fabrication of various
coordination polymers, thus organic carboxylates have been
widely used to construct or modulate molecular architectures.[29,30] Besides, N-donor ligands, which can act as both
the neutral and the anion organic ligands,[28] are of considerable current interest and extensively used to construct and tune
distinct structures and topologies due to their versatile types,
* Prof. Dr. D.-R. Xiao
Fax: +86-23-68254000
E-Mail: [email protected]
[a] College of Chemistry and Chemical Engineering
Southwest University
Chongqing, 400715, P. R. China
[b] State Key Laboratory of Structural Chemistry
Fujian Institute of Research on the Structure of Matter
Chinese Academy of Sciences
Fuzhou, Fujian 350002, P. R. China
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/zaac.201600120 or from the author.
Z. Anorg. Allg. Chem. 2016, 642, (11-12), 724–729
Experimental Section
Materials and Methods: All reagents and solvents were obtained
commercially and were used without further purification
[Cu(Ac)2·H2O, Alfa Aesar, 99.9 %; CuCl2·2H2O, Alfa Aesar, 99.9 %;
3,3⬘,4,4⬘-diphenylsulfonetetracarboxylic dianhydride, Tokyo Chemical
Industry Co., Ltd., 97.0 %; tetrachlorophthalic anhydride, Alfa Aesar,
724
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Journal of Inorganic and General Chemistry
ARTICLE
www.zaac.wiley-vch.de
Zeitschrift für anorganische und allgemeine Chemie
98.0 %; 5-(4-(1H-1,2,4-triazol-1-yl)phenyl)-1H-tetrazole (Htyty), Jinan
Henghua Sci.& Tec. Co. Ltd., 99.0 %]. Elemental analyses (C, H, and
N) were performed with a Perkin-Elmer 2400 CHN Elemental Analyzer. Cu was determined by a tps-7000 Plasma-Spec(I) inductively
coupled plasma-atomic emission spectrometer (ICP-AES). IR spectra
were recorded in the range of 400–4000 cm–1 with a Bio-Rad FTS185 FT/IR Spectrophotometer using KBr pellets. UV/Vis spectra were
obtained with a Shimadzu UV2450 spectrometer. PXRD data were
recorded with a XD-3 diffractometer using Cu-Kα radiation. TG analyses were performed with a NETZSCH STA 449C instrument with
flowing N2 with a heating rate of 10 K·min–1. Variable-temperature
magnetic susceptibility data were obtained with a SQUID magnetometer (Quantum Design, MPMS-7) in the temperature range of 2–300 K
with an applied field of 1 kOe. The magnetic susceptibility data were
corrected from diamagnetic contributions estimated from Pascal’s constants.
Synthesis of [Cu(tyty)] (1): A mixture of Cu(Ac)2·H2O (0.4 mmol),
Htyty (0.2 mmol), STBA (3,3⬘,4,4⬘-diphenylsulfonetetracarboxylic dianhydride) (0.2 mmol), HCl (five drops, 0.2 m), and H2O (10 mL) was
stirred for about 15 min in air, afterwards transferred and sealed in a
18 mL Teflon-lined autoclave, which was heated at 160 °C for 72 h.
After slow cooling to room temperature, pale yellow needle crystals
of 1 were filtered off, washed with distilled water, and dried at ambient
temperature (yield:43 % based on Cu). C9H6CuN7: calcd. C 39.20, H
2.19, N 35.56, Cu 23.05 %; found: C 39.01, H 2.43, N 35.76, Cu
22.87 %. IR (KBr): ν̃ = 3140 (m), 3059 (m), 3011 (m), 2930 (w), 2246
(w), 1767 (w), 1610 (m), 1538 (s), 1518 (s), 1461 (s), 1437 (s), 1402
(s), 1366 (m), 1313 (m), 1280 (s), 1229 (m), 1179 (w), 1152 (m), 1048
(w), 1020 (w), 1008 (w), 969 (s), 885 (w), 847 (s), 826 (w), 751 (s),
707 (w), 668 (s), 650 (w), 528 (m), 508 (w), 492 (m), 445 (w) cm–1.
Synthesis of [Cu1.5(L1)(L2)(tyty)] (2): A mixture of CuCl2·2H2O
(0.6 mmol), Htyty (0.3 mmol), tetrachlorophthalic anhydride
(0.3 mmol), and H2O (10 mL) was placed in an 18 mL Teflon-lined
autoclave and stirred for about 15 min in air. The autoclave was sealed
and heated at 160 °C for 72 h under autogenous pressure, and cooled
to room temperature naturally. Green block crystals of 2 were obtained
(yield: 22 % based on Cu). C23H7Cu1.5Cl9N7O4: calcd. C 32.13, N
11.40, Cu 11.09 %; found: C 32.34, N 11.59, Cu 11.24 %. IR (KBr):
ν̃ = 3451 (br), 3153 (m), 3067 (w), 1746 (w), 1620 (s), 1576 (s), 1553
(s), 1581 (s), 1466 (m), 1421 (s), 1377 (s), 1348 (s), 1288 (m), 1213
(m), 1151 (m), 1086 (w), 1047 (w), 1003 (w), 974 (m), 932 (w), 905
(w), 847 (m), 779 (w), 758 (w), 675 (w), 652 (m), 516 (w), 509 (w)
cm–1.
X-ray Diffraction: Crystallographic data for compounds 1 and 2 were
collected with Cu-Kα radiation (λ = 1.54184 Å) at 296.15 K and
289.63 K, respectively. Using Olex2,[37] the structure of 1 was solved
with the SHELXS[38] structure solution program using Direct Methods
and 2 was solved with the Superflip[39–41] structure solution program
using Charge Flipping. Moreover, the structures of 1 and 2 were refined with the SHELXL[42] refinement package using least square minimization. All non-hydrogen atoms were refined anisotropically. The
organic hydrogen atoms were generated geometrically. The organic
hydrogen atoms were generated geometrically from different Fourier
maps and refined with isotropic displacement parameters. Crystallographic data and structure refinement results for compounds 1 and 2
are summarized in Table 1. Selected bond lengths for 1 and 2 are listed
in Table S1 (Supporting Information).
Z. Anorg. Allg. Chem. 2016, 724–729
Table 1. Crystal data and structure refinements for compounds 1 and
2.
Empirical formula
Mr /g·mol–1
Crystal system
Space group
a /Å
b /Å
c /Å
α /°
β /°
γ /°
V /Å3
Z
ρcalcd. /g·cm–3
μ /mm–1
F(000)
2Θ range /°
Reflections collected
Unique data (Rint)
GOF on F2
R1a) /wR2b) [I⬎2σ (I)]
R1a) /wR2b) (all data)
1
2
C9H6CuN7
275.75
orthorhombic
Fdd2
17.6007(14)
19.6048(16)
21.0543(17)
90
90
90
7265.0(10)
32
2.017
2.389
4416.0
3.662–54.954
10784
3960(0.0272)
1.005
0.0307/0.0723
0.0369/0.0747
C23H7Cu1.5Cl9N7O4
859.72
triclinic
P1̄
8.74394(17)
13.4023(3)
13.7868(3)
117.355(2)
94.2555(18)
90.2961(16)
1429.63(6)
2
1.997
9.634
845.0
11.964–143.144
26720
5527(0.0324)
1.044
0.0343/0.0907
0.0356/0.0917
a) R1 = ∑||Fo|–|Fc||/∑|Fo|. b) wR2 = ∑[w(Fo2 – Fc2)2]/∑[w(Fo2)2]1/2.
Crystallographic data (excluding structure factors) for the structures in
this paper have been deposited with the Cambridge Crystallographic
Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies
of the data can be obtained free of charge on quoting the depository
numbers CCDC-1455978 and CCDC-1455979. (Fax: +44-1223-336033; E-Mail: [email protected], http://www.ccdc.cam.ac.uk).
Supporting Information (see footnote on the first page of this article):
Additional structural figures and tables, PXRD patterns, TG-DSC
curves, IR spectra, and additional details for single-crystal structural
refinements.
Results and Discussion
Structure of [Cu(tyty)] (1)
As shown in Figure 1, there are two copper atoms and two
tyty anions in the asymmetric unit. Each CuI cation displays
almost a triangle arrangement by coordinating to three nitrogen
atoms of tyty [Cu–N 1.954(4)–2.007(4) Å]. Each tyty ligand
bridges three CuI atoms (Scheme S1, Supporting Information).
Based on aforementioned coordination modes, the extension
of such asymmetric units results in an uncommon 2D doublebilayer motif with large quadrilateral cavities (dimensions
Figure 1. Coordination environment of the Cu atom in 1 (hydrogen
atoms are omitted for clarity).
725
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Journal of Inorganic and General Chemistry
www.zaac.wiley-vch.de
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
10.05 Å ⫻ 10.30 Å, Figure 2). In order to simplify the intricate
structure of 1, the CuI atoms and tyty ligands can be regarded
as 3-connected nodes, and the double-bilayer network can be
viewed as the combination of two bilayer networks (Figure 3).
In other words, in the single bilayer net (Figure 3a), a half of
Cu atoms and tyty ligands just act as 2-connected nodes, which
still remain uncoordinated, and two bilayer nets are linked
through these unsaturated Cu atoms and tyty ligands, resulting
in a double-bilayer structure (Figure 3b). Additionally, as depicted in Figure 3c and d, left-handed double helical chains,
running along the b axis with a pitch of 28.638 Å, are included
in the same double-bilayer network, indicating that an individual double-bilayer network possesses chirality. In this 2D chiral double-bilayer net, strong π···π stacking interactions exist
between adjacent tyty ligands (π···π stacking interactions are
listed in Table S2 (Supporting Information), which may be another factor for the formation of the double bilayer. So far,
compound 1 is the first example of an indigitated structure
with double-bilayer motif.
Furthermore, the tyty ligand located out of the layer can be
viewed as a “tooth”, and each 2D double bilayer is interdigitated with another 2D double-bilayer net to generate 2D saw-
Figure 2. Space-filling model of the 2D layer in 1, showing large
quadrilateral cavities with dimensions of 10.05 ⫻10.30 Å2.
Figure 3. (a) Simplified view of the single bilayer network in 1 (turquoise for Cu ions and blue for tyty anion ligands). (b) Simplified view of
the double-bilayer motif in 1. (c) Perspective view of the 2D double bilayer in 1. (d) View of the double-stranded helices running along the b
axis direction in 1.
Z. Anorg. Allg. Chem. 2016, 724–729
726
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Journal of Inorganic and General Chemistry
ARTICLE
www.zaac.wiley-vch.de
Zeitschrift für anorganische und allgemeine Chemie
tooth-like supermolecular layer (Figure 4a) that provides
enough space for the occurrence of further interdigitation.
Consequently, the adjacent 2D supermolecular layers are interdigitated with each other to yield a 2D 씮 3D interdigitated
framework (Figure 4b).
simultaneously, resulting in a 2D 씮 3D interdigitated motif
(Figure 7).
Figure 5. Coordination environment of the Cu atoms in 2 (hydrogen
atoms are omitted for clarity).
Figure 4. (a) View of two different double-bilayer networks to form a
2D sawtooth-like supermolecular layer. (b) The 2D 씮 3D interdigitated array of 1.
Structure of [Cu1.5(L1)(L2)(tyty)] (2)
The coordination environment of the central CuII atoms in
compound 2 is illustrated in Figure 5. The Cu1 atom is coordinated by two oxygen atoms belonging to two molecules of L1
[Cu–O 1.9648(16) and 1.9648(16) Å] and two nitrogen atoms
from two tyty ligands [Cu–N 2.0122(19) and 2.0123(19) Å],
to yield a roughly square-planar coordination arrangement.
However, Cu2 is situated in the center of a slightly distorted
square pyramidal arrangement, being coordinated by one oxygen atom from L1 [Cu–O 2.0215(17) Å], two oxygen atoms
from two L2 ligands [Cu–O 1.9761(18) and 2.1762(17) Å],
and two nitrogen atoms from two tyty ligands [Cu–N
1.9627(19) and 1.980(2) Å]. The tyty ligand shows a 3-connected mode linking three CuII atoms. Meanwhile, L1 and L2
similarly act as V-shaped linkers linking two CuII ions
(Scheme S1 and Scheme S2, Supporting Information). Based
on these connection modes, the CuII ions are connected by
carboxylate groups of L1 and L2 ligands to form 1D CuIIcarboxylate chains along the a axis, which can be taken as rodshaped SBUs (Figure 6a), and these chains are further extended by tyty ligands to yield a 2D sheet (Figure 6b). Additionally, the 2,3,4,5-tetrachlorobenzene rings of L1 ligands
and the 2,3,4,5,6-pentachlorobenzene rings of L2 ligands out
of the plane embed the adjacent layers above and below
Z. Anorg. Allg. Chem. 2016, 724–729
Figure 6. (a) View of the rod-shaped SBU in compound 2. (b) View
of the 2D layer in 2.
Figure 7. View of the 2D 씮 3D interdigitated array of 2.
Compared to the coordination modes of the tyty ligand in
published literature (Scheme S3, Supporting Information),[43]
727
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Journal of Inorganic and General Chemistry
ARTICLE
www.zaac.wiley-vch.de
Zeitschrift für anorganische und allgemeine Chemie
in compounds 1 and 2 the tyty ligands act in tridentate fashion
to assist to construct 2D 씮 3D interdigitated structures, however, there are distinct differences in the structures of 1 and 2.
Consequently, it has to be mentioned that the organic carboxylates may play a crucial role in adjusting the structures of the
title compounds. Especially in compound 1, no crystals suitable for single-crystal X-ray diffraction could be obtained
without the carboxylate STBA, which may act as a regulator
to influence the behaviors of the CuI atom and the tyty ligand,
however, the mechanism is still unexplored. In 2, the L1 and
L2 ligands were produced via in situ reaction from tetrachlorophthalic anhydride (Scheme S4, Supporting Information).
They both coordinate with CuII atoms to form rod-shaped
SBUs.
X-ray Powder Diffraction
In order to check the phase purity of compounds 1 and 2,
the X-ray powder diffraction (PXRD) patterns were recorded
at room temperature. As shown in Figures S2 and S3 (Supporting Information), the peak positions of simulated and experimental patterns are in good agreement with each other, demonstrating the phase purity of the products. The differences in
intensity may be due to the preferred orientation of the crystalline powder samples
magnetic properties of compound 2 were investigated in the
temperature range of 2–300 K at a direct current field of
1.0 kOe. As shown in Figure 8, the χMT value at 300 K is
0.635 cm3·K·mol–1 (2.254 μB), which is slightly higher than
the expected value (0.563 cm3·K·mol–1, 2.122 μB) of one and
a half isolated spin-only CuII ions (S = 0.5, g = 2.0). The χMT
value of compound 2 increases slowly and reaches a maximum
value at 60.3 K (0.653 cm3·K·mol–1) with decreasing temperature. This magnetic behavior is usually the signature of a ferromagnetic interaction between CuII metal ions in the structure.[44] Based on the structure analysis of 2, the ferromagnetic
interaction between the central Cu atoms is attributed to the
magnetic exchange coupling through the tetrazole and carboxylate bridges. Below this temperature, the χMT product decreases sharply to 0.455 cm3·K·mol–1 at 2 K, which is usually
the signature of weak antiferromagnetic interaction between
CuII metal ions and/or a zero-field splitting (ZFS) effect. In
the temperature range of 2–300 K, the fit of the curve for
χM–1 vs. T plot to the Curie-Weiss law results in C =
0.631 cm3·K·mol–1 and θ = 1.129 K.
Thermal Analysis
Thermogravimetric analyses (TG) of compounds 1 and 2
were performed to investigate their thermal stabilities. The
thermogravimetric analysis of 1 exhibits two weight loss steps
(Figure S4, Supporting Information). The sample keeps relatively stable from room temperature to 282 °C. Approximately
28 % weight is lost in the first step from 283 °C to 393 °C, the
second weight loss is 22 % at 394–780 °C, both assigned to
the release of tyty ligands. The total weight loss of 50.08 % is
less than the calculated value of 71.15 % if the final product is
assumed to be CuO, which indicates that the decomposing process is not complete due to the use of nitrogen protection. In
the DSC curve of 1, the exothermic peaks at 397 °C and
626 °C are both related to the release of the organic ligands.
The TG curve of 2 exhibits two weight loss steps (Figure
S5, Supporting Information). The sample keeps relatively
stable from room temperature to 247 °C. The first weight loss
(56 %) occurs at 248–367 °C and the second weight loss (22 %)
occurs at 365–780 °C corresponding to the release of organic
ligands. The total weight loss of 77.92 % is less than the calculated value of 86.12 % if the final product is assumed to be
CuO, which indicates that the decomposing process is not
complete due to the use of nitrogen protection. In the DSC
curve of 2, the exothermic peaks at 342 °C and 613 °C are
both related to the release of the organic ligands.
Figure 8. Thermal variation of χM and χMT for compound 2. Insert:
plot of the thermal variation of χM–1 for compound 2.
UV/Vis Spectroscopy
Complexes 1 and 2 are sparingly soluble in water solution
containing 1 % DMSO at 1 ⫻ 10–5 M concentration level
(25 °C) and the UV/Vis spectra of the complexes were recorded under this condition. The UV/Vis spectra for 1 are
shown in Figure S8 (Supporting Information) in the range of
240–800 nm, and the UV/Vis spectra for 2 are shown in Figure
S9 (Supporting Information) in the range of 200–800 nm. The
lower energy bands from 245 to 323 nm for 1 and from 203 to
260 nm for 2 are considered as metal-to-ligand charge-transfer
(MLCT) transitions.[45]
Magnetic Properties
Conclusions
The CuII ions in 2 are bridged by tetrazole and carboxylate
groups, which may mediate magnetic interactions. Thus, the
Two 2D 씮 3D interdigitated coordination polymers with
novel structural motifs were synthesized and characterized. In
Z. Anorg. Allg. Chem. 2016, 724–729
728
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Journal of Inorganic and General Chemistry
www.zaac.wiley-vch.de
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
1, double-bilayer sheets with large quadrilateral cavities are
further interdigitated to form a 3D framework. In 2, carboxylate ligands link metals to produce rod-shaped SBUs, which are
extended by tyty ligands to construct 2D layers, and finally a
3D network is attained by interdigitating between 2D layers.
The preparation of the two compounds with peculiar structures
not only adds new members to the family of interdigitation,
but also provides a new structural motif – double bilayer – for
the entangled system.
Acknowledgements
This work was financially supported by the National Natural Science
Foundation of China (21571149), the Program for Chongqing Excellent Talents in University, the Fundamental Research Funds for the
Central Universities (XDJK2013A027, XDJK2016C101), the Open
Foundation of State Key Laboratory of Structural Chemistry
(20160010), and the Open Foundation of Key Laboratory of Synthetic
and Natural Functional Molecule Chemistry of Ministry of Education
(338080045).
References
[1] B. Kesanli, Y. Cui, M. R. Smith, E. W. Bittner, B. C. Bockrath,
W. Lin, Angew. Chem. Int. Ed. 2005, 44, 72.
[2] Y. Q. Tian, Y. M. Zhao, Z. X. Chen, G. N. Zhang, L. H. Weng,
D. Y. Zhao, Chem. Eur. J. 2007, 13, 4146.
[3] J. Seo, N. Jin, H. Chun, Inorg. Chem. 2010, 49, 10833.
[4] N. Kornienko, Y. Zhao, C. S. Kley, C. Zhu, D. Kim, S. Lin, C. J.
Chang, O. M. Yaghi, P. Yang, J. Am. Chem. Soc. 2015, 137,
14129.
[5] L. Xu, G. C. Guo, B. Liu, M. S. Wang, J. S. Huang, Inorg. Chem.
Commun. 2004, 7, 1145.
[6] D. Yuan, D. Zhao, D. Sun, H. C. Zhou, Angew. Chem. Int. Ed.
2010, 49, 5357.
[7] H. Chen, K. Riascos Rodríguez, M. E. Marcano González, A. J.
Hernández Maldonado, Chem. Eng. J. 2016, 283, 806.
[8] L. Wen, X. Wang, H. Shi, K. Lv, C. Wang, RSC Adv. 2016, 6,
1388.
[9] R. Zhong, Z. Xu, W. Bi, S. Han, X. Yu, R. Zou, Inorg. Chim.
Acta 2016, 443, 299.
[10] L. Ma, C. Abney, W. Lin, Chem. Soc. Rev. 2009, 38, 1248.
[11] M. Yoon, R. Srirambalaji, K. Kim, Chem. Rev. 2012, 112, 1196.
[12] B. Li, M. Chrzanowski, Y. Zhang, S. Ma, Coord. Chem. Rev.
2016, 307, 106.
[13] A. M. Spokoyny, D. Kim, A. Sumrein, C. A. Mirkin, Chem. Soc.
Rev. 2009, 38, 1218.
[14] P. Horcajada, R. Gref, T. Baati, P. K. Allan, G. Maurin, P. Couvreur, G. Férey, R. E. Morris, C. Serre, Chem. Rev. 2012, 112, 1232.
[15] S. Tai, W. Zhang, J. Zhang, G. Luo, Y. Jia, M. Deng, Y. Ling,
Microporous Mesoporous Mater. 2016, 220, 148.
Z. Anorg. Allg. Chem. 2016, 724–729
[16] M. D. Allendorf, C. A. Bauer, R. K. Bhakta, R. J. T. Houk, Chem.
Soc. Rev. 2009, 38, 1330.
[17] J. Rocha, L. D. Carlos, F. A. A. Paz, D. Ananias, Chem. Soc. Rev.
2011, 40, 926.
[18] L. E. Kreno, K. Leong, O. K. Farha, M. Allendorf, R. P.
Van Duyne, J. T. Hupp, Chem. Rev. 2012, 112, 1105.
[19] C. Rovira, J. Veciana, CrystEngComm 2009, 11, 2031.
[20] J. S. Miller, D. Gatteschi, Chem. Soc. Rev. 2011, 40, 3065.
[21] Y. Tian, S. Shen, J. Cong, L. Yan, S. Wang, Y. Sun, J. Am. Chem.
Soc. 2016, 138, 782.
[22] O. Sato, J. Tao, Y. Z. Zhang, Angew. Chem. Int. Ed. 2007, 46,
2152.
[23] C. Wang, T. Zhang, W. Lin, Chem. Rev. 2012, 112, 1084.
[24] M. Munakata, L. P. Wu, T. Kuroda Sowa, M. Maekawa, K. Moriwaki, S. Kitagawa, Inorg. Chem. 1997, 36, 5416.
[25] F. F. Li, J. F. Ma, S. Y. Song, J. Yang, Y. Y. Liu, Z. M. Su, Inorg.
Chem. 2005, 44, 9374.
[26] M. Du, Z. H. Zhang, L. F. Tang, X. G. Wang, X. J. Zhao, S. R.
Batten, Chem. Eur. J. 2007, 13, 2578.
[27] G. Yuan, K. Z. Shao, D. Y. Du, X. L. Wang, Z. M. Su, J. F. Ma,
CrystEngComm 2012, 14, 1865.
[28] Y. Chen, J. Yang, X. C. Wang, Y. C. Xu, H. L. Xu, X. S. Zeng,
D. R. Xiao, RSC Adv. 2016, 6, 5729.
[29] M. O’Keeffe, O. M. Yaghi, Chem. Rev. 2012, 112, 675.
[30] J. P. Zhang, Y. B. Zhang, J. B. Lin, X. M. Chen, Chem. Rev. 2012,
112, 1001.
[31] S. L. Wang, F. L. Hu, J. Y. Zhou, Y. Zhou, Q. Huang, J. P. Lang,
Cryst. Growth Des. 2015, 15, 4087.
[32] T. Cao, Y. Peng, T. Liu, S. Wang, J. Dou, Y. Li, C. Zhou, D. Li,
J. Bai, CrystEngComm 2014, 16, 10658.
[33] Y. C. Xu, Y. Chen, X. Li, Q. Yang, J. L. Zhang, H. L. Xu, X. S.
Zeng, X. C. Wang, D. R. Xiao, Inorg. Chem. Commun. 2015, 61,
64.
[34] X. Guo, Y. Yan, H. Guo, N. Wang, Y. Qi, Inorg. Chem. Commun.
2016, 64, 59.
[35] X. Wang, S. W. Yan, J. Yang, D. R. Xiao, H. Y. Zhang, J. L.
Zhang, X. L. Chi, E. B. Wang, Inorg. Chim. Acta 2014, 409, 208.
[36] X. L. Wang, C. Qin, E. B. Wang, L. Xu, Z. M. Su, C. W. Hu,
Angew. Chem. Int. Ed. 2004, 43, 5036.
[37] O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H.
Puschmann, J. Appl. Crystallogr. 2009, 42, 339.
[38] G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112.
[39] L. Palatinus, G. Chapuis, J. Appl. Crystallogr. 2007, 40, 786.
[40] L. Palatinus, A. van der Lee, J. Appl. Crystallogr. 2008, 41, 975.
[41] L. Palatinus, S. J. Prathapa, S. van Smaalen, J. Appl. Crystallogr.
2012, 45, 575.
[42] G. M. Sheldrick, Acta Crystallogr., Sect. C 2015, 72, 3.
[43] T. P. Hu, Y. Q. Zhao, Z. Jaglicic, K. Yu, X. P. Wang, D. Sun,
Inorg. Chem. 2015, 54, 7415.
[44] H. Zhou, G. X. Liu, X. F. Wang, Y. Wang, CrystEngComm 2013,
15, 1377.
[45] J. Guo, J. Yang, Y. Y. Liu, J. F. Ma, CrystEngComm 2012, 14,
6609.
Received: April 6, 2016
Published Online: June 8, 2016
729
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim