DOI: 10.1039/C3TC31633E
Page 5 of 6
Journal of Materials Chemistry C
c
4H), 0.47 (s, 6H). 13C NMR (100 MHz, CDCl3), (TMS, ppm):
Guangdong Innovative Research Team, SCUT-HKUST Joint Research
60 Laboratory, State Key Laboratory of Luminescent Materials and Devices,
South China University of Technology (SCUT), Guangzhou 510640,
China
154.3, 141.3, 139.9, 138.5, 132.4, 129.9, 129.1, 127.9, 127.5,
126.3, 54.6, 3.9. HRMS (MALDI-TOF): m/z 524.2200 (M+,
calcd 524.2145).
d HKUST Shenzhen Research Institute, Nanshan, Shenzhen 518057, China
5
65 † Electronic Supplementary Information (ESI) available: 1H and 13C
NMR spectra of 1 (Fig. S1 and S2), MS and Particle size distribution of 1
(Fig. S3 and S4), UV and CD spectra of 1 in the absence and presence of
chiral hydroxy acids (Fig. S57). TEM and powder XRD of 1, pure R-()-
mandelic acid, S-(+)-mandelic acid and the corresponding complexes
70 (Fig. S7S9).
Preparation
of
1,1-dimethyl-2,5-bis[4-
(isothiocyanatomethyl)phenyl]-3,4-diphenylsilole (7).28
To a solution of 6 (131 mg, 0.25 mmol) and CS2 (0.24 ml, 4.0
mmol) in CHCl3 (1.0 ml) was added PPh3 (131.1 mg, 0.5 mmol)
10 at room temperature. The mixture was stirred for 1.5 h. After
solvent evaporation under reduced pressure, the crude product
was purified by a silica-gel column using ethyl acetate/hexane
(1:10 v/v) as eluent. The product was obtained as a yellow solid
in 58.6% yield. 1H NMR (400 MHz, CDCl3), δ (TMS, ppm): 7.04
15 (d, J = 6.4 Hz, 4H, Ar), 7.00 (m, 6H, Ar), 6.93 (d, J = 8.4Hz, 4H,
Ar), 6.79 (m, 4H, Ar), 4.62 (s, 4H, CH2), 0.47 (s, 6H, CH3). 13C
NMR (100 MHz, CDCl3), δ (TMS, ppm): 154.5, 141.2, 139.9,
138.4, 131.2, 129.9, 129.2, 127.5, 126.5, 126.4, 48.4, −3.9.
HRMS (MALDI-TOF): m/z 556.1462 (M+, calcd 556.1463).
1
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Muller, D. K. Shuh, J. K. Gibson, and K. N. Raymond, J. Am.
Chem. Soc., 2012, 134, 15545−15549
75
80
2
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4
20 Preparation of 1
Into a Schlenk tube equipped with a magnetic stirrer were added
0.14 g (0.25 mmol) of 7 and 0.73ml (0.553 mmol) of 8 in 6 mL of
distilled THF protected under nitrogen, the setup was stirred at
room temperature for 30 hours. After solvent evaporation under
25 reduced pressure, the residue was purified by a silica-gel column
using gradient DCM/hexane (80/20 to 100/0, v/v) mixture as
eluent. A yellow solid was obtained in 97.6% yield. 1H NMR
5
6
7
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85
(400 MHz, MeOD),
δ (TMS, ppm): 7.297.27 (m, 4H),
90
8
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7.227.18 (m, 1H), 7.026.88 (m, 5H), 6.856.83 (d, 2H),
30 6.786.76 (m, 2H), 5.48 (s, 1H), 4.46 (s, 1H), 4.504.47 (d, 1H),
1.461.44 (d, 3H), 0.40 (t, 3H). 13C NMR (100 MHz, MeOD),
(TMS, ppm): 183.1, 155.8, 145.3, 142.9, 140.6, 140.2, 137.4,
131.4, 130.3, 129.9, 128.9, 128.4, 127.7, 127.5, 54.7, 31.5, 23.1,
3.50. HRMS (MALDI-TOF): m/z 798.32 (M+, calcd 798.32).
35 The optical rotation of 1 in THF at room temperature is 51.9o
(concentration of 1: 0.4 g/L).
95
100
105
110
115
120
125
Thin Film Preparation
9
The thin films for CD and CPL measurement were prepared by
dissolving 1 and enantiopure chiral acid (1:40 molar ratio) in
40 THF. The solution was casted on a quartz plate and solvent was
then naturally evaporated.
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Acknowledgments
This work was partially supported by the National Basic
45 Research Program of China (973 Program; 2013CB834701),
Research Grants Council of Hong Kong (HKUST2/CRF/10 and
N_HKUST620/11), and the University Grants Committee of
Hong Kong (AoE/P-03/08). B.Z.T. thanks the support from
Guangdong Innovative Research Team Program of China
50 (201101C0105067115).
Notes and references
a
Department of Chemistry, Institute for Advanced Study, Institute of
Molecular Functional Materials, and Division of Biomedical
Engineering, The Hong Kong University of Science & Technology
55 (HKUST), Clear Water Bay, Kowloon, Hong Kong, China. Email:
b
Department of Physics, HKUST, Clear Water Bay, Kowloon, Hong