Skip to main content
Log in

Synthesis of substituted 4,4´-dihalobiphenyls and their use for the preparation of isomeric bis(carbazolyl)biphenyls

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. T. I. Gorbunova, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Rev., 2010, 79, 511 [Usp. Khim., 2010, 79, 565].

    Article  CAS  Google Scholar 

  2. 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).

    Google Scholar 

  3. L. N. Zanaveskin, V. A. Averyanov, Russ. Chem. Rev., 1998, 67, 713 [Usp. Khim., 1998, 67, 788].

    Article  Google Scholar 

  4. 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.

  5. V. V. Khudolei, I. V. Mizgirev, Ekologicheski opasnye faktory [Environmental Risk Factors], Bank Petrovskii Publishing, St. Petersburg, 1996, 186 pp. (in Russian).

    Google Scholar 

  6. S. H. Safe, A. McDougal, Endocrine-Related Cancer, 1997, 4, 113.

    Article  CAS  Google Scholar 

  7. L. H. Keith, Environmental Endocrine Disrupters, J. Wiley and Sons, New York, 1997, 142 p.

    Google Scholar 

  8. 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].

    Article  CAS  Google Scholar 

  9. P. De Filippis, A. Chianese, F. Pochetti, Chemosphere, 1997, 35, 1659.

    Article  CAS  Google Scholar 

  10. D. O. Egorova, T. I. Gorbunova, M. G. Pervova, V. A. Demakov, Biotekhnologiya, 2013, 4, 56 [Russ. J. Biotech., 2013, 4].

    Google Scholar 

  11. H. Pellissier, M. Santelli, Tetrahedron, 2003, 59, 70.

    Google Scholar 

  12. 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].

    Article  CAS  Google Scholar 

  13. R. Karmakar, S. Y. Yun, K.-P. Wang, D. Lee, Org. Lett., 2014, 16, 6.

    Article  CAS  Google Scholar 

  14. 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].

    Article  CAS  Google Scholar 

  15. A. Bhunia, T. Kaicharla, D. Porwal, R. G. Gonnadeb, A. T. Biju, Chem. Commun., 2014, 50, 11389.

    Article  CAS  Google Scholar 

  16. 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.

    Article  CAS  Google Scholar 

  17. G. V. Zyryanov, M. A. Palacios, P. Anzenbacher, Jr., Org. Lett., 2008, 10(17), 3681.

    Article  CAS  Google Scholar 

  18. J. H. Park, C. Yun, T.-W. Koh, Y. Do, S. Yoo, M. H. Lee, J. Mater. Chem., 2011, 21, 5422.

    Article  CAS  Google Scholar 

  19. 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.

    Article  CAS  Google Scholar 

  20. T. Sandmeyer, Ber., 1884, 17, 2653.

    Google Scholar 

  21. E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis, 2007, 81.

    Google Scholar 

  22. P. Anzenbacher, Jr., S. Takizawa, Pat. US 2014/8785002 B1; CA 2014, 161, 255140.

    Google Scholar 

  23. H. Gilman, J. Honeycutt, Jr., J. Org. Chem., 1957, 22, 226.

    Article  CAS  Google Scholar 

  24. 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].

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. V. Zyryanov.

Additional information

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.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-1104-2

Key words

Navigation