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Russian Chemical Bulletin

, Volume 56, Issue 9, pp 1860–1883 | Cite as

Styryl dyes. Synthesis and study of the solid-state [2+2] autophotocycloaddition by NMR spectroscopy and X-ray diffraction

  • A. I. Vedernikov
  • L. G. Kuz’mina
  • S. K. Sazonov
  • N. A. Lobova
  • P. S. Loginov
  • A. V. Churakov
  • Yu. A. Strelenko
  • J. A. K. Howard
  • M. V. Alfimov
  • S. P. Gromov
Article

Abstract

New styryl dyes of the pyridine and benzothiazole series were synthesized with the aim of investigating the solid-state [2+2] autophotocycloaddition (PCA) reaction. The 1H NMR spectroscopy showed that for most of the compounds under study, the visible light irradiation of thin polycrystalline films of the dyes affords cyclobutane derivatives. The rate of the photoreaction depends on the structure of the dye and is higher for compounds, which contain a short N-substituent in the heterocyclic moiety and have strong absorption in the visible region. Dyes bearing electron-releasing substituents in the benzene ring undergo the stereospecific PCA in the syn-head-to-tail dimeric pair to give the only rctt isomer of cyclobutane derivatives. Electron-withdrawing and bulky substituents in the benzene fragment of styryl dyes extend the range of the mutual orientations of the molecules in the dimeric pairs, resulting in the formation of two or even four isomeric cyclobutanes in the PCA reactions. The structures of some dyes were established by X-ray diffraction. In the overwhelming majority of the structures, one of two packing modes, either syn-head-to-tail or syn-head-to-head, with extensive stacking interactions is observed. A rare example of the anti-head-to-head stacking mode was found for the dicationic dye containing the bulky N+(Et)Me2 substituent in the benzene ring. The syn-head-to-tail and anti-head-to-head stacking modes can facilitate the PCA reaction due to the close spatial proximity of the ethylenic bonds and their parallel orientation in the dimeric pairs of the dye molecules.

Key words

styryl dyes crown ethers structure [2+2] photocycloaddition topochemical reaction cyclobutanes X-ray diffraction 1H NMR spectroscopy 

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References

  1. 1.
    M. D. Cohen and G. M. Schmidt, J. Chem. Soc., 1964, 1996.Google Scholar
  2. 2.
    G. M. Schmidt, J. Pure Appl. Chem., 1971, 27, 647.Google Scholar
  3. 3.
    V. Ramamurthy and K. Venkatesan, Chem. Rev., 1987, 87, 433.CrossRefGoogle Scholar
  4. 4.
    K. S. S. P. Rao, S. M. Hubig, J. N. Moorthy, and J. K. Kochi, J. Org. Chem., 1999, 64, 8098.CrossRefGoogle Scholar
  5. 5.
    T. D. Hamilton, G. S. Papaefstathiou, and L. R. MacGillivray, J. Am. Chem. Soc., 2002, 124, 11606.CrossRefGoogle Scholar
  6. 6.
    L. R. MacGillivray, Cryst. Eng. Commun., 2002, 4, 37.Google Scholar
  7. 7.
    V. Darcos, K. Griffith, X. Sallenave, J.-P. Desvergne, C. Guyard-Duhayon, B. Hasenknopf, and D. M. Bassani, Photochem. Photobiol. Sci., 2003, 2, 1152.CrossRefGoogle Scholar
  8. 8.
    J. Hockemeyer, J. C. Burbiel, and C. E. Müller, J. Org. Chem., 2004, 69, 3308.CrossRefGoogle Scholar
  9. 9.
    T. Caronna, R. Liantonio, T. A. Logothetis, P. Metrangolo, T. Pilati, and G. Resnati, J. Am. Chem. Soc., 2004, 126, 4500.CrossRefGoogle Scholar
  10. 10.
    H. Maeda, K. Nishimura, K. Mizuno, M. Yamaji, J. Oshima, and S. Tobita, J. Org. Chem., 2005, 70, 9693.CrossRefGoogle Scholar
  11. 11.
    F. H. Allen, M. F. Mahon, P. R. Raithby, G. P. Shields, and H. A. Sparkes, New J. Chem., 2005, 29, 182.CrossRefGoogle Scholar
  12. 12.
    Y. Ohashi, Acta Crystallogr., Sect. A, 1998, 54, 842.CrossRefGoogle Scholar
  13. 13.
    H. Hosomi, S. Ohba, K. Tanaka, and F. Toda, J. Am. Chem. Soc., 2000, 122, 1818.CrossRefGoogle Scholar
  14. 14.
    I. Turowska-Tyrk, J. Phys. Org. Chem., 2004, 17, 837.CrossRefGoogle Scholar
  15. 15.
    H. Nalanishi, W. Jones, J. M. Thomas, and K. Honda, Bull. Chem. Soc. Jpn, 2002, 75, 2383.CrossRefGoogle Scholar
  16. 16.
    S. P. Gromov and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1997, 641 [Russ. Chem. Bull., 1997, 46, 611 (Engl. Transl.)].Google Scholar
  17. 17.
    S. P. Gromov, E. N. Ushakov, O. A. Fedorova, I. I. Baskin, A. V. Buevich, E. N. Andryukhina, M. V. Alfimov, D. Johnels, U. G. Edlund, J. K. Whitesell, and M. A. Fox, J. Org. Chem., 2003, 68, 6115.CrossRefGoogle Scholar
  18. 18.
    A. I. Vedernikov, N. A. Lobova, E. N. Ushakov, M. V. Alfimov, and S. P. Gromov, Mendeleev Commun., 2005, 15, 173.CrossRefGoogle Scholar
  19. 19.
    A. I. Vedernikov, S. K. Sazonov, P. S. Loginov, N. A. Lobova, M. V. Alfimov, and S. P. Gromov, Mendeleev Commun., 2007, 17, 29.CrossRefGoogle Scholar
  20. 20.
    A. I. Vedernikov, S. P. Gromov, N. A. Lobova, L. G. Kuz’mina, Yu. A. Strelenko, J. A. K. Howard, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 2005, 1896 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1954].Google Scholar
  21. 21.
    S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. N. Dmitrieva, O. V. Tikhonova, and M. V. Alfimov, Pat. RF 2278134; Byul. izobret. [Inventor Bull.], 2006, No. 17 (in Russian).Google Scholar
  22. 22.
    L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, A. V. Churakov, J. A. K. Howard, M. V. Alfimov, and S. P. Gromov, New J. Chem., 2007, 31, 980.CrossRefGoogle Scholar
  23. 23.
    L. G. Kuz’mina, A. I. Vedernikov, S. K. Sazonov, N. A. Lobova, P. S. Loginov, J. A. K. Howard, M. V. Alfimov, and S. P. Gromov, Kristallografiya, 2008, 53, No 2 [Crystallogr. Repts, 2008, 53 (Engl. Transl.)].Google Scholar
  24. 24.
    J. L. R. Williams, R. E. Adel, J. M. Carlson, G. A. Reynolds, D. G. Borden, and J. A. Ford, J. Org. Chem., 1963, 28, 387.CrossRefGoogle Scholar
  25. 25.
    A. K. Yatsimirskii, Itogi nauki i tekhniki. Bioorganicheskaya khimiya [Advances in Science and Technology, Ser. Bioorganic Chemistry], VINITI, Moscow, 1990, 17, 148 (in Russian).Google Scholar
  26. 26.
    T. Steiner, Acta Crystallogr., Sect. B, 1998, 54, 456.CrossRefGoogle Scholar
  27. 27.
    D. A. Dickie, D. Abeysekera, I. D. VcKenzie, H. A. Jenkins, and J. C. Clyburne, Cryst. Eng., 2003, 6, 79.CrossRefGoogle Scholar
  28. 28.
    T. Sakurai, J. Nucl. Sci. Technol., 1996, 33, 266.Google Scholar
  29. 29.
    R. Grünwald and H. Tributsch, J. Phys. Chem. B, 1997, 101, 2564.CrossRefGoogle Scholar
  30. 30.
    S. P. Gromov, D. E. Levin, K. Ya. Burshtein, V. E. Krasnovskii, S. N. Dmitrieva, A. A. Golosov, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1997, 999 [Russ. Chem. Bull., 1997, 46, 959 (Engl. Transl.)].Google Scholar
  31. 31.
    S. P. Gromov, E. N. Ushakov, O. A. Fedorova, V. A. Soldatenkova, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1997, 1192 [Russ. Chem. Bull., 1997, 46, 1143 (Engl. Transl.)].Google Scholar
  32. 32.
    H. Görner and H. Gruen, J. Photochem., 1985, 28, 329.CrossRefGoogle Scholar
  33. 33.
    S. P. Gromov, A. I. Vedernikov, Yu. V. Fedorov, O. A. Fedorova, E. N. Andryukhina, N. E. Shepel’, Yu. A. Strelenko, D. Johnels, U. G. Edlund, J. Saltiel, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 2005, 1524 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1569].Google Scholar
  34. 34.
    M. V. Alfimov, S. P. Gromov, O. B. Stanislavskii, E. N. Ushakov, and O. A. Fedorova, Izv. Akad. Nauk, Ser. Khim., 1993, 1449 [Russ. Chem. Bull., 1993, 42, 1385 (Engl. Transl.)].Google Scholar
  35. 35.
    S. P. Gromov, O. A. Fedorova, E. N. Ushakov, A. V. Buevich, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1995, 2225 [Russ. Chem. Bull., 1995, 44, 2131 (Engl. Transl.)].Google Scholar
  36. 36.
    O. A. Fedorova, Yu. V. Fedorov, A. I. Vedernikov, S. P. Gromov, O. V. Yescheulova, M. V. Alfimov, M. Woerner, S. Bossmann, A. Braun, and J. Saltiel, J. Phys. Chem. A, 2002, 106, 6213.CrossRefGoogle Scholar
  37. 37.
    D. Donati, M. Fiorenza, and P. S. Fautoni, J. Heterocycl. Chem., 1979, 16, 253.CrossRefGoogle Scholar
  38. 38.
    S. K. Kearsley, Studies in Organic Chemistry. 32. Organic Solid State Chemistry, Ed. G. R. Desiraju, Elsevier, Amsterdam, 1987, 32, 69.Google Scholar
  39. 39.
    M. V. Alfimov, A. V. Churakov, Yu. V. Fedorov, O. A. Fedorova, S. P. Gromov, R. E. Hester, J. A. K. Howard, L. G. Kuz’mina, I. K. Lednev, and J. N. Moore, J. Chem. Soc., Perkin Trans. 2, 1997, 2249.Google Scholar
  40. 40.
    O. A. Fedorova, Yu. V. Fedorov, A. I. Vedernikov, O. V. Yescheulova, S. P. Gromov, M. V. Alfimov, L. G. Kuz’mina, A. V. Churakov, J. A. K. Howard, S. Yu. Zaitsev, T. I. Sergeeva, and D. Möbius, New J. Chem., 2002, 26, 543.CrossRefGoogle Scholar
  41. 41.
    S. P. Gromov, A. I. Vedernikov, E. N. Ushakov, L. G. Kuz’mina, A. V. Feofanov, V. G. Avakyan, A. V. Churakov, Yu. S. Alaverdian, E. V. Malysheva, M. V. Alfimov, J. A. K. Howard, B. Eliasson, and U. G. Edlund, Helv. Chim. Acta, 2002, 85, 60.CrossRefGoogle Scholar
  42. 42.
    S. P. Gromov, S. A. Sergeev, S. I. Druzhinin, M. V. Rusalov, B. M. Uzhinov, L. G. Kuz’mina, A. V. Churakov, J. A. K. Howard, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1999, 530 [Russ. Chem. Bull., 1999, 48, 525 (Engl. Transl.)].Google Scholar
  43. 43.
    E. N. Andryukhina, M. M. Mashura, O. A. Fedorova, L. G. Kuz’mina, J. A. K. Howard, and S. P. Gromov, Izv. Akad. Nauk, Ser. Khim., 2005, 1650 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1700].Google Scholar
  44. 44.
    A. K. Sheinkman and L. G. Piotrkovskaya, Metody polucheniya khimicheskikh reaktivov i preparatov [Methods for the Synthesis of Chemical Reagents and Preparations], IREA, Moscow, 1965, Vol. 13, 29 (in Russian).Google Scholar
  45. 45.
    O. A. Fedorova, E. N. Andryukhina, A. V. Lindeman, S. S. Basok, T. Yu. Bogashchenko, and S. P. Gromov, Izv. Akad. Nauk, Ser. Khim., 2002, 302 [Russ. Chem. Bull., Int. Ed., 2002, 51, 319].Google Scholar
  46. 46.
    F. Cherioux, P. Audebert, and P. Hapiot, Chem. Mater., 1998, 10, 1984.CrossRefGoogle Scholar
  47. 47.
    SAINT, Version 6.02A, Bruker AXS Inc., Madison (Wisconsin, USA), 2001.Google Scholar
  48. 48.
    SHELXTL-Plus, Version 5.10, Bruker AXS Inc., Madison (Wisconsin, USA), 1997.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • A. I. Vedernikov
    • 1
  • L. G. Kuz’mina
    • 2
  • S. K. Sazonov
    • 1
  • N. A. Lobova
    • 1
  • P. S. Loginov
    • 1
  • A. V. Churakov
    • 2
  • Yu. A. Strelenko
    • 3
  • J. A. K. Howard
    • 4
  • M. V. Alfimov
    • 1
  • S. P. Gromov
    • 1
  1. 1.Photochemistry CenterRussian Academy of SciencesMoscowRussian Federation
  2. 2.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  4. 4.Department of ChemistryUniversity of DurhamDurhamUK

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