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Journal of Materials Chemistry C
Page 8 of 10
ARTICLE
Journal Name
Anal. calcd (%) for C13H11NO: C, 79.17; H, 5.62; N, 7.10. Found: C, stirred for 3 h and then cooled to 0 °C. 4-VinylbenzylVciehwloArritidcele O(0n.l7in6e
79.17; H, 5.62; N, 7.07.
mL, 5.4 mmoL) was added drop-wise. ThDeOrIe:a1c0t.1io0n39/mCi6xTtCur0e26w34aFs
stirred for 24 h at 60 °C and then quenched with water. The aqueous
layer was extracted with CH2Cl2. The combined organic layers were
Preparation
of
bis[4-(3-methoxycarbazole)phenyl]sulfone
(MOC-DPS)
To a stirred solution of 3-Methoxy-9H-carbazole (1.5 g, 7.6 washed with brine, dried with MgSO4 and concentrated in vacuo.
mmol) in dehydrated dimethylformamide (DMF) at room The crude material was purified using column chromatography to
temperature was added sodium hydride (0.4 g, 16 mmoL). After the produce a white solid (0.44 g, 32%). 1H NMR (300 MHz, CDCl3, δ):
solution was stirred at room temperature for 30 min, bis(p- 5.18 (s, 4H), 5.24-5.29 (t, 2H), 7.74 (d, J= 10.8 Hz, 2H), 6.70-6.76
fluorophenyl)sulfone (0.75 g, 3.0 mmol) in dehydrated DMF (15 (m, 2H), 7.10 (d, J= 6.6 Hz, 2H), 7.28-7.31 (t, 2H), 7.39-7.47 (m,
mL) was added, following which the mixture was stirred at 100 °C 4H), 7.67 (s, 2H), 7.79 (d, J= 5.1 Hz, 4H), 8.05 (d, J= 4.5 Hz, 2H),
for an additional 1 h. After cooling, the mixture was poured into 300 8.23 (d, J= 5.1 Hz, 4H); 13C NMR (300 MHz, CDCl3, δ): 70.89,
mL of water, and the yellow precipitate was filtered and dried. The 76.73, 76.98, 77.23, 105.16, 109.72, 110.43, 114.05, 115.95, 120.53,
crude product was isolated by silica gel column chromatography 120.72, 123.95, 124.71, 126.43, 126.84, 134.99, 136.46, 136.74,
using petroleum ether/ethyl acetate as eluent to produce pale green 137.37, 140.41, 142.94, 154.09; MS (MALDI-TOF) [m/z]:
solid (1.56 g, 86%).1H NMR (300 MHz, DMSO-d6, δ ): 3.88 (s, 6H), C54H40N2O4S: 812.98, found: 812.82. Anal. calcd (%) for
7.01 (d, J= 10.5 Hz, 2H), 7.26-7.31 (t, 2H), 7.37-7.45 (m, 4H), 7.49 C54H40N2O4S: C, 79.78; H, 4.96; N, 3.45. Found: C, 79.76; H, 4.96;
(d, J= 8.4 Hz, 2H), 7.82 (s, 2H), 7.92 (d, J= 9 Hz, 4H), 8.26 (d, J= N, 3.44.
7.8 Hz, 2H), 8.34 (d, J= 8.1 Hz, 4H); 13C NMR (300 MHz, DMSO-
Acknowledgements
d6, δ): 56.15, 104.07, 110.36, 111.20, 115.61, 121.24, 123.85,
126.94, 130.14, 134.41, 138.93, 140.11, 142.49, 155.07; MS
(MALDI-TOF) [m/z]: C38H28N2O4S: 608.71, found: 608.01. Anal.
calcd (%) for C38H28N2O4S: C, 74.98; H, 4.64; N, 4.60. Found: C,
74.95; H, 4.64; N, 4.60.
We are grateful for the grants from the National Natural Science
Foundation of China (51103023 and 21173042), National Basic
Research Program China (2013CB932902). We are also thankful for
the support of the Scientific Research Foundation of Graduate
School of Southeast University (NO. YBJJ1631).
Preparation of bis[4-(carbazole-3-ol)phenyl]sulfone (5)
Notes and references
To a stirred solution of bis[4-(3-methoxycarbazole)phenyl]sulfone
(1 g, 1.6 mmol) in dehydrated dichloromethane at 0 °C was added
BBr3 (0.9 g, 3.6 mmoL). After the addition was completed the
mixture was stirred for 24 h. The reaction was quenched by methyl
alcohol. The solution was evaporated in vacuo. The crude product
was further purified using column chromatography to produce pale
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green solid (0.88 g, 92%). H NMR (300 MHz, DMSO-d6, δ): 6.93
(d, J= 8.7 Hz, 2H), 7.24-7.29 (t, 2H), 7.37-7.41 (t, 4H), 7.51-7.56
(m, 4H), 7.93-7.96 (d, J= 8.4 Hz, 4H), 8.12-8.15 (d, J= 7.8 Hz, 2H),
8.29 (d, J= 8.7 Hz, 4H), 9.33 (s, 2H); 13C NMR (300 MHz, DMSO-
d6, δ): 105.87, 110.28, 111.03, 115.88, 120.89, 121.07,
123.78,126.80, 127.14, 130.09, 133.59, 138.72, 140.06, 142.69,
152.82; MS (MALDI-TOF) [m/z]: C36H24N2O4S: 580.66, found:
580.50. Anal. calcd (%) for C36H24N2O4S: C, 74.47; H, 4.17; N,
4.82. Found: C, 74.47; H, 4.15; N, 4.81.
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Preparation of bis[3-((4-vinylbenzyl)oxy)-9H-carbazole]sulfone
(DV-MOC-DPS)
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To a solution of bis[4-(carbazole-3-ol)phenyl]sulfone (1.00 g, 1.80
mmol) in DMF (30 mL) was added NaH (0.13 g, 5.4 mmol) at room
temperature under a nitrogen atmosphere. The reaction mixture was
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8 | J. Name., 2012, 00, 1-3
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