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Photochromism of 6′-cyanosubstituted spirooxazines in frozen alcohol matrices

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Abstract

For three 6′-cyanosubstituted spironaphthooxazines, spectral characteristics of an open form and quantum yields of photoisomerization were determined both at room temperature and in frozen alcohol matrices. Spironaphthooxazines have demonstrated fairly high (0.01–0.02) quantum yields of open form appearance at 77 K. The observed peculiarities of the open form UV spectra were explained by the temperature dependence of the open form isomers distribution. Partial stabilization of the nonequilibrium isomers of an open form in the low-temperature matrices was revealed.

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References

  1. Maeda, S., Organic Photochromic and Termochromic Compounds, Crano, J.C. and Guglielmetti, R.J., Eds., New York: Plenum, 1999, vol. 1, p. 85.

    Google Scholar 

  2. Malatesta, V., Organic Photochromic and Termochromic Compounds, Crano, J.C. and Guglielmetti, R.J., Eds., New York: Plenum, 1999, vol. 2, p. 65.

    Google Scholar 

  3. Appriou, P., Guglielmetti, R., and Garnier, F., J. Photochem., 1978, vol. 8, no. 2, p. 145.

    Article  CAS  Google Scholar 

  4. Tamai, N. and Miyasaka, H., Chem. Rev., 2000, vol. 100, no. 5, p. 1875.

    Article  CAS  Google Scholar 

  5. Ortica, F. and Favaro, G., J. Phys. Chem. B, 2000, vol. 104, no. 51, p. 12179.

    Article  CAS  Google Scholar 

  6. Metelitsa, A.V., Lokshin, V., Micheau, J.C., Samat, A., Guglielmetti, R., and Minkin, V.I., Phys. Chem. Chem. Phys., 2002, vol. 4, no. 18, p. 4340.

    Article  CAS  Google Scholar 

  7. Kellmann, A., Tfibel, F., Dubest, R., Levoir, P., Aubard, J., Pottier, E., and Guglielmetti, R., J. Photochem. Photobiol., A, 1989, vol. 49, nos. 1–2, p. 63.

    Article  CAS  Google Scholar 

  8. Chibisov, A.K. and Gorner, H., J. Phys. Chem. A, 1999, vol. 103, no. 26, p. 5211.

    Article  CAS  Google Scholar 

  9. Chibisov, A.K., Marevtsev, V.S., and Gorner, H., J. Photochem. Photobiol., A, 2003, vol. 159, no. 3, p. 233.

    Article  CAS  Google Scholar 

  10. Schneider, S., Mindl, A., Elfinger, G., and Melzig, M., Ber. Bunsen-Ges. Phys. Chem., 1987, vol. 91, no. 11, p. 1222.

    CAS  Google Scholar 

  11. Aramaki, S. and Atkinson, G.H., Chem. Phys. Lett., 1990, vol. 170, nos. 2–3, p. 181.

    Article  CAS  Google Scholar 

  12. Wilkinson, F., Worrall, D.R., Hobley, J., Jansen, L., Williams, S.L., Langley, A.J., and Matousek, P., J. Chem. Soc., Faraday Trans., 1996, vol. 92, no. 9, p. 1331.

    Article  CAS  Google Scholar 

  13. Antipin, S.A., Petrukhin, A.N., Gostev, F.E., Marevtsev, V.S., Titov, A.A., Barachevsky, V.A., Strokach, Yu.P., and Sarkisov, O.M., Chem. Phys. Lett., 2000, vol. 331, nos. 5–6, p. 378.

    Article  CAS  Google Scholar 

  14. Suzuki, M., Asahi, T., and Masuhara, H., Phys. Chem. Chem. Phys., 2002, vol. 4, no. 2, p. 185.

    Article  CAS  Google Scholar 

  15. Buntinx, G., Foley, S., Lefumeux, C., Lokshin, V., Poizat, O., and Samat, A., Chem. Phys. Lett., 2004, vol. 391, nos. 1–3, p. 33.

    Article  CAS  Google Scholar 

  16. Lenoble, C. and Becker, R.S., J. Phys. Chem., 1986, vol. 90, no. 1, p. 62.

    Article  CAS  Google Scholar 

  17. Heiligman-Rim, R., Hirshberg, Y., and Fischer, E., J. Phys. Chem., 1962, vol. 66, no. 12, p. 2464.

    Google Scholar 

  18. Heiligman-Rim, R., Hirshberg, Y., and Fischer, E., J. Phys. Chem., 1962, vol. 66, no. 12, p. 2470.

    Article  CAS  Google Scholar 

  19. Dvornikov, S., Malkin, J., and Rentzepis, P.M., J. Phys. Chem., 1994, vol. 98, no. 27, p. 6746.

    Article  CAS  Google Scholar 

  20. Asahi, T., Suzuki, M., and Masuhara, H., J. Phys. Chem. A, 2002, vol. 106, no. 9, p. 2335.

    Article  CAS  Google Scholar 

  21. Ernsting, N.P. and Arthen-Engeland, T., J. Phys. Chem., 1991, vol. 95, no. 15, p. 5502.

    Article  CAS  Google Scholar 

  22. Krysanov, S.A. and Alfimov, M.V., Chem. Phys. Lett., 1982, vol. 91, no. 1, p. 77.

    Article  CAS  Google Scholar 

  23. Malkin, Ya.N., Krasieva, T.B., and Kuz’min, V.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1990, no. 2, p. 236.

  24. Tamaki, T., Sakuragi, M., Ichimura, K., and Aoki, K., Chem. Phys. Lett., 1989, vol. 161, no. 1, p. 23.

    Article  CAS  Google Scholar 

  25. Marevtsev, V.S., Gradyushko, A.T., Ermakova, V.D., Linskii, V.A., and Cherkashin, M.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1981, no. 9, p. 1249.

  26. Luchina, V.G., Khamchukov, Yu.D., Marevtsev, V.S., Lyubimov, A.V., Gradyushko, A.T., and Cherkashin, M.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1988, no. 10, p. 2255.

  27. Glebov, E.M., Vorobyev, D.Yu., Grivin, V.P., Plyusnin, V.F., Metelitsa, A.V., Voloshin, N.A., Minkin, V.I., and Micheau, J.C., Chem. Phys., 2006, vol. 323, nos. 2–3, p. 490.

    Article  Google Scholar 

  28. Marevtsev, V.S. and Zaichenko, N.L., J. Photochem. Photobiol., A, 1997, vol. 104, nos. 1–3, p. 197.

    Article  CAS  Google Scholar 

  29. Lee, I.-J., J. Photochem. Photobiol., A, 1999, vol. 124, no. 3, p. 141.

    Article  CAS  Google Scholar 

  30. Voloshin, N.A., Metelitsa, A.V., Micheau, J.C., Voloshina, E.N., Besugliy, S.O., Shelepin, N.E., Minkin, V.I., Tkachev, V.V., Safoklov, B.B., and Aldoshin, S.M., Izv. Akad. Nauk, Ser. Khim., 2003, no. 9, p. 1929.

  31. Metelitsa, A.V., Micheau, J.C., Besugliy, S.O., Gaeva, E.B., Voloshin, N.A., Voloshina, E.N., Samat, A., and Minkin, V.I., Int. J. Photoenergy, 2004, vol. 6, no. 4, p. 199.

    Article  CAS  Google Scholar 

  32. Korolev, V.V., Plyusnin, V.F., and Bazhin, N.M., Zh. Fiz. Khim., 1975, vol. 49, no. 9, p. 2440.

    CAS  Google Scholar 

  33. Kurien, K.C., J. Chem. Soc. B, 1971, p. 2081.

  34. Korolev, V.V., Gritsan, N.P., and Bazhin, N.M., Khim. Fiz., 1986, vol. 5, no. 6, p. 730.

    CAS  Google Scholar 

  35. Takahashi, H., Yoda, K., Isaka, H., Ohzeki, T., and Sakaino, Y., Chem. Phys. Lett., 1987, vol. 140, no. 1, p. 90.

    Article  CAS  Google Scholar 

  36. Delbaere, S., Bochu, C., Azaroual, N., Buntinx, G., and Vermeersch, G., J. Chem. Soc., Perkin Trans. 2, 1997, no. 8, p. 1499.

  37. Perrier, A., Perpete, E.A., Wathelet, V., and Jacquemin, D., J. Phys. Chem. A, 2009, vol. 113, no. 46, p. 13004.

    Article  CAS  Google Scholar 

  38. Burdzinski, G.T., Middleton, C.T., Gustafson, T.L., and Platz, M.S., J. Am. Chem. Soc., 2006, vol. 128, no. 46, p. 14804.

    Article  CAS  Google Scholar 

  39. Gritsan, N.P., Usp. Khim., 2007, vol. 76, no. 12, p. 1218.

    Google Scholar 

  40. Maurel, F., Aubard, A., Millie, P., Dognon, J.P., Rajzman, M., Guglielmetti, R., and Samat, A., J. Phys. Chem. A, 2006, vol. 110, no. 14, p. 4759.

    Article  CAS  Google Scholar 

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Correspondence to E. M. Glebov.

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Original Russian Text © M.I. Nikolaeva, V.V. Korolev, E.A. Pritchina, E.M. Glebov, V.F. Plyusnin, A.V. Metelitsa, N.A. Voloshin, V.I. Minkin, 2011, published in Kinetika i Kataliz, 2011, Vol. 52, No. 2, pp. 209–217.

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Nikolaeva, M.I., Korolev, V.V., Pritchina, E.A. et al. Photochromism of 6′-cyanosubstituted spirooxazines in frozen alcohol matrices. Kinet Catal 52, 202–209 (2011). https://doi.org/10.1134/S0023158411020145

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