Skip to main content
Log in

Reverse Photochromism of Nitrosubstituted Bisspiropyran Based on Benzopyrroloindole

  • PHOTONICS
  • Published:
High Energy Chemistry Aims and scope Submit manuscript

Abstract

The photochromic properties of new di- and tetranitrobisspiropyrans have been studied. Dinitrobisspiropyran solutions are characterized by direct photochromism, whereas reverse photochromism—coloration of the solution in the dark and its discoloration under the action of visible or UV light—is observed in solutions of tetranitrobisspiropyran in polar and weakly polar solvents and in polymer matrices of poly(methyl methacrylate) (PMMA) and polyvinyl butyral (PVB). The features of reverse photochromism are discussed, and a comparison with the photochromism of model nitrosubstituted monospiropyrans and dinitrobisspiropyran is carried out.

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.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. Organic Photochromic and Thermochromic Compounds, Grano, Y.C. and Guglielmetti, R.Y., Eds., New York: Kluwer Academic, 2002, vol. 1.

    Google Scholar 

  2. Aiken, S., Edgar, R.J.L., Gubbutt, C.D., and Heron, B.M., Dyes Pigments, 2018, vol. 149, p. 92.

    Article  CAS  Google Scholar 

  3. Barachevsky, V.A., Rev. J. Chem., 2017, vol. 7, no. 3, p. 334.

    Article  CAS  Google Scholar 

  4. Barachevskii, V.A. and Karpov, R.E., High Energy Chem., 2007, vol. 41, no. 3, p. 188.

    Article  CAS  Google Scholar 

  5. Barachevsky, V.A., Valova, T.M., Atabekyan, L.S., and Lyubimov, A.V., High Energy Chem., 2017, vol. 51, no. 6, p. 415.

    Article  CAS  Google Scholar 

  6. Levy, D. and Avnir, D., J. Phys. Chem., 1988, vol. 92, p. 4734.

    Article  CAS  Google Scholar 

  7. Dzhaparidze, K.G., Spirokhromeny (Spirochromenes), Tbilisi: Metsniereba, 1979.

    Google Scholar 

  8. Zakharova, M.I., Coudret, C., Pimienta, V., Micheau, J.C., Delbaere, S., Vermeersch, G., Metelitsa, A.V., Voloshin, N., and Minkin, V.I., Photochem. Photobiol. Sci., 2010, vol. 9, p. 199.

    Article  CAS  PubMed  Google Scholar 

  9. Minkin, V.I., Usp. Khim., 2013, vol. 82, no. 1. p. 1.

    Article  CAS  Google Scholar 

  10. Mardaleishvili, I.R., Kol’tsova, L.S., Zaichenko, N.L., Shienok, A.I., Levin, P.P., and Tatikolov, A.S., High Energy Chem., 2015, vol. 49, no. 1, p. 30.

    Article  CAS  Google Scholar 

  11. Corley, C., Gillmore, J.G., Crisman, J., Kodis, G., Gray, C.L., Cherry, B.R., Sherman, B.D., Liddell, P.A., Paquette, M.M., Kelbaukas, L., Frank, N.L., Moore, A.L., Moore, T.A., and Gust, D., J. Am. Chem. Soc., 2014, vol. 136, p. 11994.

    Article  CAS  Google Scholar 

  12. Arsenov, V.D., Parshutkin, A.A., Marevtsev, V.S., and Cherkashin, M.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1984, p. 1987.

  13. Samsoniya, Sh.A., Trapaidze, M.V., Nikolei-shvili, N.N., Japaridze, K.G., Maisuradze, J.P., and Kazmaier, U., Chem. Heterocycl. Compd., 2011, vol. 47, no. 9, p. 1098.

    Article  CAS  Google Scholar 

  14. Samsoniya, Sh.A., Trapaidze, M.V., Nikolei-shvili, N.N., Dzhaparidze, K.G., Maisuradze, Dzh.P., and Katsmaier, U., Khim. Geterotsikl. Soedin., 2010, no. 8, p. 1259.

  15. Lyubimov, A.V., Lyubimova, G.V., and Shienok, A.I., Evraz. Soyuz Uchenykh (ESU), 2016, vol. 23, p. 2.

    Google Scholar 

  16. Hinnen, A. and Audio, G., Gautron, Bull. Soc. Chim. Fr., 1968, p. 2066.

  17. Fihey, A., Perrier, A., Browne, W.R., and Jacquemin, D., Chem. Soc. Rev., 2015, vol. 44, p. 3719.

    Article  CAS  PubMed  Google Scholar 

  18. Malkin, Ya.N., Kuz’min, V.A., Mikhailenko, F.A., and Dyadyusha, G.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1976, no. 3, p. 555.

  19. Malkin, Ya.N., Kuz,min, V.A., and Mikhailenko, F.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1977, no. 1, p. 83.

  20. Mukhanov, E.S., Alekseenko, Yu.S., Luk’yanov, B.S., Dorogan, I.V., and Bezuglyi, S.O., High Energy Chem., 2010, vol. 44, no. 3, p. 210.

    Article  CAS  Google Scholar 

  21. Lee, S., Ji, S., and Kang, Y., Bull. Korean Chem. Soc., 2012, vol. 33, no. 11, p. 3740.

    Article  CAS  Google Scholar 

  22. Li, Y., Zhou, J., Wang, Y., Zhang, F., and Song, X., J. Photochem. Photobiol., A, 1998, vol. 113, p. 65.

    Article  CAS  Google Scholar 

  23. Dzhaparidze, K.G., Gachechiladze, G.G., Pavlenishvili, Ya.I., Gugava, M.T., Maisuradze, D.P., and Mamistvalova, N., Soobshch. Akad. Nauk. Gruz. SSR, 1973, vol. 69, p. 329.

    CAS  Google Scholar 

  24. Kundu, P.K., Lerner, A., Kucanda, K., Leitus, G., and Klajn, R., J. Am. Chem. Soc.,2014, vol. 136, p. 11270.

    Article  CAS  Google Scholar 

  25. Samsoniya, Sh.A., Trapaidze, M.V., Nikolei-shvili, N.N., Japaridze, K.G., and Maisuradze, J.P., Bull. Georgian Natl. Acad. Sci., 2013, vol. 7, no. 3, p. 51.

    CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

This work was carried out under the program of the State Assignment 0082-2018-0006 and 0082-2014-0015 and supported by the Russian Foundation for Basic Research, project no. 16-03-00275.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. R. Mardaleishvili.

Additional information

Translated by A. Tatikolov

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mardaleishvili, I.R., Lyubimova, G.V., Lyubimov, A.V. et al. Reverse Photochromism of Nitrosubstituted Bisspiropyran Based on Benzopyrroloindole. High Energy Chem 53, 13–21 (2019). https://doi.org/10.1134/S0018143919010089

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0018143919010089

Keywords:

Navigation