Abstract
Model compounds of some polychlorobiphenyl congeners, viz., 4,4´-dihalobiphenyls, were synthesized. These compounds can be successfully utilized by a chemical method for the in situ generation of arynes followed by the reaction with carbazole in order to prepare appropriate bis(carbazolyl)biphenyls as components for molecular electronics and OLED devices.
References
T. I. Gorbunova, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Rev., 2010, 79, 511 [Usp. Khim., 2010, 79, 565].
T. I. Gorbunova, M. G. Pervova, O. N. Zabelina, V. I. Saloutin, O. N. Chupakhin, Polikhlorbifenily: Problemy ekologii, analiza i khimicheskoi utilizatsii [Polychlorobiphenyls: Problems of Ecology, Analysis, and Chemical Utilization], KRASAND, UrO RAN, 2011, 400 pp. (in Russian).
L. N. Zanaveskin, V. A. Averyanov, Russ. Chem. Rev., 1998, 67, 713 [Usp. Khim., 1998, 67, 788].
PCBs: Recent Advances in Environmental Toxicology and Health Effects, Ed. L. W. Robertson, L. G. Hansen, Lexington, Ky., University Press of Kentucky, 2001, p.11.
V. V. Khudolei, I. V. Mizgirev, Ekologicheski opasnye faktory [Environmental Risk Factors], Bank Petrovskii Publishing, St. Petersburg, 1996, 186 pp. (in Russian).
S. H. Safe, A. McDougal, Endocrine-Related Cancer, 1997, 4, 113.
L. H. Keith, Environmental Endocrine Disrupters, J. Wiley and Sons, New York, 1997, 142 p.
T. I. Gorbunova, M. G. Pervova, V. I. Saloutin, O. N. Chupakhin, J. Gen. Chem. (Engl. Transl.), 2012, 82, 138 [Zh. Obshch. Khim., 2012, 82, 142].
P. De Filippis, A. Chianese, F. Pochetti, Chemosphere, 1997, 35, 1659.
D. O. Egorova, T. I. Gorbunova, M. G. Pervova, V. A. Demakov, Biotekhnologiya, 2013, 4, 56 [Russ. J. Biotech., 2013, 4].
H. Pellissier, M. Santelli, Tetrahedron, 2003, 59, 70.
I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin, Chem. Heterocyc. Compd. (Engl. Transl.), 2012, 48, 536 [Khim. Geterotsikl. Soedin., 2012, 4, 576].
R. Karmakar, S. Y. Yun, K.-P. Wang, D. Lee, Org. Lett., 2014, 16, 6.
G. V. Zyryanov, I. S. Kovalev, I. N. Egorov, V. L. Rusinov, O. N. Chupakhin, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 303 [Izv. Akad. Nauk, Ser. Khim., 2012, 302].
A. Bhunia, T. Kaicharla, D. Porwal, R. G. Gonnadeb, A. T. Biju, Chem. Commun., 2014, 50, 11389.
I. L. Nikonov, D. S. Kopchuk, I. S. Kovalev, G. V. Zyryanov, A. F. Khasanov, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin, Tetrahedron Lett., 2013, 54, 6427.
G. V. Zyryanov, M. A. Palacios, P. Anzenbacher, Jr., Org. Lett., 2008, 10(17), 3681.
J. H. Park, C. Yun, T.-W. Koh, Y. Do, S. Yoo, M. H. Lee, J. Mater. Chem., 2011, 21, 5422.
S. Zhang, R. Chen, J. Yin, F. Liu, H. Jiang, N. Shi, Z. An, C. Ma, B. Liu, W. Huang, Org. Lett., 2010, 12, 3438.
T. Sandmeyer, Ber., 1884, 17, 2653.
E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis, 2007, 81.
P. Anzenbacher, Jr., S. Takizawa, Pat. US 2014/8785002 B1; CA 2014, 161, 255140.
H. Gilman, J. Honeycutt, Jr., J. Org. Chem., 1957, 22, 226.
G. V. Zyryanov, I. S. Kovalev, I. N. Egorov, V. L. Rusinov, O. N. Chupakhin, Chem. Heterocycl. Compd. (Engl. Transl.), 2011, 47, 571 [Khim. Geterotsikl. Soedin., 2011, 5, 692].
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Based on the materials of the XXVI International Chugaev Conference on Coordination Chemistry (October 6—10, 2014, Kazan).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1978—1981, August, 2015.
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Kovalev, I.S., Pavlyuk, D.E., Zaripov, V.A. et al. Synthesis of substituted 4,4´-dihalobiphenyls and their use for the preparation of isomeric bis(carbazolyl)biphenyls. Russ Chem Bull 64, 1978–1981 (2015). https://doi.org/10.1007/s11172-015-1104-2
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DOI: https://doi.org/10.1007/s11172-015-1104-2