Skip to main content
Log in

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Syntheses are reported for cationic indoline spiropyrans with a quaternized pyridinium fragment in the aliphatic side chain, which display photochromic properties in solution. The major effect of introducing a quaternized pyridinium fragment into the benzopyran part of the spiropyran entails a significant decrease in the rate of thermal relaxation processes.

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.

Similar content being viewed by others

References

  1. B. S. Lukyanov, A. N. Utenyshev, V. V. Tkachev, S. M. Aldoshin, V. I. Minkin, M. B. Lukyanova, and Yu. S. Alekseenko, Khim. Geterotsikl. Soedin., 221 (2008). [Chem. Heterocycl. Comp., 44, 163 (2008)].

    Google Scholar 

  2. R. Guglielmetti, in: H. Dürr and H. Bouas-Laurent (editors), Photochroism, Elsevier, Amsterdam (1990), Ch. 8.

    Google Scholar 

  3. R. C. Bertelson, in: J. C. Crano and R. J. Guglielmetti (editors), Organic Photochromic and Thermochromic Compounds, vol. 1, Plenum Press, New York (1999), Ch. 1.

    Google Scholar 

  4. G. Bercovic, V. Krongauz, and V. Weiss, Chem. Rev., 100, 1741 (2000).

    Article  Google Scholar 

  5. V. I. Minkin, Chem. Rev., 104, 2751 (2004).

    Article  CAS  Google Scholar 

  6. S. Bénard and P. Yu, Chem. Commun., 65 (2000).

  7. S. Bérnard, E. Riviere, and P. Yu, Chem. Mater., 13, 159 (2001).

    Article  Google Scholar 

  8. I. Kashima, M. Okubo, Y. Ono, M. Itoi, N. Kida, M. Hikita, M. Enomoto, and N. Kojima, Synth. Meth., 153, 473 (2005).

    Article  CAS  Google Scholar 

  9. S. M. Aldoshin, N. A. Sanina, V. I. Minkin, V. A. Voloshin, V. N. Ikorskii, V. I. Ovcharenko, V. A. Smirnov, and N. K. Nagaeva, J. Mol. Struct., 826, 69 (2007).

    Article  CAS  Google Scholar 

  10. I. Shevyakova, L. Buravov, V. Tkacheva, L. Zorina, S. Khasanov, S. Simonov, J. Yamada, E. Canadell, R. Shibaeva, and E. Yagubskii, Adv. Funct. Mater., 14, 660 (2004).

    Article  CAS  Google Scholar 

  11. S. V. Simonov, I. Yu. Shevyakova, L. V. Zorina, S. S. Khasanov, L. I. Buravov, V. A. Emel'yanov, E. Canadell, R. P. Shibaeva, and E. B. Yagubskii, J. Mater. Chem., 15, 2476 (2005).

    Article  CAS  Google Scholar 

  12. T. G. Prokhorova, S. S. Khasanov, L. V. Zorina, L. I. Buravov, V. A. Tkacheva, A. A. Baskakov, R. B. Morgunov, M. Gener, E. Canadell, R. P. Shibaeva, and E. B. Yagubskii, Adv. Funct. Mater., 13, 403 (2003).

    Article  CAS  Google Scholar 

  13. N. S. Ovanesyan, V. D. Makhaev, S. M. Aldoshin, P. Gredin, K. Boubekeur, C. Train, and M. Gruselle, J. Chem. Soc., Dalton Trans., 18, 3101 (2005).

    Google Scholar 

  14. S. Bénard and P. Yu, Adv. Mater., 12, 48 (2000).

    Article  Google Scholar 

  15. S. M. Aldoshin, L. A. Nikonova, V. A. Smirnov, G. V. Shilov, and N. K. Nagaeva, J. Mol. Struct., 750, 158 (2005).

    Article  CAS  Google Scholar 

  16. K. Nakatani and P. Yu, Adv. Mater., 13, 1411 (2001).

    Article  CAS  Google Scholar 

  17. S. M. Aldoshin, L. A. Nikonova, V. A. Smirnov, G. V. Shilov, and N. K. Nagaeva, Izv. Akad. Nauk, Ser. Khim., 2050 (2005).

  18. S. Bénard, E. Riviere, P. Yu, K. Nakatani, and J. F. Delouis, Chem. Mater., 13, 159 (2001).

    Article  Google Scholar 

  19. I. Kashima, M. Okubo, Y. Ono, M. Itoi, N. Kida, M. Hikita, M. Enomoto, and N. Kojima, Synth. Meth., 155, 703 (2005).

    Article  Google Scholar 

  20. K. Takagi, T. Kurematsu, and Y. Sawaki, J. Chem. Soc., Perkin Trans. 2, 1667 (1995).

  21. N. K. Artemova, V. A. Smirnov, B. G. Rogachev, G. V. Shilov, and S. M. Aldoshin, Izv. Akad. Nauk, Ser. Khim., 1548 (2006).

  22. N. W. Tyer, Jr. and R. S. Becker, J. Am. Chem. Soc., 92, 1289 (1970).

    Article  CAS  Google Scholar 

  23. A. V. Metelitsa, V. Lokshin, J. C. Micheau, A. Samat, R. Guglielmetti, and V. I. Minkin, Phys. Chem. Chem. Phys., 4, 4340 (2002).

    Article  CAS  Google Scholar 

  24. V. Lokshin, A. Samat, and A. V. Metelitsa, Usp. Khim., 71, 1015 (2002).

    Google Scholar 

  25. E. Pottier, M. Sergent, R. Phan Tan Luu, and R. Guglielmetti, Bull. Soc. Chim. Belg., 101, 719 (1992).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Solov’eva.

Additional information

*2Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his 70th jubilee.

*For Communication 30 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1513-1522, October, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voloshin, N.A., Bezugliy, S.O., Solov’eva, E.V. et al. Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2 . Chem Heterocycl Comp 44, 1229–1237 (2008). https://doi.org/10.1007/s10593-009-0175-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-009-0175-0

Keywords

Navigation