Advertisement

Russian Chemical Bulletin

, Volume 62, Issue 8, pp 1726–1739 | Cite as

Design of crystal packings of styryl heterocycles and regularities of [2+2] photocycloaddition in their single crystals 8. Topochemical [2+2] autophotocycloaddition and back reaction in styryl dye of the benzothiazole series

  • L. G. Kuz’mina
  • A. I. Vedernikov
  • E. Kh. Lermontova
  • J. A. K. Howard
  • M. V. Alfimov
  • S. P. Gromov
Full Articles

Abstract

New styryl dye of the 2-benzothiazole series was synthesized. The new dye contains two methoxy groups in the benzene ring and tosylate counterion. The [2+2] photocycloaddition (PCA) of the dye was studied in the polycrystalline film and in single crystal. Two modifications of the dye cocrystallizate with hydroquinone differed in the ratio of components were obtained, and their ability to enter PCA was studied. According to the X-ray diffraction data, molecular cations of the dye form stack packings either of syn-“head-to-tail” type or relatively isolated stacking dimers. In all cases, the ethylene bonds of the adjacent cations are brought together and antiparallel, favoring PCA to form the centrosymmetric rctt-isomer of 1,2,3,4-tetrasubstituted cyclobutane. In two cases, the PCA reaction proceeded as the “single crystal-to-single crystal” transformation. Hydrogen bonds in crystals including hydroquinone molecules strengthen the crystal packing retarding the PCA. The back photoreaction (retro-PCA) was detected: it occurs without single crystal decomposition and results in the accumulation of the initial styryl dye in crystal consisting of the cyclobutane derivative. This is the first example of such a transformation in single crystals.

Key words

styryl dye X-ray diffraction analysis solid phase [2+2] photocycloaddition retro[2+2] photocycloaddition cyclobutanes NMR spectroscopy 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    L. G. Kiz’mina, A. I. Vedernikov, S. K. Sazonov, N. A. Lobova, A. V. Churakov, E. Kh. Lermontova, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 1734 [Izv. Akad. Nauk, Ser. Khim., 2011, 1708].CrossRefGoogle Scholar
  2. 2.
    G. J. M. Schmidt, J. Pure Appl. Chem., 1971, 27, 647.CrossRefGoogle Scholar
  3. 3.
    L. R. MacGillivray, CrystEngComm, 2002, 4, No. 7, 37.CrossRefGoogle Scholar
  4. 4.
    I. Turowska-Tyrk, J. Phys. Org. Chem., 2004, 17, 837.CrossRefGoogle Scholar
  5. 5.
    C.-H. Huang, D. M. Bassani, Eur. J. Org. Chem., 2005, 4041.Google Scholar
  6. 6.
    T. Friščić, L. R. MacGillivray, Supramol. Chem., 2005, 17, 47.CrossRefGoogle Scholar
  7. 7.
    M. Nagarathinam, J. J. Vittal, Macromol. Rapid Commun., 2006, 27, 1091.CrossRefGoogle Scholar
  8. 8.
    J. Svoboda, B. König, Chem. Rev., 2006, 106, 5413.CrossRefGoogle Scholar
  9. 9.
    D.-K. Bu ar, G. S. Papaefstathiou, T. D. Hamilton, Q. L. Chu, I. G. Georgiev, L. R. MacGillivray, Eur. J. Inorg. Chem., 2007, 4559.Google Scholar
  10. 10.
    S. P. Gromov, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 1325 [Izv. Akad. Nauk, Ser. Khim., 2008, 1299].CrossRefGoogle Scholar
  11. 11.
    N. Hoffmann, Chem. Rev., 2008, 108, 1052.CrossRefGoogle Scholar
  12. 12.
    L. R. MacGillivray, J. Org. Chem., 2008, 73, 3311.CrossRefGoogle Scholar
  13. 13.
    L. R. MacGillivray, G. S. Papaefstathiou, T. Friščić, T. D. Hamilton, D.-K. Buèar, Q. Chu, D. B. Varshney, I. G. Georgiev, Acc. Chem. Res., 2008, 41, 280.CrossRefGoogle Scholar
  14. 14.
    J. A. K. Howard, M. F. Mahon, P. R. Raithby, H. A. Sparkes, Acta Crystallogr., Sect. B, 2009, B65, 230.CrossRefGoogle Scholar
  15. 15.
    A. Briceño, Y. Hill, T. González, G. D. de Delgado, Dalton Trans., 2009, 1602.Google Scholar
  16. 16.
    S. Yamada, Y. Tokugawa, J. Am. Chem. Soc., 2009, 131, 2098.CrossRefGoogle Scholar
  17. 17.
    J. W. Chung, Y. You, H. S. Huh, B.-K. An, S.-J. Yoon, S.-H. Kim, S. W. Lee, S. Y. Park, J. Am. Chem. Soc., 2009, 131, 8163.CrossRefGoogle Scholar
  18. 18.
    M. H. Mir, L. L. Koh, G. K. Tan, J. J. Vittal, Angew. Chem., Int. Ed., 2010, 49, 390.CrossRefGoogle Scholar
  19. 19.
    D. Liu, Z.-G. Ren, H.-X. Li, J.-P. Lang, N.-Y. Li, B. F. Abrahams, Angew. Chem., Int. Ed., 2010, 49, 4767.CrossRefGoogle Scholar
  20. 20.
    E. Elacqua, L. R. MacGillivray, Eur. J. Org. Chem., 2010, 6883.Google Scholar
  21. 21.
    B. R. Bhogala, B. Captain, A. Parthasarathy, V. Ramamurthy, J. Am. Chem. Soc., 2010, 132, 13434.CrossRefGoogle Scholar
  22. 22.
    S. Clément, F. Meyer, J. De Winter, O. Coulembier, C. M. L. Vande Velde, M. Zeller, P. Gerbaux, J.-Y. Balandier, S. Sergeyev, R. Lazzaroni, Y. Geerts, P. Dubois, J. Org. Chem., 2010, 75, 1561.CrossRefGoogle Scholar
  23. 23.
    M. Linares, A. Briceño, New J. Chem., 2010, 34, 587.CrossRefGoogle Scholar
  24. 24.
    I. G. Ovchinnikova, D. K. Nikulov, E. V. Bartashevich, E. G. Matochkina, M. I. Kodess, P. A. Slepukhin, A. V. Druzhinin, O. V. Fedorova, G. L. Rusiniv, V. N. Charushin, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 824 [Izv. Akad. Nauk, Ser. Khim., 2011, 805].CrossRefGoogle Scholar
  25. 25.
    R. Santra, K. Banerjee, K. Biradha, Chem. Commun., 2011, 47, 10740.CrossRefGoogle Scholar
  26. 26.
    G. K. Kole, G. K. Tan, J. J. Vittal, J. Org. Chem., 2011, 76, 7860.CrossRefGoogle Scholar
  27. 27.
    Y. Sonoda, Molecules, 2011, 16, 119.CrossRefGoogle Scholar
  28. 28.
    D.-K. Buèar, A. Sen, S. V. S. Mariappan, L. R. MacGillivray, Chem. Commun., 2012, 48, 1790.CrossRefGoogle Scholar
  29. 29.
    P. Zhang, Y. Wang, R. Bao, T. Luo, Z. Yang, Y. Tang, Org. Lett., 2012, 14, 162.CrossRefGoogle Scholar
  30. 30.
    E. Elacqua, P. Kaushik, R. H. Groeneman, J. C. Sumrak, D.-K. Buèar, L. R. MacGillivray, Angew. Chem. Int. Ed., 2012, 51, 1037.CrossRefGoogle Scholar
  31. 31.
    X.-M. Cheng, M. Chen, Z.-T. Huang, Q.-Y. Zheng, Synthesis, 2012, 3693.Google Scholar
  32. 32.
    R. Santra, M. Garai, D. Mondal, K. Biradha, Chem. Eur. J., 2013, 19, 489.CrossRefGoogle Scholar
  33. 33.
    S. Bhattacharya, J. Stojakovic’, B. K. Saha, L. R. Mac-Gillivray, Org. Lett., 2013, 15, 744.CrossRefGoogle Scholar
  34. 34.
    F. Li, J. Zhuang, G. Jiang, H. Tang, A. Xia, L. Jiang, Y. Song, Y. Li, D. Zhu, Chem. Mater., 2008, 20, 1194.CrossRefGoogle Scholar
  35. 35.
    A. Papagni, P. Del Buttero, C. Bertarelli, L. Miozzo, M. Moret, M. T. Pryce, S. Rizzato, New J. Chem., 2010, 34, 2612.CrossRefGoogle Scholar
  36. 36.
    A. I. Vedernikov, S. P. Gromov, N. A. Lobova, L. G. Kuz’mina, Yu. A. Strelenko, J. A. K. Howard, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 1954 [Izv. Akad. Nauk, Ser. Khim., 2005, 1896].CrossRefGoogle Scholar
  37. 37.
    L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, A. V. Churakov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, New J. Chem., 2007, 31, 980.CrossRefGoogle Scholar
  38. 38.
    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, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1860 [Izv. Akad. Nauk, Ser. Khim., 2007, 1797].CrossRefGoogle Scholar
  39. 39.
    L. G. Kuz’mina, A. I. Vedernikov, S. K. Sazonov, N. A. Lobova, P. S. Loginov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, Crystallogr. Repts (Engl. Transl.), 2008, 53, 428 [Kristallografiya, 2008, 53, 460].Google Scholar
  40. 40.
    L. G. Kuz’mina, A. I. Vedernikov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, Nanotechnologies in Russia (Engl. Transl.), 2008, 3, 408 [Rossiiskie nanotekhnologii, 2008, 3, Nos 7–8, 32].CrossRefGoogle Scholar
  41. 41.
    S. P. Gromov, A. I. Vedernikov, L. G. Kuz’mina, D. V. Kondratuk, S. K. Sazonov, Yu. A. Strelenko, M. V. Alfimov, J. A. K. Howard, Eur. J. Org. Chem., 2010, 2587.Google Scholar
  42. 42.
    L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, S. K. Sazonov, S. S. Basok, J. A. K. Howard, S. P. Gromov, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 1192 [Izv. Akad. Nauk, Ser. Khim., 2009, 1161].CrossRefGoogle Scholar
  43. 43.
    F. H. Allen, Acta Crystallogr., Sect. B, 2002, B58, 380.CrossRefGoogle Scholar
  44. 44.
    O. A. Fedorova, E. N. Andrjukhina, A. V. Lindeman, S. S. Basok, T. Yu. Bogaschenko, S. P. Gromov, Russ. Chem. Bull. (Int. Ed.), 2002, 51, 319 [Izv. Akad. Nauk, Ser. Khim., 2002, 302].CrossRefGoogle Scholar
  45. 45.
    A. C. Pardal, S. S. Ramos, P. F. Santos, L. V. Reis, P. Almeida, Molecules, 2002, 7, 320.CrossRefGoogle Scholar
  46. 46.
    SHELXTL-Plus, Version 5.10, Bruker AXS Inc., Madison, Wisconsin (USA), 1997.Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • L. G. Kuz’mina
    • 1
  • A. I. Vedernikov
    • 2
  • E. Kh. Lermontova
    • 1
  • J. A. K. Howard
    • 3
  • M. V. Alfimov
    • 2
  • S. P. Gromov
    • 2
  1. 1.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Photochemistry CentreRussian Academy of SciencesMoscowRussian Federation
  3. 3.Department of ChemistryUniversity of DurhamDurhamUK

Personalised recommendations