High Energy Chemistry

, Volume 53, Issue 3, pp 198–203 | Cite as

Photoprocesses in 2-Benzylidene-5-(pyridin-4-ylmetylidene)cyclopentanone and Its Derivatives in Acetonitrile

  • V. N. Gutrov
  • G. V. ZakharovaEmail author
  • M. A. Artsiusheuski
  • V. N. Nuriev
  • S. Z. Vatsadze
  • S. P. GromovEmail author
  • A. K. Chibisov


The results of the study of the spectral, luminescent, and spectral–kinetic properties of 2-benzylidene-5-(pyridin-4-ylmethylidene)cyclopentanone and its diethylamino, methoxy, methylthio, and dimethoxy derivatives in acetonitrile at room temperature are presented. The introduction of electron-donating substituents leads to a bathochromic shift of the absorption maximum by 121 nm with respect to the maximum of the unsubstituted dienone and a bathochromic shift of the fluorescence maximum by 129 nm with respect to the maximum of the methoxy derivative. Upon laser irradiation of deoxygenated solutions of the dienones, intersystem crossing to the triplet state with a lifetime of 0.7–3.0 μs occurs, whereas for the methoxy, methylthio, and dimethoxy derivatives of the dienone, the formation of a stable photoproduct is observed.


ketocyanine dyes absorption fluorescence nanosecond laser flash photolysis 



This work was supported by the Russian Science Foundation (project no. 14-13-00076) in part of the synthesis of ketоcyanines and by the Ministry of Science and Higher Education within the State assignment FSRC “Crystallography and Photonics” of the Russian Academy of Sciences in part of the spectral–kinetic measurements of ketоcyanines.


  1. 1.
    Doroshenko, A.O. and Pivovarenko, V.G., J. Photochem. Photobiol., A, 2003, vol. 156, nos. 1–3, p. 55.CrossRefGoogle Scholar
  2. 2.
    Khalaf, A.A., Etaiw, S.H., Issa, R.M., and El-Shafei, A.K., Rev. Roum. Chim., 1977, vol. 22, p. 1251.Google Scholar
  3. 3.
    Kessler, M.A. and Wolfbeis, O.S., Spectrochim. Acta, Part A, 1991, vol. 47, no. 2, p. 187.CrossRefGoogle Scholar
  4. 4.
    Barnabas, M.V., Liu, A., and Trifunac, A.D., et al., J. Phys. Chem., 1992, vol. 96, no. 1, p. 212.CrossRefGoogle Scholar
  5. 5.
    Zoto, C.A., Ucak-Astarlioglu, M.G., and Connors, R.E., J. Mol. Struct., 2016, vol. 1105, p. 396.CrossRefGoogle Scholar
  6. 6.
    Vatsadze, S.Z., Manaenkova, M.A., Sviridenkova, N.V., et al., Izv. Akad. Nauk, Ser. Khim., 2006, vol. 55, p. 1141.Google Scholar
  7. 7.
    Vatsadze, S.Z., Golikov, A.G., Kriven’ko, A.P., and Zyk, N.V., Usp. Khim., 2008, vol. 77, no. 8, p. 707.CrossRefGoogle Scholar
  8. 8.
    Doroshenko, A.O., Grigorovich, A.V., and Posokhov, E.A., et al., Mol. Eng., 1998, vol. 8, no. 3, p. 199.CrossRefGoogle Scholar
  9. 9.
    Rurack, K., Dekhtyar, M.L., and Bricks, J.L., et al., J. Phys. Chem. A, 1999, vol. 103, no. 48, p. 9626.CrossRefGoogle Scholar
  10. 10.
    Rurack, K., Bricks, J.L., and Reck, G., et al., J. Phys. Chem. A, 2000, vol. 104, no. 14, p. 3087.CrossRefGoogle Scholar
  11. 11.
    Doroshenko, A.O., Sychevskaya, L.B., Grygorovych, A.V., and Pivovarenko, V.G., J. Fluoresc., 2002, vol. 12, nos 3-4, p. 455.CrossRefGoogle Scholar
  12. 12.
    Zakharova, G.V., Zyuz’kevich, F.S., Gutrov, V.N., et al., High Energy Chem., 2017, vol. 51, no. 2, p. 113.CrossRefGoogle Scholar
  13. 13.
    Atabekyan, L.S., Chibisov, A.K., and Alfimov, M.V., High Energy Chem., 1997, vol. 31, no. 5, p. 344.Google Scholar
  14. 14.
    Zakharova, G.V., Avakyan, V.G., Markelov, V.P., et al., High Energy Chem., 2015, vol. 49, no. 6, p. 407.CrossRefGoogle Scholar
  15. 15.
    Mondal, J.A.L., Verma, S., Ghosh, H.N., and Palit, D.K., J. Chem. Sci., 2008, vol. 120, no. 1, p. 45.CrossRefGoogle Scholar
  16. 16.
    Marcotte, N., Feryforgues s, J. Photochem. Photobiol., A, 2000, vol. 130, p. 133.CrossRefGoogle Scholar
  17. 17.
    Gutrov, V.N., Zakharova, G.V., Zyuz’kevich, F.S., et al., High Energy Chem., 2018, vol. 52, no. 6, p. 475.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • V. N. Gutrov
    • 1
  • G. V. Zakharova
    • 1
    Email author
  • M. A. Artsiusheuski
    • 2
  • V. N. Nuriev
    • 1
    • 2
  • S. Z. Vatsadze
    • 1
    • 2
  • S. P. Gromov
    • 1
    • 2
    Email author
  • A. K. Chibisov
    • 1
  1. 1.Photochemistry Center of Federal Scientific Research Center “Crystallography and Photonics”, Russian Academy of SciencesMoscowRussia
  2. 2.Faculty of Chemistry, Moscow State UniversityMoscowRussia

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