Skip to main content
SpringerLink
Log in

New Tetrathiafulvalenes Containing Carbazole and 1,3,5-Triazine Fragments: Synthesis, Electro-Chemical and Optical Properties

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

New tetrathiafulvalenes, containing carbazole and 1,3,5-triazine fragments added to the tetrathia-fulvalene ring by means of a S–CH2–CH2–O bridge, were synthesized. The electrochemical properties of the initial compounds and of the final products were investigated by cyclic voltammetry. The optical characteristics of their solutions were studied by UV absorption spectroscopy and fluorescence spectroscopy.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. P. Leriche, F. Piron, E. Ripaud, P. Frère, M. Allain, and J. Roncali, Tetrahedron Lett., 50, 5673 (2009).

    Article  CAS  Google Scholar 

  2. M. Ak and L. Toppare, Mater. Chem. Phys., 114, 789 (2009).

    Article  CAS  Google Scholar 

  3. J. Liu, M.-Y. Teng, X.-P. Zhang, K. Wang, C.-H. Li, Y.-X. Zheng, and X.-Z. You, Org. Electron., 13, 2177 (2012).

    Article  CAS  Google Scholar 

  4. J. Zhuang, W. Su, W. Li, Y. Zhou, Q. Shen, and M. Zhou, Org. Electron., 13, 2210 (2012).

    Article  CAS  Google Scholar 

  5. E. Orselli, J. Maunoury, D. Bascour, and J.-P. Catinat, Org. Electron., 13, 1506 (2012).

    Article  CAS  Google Scholar 

  6. A. Luechai, N. Pootrakulchote, T. Kengthanomma, P. Vanalabhpatana, and P. Thamyongkit, J. Organomet. Chem., 753, 27 (2014).

    Article  CAS  Google Scholar 

  7. J. Liu, K. Wang, X. Zhang, C. Li, and X. You, Tetrahedron, 69, 190 (2013).

    Article  CAS  Google Scholar 

  8. G. Lai, Y. Liu, M. Li, and Y. Shen, Front. Chem. Eng. China, 3, 192 (2009).

    Article  CAS  Google Scholar 

  9. G. G. Abashev, E. V. Shklyaeva, R. V. Syutkin, K. Yu. Lebedev, I. V. Osorgina, V. A. Romanova, and A. Yu. Bushueva, Solid State Sci., 10, 1710 (2008).

    Article  CAS  Google Scholar 

  10. G. G. Abashev, K. Yu. Lebedev, I. V. Osorgina, and E. V. Shklyaeva, Zh. Org. Khim., 42, 1880 (2006). [Rus. J. Org. Chem., 42, 1873 (2006).]

  11. G. G. Abashev, A. Yu. Bushueva, and K. Yu. Lebedev, Zh. Org. Khim., 43, 129 (2007). [Rus. J. Org. Chem., 43, 135 (2007).]

  12. E. V. Shklyaeva, E. A. Ignatenko, and G. G. Abashev, Zh. Org. Khim., 49, 1394 (2013). [Rus. J. Org. Chem., 49, 1379 (2013).]

  13. E. A. Ignatenko, P. A. Slepukhin, E. V. Shklyaeva, and G. G. Abashev, Mendeleev Commun., 22, 145 (2012).

    Article  CAS  Google Scholar 

  14. X.-C. Zhang, C.-Y. Wang, G.-Q. Lai, L. Zhang, and Y.-J. Shen, Polym. Bull., 66, 893 (2011).

    Article  CAS  Google Scholar 

  15. S. Liang, Y. Zhao, and A. Adronov, J. Am. Chem. Soc., 136, 970 (2014).

    Article  CAS  Google Scholar 

  16. K. A. Nielsen, Tetrahedron Lett., 53, 5616 (2012).

    Article  CAS  Google Scholar 

  17. J. Xiong, L. Sun, Y. Liao, G.-N. Li, J.-L. Zuo, and X.-Z. You, Tetrahedron Lett., 52, 6157 (2011).

    Article  CAS  Google Scholar 

  18. M. Kato, D. Ogi, M. Yao, and Y. Misaki, Chem. Lett., 42, 1556 (2013).

    Article  CAS  Google Scholar 

  19. T. Marszalek, A. Nosal, R. Pfattner, J. Jung, S. Kotarba, M. Mas-Torrent, B. Krause, J. Veciana, M. Gazicki-Lipman, C. Crickert, G. Schmidt, C. Rovira, and J. Ulanski, Org. Electron., 13, 121 (2012).

    Article  CAS  Google Scholar 

  20. H. Jiang, X. Yang, E. Wang, Y. Fu, Y. Liu, H. Li, Z. Cui, Y. Liu, and W. Hu, Synth. Met., 161, 136 (2011).

    Article  CAS  Google Scholar 

  21. N. Borjigin, J.-I. Nishida, S. Tokito, L. Theogarajan, and Y. Yamashita, Synth. Met., 160, 2323 (2010).

    Article  CAS  Google Scholar 

  22. K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, M. Mørk, G. J. Kristensen, and J. Becher, Synthesis, 407 (1996).

  23. J. Lau, O. Simonsen, and J. Becher, Synthesis, 521 (1995).

  24. G. G. Abashev, E. V. Shklyaeva, A. G. Tenishev, and A. B. Sheremetev, in: Prospects for Development of Natural Sciences in High School (Proceedings of International Scientific Conference) [in Russian], Vol. 1, Izd-vo Perm. Gos. Univ., Perm (2001), p. 15.

    Google Scholar 

  25. K. Hartke, T. Kissel, J. Quante, and R. Matusch, Chem. Ber., 113, 1898 (1980).

    Article  CAS  Google Scholar 

  26. J. Becher, J. Lau, P. Leriche, P. Mørk, and N. Svenstrup, J. Chem. Soc., Chem. Commun., 2715 (1994).

  27. N. Svenstrup, R. M. Rasmussen, T. K. Hansenm, and J. Becher, Synthesis, 809 (1994).

  28. G. Steimecke, H.-J. Sieler, R. Kirmse, and E. Hoyer, Phosphorus, Sulfur Silicon Relat. Elem., 7, 49 (1979).

    Article  CAS  Google Scholar 

  29. G. G. Abashev, V. S. Russkikh, and E. V. Shklyaeva, in: Electronics of Organic Materials (ELORMA-90), Proceedings of All-Union Conference [in Russian], Dombai, (1990), p. 81.

  30. G. G. Abashev, V. S. Russkikh, E. V. Shklyaeva, and V. I. Vladykin, Zh. Org. Khim., 31, 1705 (1995).

    CAS  Google Scholar 

  31. H. Meng, J. Zheng, A. J. Lovinger, B.-C. Wang, P. G. Van Patten, and Z. Bao, Chem. Mater., 15, 1778 (2003).

    Article  CAS  Google Scholar 

  32. C. K. Kim, E. S. Song, H. J. Kim, C. Park, Y. C. Kim, J. K. Kim, J. W. Yu, and C. Kim, J. Polym. Sci., Part A: Polym. Chem., 44, 254 (2006).

    Article  CAS  Google Scholar 

Download references

The work was carried out with financial support from the Russian Foundation for Basic Research (grants 14-03-00341A and 14-03-96003).

Author information

Authors and Affiliations

  1. Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, 3 Akademika Koroleva St., Perm, 614013, Russia

    E. A. Ignatenko, A. A. Gorbunov & G. G. Abashev

  2. Natural Science Institute, Perm State University, 4 Genkel St., Perm, 614990, Russia

    E. V. Shklyaeva

Authors
  1. E. A. Ignatenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Gorbunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Shklyaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. G. Abashev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. A. Ignatenko.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 752-760, May, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ignatenko, E.A., Gorbunov, A.A., Shklyaeva, E.V. et al. New Tetrathiafulvalenes Containing Carbazole and 1,3,5-Triazine Fragments: Synthesis, Electro-Chemical and Optical Properties. Chem Heterocycl Comp 50, 691–698 (2014). https://doi.org/10.1007/s10593-014-1522-3

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1522-3

Keywords

Search

Navigation