Supporting Information
Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013
Energy-Transfer Properties of a [2.2]Paracyclophane-Based
Through-Space Dimer
Yasuhiro Morisaki,* Naoya Kawakami, Tatsuya Nakano, and Yoshiki Chujo*[a]
chem_201303108_sm_miscellaneous_information.pdf
Supporting information
Energy Transfer Property of the [2.2]Paracyclophane-based Through-space Dimer
Yasuhiro Morisaki,* Naoya Kawakami, Tatsuya Nakano, and Yoshiki Chujo*
Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University
Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
E-mail: [email protected] or [email protected]
Contents
General and Materials
Synthetic Procedures and NMR spectra
Compound 3
Compound 4
Compound 5
Compound D1
Compound M2
Optical Properties
Compound M1
Compound M2
Compound D1
Compound D1 vs mixture of M1 and M2
DFT and TD-DFT calculation for M1, M2, and D1
Data of Energy Transfer in D1
References
S–1
page
S–2
S–3
S–4
S–7
S–10
S–13
S–16
S–19
S–19
S–20
S–21
S–23
S–24
S–26
S–27
General
1
H and 13C NMR spectra were recorded on a JEOL JNM-EX400 instrument at 400 and 100 MHz,
respectively. The chemical shift values were expressed relative to Me4Si as an internal standard.
High-resolution mass spectra (HRMS) were obtained on a JEOL JMS-MS700 spectrometer for
electron ionization (EI), a Thermo Fisher Scientific EXACTIVE spectrometer for atmospheric
pressure chemical ionization (APCI), and a Thermo Fisher Scientific orbitrapXL spectrometer for
matrix assisted laser desorption/ionization (MALDI).
Analytical thin-layer chromatography
(TLC) was performed with silica gel 60 Merck F254 plates.
performed with Wakogel C-300 silica gel.
Column chromatography was
Recyclable preparative high-performance liquid
chromatography (HPLC) was performed on a Japan Analytical Industry LC-918R (JAIGEL-1H and
2H columns) using CHCl3 as an eluent.
SHIMADZU UV3600 spectrophotometer.
UV-vis absorption spectra were obtained on a
Photoluminescence spectra were obtained on a Perkin-
Elmer LS50B luminescence spectrometer or a Horiba FluoroMax-4 luminescence spectrometer.
Fluorescence lifetime measurement was performed on a Horiba FluoreCube spectrofluorometer
system; excitation was carried out using a UV diode laser (NanoLED 375 nm).
Elemental
analyses were performed at the Microanalytical Center of Kyoto University.
Materials
THF and Et3N were purchased and purified by passage through purification column under Ar
pressure.1 Pd2(dba)3, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (X-Phos), PPh3, CuI,
FNBu4 (1.0 M in THF), 2-ethynyl-1,4-dimethylbenzene (7) were obtained commercially, and used
without further purification.
Compounds 1,2 2,2 6,3 and M14 were prepared as described in the
literature. All reactions were performed under Ar atmosphere.
S–2
Synthetic Procedures
Scheme S1.
Synthetic outlines of new compounds 3, 4, 5, D1 and M2.
S–3
Synthesis of Compound 3
The mixture of 1 (212 mg, 0.324 mmol), 2 (97.4 mg, 0.270 mmol), Pd2(dba)3 (6.18 mg, 6.76
mmol), X-Phos (12.8 mg, 0.027 mmol), and CuI (2.57 mg, 0.0135 mmol) were placed in a 50 mL
flask.
To this mixture THF (10 mL) and Et3N (6 mL) were added.
The reaction was carried out
at 70 °C for 44 h. After the reaction mixture was cooled to room temperature, 28% aqueous NH3
was added.
The organic layer was extracted three times with CHCl3 and washed with brine.
combined organic layer was dried over Mg2SO4.
The
After Mg2SO4 was removed, solvent was dried
in vacuo. The residue was purified by SiO2 column chromatography (eluent: hexane/CHCl3 = 3/1
v/v).
Solvent was evaporated, and the solid was recrystallized from CHCl3 and MeOH to obtain 3
(227.5 mg, 0.23 mmol, 85%) as a yellow solid.
Rf = 0.18 (hexane/CHCl3 = 3/1 v/v).
1
H NMR (CD2Cl2, 400 MHz)
0.86-0.89 (m, 6H), 1.15-
1.75 (m, 57H), 1.80-2.00 (m, 4H), 2.32 (s, 3H), 2.51 (s, 3H), 2.80-3.10 (m, 4H), 3.15-3.35 (m, 2H),
3.58-3.82 (m, 2H), 4.00-4.15 (m, 4H), 6.47 (d, J = 1.9 Hz, 1H), 6.49 (d, J =1.9, 1H), 6.56 (d, J = 1.9,
1H), 6.57 (d, J = 1.9, 1H), 7.00-7.10 (m, 5H), 7.34 (s, 1H) ppm.
13
C NMR (CD2Cl2, 100 MHz) δ
12.0, 14.0, 19.1, 19.1, 20.5, 21.0, 23.2, 26.7, 26.7, 29.8, 30.0, 30.0, 30.0, 30.1, 30.2, 32.4, 34.1, 34.4,
34.5, 69.9, 70.0, 89.9, 90.0, 94.0, 94.3, 95.4, 107.8, 114.2, 114.4, 116.5, 116.8, 123.3, 125.3, 129.6,
129.7, 130.5, 130.9, 132.4, 133.4, 133.5, 135.5, 137.5, 137.5, 138.2, 138.2, 139.9, 140.1, 142.7,
153.8, 153.9 ppm.
HRMS (APCI) calcd. for C69H97O2Si [M+H]+: 985.7252, found 985.7260.
Anal. calcd. for C69H96O2Si: C 84.09 H 9.82, found: C 84.08 H 9.89.
S–4
Figure S1.
1
H NMR spectrum of 3, 400 MHz, CD2Cl2.
S–5
Figure S2.
13
C NMR spectrum of 3, 100 MHz, CD2Cl2.
S–6
Synthesis of Compound 4
FNBu4 (1.0 M in hexane, 0.46 mL, 0.46 mmol) was added to the THF solution of 3 (228 mg,
0.231 mmol, THF 10 mL) at room temperature. The solution was stirred for 10 min, and H2O was
added to reaction mixture.
The organic layer was extracted three times with CHCl3 and washed
with brine. The organic layer was dried over Mg2SO4.
dried in vacuo.
After Mg2SO4 was removed, solvent was
The residue was purified by SiO2 column chromatography (eluent: hexane/CHCl3
= 2/1 v/v) and HPLC to obtain 4 (170 mg, 0.205 mmol, 89%) as a right green solid.
Rf = 0.33 (hexane/CHCl3 = 2/1 v/v).
1
H NMR (CD2Cl2, 400 MHz) δ 0.88 (m, 6H), 1.10-1.70
(m, 36H), 1.80-2.00 (m, 4H), 2.33 (s, 3H), 2.52 (s, 3H), 2.80-3.10 (m, 4H), 3.15-3.3.35 (m, 3H),
3.60 (m, 1H), 3.75 (m, 1H), 4.00-4.20 (m, 4H), 6.40-6.55 (m, 4H), 6.59 (s, 2H), 6.98-7.20 (m, 6H),
7.34 (s, 1H) ppm.
13
C NMR (CD2Cl2, 100 MHz) δ 14.4, 20.5, 21.0, 23.2, 26.7, 26.7, 29.8, 30.0,
30.0, 30.1, 30.1, 30.1, 30.2, 32.4, 34.2, 34.2, 34.5, 69.9, 70.0, 80.6, 84.2, 90.0, 90.0, 94.4, 95.4,
114.3, 114.4, 116.5, 116.9, 123.3, 123.9, 125.3, 129.6, 129.7, 130.5, 131.3, 132.5, 133.5, 133.6,
135.5, 137.4, 137.5, 138.1, 140.0, 140.2, 142.7, 143.0, 153.8, 154.0 ppm. HRMS (APCI) calcd.
For C60H77O2 [M+H]+: 829.5918, found 829.5901.
found: C 86.87 H 9.48.
S–7
Anal. calcd. for C60H76O2: C 86.90 H 9.24,
Figure S3.
1
H NMR spectrum of 4, 400 MHz, CD2Cl2.
S–8
Figure S4.
13
C NMR spectrum of 4, 100 MHz, CD2Cl2.
S–9
Synthesis of Compound 5
The mixture of 6 (147 mg, 0.431 mmol), PdCl2(PPh3)2 (14.6 mg, 0.0208 mmol), PPh3 (10.9 mg,
0.0416 mmol), and CuI (3.9 mg, 0.0205 mmol) were placed in a 50 mL flask.
This flask was
purged with Ar, and THF (10 mL), Et3N (6 mL), and 7 (64.7 mg, 0.497 mmol) were added.
reaction was carried out at 50 °C for 35 h.
The
After reaction mixture was cooled to room temperature,
28% aqueous NH3 was added to the reaction mixture.
The organic layer was extracted three times
with CHCl3 and washed with brine. The organic layer was dried over Mg2SO4.
was removed, solvent was dried in vacuo.
After Mg2SO4
The residue was purified by SiO2 column
chromatography (eluent: hexane/CHCl3 = 3/1 v/v) and HPLC (eluent: CHCl3) to obtain 5 (108 mg,
0.315 mmol, 73%) as a yellow solid.
Rf = 0.20 (hexane/CHCl3 = 3/1 v/v).
1
H NMR (CD2Cl2, 400 MHz) δ 2.33 (s, 3H), 2.56 (s, 3H),
7.12 (d, J = 7.8, 1H), 7.17 (, J = 7.8, 1H), 7.41 (s, 1H), 7.65 (d, J = 7.8, 1H), 7.84 (d, J = 7.6, 1H)
ppm.
13
C NMR (CD2Cl2, 100 MHz) δ 20.4, 20.9, 88.6, 96.4, 114.7, 117.4, 122.3, 130.0, 130.5,
132.4, 132.8, 135.8, 138.2, 153.6, 154.2 ppm.
found 341.9831.
HRMS (EI) calcd. for C16H11N2BrS [M]+: 341.9826,
Anal. calcd. for C69H96BrN2S: C 55.99 H 3.23 N 8.16, found: C 55.85 H 3.17 N
7.99.
S–10
Figure S5.
1
H NMR spectrum of 5, 400 MHz, CD2Cl2.
S–11
Figure S6.
13
C NMR spectrum of 5, 100 MHz, CD2Cl2.
S–12
Synthesis of Compound D1
The mixture of 4 (170 mg, 0.205 mmol), 5 (84.5 mg, 0.246 mmol), Pd2(dba)3 (4.70 mg, 5.13
mol), X-Phos (9.78 mg, 2.05
mol), and CuI (2.00 mg, 1.03
mol) were placed in 50 mL flask.
This flask was purged with Ar, and THF (8 mL) and Et3N (2 mL) were added. The reaction was
carried out at 70 °C for 52 h.
After the reaction mixture was cooled to room temperature, 28%
aqueous NH3 was added. The organic layer was extracted three times with CHCl3 and washed
with brine. The organic layer was dried over Mg2SO4.
dried in vacuo.
After Mg2SO4 was removed, solvent was
The residue was purified by SiO2 column chromatography (eluent: hexane/CHCl3
= 3/2 v/v) and HPLC (eluent: CHCl3).
The solvent was removed in vacuo, and the solid was
recrystallized from CHCl3 and MeOH to obtain D1 (168 mg, 0.154 mmol, 75%) as a yellow solid.
Rf = 0.22 (hexane/CHCl3 = 3/2 v/v).
1
H NMR (CD2Cl2, 400 MHz) δ 0.80-0.9.5 (m, 6H), 1.15-
1.65 (m, 36H), 1.80-2.00 (m, 4H), 2.37 (s, 3H), 2.39 (s, 3H), 2.56 (s, 3H), 2.65 (s, 3H), 2.95-3.20
(m, 4H), 3.30-3.55 (m, 2H), 3.80-4.00 (m, 2H), 4.00-4.20 (m, 4H), 6.55-6.80 (m, 4H), 7.10-7.25 (m,
8H), 7.38 (s, 1H), 7.49 (s, 1H), 7.86 (s, 2H) ppm.
13
C NMR (CD2Cl2, 100 MHz) δ 14.3, 20.5, 20.5,
20.9, 20.9, 23.2, 26.6, 26.7, 29.8, 30.0, 30.0, 30.1, 30.1, 32.4, 34.2, 34.3, 34.5, 34.6, 69.8, 70.0, 89.5,
89.6, 90.0, 90.0, 94.4, 95.4, 96.9, 98.3, 116.5, 116.8, 117.5, 117.8, 122.4, 123.2, 124.3, 125.3, 129.6,
129.7, 129.9, 130.4, 130.9, 131.6, 131.9, 132.4, 132.4, 132.7, 133.5, 133.7, 137.5, 137.6, 138.0,
140.1, 140.4, 142.7, 143.4, 153.8, 153.9, 154.9, 155.2 ppm.
C76H86N2O2S1 [M]+: 1090.6405, found 1090.6419.
N 2.57, found: C 83.60 H 7.99 N 2.36.
S–13
HRMS (MALDI) calcd. for
Anal. calcd. for C76H86N2O2S: C 83.62 H 7.94
Figure S7.
1
H NMR spectrum of D1, 400 MHz, CD2Cl2.
S–14
Figure S8.
13
C NMR spectrum of D1, 100 MHz, CD2Cl2.
S–15
Synthesis of Compound M2
The mixture of 6 (112 mg, 0.381 mmol), PdCl2(PPh3)2 (26.8 mg, 0.0381 mmol), PPh3 (24 mg,
0.092 mmol), and CuI (7.3 mg, 0.038 mmol) were placed in 100 mL flask.
This flask was purged
with Ar, and THF (10 mL), Et3N (6 mL), and 7 (0.17 mL, 1.19 mmol) was added.
The reaction
was carried out at 70 °C for 22 h. After the reaction mixture was cooled to room temperature,
28% aqueous NH3 was added. The organic layer was extracted three times with CHCl3 and
washed with brine. The organic layer was dried over Mg2SO4.
solvent was dried in vacuo.
hexane/CHCl3 = 3/1 v/v).
After Mg2SO4 was removed,
The residue was purified by SiO2 column chromatography (eluent:
Solvent was removed in vacuo, and the solid was recrystallized from
CHCl3 and MeOH to obtain M2 (110 mg, 0.280 mmol, 73%) as a yellow solid.
Rf = 0.15 (hexane/CHCl3 = 3/1 v/v).
1
H NMR (CD2Cl2, 400 MHz) δ 2.35 (s, 6H), 2.59 (s, 6H),
7.10-7.30 (m, 4H), 7.44 (s, 2H), 7.79 (s, 2H) ppm.
13
C NMR (CD2Cl2, 100 MHz) δ 20.5, 20.9,
89.5, 97.0, 117.6, 122.5, 130.0, 130.5, 132.4, 132.8, 135.8, 138.2, 155.0 ppm.
calcd. for C26H21N2S [M+H]+: 393.1420, found 393.1413.
5.14 N 7.14, found: C 79.58 H 5.19 N 7.07.
S–16
HRMS (APCI)
Anal. calcd. for C26H20N2S: C 79.56 H
Figure S9.
1
H NMR spectrum of M2, 400 MHz, CD2Cl2.
S–17
Figure S10.
13
C NMR spectrum of M2, 100 MHz, CD2Cl2.
S–18
Optical properties
Compound M1
0.7
5x10
5
4x10
5
3x10
5
2x10
5
1x10
5
–1
–5
ε x 10
0.5
0.4
0.3
Intensity / a.u.
/ M cm
–1
0.6
0.2
0.1
0
0
250
350
450
550
650
750
Wavelength / nm
Figure S11.
UV-vis absorption spectra (in CHCl3, 1.0 × 10–5 M) and photoluminescence spectra
(in CHCl3, 1.0 × 10–6 M, excited at 372 nm) of M1.
1 x 10
5
ΦPL = 0.94
1 x 10
τ = 1.25 ns
4
χ2 = 1.13
Counts
1 x 10
rate constant:
3
radiative kr = 0.75 × 109 s–1
non-radiative knr = 0.048 × 109 s–1
100
10
1
0
1
2
3
4
5
6
7
8
Time / ns
Figure S12.
Fluorescence decay curves at 401 nm and data of M1 in CHCl3 (1.0 × 10–6 M)
S–19
excited at 375 nm with LED laser.
S–20
Compound M2
0.7
5x10
5
4x10
5
3x10
5
2x10
5
1x10
5
–1
–5
ε x 10
0.5
0.4
0.3
Intensity / a.u.
/ M cm
–1
0.6
0.2
0.1
0
0
250
350
450
550
650
750
Wavelength / nm
Figure S13.
UV-vis absorption spectra (in CHCl3, 1.0 × 10–5 M) and photoluminescence spectra
(in CHCl3, 1.0 × 10–6 M, excited at 372 nm) of M2.
1 x 10
5
ΦPL = 0.78
1 x 10
τ = 6.05 ns
4
χ2 = 1.01
Counts
1 x 10
rate constant:
3
radiative kr = 0.13 × 109 s–1
non-radiative knr = 0.036 × 109 s–1
100
10
1
0
1
2
3
4
5
6
7
8
Time / ns
Figure S14.
Fluorescence decay curves at 508 nm and data of M2 in CHCl3 (1.0 × 10–6 M)
excited at 375 nm with LED laser.
S–21
Compound D1
0.7
5x10
5
4x10
5
3x10
5
2x10
5
1x10
5
–1
–5
ε x 10
0.5
0.4
0.3
Intensity / a.u.
/ M cm
–1
0.6
0.2
0.1
0
0
250
350
450
550
650
750
Wavelength / nm
Figure S15. UV-vis absorption spectra (in CHCl3, 1.0 × 10–5 M) and photoluminescence spectra
(in CHCl3, 1.0 × 10–6 M, excited at 372 nm) of D1.
1.2
–5
M
–6
M
–7
M
1.0 x 10
Normalized intensity
1
1.0 x 10
1.0 x 10
0.8
0.6
0.4
0.2
0
400 440 480 520 560 600 640 680 720
Wavelength / nm
Figure S16. Normalized PL spectra of D1 in CHCl3 1.0 × 10–5 M, 1.0 × 10–6 M, and 1.0 × 10–7 M
S–22
excited at 372 nm.
S–23
1 x 10
5
ΦPL = 0.68
1 x 10
τ = 5.67 ns
4
χ2 = 1.16
Counts
1 x 10
rate constant:
3
radiative kr = 0.12 × 109 s–1
non-radiative knr = 0.056 × 109 s–1
100
10
1
0
1
2
3
4
5
6
7
8
Time / ns
Figure S17.
Fluorescence decay curves at 522 nm and data of D1 in CHCl3 (1.0 × 10–6 M) excited
at 375 nm with LED laser.
S–24
(A)
0.7
5x10
5
4x10
5
3x10
5
2x10
5
1x10
5
–1
–5
ε x 10
0.5
0.4
Emission
from the M2 moiety
0.3
Intensity / a.u.
/ M cm
–1
0.6
0.2
0.1
0
0
250
350
450
550
650
750
Wavelength / nm
(B)
Emission
from M1
Emission
from M2
Figure S18. UV-vis absorption (in CHCl3, 1.0 × 10–5 M) and PL spectra (in CHCl3, 1.0 × 10–6 M,
S–25
excited at 372 nm) of (A) D1 and (B) the 1:1 mixture of M1 and M2.
S–26
DFT and TD-DFT calculation
CAM-B3LYP/6-31G*,5 Gaussian09 package6
(A)
(B)
Figure S19. (A) Molecular orbitals (top views) of M1, M2, and D1.
(experiment and simulation) of D1.
S–27
(B) Absorption spectra
Table S1. Oscillator strength (f) and dipole moment of D1
Transition
Coefficient
f
µx
µy
µz
HOMO-1 to LUMO
0.64787
1.2383
4.1338
0.1414
0.3327
HOMO to LUMO+1
0.59474
1.4432
–3.9615
0.6137
–0.4500
HOMO-1 to LUMO+2
0.49019
0.6274
–2.4493
–0.0089
–0.1658
general view
x-z plane
y-z plane
Figure S20. Optimized structure of D1 calculated at CAM-B3LYP/6-31G* level.
S–28
Data of Energy Transfer in D17,8
µx
Dipole moment of the donor moiety (M1)
Dipole moment of the acceptor moiety (M2)
4.1338
-3.9615
µy
0.1414
0.6137
µz
0.3327
-0.4500
x
y
Center of gravity of the donor moiety (M1)
-7.2104
-0.0979
0.4378
Center of gravity of the acceptor moiety (M2)
7.2487
0.1556
-0.4399
Distance between the centers: R / Å
14.4879
µx
DA vector (between centers of gravity)
DA unit vector: RDA
µy
z
µz
14.4591
0.2535
-0.8777
0.99801
0.01750
-0.06058
Orientation factor: κ = (µD·µA)–3(µD·RDA)( µA·RDA) = 1.90071, κ2 = 3.6127
Dipole moment unit vector of the donor: µD
Dipole moment unit vector of the acceptor: µA
Spectral overlap integral:
∫F
J =
D
( λ )ε A ( λ ) λ 4 d λ
∫F
D
(λ ) dλ
= 5.84 × 1014 M–1cm3
Intensity of fluorescence spectrum of the donor: FD(λ)
Molar absorption coefficient of the acceptor: εA(λ)
Förster radius: R0 = 0.879 × 10–5(κ2n–4ΦPL,D)J(λ) = 59.0 Å
Refractive index of CHCl3: n = 1.446
PL quantum efficiency of the donor: ΦPL,D = 0.94
1.6
1.6
1.4
1.4
1.2
1.2
1
1
0.8
0.8
0.6
0.6
0.4
0.4
0.2
0.2
0
250
Normalized intensity
Normalized absorbance
Energy transfer efficiency: ΦET = 1/{1+(R/R0)6} = 0.999
Energy transfer rate: kET = (R0/R)6/τD = 3.64 × 1012 s–1
PL lifetime of the donor: τD =1.25 ns
0
300
350
400
450
500
550
600
Wavelength / nm
Figure S21.
Normalized (at 424 nm) absorption spectrum of M2 (in CHCl3, 1.0 × 10–5 M) and normalized
S–29
PL spectrum (in CHCl3, 1.0 × 10–6 M, excited at 372 nm) of M1.
S–30
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