Advertisement

Review Journal of Chemistry

, Volume 1, Issue 1, pp 1–26 | Cite as

Self-assembly and [2 + 2]-photocycloaddition to give cyclobutanes of unsaturated and macrocyclic compounds

  • S. P. Gromov
Article

Abstract

The effect of complexation with crown compounds and cucurbiturils on the photochemical behavior of styryl, bis-styryl, and butadienyl dyes containing various heterocyclic residues and N-substituents was studied by electronic and NMR spectroscopy and X-ray analysis. In solutions, these dyes and macrocyclic compounds are capable of undergoing self-assembly into highly stable dimeric, pseudodimeric, sandwich, bis-sandwich, pseudosandwich, bis-pseudosandwich, and bi- and trimolecular pseudorotaxane complexes. In these supramolecular complexes, the dye molecules can undergo two competing photoreactions: stereoselective [2 + 2]-cycloaddition to form cyclobutane and geometrical trans-cis-isomerization. The path of the photochemical transformation of the unsaturated dye and the quantum yields of the competing photoreactions can be controlled by selectively modifying the N-substituent containing a terminal functional group. The potential applications of these studies are considered and a new strategy for the design of materials for nanophotonics is suggested.

Keywords

[2 + 2]-photocycloaddition trans-cis-photoisomerization unsaturated compounds crown compounds cucurbiturils molecular devices molecular machines 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Barltrop, J. and Coyle, J., Excited States in Organic Chemistry, London: Wiley, 1975Google Scholar
  2. 2.
    Wayne, R.P., Principles and Applications of Photochemistry, Oxpord: Oxford Univ. Press, 1988.Google Scholar
  3. 3.
    Razumov, V.F. and Alfimov, M.V., Zh. Nauchn. Prikl. Fotogr., 2003, vol. 48, no. 6, p. 28.Google Scholar
  4. 4.
    Organicheskie fotokhromy (Organic Photochromes), El’tsov, A.V., Ed., Leningrad: Khimiya, 1982.Google Scholar
  5. 5.
    Photochromism: Molecules and Systems, Durr, H. and Bouas-Laurent, H., Eds., Amsterdam: Elsevier, 1990.Google Scholar
  6. 6.
    Gromov, S.P. and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1997, no. 4, p. 641 [Russ. Chem. Bull., Int. Ed., 1997, vol. 46, p. 611].Google Scholar
  7. 7.
    Molecular Switches, Feringa, B.L., Ed., Weinheim: Wiley, 2001.Google Scholar
  8. 8.
    Host-Guest Complex Chemistry of Macrocycles, Vögtle, F. and Weber, E., Eds., Berlin: Springer, 1985.Google Scholar
  9. 9.
    Cation Binding by Macrocycles, Inoue, Y. and Gokel, G.W., Eds., New York: Marcel Dekker, 1990.Google Scholar
  10. 10.
    Shinkai, S., in Comprehensive Supramolecular Chemistry, Lehn, J.M., Ed., New York: Pergamon, 1996, vol. 1, p. 671.Google Scholar
  11. 11.
    Lehn, J.M., Supramolecular Chemistry: Concepts and Perspectives, Weinheim: VCH, 1995.Google Scholar
  12. 12.
    Steed, J.W. and Atwood, J.L., Supramolecular Chemistry, Chichester: Wiley, 2000.Google Scholar
  13. 13.
    Gromov, S.P., Ross. Khim. Zh., 2001, vol. 45, no. 3, p. 116.Google Scholar
  14. 14.
    Gromov, S.P., Ross. Nanotekhnol., 2006, vol. 1, nos. 1–2, p. 29.Google Scholar
  15. 15.
    Gromov, S.P., Izv. Akad. Nauk, Ser. Khim., 2008, no. 7, p. 1299 [Russ. Chem. Bull., Int. Ed., 2008, vol. 57, p. 1325].Google Scholar
  16. 16.
    Gromov, S.P., Fedorova, O.A., Alfimov, M.V., Tkachev, V.V., and Atovmyan, L.O., Dokl. Akad. Nauk SSSR, 1991, vol. 319, p. 1141.Google Scholar
  17. 17.
    Gromov, S.P., Sergeev, S.A., Druzhinin, S.I., Rusalov, M.V., Uzhinov, B.M., Kuz’mina, L.G., Churakov, A.V., Khovard, Dzh.A.K., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1999, no. 3, p. 530 [Russ. Chem. Bull., Int. Ed., 1999, vol. 48, p. 525].Google Scholar
  18. 18.
    Gromov, S.P., Fomina, M.V., Ushakov, E.N., Lednev, I.K., and Alfimov, M.V., Dokl. Akad. Nauk SSSR, 1990, vol. 314, p. 1135.Google Scholar
  19. 19.
    Gromov, S.P., Fomina, M.V., Chudinova, G.K., Barachevskii, V.A., and Alfimov, M.V., Dokl. Akad. Nauk SSSR, 1991, vol. 321, p. 739.Google Scholar
  20. 20.
    Gromov, S.P., Fomina, M.V., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1993, no. 9, p. 1625 [Russ. Chem. Bull., Int. Ed., 1993, vol. 42, p. 1561].Google Scholar
  21. 21.
    Lednev, K., Fomina, M.V., Gromov, S.P., Stanislavsky, O.B., Alfimov, M.V., Moore, J.N., and Hester, R.E., Spectrochim. Acta, A 1992, vol. 48, p. 931.CrossRefGoogle Scholar
  22. 22.
    Gromov, S.P., Fedorova, O.A., Fomina, M.V., and Alfimov, M.V., RF Patent 2012574, Byull. izobret., 1994, no. 9.Google Scholar
  23. 23.
    Gromov, S.P., Levin, D.E., Burshtein, K.Ya., Krasnovskii, V.A., Dmitrieva, S.N., Golosov, A.A., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1997, no. 5, p. 999 [Russ. Chem. Bull., Int. Ed., 1997, vol. 46, p. 959].Google Scholar
  24. 24.
    Alfimov, M.V., Gromov, S.P., and Lednev, I.K., Chem. Phys. Lett., 1991, vol. 185, nos. 5–6, p. 455.CrossRefGoogle Scholar
  25. 25.
    Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Stanislavskii, O.B., Lednev, I.K., and Alfimov, M.V., Dokl. Akad. Nauk SSSR, 1991, vol. 317, no. 5, p. 1134.Google Scholar
  26. 26.
    Lednev, I.K., Gromov, S.P., Ushakov, E.N., Alfimov, M.V., Moore, J.N., and Hester, R.E., Spectrochim. Acta, 1992, vol. 48, no. 6, p. 799.CrossRefGoogle Scholar
  27. 27.
    Barzykin, A.V., Fox, M.A., Ushakov, E.N., Stanislavsky, O.B., Gromov, S.P., Fedorova, O.A., and Alfimov, M.V., J. Am. Chem. Soc., 1992, vol. 114, no. 16, p. 6381.CrossRefGoogle Scholar
  28. 28.
    Baskin, I.I., Burshtein, K.Ya., Bagatur’yants, A.A., Gromov, S.P., and Alfimov, M.V., Dokl. Akad. Nauk, 1992, vol. 325, no. 2, p. 306.Google Scholar
  29. 29.
    Baskin, I.I., Burstein, K.Ya., Bagatur’yants, A.A., Gromov, S.P., and Alfimov, M.V., J. Mol. Struct., 1992, vol. 274, p. 93.CrossRefGoogle Scholar
  30. 30.
    Baskin, I.I., Burshtein, K.Ya., Bagatur’yants, A.A., Gromov, S.P., and Alfimov, M.V., Zh. Strukt. Khim., 1993, vol. 33, p. 29.Google Scholar
  31. 31.
    Stanislavskii, O.B., Ushakov, E.N., Gromov, S.P., Fedorova, O.A., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1996, no. 3, p. 605 [Russ. Chem. Bull., Int. Ed., 1996, vol. 45, p. 564].Google Scholar
  32. 32.
    Ushakov, E.N., Stanislavskii, O.B., Gromov, S.P., Fedorova, O.A., and Alfimov, M.V., Dokl. Akad. Nauk, 1992, vol. 323, no. 4, p. 702.Google Scholar
  33. 33.
    Alfimov, M.V., Gromov, S.P., Stanislavskii, O.B., Ushakov, E.N., and Fedorova, O.A., Izv. Akad. Nauk, Ser. Khim., 1993, no. 8, p. 1449 [Russ. Chem. Bull., Int. Ed., 1993, vol. 42, p. 1385].Google Scholar
  34. 34.
    Baskin, I.I., Bagatur’yants, A.A., Gromov, S.P., and Alfimov, M.V., Dokl. Akad. Nauk, 1994, vol. 335, no. 3, p. 313.Google Scholar
  35. 35.
    Alfimov, M.V. and Gromov, S.P., in Applied Fluorescence in Chemistry, Biology, and Medicine, Rettig, W., Strehmel, B., Schrader, S., and Seifert, H., Eds., Berlin: Springer, 1999, p. 161.Google Scholar
  36. 36.
    Fedorova, O.A., Fedorov, Y.V., Vedernikov, A.I., Gromov, S.P., Yescheulova, O.V., Alfimov, M.V., Woerner, M., Bossmann, S., Braun, A., and Saltiel, J., J. Phys. Chem., A, 2002, vol. 106, p. 6213.CrossRefGoogle Scholar
  37. 37.
    Gromov, S.P., Ushakov, E.N., Fedorova, O.A., Buevich, A.V., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1996, no. 3, p. 693 [Russ. Chem. Bull., Int. Ed., 1996, vol. 45, p. 654].Google Scholar
  38. 38.
    Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Baskin, I.I., Lindeman, A.V., Malysheva, E.V., Balashova, T.A., Arsen’ev, A.S., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1998, no. 1, p. 99 [Russ. Chem. Bull., Int. Ed., 1998, vol. 47, p. 97].Google Scholar
  39. 39.
    Ushakov, E.N., Gromov, S.P., Buevich, A.V., Baskin, I.I., Fedorova, O.A., Vedernikov, A.I., Alfimov, M.V., Eliasson, B., and Edlund, U., J. Chem. Soc., Perkin Trans., 1999, no. 3, p. 601.Google Scholar
  40. 40.
    Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Buevich, A.V., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1995, no. 11, p. 2225 [Russ. Chem. Bull., Int. Ed., 1995, vol. 44, p. 2131].Google Scholar
  41. 41.
    Gromov, S.P., Ushakov, E.N., Fedorova, O.A., Baskin, I.I., Buevich, A.V., Andryukhina, E.N., Alfimov, M.V., Johnels, D., Edlund, U.G., Whitesell, J.K., and Fox, M.A., J. Org. Chem., 2003, vol. 68, no. 16, p. 6115.CrossRefGoogle Scholar
  42. 42.
    Freidzon, A.Ya., Baskin, I.I., Bagatur’yants, A.A., Gromov, S.P., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 1998, no. 11, p. 2185 [Russ. Chem. Bull., Int. Ed., 1998, vol. 47, p. 2117].Google Scholar
  43. 43.
    Gromov, S.P., Vedernikov, A.I., Ushakov, E.N., Kuz’mina, L.G., Feofanov, A.V., Avakyan, V.G., Churakov, A.V., Alaverdyan, Yu.S., Malysheva, E.V., Alfimov, M.V., Howard, J.A.K., Eliasson, B., and Edlund, U.G., Helv. Chim. Acta, 2002, vol. 85, no. 1, p. 60.CrossRefGoogle Scholar
  44. 44.
    Ushakov, E.N., Gromov, S.P., Kuz’mina, L.G., Vedernikov, A.I., Avakyan, V.G., Khovard, Dzh.A.K., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 2004, no. 7, p. 1491 [Russ. Chem. Bull., Int. Ed., 2004, vol. 53, p. 1549].Google Scholar
  45. 45.
    Vedernikov, A.I., Ushakov, E.N., Kuz’mina, L.G., Zaitsev, S.Yu., Karishnikova, M.S., Strelenko, Yu.A., Alfimov, M.V., Shurakov, A.V., Sergeeva, T.I., Howard, J.A.K., Johnels, D., Edlund, U.G., Gloe, K., and Gromov, S.R., XVII Mendeleevskii S”ezd po Obshchei i Prikladnoi Khimii (Proc. XVII Mendeleev Conf. on General and Applied Chemistry), Kazan, 2003, p. 21.Google Scholar
  46. 46.
    Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Buevich, A.V., Baskin, I.I., Pershina, Y.V., Eliasson, B., Edlund, U., and Alfimov, M.V., J. Chem. Soc., Perkin Trans., 1999, no. 7, p. 1323.Google Scholar
  47. 47.
    Ushakov, E.N., Gromov, S.P., Fedorova, O.A., Pershina, Y.V., Alfimov, M.V., Barigelletti, F., Flamigni, L., and Balzani, V., J. Phys. Chem., A, 1999, vol. 103, no. 50, p. 11188.CrossRefGoogle Scholar
  48. 48.
    Kuz’mina, L.G., Churakov, A.V., Khovard, Dzh.A.K., Fedorova, O.A., Gromov, S.P., and Alfimov, M.V., Kristallografiya, 2003, vol. 48, no. 4, p. 664 [Crystallogr. Rep. (Engl. Transl.), vol. 48, no. 4, p. 613].Google Scholar
  49. 49.
    Gromov, S.P., Vedernikov, A.I., Fedorov, Yu.V., Fedorova, O.A., Andryukhina, E.N., Shepel’, N.E., Strelenko, Yu.A., Dzhonels, D., Edlund, U., Saltiel, Zh., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 2005, no. 7, p. 1524 [Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 1569].Google Scholar
  50. 50.
    Gromov, S.P., Vedernikov, A.I., Lobova, N.A., Basok, S.S., Strokach, Yu.P., Kuz’mina, L.G., Valova, T.M., Ivanov, E.I., Howard, J.A.K., and Alfimov, M.V., XXX Int. Symp. on Macrocyclic Chemistry, Drezden, 2005, p. 114.Google Scholar
  51. 51.
    Vedernikov, A.I., Kondratuk, D.V., Lobova, N.A., Valova, T.M., Barachevsky, V.A., Alfimov, M.V., and Gromov, S.P., Mendeleev Commun., 2007, vol. 17, no. 5, p. 264.CrossRefGoogle Scholar
  52. 52.
    Avakyan, V.G., Kondratuk, D.V., Vedernikov, A.I., Kuz’mina, L.G., Rudyak, V.Yu., Alfimov, M.V., Howard, J.A.K., and Gromov, S.P., J. Mol. Struct., 2009, vol. 935, p. 136.CrossRefGoogle Scholar
  53. 53.
    Gromov, S.P., Vedernikov, A.I., Lobova, N.A., Kuz’mina, L.G., Dmitrieva, S.N., Tikhonova, O.V., and Alfimov, M.V., RF Patent 2278134, Byull. izobret., 2006, no. 17.Google Scholar
  54. 54.
    Gromov, S.P., Lobova, N.A., Vedernikov, A.I., Kuz’mina, L.G., Khovard, Dzh.A.K., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 2009, no. 6, p. 1179 [Russ. Chem. Bull., Int. Ed., 2009, vol. 58, p. 1211].Google Scholar
  55. 55.
    Vedernikov, A.I., Gromov, S.P., Lobova, N.A., Kuz’mina, L.G., Strelenko, Yu.A., Khovard, Dzh.A.K., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 2005, no. 8, p. 1896 [Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 1954].Google Scholar
  56. 56.
    Vedernikov, R.I., Sazonov, S.K., Loginov, P.S., Lobova, N.A., Alfimov, M.V., and Gromov, S.P., Mendeleev Commun., 2007, vol. 17, no. 1, p. 29.CrossRefGoogle Scholar
  57. 57.
    Vedernikov, A.I., Sazonov, S.K., Kuz’mina, L.G., Khovard, Dzh.A.K., Alfimov, M.V., and Gromov, S.P., Izv. Akad. Nauk, Ser. Khim., 2009, no. 9, p. 1893 [Russ. Chem. Bull., Int. Ed., 2009, vol. 58, p. 2289].Google Scholar
  58. 58.
    Gromov, S.P., Vedernikov, A.I., Sazonov, S.K., Lobova, N.A., and Alfimov, M.V., RF Patent 2383571, Byull. izobret., 2010, no. 7.Google Scholar
  59. 59.
    Vedernikov, A.I., Ushakov, E.N., Lobova, N.A., Kiselev, A.A., Alfimov, M.V., and Gromov, S.P., Izv. Akad. Nauk, Ser. Khim., 2005, no. 3, p. 656 [Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 666].Google Scholar
  60. 60.
    Vedernikov, A.I., Lobova, N.A., Ushakov, E.N., Alfimov, M.V., and Gromov, S.P., Mendeleev Commun., 2005, vol. 15, no. 5, p. 173.CrossRefGoogle Scholar
  61. 61.
    Gromov, S.P., Vedernikov, A.I., Kuz’mina, L.G., Lobova, N.A., Basok, S.S., Strelenko, Yu.A., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 2009, no. 1, p. 108 [Russ. Chem. Bull., Int. Ed., 2009, vol. 58, p. 108].Google Scholar
  62. 62.
    Kim, K., Chem. Soc. Rev., 2002, vol. 31, p. 96.CrossRefGoogle Scholar
  63. 63.
    Lee, J.W., Samal, S., Selvapalam, N., Kim, H.-J., and Kim, K., Acc. Chem. Res., 2003, vol. 36, p. 621.CrossRefGoogle Scholar
  64. 64.
    Balzani, V., Gómez-López, M., and Stoddart, J.F., Acc. Chem. Res., 1998, vol. 31, no. 7, p. 405.CrossRefGoogle Scholar
  65. 65.
    Sauvage, J.-P., Acc. Chem. Res., 1998, vol. 31, no. 10, p. 611.CrossRefGoogle Scholar
  66. 66.
    Molecular Machines, Topics in Current Chemistry, Kelly, T.R., Ed., Berlin: Springer, 2005.Google Scholar
  67. 67.
    Vedernikov, A.I., Lobova, N.A., Kuz’mina, L.G., Strelenko, Yu.A., Khovard, Dzh.A.K., Alfimov, M.V., and Gromov, S.P., Ross. Nanotekhnol., 2007, vol. 2, nos. 5–6, p. 56.Google Scholar
  68. 68.
    Kuz’mina, L.G., Vedernikov, A.I., Lobova, N.A., Howard, J.A.K., Strelenko, Y.A., Fedin, V.P., Alfimov, M.V., and Gromov, S.P., New J. Chem., 2006, vol. 30, no. 3, p. 458.CrossRefGoogle Scholar
  69. 69.
    Gromov, S.P., Vedernikov, A.I., Kuz’mina, L.G., Kondratuk, D.V., Sazonov, S.K., Strelenko, Y.A., Alfimov, M.V., and Howard, J.A.K., Eur. J. Org. Chem., 2010, no. 13, p. 2587.Google Scholar
  70. 70.
    Drexler, K.E., Engines of Creation: The Coming Era of Nanotechnology, New York: Anchor Books, 1986.Google Scholar
  71. 71.
    Sergeeva, T.I., Zaitsev, S.Yu., Tsarkova, M.S., Gromov, S.P., Vedernikov, A.I., Kapichnikova, M.S., Alfimov, M.V., Druzhinina, T.S., and Möbius, D., J. Colloid Interface Sci., 2003, vol. 265, p. 77.CrossRefGoogle Scholar
  72. 72.
    Zaitsev, S.Yu., Sergeeva, T.I., Möbius, D., Vedernikov, A.I., Kapichnikova, M.S., Gromov, S.P., and Alfimov, M.V., Mendeleev Commun., 2004, vol. 14, no. 5, p. 199.CrossRefGoogle Scholar
  73. 73.
    Turshatov, A.A., Bossi, M.L., Möbius, D., Hell, S.W., Vedernikov, A.I., Gromov, S.P., Lobova, N.A., Alfimov, M.V., and Zaitsev, S.Yu., Thin Solid Films, 2005, vol. 476, p. 336.CrossRefGoogle Scholar
  74. 74.
    Sergeeva, T.I., Gromov, S.P., Vedernikov, A.I., Kapichnikova, M.S., Alfimov, M.V., Lieu, V.T., Möbius, D., Tsarkova, M.S., and Zaitsev, S.Yu., Colloids Surf., A, 2005, vol. 255, p. 201.CrossRefGoogle Scholar
  75. 75.
    Sergeeva, T.I., Gromov, S.P., Vedernikov, A.I., Kapichnikova, M.S., Alfimov, M.V., Möbius, D., and Zaitsev, S.Yu., Appl. Surf. Sci., 2005, vol. 246, p. 377.CrossRefGoogle Scholar
  76. 76.
    Sergeeva, T.I., Gromov, S.P., Vedernikov, A.I., Kapichnikova, M.S., Alfimov, M.V., Möbius, D., and Zaitsev, S.Yu., Colloids Surf., A, 2005, vol. 264, p. 207.CrossRefGoogle Scholar
  77. 77.
    Sergeeva, T.I., Gromov, S.P., Zaitsev, S.Yu., and Möbius, D., Colloids Surf., B, 2009, vol. 74, no. 2, p. 410.CrossRefGoogle Scholar
  78. 78.
    Kuz’mina, L.G., Vedernikov, A.I., Lobova, N.A., Churakov, A.V., Howard, J.A.K., Alfimov, M.V., and Gromov, S.P., New J. Chem., 2007, vol. 31, p. 980.CrossRefGoogle Scholar
  79. 79.
    Vedernikov, A.I., Kuz’mina, L.G., Sazonov, S.K., Lobova, N.A., Loginov, P.S., Churakov, A.V., Strelenko, Yu.A., Khovard, Dzh.A.K., Alfimov, M.V., and Gromov, S.P., Izv. Akad. Nauk, Ser. Khim., 2007, no. 9, p. 1797 [Russ. Chem. Bull., Int. Ed., 2007, vol. 56, p. 1860].Google Scholar
  80. 80.
    Kuz’mina, L.G., Vedernikov, A.I., Sazonov, S.K., Lobova, N.A., Loginov, P.S., Khovard, Dzh.A.K., Alfimov, M.V., and Gromov, S.P., Kristallografiya, 2008, vol. 53, no. 3, p. 460 [Crystallogr. Rep. (Engl. Transl.), vol. 53, no. 3, p. 428].Google Scholar
  81. 81.
    Kuz’mina, L.G., Vedernikov, A.I., Khovard, Dzh.A.K., Alfimov, M.V., and Gromov, S.P., Ross. Nanotekhnol., 2008, vol. 3, nos. 7–8, p. 32.Google Scholar
  82. 82.
    Kuz’mina, L.G., Vedernikov, A.I., Lobova, N.A., Sazonov, S.K., Basok, S.S., Khovard, Dzh.A.K., and Gromov, S.P., Izv. Akad. Nauk, Ser. Khim., 2009, no. 6, p. 1161 [Russ. Chem. Bull., Int. Ed., 2009, vol. 58, p. 1192].Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  1. 1.Photochemistry CenterRussian Academy of SciencesMoscowRussia

Personalised recommendations