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All reagents and solvents were obtained from Aldrich, Acros or
the Energy Chemical Co. and the solvents were treated as
required prior to use. Commercially available reagents were used
without further purification unless otherwise stated. All reactions
were performed under a nitrogen atmosphere. The important
intermediates, including 4-(9-carbazolyl)-1-phenylboronic acid,
4-[9-(3,6-(di-tert-butyl)carbazolyl)]-1-phenylboronic acid,32 1,4-
diiododurene31 and the reference compound CDBP,23 were
synthesized and characterized according to the literature
methods.
€
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General procedure for the preparation of 1,4-bis-[4-(9-carba-
zolyl)-phenyl]-durene (CPD) and 1,4-bis-{4-[9-(3,6-(di-tert-
butyl)carbazoyl)]-phenyl}-durene (t-BuCPD):
a mixture of
1,4-diiododurene (385.9 mg, 1 mmol), 4-(9-carbazolyl)-1-phe-
nylboronic acid or 4-[9-(3,6-(di-tert-butyl)carbazolyl)]-1-phenyl-
boronic acid (2.5 mmol), tetrakis(triphenylphosphine)
palladium(0) (69.3 mg, 0.06 mmol), 2 M potassium carbonate
(2 mL), toluene (20 mL) and ethanol (4 mL) was stirred under an
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ꢁ
atmosphere of nitrogen at 80 C for 6 h. After cooling to room
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temperature, the reaction mixture was poured into cool water
and extracted with dichloromethane (3 ꢂ 50 mL). The combined
organic layers were dried over anhydrous sodium sulfate, filtered
and evaporated to dryness. The crude product was then
purified by silica gel column chromatography with light petro-
leum : dichloromethane ¼ 10 : 1 as an eluent to afford the pure
product as a white solid.
1
CPD: Yield 85%. H NMR (400 MHz, CDCl3) d (ppm): 2.13
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(s, 12H, CH3), 7.31–7.35(t, 4H, Ar), 7.45–7.49 (t, 8H, Ar), 7.54–
7.56 (d, 4H, Ar), 7.66–7.68 (d, 4H, Ar), 8.18–8.20 (d, 4H, Ar). 13
C
NMR (100 MHz, CDCl3): 142.0, 141.0, 140.7, 136.0, 132.2,
130.9, 127.0, 125.9, 123.4, 120.3, 119.9, 109.8, 18.37. MALDI-
TOF-MS (m/z): 616.1 [M]+. Anal. Calcd. For C46H36N2: C,
89.58; H, 5.88; N, 4.54%. Found: C, 89.46; H, 5.92; N, 4.58%.
A.
Matoliukstyte,
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Simokaitiene,
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1
t-BuCPD: Yield 80%. H NMR (400 MHz, CDCl3) d (ppm):
1.49 (s, 36H, CH3), 2.11 (s, 12H, CH3), 7.41–7.43(d, 4H, Ar),
7.48–7.53 (m, 8H, Ar), 7.64–7.66 (d, 4H, Ar), 8.18 (s, 4H, Ar).
13C NMR (100 MHz, CDCl3): 142.8, 141.4, 140.7, 139.2, 136.4,
132.1, 130.8, 126.5, 123.6, 123.3, 116.2, 109.3, 34.7, 32.0, 18.3.
MALDI-TOF-MS (m/z): 840.5 [M]+. Anal. Calcd. For
C62H68N2: C, 88.52; H, 8.15; N, 3.33%. Found: C, 88.47; H, 8.20;
N, 3.39%.
€
€
24 P. Schrogel, A. Tomkeviciene, P. Strohriegl, S. T. Hoffmann, Anna
€
Kohler and C. Lennartz, J. Mater. Chem., 2011, 21, 2266.
€
25 S. T. Hoffmann, P. Schrogel, M. Rothmann, R. Q. Albuquerque,
€
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26 D. R. Whang, Y. You, S. H. Kim, W.-I. Jeong, Y.-S. Park, J.-J. Kim
and S. Y. Park, Appl. Phys. Lett., 2007, 91, 233501.
Acknowledgements
27 J. He, H. Liu, Y. Dai, X. Ou, J. Wang, S. Tao, X. Zhang, P. Wang and
D. Ma, J. Phys. Chem. C, 2009, 113, 6761.
28 D. Hu, P. Lu, C. Wang, H. Liu, H. Wang, Z. Wang, T. Fei, X. Gu and
Y. Ma, J. Mater. Chem., 2009, 19, 6143.
29 S. Gong, X. He, Y. Chen, Z. Jiang, C. Zhong, D. Ma, J. Qin and
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30 Y. Liu, X. Xu, F. Zheng and Y. Cui, Angew. Chem., Int. Ed., 2008, 47,
4538.
We thank the National Natural Science Foundation of China
(21072026 and 20923006), the Ministry of Education for the New
Century Excellent Talents in University (Grant NCET-08-0074),
the NKBRSF (2009CB220009) and the Fundamental Research
Funds for the Central Universities (DUT12ZD211) for the
financial support of this work.
31 M. S. Yusubov, T. V. Funk, K.-W. Chi, E.-H. Cha, G. H. Kim,
A. Kirschning and V. V. Zhdankin, J. Org. Chem., 2008, 73, 295.
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