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Synthesis and kinetics of photochemical reactions of novel bifunctional salicylideneiminospironaphthoxazines

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Abstract

A series of novel photochemically bifunctional compounds was synthesized. Their molecules combine the photochromic spironaphthoxazine fragment with a salicylideneimine fragment containing various substituents. The latter can undergo intramolecular proton transfer in the electron-excited state. Photolysis products of three types, namely, open merocyanine forms having an enol or cis-keto form of the salicylideneimine moiety and a trans-keto form with the closed spiro fragment, were detected using pulse photolysis technique in toluene and methanol solutions. The spectral kinetic characteristics of the photoproducts were studied, and their quantum yields were measured. The effects of substituents in the salicylideneimine fragment and the solvent nature were discussed.

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References

  1. V. A. Barachevskii, Zh. Nauchn. Prikl. Fotografii [Journal of Scientific and Applied Photography], 1998, 43, 79 (in Russian).

    CAS  Google Scholar 

  2. G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev., 2000, 100, 1741.

    Article  CAS  Google Scholar 

  3. M. Irie, Chem. Rev., 2000, 100, 1685.

    Article  CAS  Google Scholar 

  4. M. Figoli, G. H. Mehl, Angew. Chem., Int. Ed., 2005, 44, 5048.

    Article  Google Scholar 

  5. G. J. Brown, A. P. De Silva, S. Pagliari, Chem. Commun., 2002, 2461.

  6. S. Kobatake, M. Irie, Tetrahedron, 2003, 59, 8359.

    Article  CAS  Google Scholar 

  7. B. Z. Chen, M. Z Wang, Q. F. Luo, H. Tian, Synth. Met., 2003, 137, 985.

    Article  CAS  Google Scholar 

  8. A. J. Myles, T. J. Wigglesworth, N. R. Branda, Adv. Mater., 2003, 745.

  9. K. Yagi, M. Irie, Chem. Lett., 2003, 32, 848.

    Article  CAS  Google Scholar 

  10. A. I. Shienok, N. L. Zaichenko, L. S. Kol’tsova, V. S. Marevtsev, Izv. Akad. Nauk, Ser. Khim., 2003, 2169 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2294].

    Google Scholar 

  11. A. K. Frolov, F. E. Gostev, I. V. Shelaev, A. I. Shienok, N. L. Zaichenko, L. S. Kol’tsova, V. A. Barachevskii, O. M. Sarkisov, Khim. Fiz. [Chemical Physics], 2007, 26, 1021 (in Russian).

    Google Scholar 

  12. S. A. Antipin, A. N. Petrukhin, F. E. Gostev, V. S. Marevtsev, A. A. Titov, V. A. Barachevskii, Yu. P. Strokach, O. M. Sarkisov, Khim. Fiz. [Chemical Physics], 2002, 21, 10 (in Russian).

    CAS  Google Scholar 

  13. R. S. Becker, W. F. Richey, J. Am. Chem. Soc., 1967, 89, 1298.

    Article  CAS  Google Scholar 

  14. M. Z. Zgierski, A. Grabowska, J. Chem. Phys., 2000, 112, 6329.

    Article  CAS  Google Scholar 

  15. W. V. F. Fabian, L. Antonov, D. Nedeltcheva, F. S. Kamounah, P. J. Taylor, J. Phys. Chem. A, 2004, 108, 7603.

    Article  CAS  Google Scholar 

  16. M. Ziotek, J. Kubicki, R. Naskrecki, A. Grabowska, J. Chem. Phys., 2006, 124, 124518.

    Article  Google Scholar 

  17. P. Fita, E. Lusina, Cz. Radzewicz, A. Grabowska, J. Chem. Phys., 2006, 125, 184508.

    Article  CAS  Google Scholar 

  18. F. E Gostev, A. N. Petrukhin, A. A. Titov, V. A. Nadtochenko, O. M. Sarkisov, A. V. Metelitsa, V. I. Minkin, Khim. Fiz. [Chemical Physics], 2004, 23, 3 (in Russian).

    Google Scholar 

  19. Tables of Spectral Data for Structure Determination of Organic Compounds, Ed. W. Fresenius, J. F. K. Huber, E. Pungor, G. A. Rechnitz, W. Simon, Th. S. West, Springer-Verlag, Berlin—Heidelberg—New York—London—Paris—Tokio—Hong Kong, 1989, 426 pp.

    Google Scholar 

  20. V. Lokshin, A. Sama, A. V. Metelitsa, Usp. Khim., 2002, 71, 1015 [Russ. Chem. Rev., 2002, 71 (Engl. Transl.)].

    Google Scholar 

  21. V. Vargas C., J. Phys. Chem. A, 2004, 108, 281.

    Article  CAS  Google Scholar 

  22. J. S. Stephan, A. Mordzinski, C. Rios Rodriguez, K. H. Grellmann, Chem. Phys. Lett., 1994, 229, 541.

    Article  CAS  Google Scholar 

  23. A. Grabowska, K. Kownacki, J. Karpiuk, S. Dobrin, L. Kaczmarek, Chem. Phys. Lett., 1997, 267, 132.

    Article  CAS  Google Scholar 

  24. F. Bayrakceken, P. C. Sevinc, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 2007, 66, 184.

    Article  Google Scholar 

  25. G. O. Dudek, E. P. Dudek, J. Am. Chem. Soc., 1966, 88, 2407.

    Article  CAS  Google Scholar 

  26. R. N. Christie, C. K. Agyako, K. Mitchell, Dyes and Pigments, 1995, 29, 241.

    Article  CAS  Google Scholar 

  27. P. P. Levin, N. B. Sul’timova, O. N. Chaikovskaya, Izv. Akad. Nauk, Ser. Khim., 2005, 1391 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1433].

    Google Scholar 

  28. N. B. Sul’timova, P. P. Levin, O. N. Chaikovskaya, Izv. Akad. Nauk, Ser. Khim., 2005, 1397 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1439].

    Google Scholar 

  29. A. S. Tatikolov, S. M. B. Costa, J. Photochem. Photobiol. A: Chem., 2001, 140, 147.

    Article  CAS  Google Scholar 

  30. J.-L. Pozzo, A. Samat, R. Guglielmetti, D. De Keukeleire, J. Chem. Soc., Perkin Trans. 2, 1993, 1327.

  31. V. Yu. Nedoshivin, N. L. Zaichenko, N. N. Glagolev, V. S. Marevtsev, Izv. Akad. Nauk, Ser. Khim., 1996, 1243 [Russ. Chem. Bull., 1996, 45, 1182 (Engl. Transl.)].

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Correspondence to N. L. Zaichenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2346–2352, November, 2008.

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Zaichenko, N.L., Levin, P.P., Mardaleishvili, I.R. et al. Synthesis and kinetics of photochemical reactions of novel bifunctional salicylideneiminospironaphthoxazines. Russ Chem Bull 57, 2394–2401 (2008). https://doi.org/10.1007/s11172-008-0341-z

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  • DOI: https://doi.org/10.1007/s11172-008-0341-z

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