Skip to main content
SpringerLink
Log in

Synthesis and photochemical properties of 3,6-di-tert-butyl-9H-carbazole derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Method of synthesis has been developed for a series of 3,6-di-tert-butyl-9H-carbazole derivatives and their photochemical properties have been investigated. The dependence of the Steglich esterification reaction on the nature of the catalyst was studied. The synthesized compounds show fluorescent emission in the range 400–600 nm with a high quantum yield.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Luminescence. From Theory to Applications, Ronda, C., Ed., Weinheim: Wiley-VCH, 2007.

    Google Scholar 

  2. Campbell, N. and Barclay, B.M., Chem. Rev., 1947, vol. 40, no. 3, p. 359. DOI: 10.1021/cr60127a001.

    Article  CAS  Google Scholar 

  3. Schmidt, A.W., Reddy, K.R., and Knolker, H.-J., Chem. Rev., 2012, vol. 112, p. 3193. DOI: 10.1021/cr200447s.

    Article  CAS  Google Scholar 

  4. Ambrose, J.F., Caprenter, L.L., and Nelson, R.F., J. Electrochem. Soc., 1975, vol. 122, no. 7, p. 876. DOI:10.1149/1.2134365.

    Article  CAS  Google Scholar 

  5. Ambrose, J.F. and Nelson, R.F., J. Electrochem. Soc., 1968, vol. 115, no. 11, p. 1159. DOI: 10.1149/1.2410929.

    Article  CAS  Google Scholar 

  6. Lamm, W., Pragst, F., and Jugelt, W., J. Prakt. Chem., 1975, vol. 317, no. 6, p. 995. DOI: 10.1002/prac.19753170616.

    Article  CAS  Google Scholar 

  7. Maes, W., Vanderhaeghen, J., Smeets, S., Asokan, C.V., Van Renterghem, L.M., Duprez, F.E., Smet, M., and Dehaen, W., J. Org. Chem., 2006, vol. 71, no. 8, p. 2987. DOI: 10.1021/jo052534u.

    Article  CAS  Google Scholar 

  8. Zhu, Z. and Moore, J.S., J. Org. Chem., 2000, vol. 65, no. 1, p. 116. DOI: 10.1021/jo991167h.

    Article  CAS  Google Scholar 

  9. Liu, Y., Di, C., Xin, Y., Yu, G., Liu, Y., He, Q., Bai, F., Xu, S., and Cao, S., Synt. Met., 2006, vol. 156, nos. 11–13, p. 824. DOI: 10.1016/j.synthmet.2006.04.011.

    Article  CAS  Google Scholar 

  10. Moss, K.C., Bourdakos, K.N., Bhalla, V., Kamtekar, K.T., Bryce, M.R., Fox, M.A., Vaughan, H.L., Dias, F.B., and Monkman, A.P., J. Org. Chem., 2010, vol. 75, no. 20, p. 6771. DOI: 10.1021/jo100898a.

    Article  CAS  Google Scholar 

  11. Thongkasee, P., Thangthong, A., Janthasing, N., Sudyoadsuk, T., Namuangruk, S., Keawin, T., Jungsuttiwong, S., and Promarak, V., Appl. Mater. Interf., 2014, vol. 6, no. 11, p. 8212. DOI: 10.1021/am500947k.

    Article  CAS  Google Scholar 

  12. Yang, X., Lu, R., Xu, T., Xue, P., Liu, X., and Zhao, Y., Chem. Commun., 2008, p. 453. DOI: 10.1039/B713734F.

    Google Scholar 

  13. Yang, X., Lu, R., Gai, F., Xue, P., and Zhan, Y., Chem. Commun., 2010, vol. 46, p. 1088. DOI: 10.1039/B918986F.

    Article  CAS  Google Scholar 

  14. Chervonova, U.V., Gruzdev, M.S., and Kolker, A.M., Russ. J. Gen. Chem., 2011, vol. 81, no. 9, p. 1853. DOI:10.1134/S1070363211090192.

    Article  CAS  Google Scholar 

  15. Chervonova, U.V., Gruzdev, M.S., Kolker, A.M., Manin, N.G., and Domracheva, N.E., Russ. J. Gen. Chem., 2010, vol. 80, no. 10, p. 1954. DOI: 10.1134/S1070363210100130.

    Article  CAS  Google Scholar 

  16. Neises, B. and Steglich, W., Angew. Chem. Int. Ed., 1978, vol. 17, no. 7, p. 522. DOI: 10.1002/anie.197805221.

    Article  Google Scholar 

  17. Otera, J. and Nishikido, J., Esterification. Methods, Reactions and Applications, Weinheim: Wiley-VCH, 2010.

    Google Scholar 

  18. Hassner, A. and Alexanian, V., Tetrahedron Lett., 1978, vol. 46, p. 4475. DOI: 10.1016/S0040-4039(01)95256-6.

    Article  Google Scholar 

  19. Hassner, A., Krepski, L., and Alexanian, V., Tetrahedron, 1978, vol. 34, no. 14, p. 2069. DOI:10.1016/0040-4020(78)89005-X.

    Article  CAS  Google Scholar 

  20. Haslam, E., Tetrahedron, 1980, vol. 36, no. 17, p. 2409. DOI: 10.1016/0040-4020(80)80219-5.

    Article  CAS  Google Scholar 

  21. Lakowicz, J.R., Principles of Fluorescence Spectroscopy, New York: Springer, 2006.

    Book  Google Scholar 

  22. Eksperimental’nye metody khimicheskoi kinetiki (Experimental Methods of Chemical Kinetics), Emmanuel, N.M. and Kuz’min, M.G., Eds., Moscow: Mosk. Gos. Univ., 1985.

    Google Scholar 

  23. Rabek, J.F., Experimental Methods in Photochemistry and Photophysics, New York: John Wiley & Sons, 1982.

    Google Scholar 

  24. Moore, J.S. and Stupp, S.I., Macromolecules, 1990, vol. 23, no. 1, p. 65. DOI: 10.1021/ma00203a013.

    Article  CAS  Google Scholar 

  25. McAdam, C.J. and Simpson, J., Acta Crystallogr. E, 2008, vol. 64, p. o627. DOI: 10.1107/S1600536808004856.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, ul. Akademicheskaya 1, Ivanovo, 153045, Russia

    M. S. Gruzdev, U. V. Chervonova, E. A. Venediktov, E. P. Rozhkova, A. M. Kolker & N. A. Dudina

  2. Ivanovo State University of Chemistry and Technology, Ivanovo, Russia

    E. A. Mazaev

  3. Kazan Physico-Technical Institute, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    N. E. Domracheva

Authors
  1. M. S. Gruzdev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. U. V. Chervonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Venediktov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. P. Rozhkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. M. Kolker
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. A. Mazaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. A. Dudina
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. N. E. Domracheva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. S. Gruzdev.

Additional information

Original Russian Text © M.S. Gruzdev, U.V. Chervonova, E.A. Venediktov, E.P. Rozhkova, A.M. Kolker, E.A. Mazaev, N.A. Dudina, N.E. Domracheva, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 6, pp. 964–972.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gruzdev, M.S., Chervonova, U.V., Venediktov, E.A. et al. Synthesis and photochemical properties of 3,6-di-tert-butyl-9H-carbazole derivatives. Russ J Gen Chem 85, 1431–1439 (2015). https://doi.org/10.1134/S1070363215060122

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215060122

Keywords

Search

Navigation