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carbazole, J 8.4 Hz), 7.62 d (4Н, 2Ph, J 7.8 Hz), 7.69 d
REFERENCES
(
2Н, carbazole, J 8.4 Hz), 8.32 s (2Н, carbazole). Mass
+
1
. Burroughes, J.H., Bradley, D.D.C., Brown, A.R.,
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spectrum, m/z (I , %): 572.45 (100) [М] , 572.45
rel
+
+
(
(
46.29) [М + H] , 429.1 (4.26) [М – H] , 377.05
10.24), 361.15 (30.30), 360.15 (96.78), 347.1 (11.32),
2
3
46.1 (12.95), 344.1 (17.27), 331.05 (11.10), 254
(
(
5
11.05), 253 (38.41), 251.05 (36.06), 208 (15.58), 207
16.80), 204.9 (10.42), 158.1 (29.08), 96 (17.57),
4.95 (13.04), 43.05 (35.60), 41.05 (11.10). UV
3
absorption and fluorescence spectral features are given
in the table.
3
,6-Di(4-bromomethylphenyl)-9-hexadecyl-9Н-
4
carbazole (IV). A mixture of 10.9 g (0.02 mol) of
compound III and catalytic amount of benzoyl
peroxide in 60 mL of CCl was stirred during 30 min.
4
Then 7.1 g (0.04 mol) of NBS was added in portions,
and the mixture was refluxed during 5 h. The solvent
was then distilled off, and the residue was purified by
column chromatography (silica gel, hexane–CH Cl ,
6
2
2
2
010, vol. 223.
2
: 1, as eluent, chloranil in benzene as developer).
1
7. Cho, M.J., Kim, J.Y., Kim, J.H., Lee, S.H., Dalton, L.R.,
and Choi, D.H., Bull. Korean Chem. Soc., 2005, vol. 26,
p. 77.
. Boudreault, P-L.T., Beaupr, S., and Leclerc, M., Polym.
Chem., 2010, vol. 1, p. 127.
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Chem. Asian J., 2012, vol. 7, p. 343.
0. Moonsin, P., Prachumrak, N., Namuangruk, S., Jun-
gsuttiwong, S., Keawin, T., Sudyoadsuka, T., and
Promarak, V., Chem. Commun., 2013, vol. 49, p. 6388.
Yield 15%, pale-yellow amorphous substance.
H
NMR spectrum (CDCl ), δ, ppm: 0.86 t (3Н, СН ,
3
3
J 5.3 Hz), 1.24 m (26Н, 13СН ), 1.90 m (2Н,
2
8
СН СН N), 4.32 t (2Н, CH N, J 6.9 Hz), 4.57 s (3Н,
2
2
2
СН ), 7.28 d (4Н, 2Ph, J 8.1 Hz), 7.46 d (2Н,
3
9
carbazole, J 8.4 Hz), 7.62 d (4Н, 2Ph, J 7.8 Hz), 7.69 d
(
2Н, carbazole, J 8.4 Hz), 8.32 s (2Н, carbazole). UV
1
absorption and fluorescence spectral features are given
in the table.
1
1
1. Iraqi, A. and Wataru, I., J. Polymer Sci. (A), 2004,
Poly(9-hexadecyl-3-phenyl-6-(4-vinylphenyl)-9H-
carbazole (V). A slurry of 0.19 g (0.64 mmol) of
compound IV and 1.12 g (0.01 mol) of t-BuOK in
vol. 42, p. 6041.
2. Khanasa, T., Prachumrak, N., Rattanawan, R., Jung-
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4
0 mL of anhydrous THF was stirred during 12 h at
room temperature. Pale-yellow precipitate was formed
immediately after mixing. After stirring, the solvent
was distilled off, the residue was washed with water,
dried, and treated with methanol. The product was
viscous yellow oil, soluble in CHCl , CH Cl , acetone,
1
1
1
1
3. Lei, Y., Nui, Q., Hongu, Yongli, W., Narulla, I., and
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3
2
2
5. Luo, J., Yang, C., Zheng, J., Ma, J., Liang, L., and Lu, M.,
hexane, benzene, toluene, DMF, and DMSO; poorly
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soluble in ethanol; insoluble in methanol and aceto-
6. Doskocz, J., Doskocz, M., Roszak, S., Soloducho, J.,
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p. 13989.
–
1
nitrile. IR spectrum (CНCl ), ν, cm : 852, 872, 887,
3
9
1
1
64, 1012, 1027 (sh.), 1053, 1073 (sh.), 1113, 1150,
289, 1312, 1351, 1378, 1481, 1470 (sh.), 1517, 1544,
599, 1627, 1649, 1689. UV absorption and fluore-
1
1
7. Aizawa, N., Pu, Y-J., Sasabe, H., and Kido, J., Org.
Electronic., 2012, vol. 13, p. 2235.
scence spectral features are given in the table.
8. Zhang, C., Seggern, H., Pakbaz, K., Kraabel, B.,
Schmidt, H.-W., and Heeger, A.J., Synth. Met., 1994,
vol. 62, p. 35.
9. Zhang, Z.G., Yang, Y., Zhang, S., Min, J., Zhang, J.,.
Zhang, M, Guo, X., and Li, Y., Synth. Met., 2011,
vol. 161, p. 1383.
ACKNOWLEDGMENTS
This work was financially supported by the
Ministry of Education and Science of the Russian
Federation (project no. 3.3304.2011).
1
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 7 2014