Advertisement

Russian Chemical Bulletin

, Volume 65, Issue 11, pp 2686–2703 | Cite as

Synthesis, structure and complexation of biscrown-containing 1,4-distyrylbenzenes

  • A. I. Vedernikov
  • V. N. Nuriev
  • O. V. Fedorov
  • A. A. Moiseeva
  • N. A. Kurchavov
  • L. G. Kuz’mina
  • A. Ya. Freidzon
  • E. S. Pod’yacheva
  • A. V. Medved’ko
  • S. Z. Vatsadze
  • S. P. Gromov
Full Articles

Abstract

An improved method for the synthesis of two symmetric biscrown-containing and one model tetramethoxy-substituted 1,4-distyrylbenzenes was suggested. The structures of compounds were established by 1H and 13C NMR spectroscopy and X-ray diffraction analysis. Spectrophotometric and fluorescent titration were used to determine spectral properties, stoichiometry, and stability of complexes of biscrown-containing 1,4-distyrylbenzenes with alkali and alkaline-earth metal cations. The stability of the complexes was found to depend on the metal cation size and charge, as well as on the size of the crown ether fragment. The electrochemical oxidation and reduction potentials of the biscrown-containing 1,4-distyrylbenzenes and the model compound in solution were determined and their basic differences from the corresponding characteristics of biscrown-containing stilbenes were identified.

Key words

distyrylbenzenes crown ethers complexes stoichiometry of complexes electronic spectroscopy NMR spectroscopy X-ray diffraction analysis electrochemistry 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J. W. Steed, J. L. Atwood, Supramolecular Chemistry, Wiley, Chichester, 2000, Vol. 1, 2.Google Scholar
  2. 2.
    H.-G. Lцhr, F. Vögtle, Acc. Chem. Res., 1985, 18, 65.CrossRefGoogle Scholar
  3. 3.
    S. Shinkai, Comprehensive Supramolecular Chemistry, Ed. J.-M. Lehn, Pergamon, New York, 1996, Vol. 1, 671.Google Scholar
  4. 4.
    E. N. Ushakov, M. V. Alfimov, S. P. Gromov, Russ. Chem. Rev. (Int. Ed.), 2008, 77, 39.CrossRefGoogle Scholar
  5. 5.
    S. P. Gromov, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 1325 [Izv. Akad. Nauk, Ser. Khim., 2008, 1299].CrossRefGoogle Scholar
  6. 6.
    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, D. Möbius, New J. Chem., 2002, 26, 543.CrossRefGoogle Scholar
  7. 7.
    E. N. Ushakov, S. P. Gromov, Russ. Chem. Rev. (Int. Ed.), 2015, 84, 787.CrossRefGoogle Scholar
  8. 8.
    S. P. Gromov, O. A. Fedorova, E. N. Ushakov, O. B. Stanislavskii, M. V. Alfimov, Dokl. Chem. (Engl. Transl.), 1991, 321, 104 [Dokl. Akad. Nauk SSSR, 1991, 321, 104].Google Scholar
  9. 9.
    I. I. Baskin, K. Ya. Burstein, A. A. Bagatur’yants, S. P. Gromov, M. V. Alfimov, J. Mol. Struct., 1992, 274, 93.CrossRefGoogle Scholar
  10. 10.
    S. P. Gromov, E. N. Ushakov, O. A. Fedorova, V. A. Soldatenkova, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 1997, 46, 1143 [Izv. Akad. Nauk, Ser. Khim., 1997, 1192].CrossRefGoogle Scholar
  11. 11.
    M. V. Alfimov, S. P. Gromov, O. B. Stanislavskii, E. N. Ushakov, O. A. Fedorova, Russ. Chem. Bull. (Int. Ed.), 1993, 42, 1385 [Izv. Akad. Nauk, Ser. Khim., 1993, 1449].CrossRefGoogle Scholar
  12. 12.
    E. N. Ushakov, S. P. Gromov, A. V. Buevich, I. I. Baskin, O. A. Fedorova, A. I. Vedernikov, M. V. Alfimov, B. Eliasson, U. Edlund, J. Chem. Soc., Perkin Trans. 2, 1999, 601.Google Scholar
  13. 13.
    S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. N. Dmitrieva, Yu. A. Strelenko, J. A. K. Howard, J. Org. Chem., 2014, 79, 11416.CrossRefGoogle Scholar
  14. 14.
    E. N. Ushakov, A. I. Vedernikov, N. A. Lobova, S. N. Dmitrieva, L. G. Kuz’mina, A. A. Moiseeva, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, J. Phys. Chem. A, 2015, 119, 13025.CrossRefGoogle Scholar
  15. 15.
    A. I. Vedernikov, E. N. Ushakov, A. A. Efremova, L. G. Kuz’mina, A. A. Moiseeva, N. A. Lobova, A. V. Churakov, Yu. A. Strelenko, M. V. Alfimov, J. A. K. Howard, S. P. Gromov, J. Org. Chem., 2011, 76, 6768.CrossRefGoogle Scholar
  16. 16.
    M. V. Fomina, A. S. Nikiforov, A. I. Vedernikov, N. A. Kurchavov, S. P. Gromov, Mendeleev Commun., 2014, 24, 295.CrossRefGoogle Scholar
  17. 17.
    S. P. Gromov, A. I. Vedernikov, E. N. Ushakov, N. A. Lobova, A. A. Botsmanova, L. G. Kuz’mina, A. V. Churakov, Yu. A. Strelenko, M. V. Alfimov, E. I. Ivanov, J. A. K. Howard, D. Johnels, U. G. Edlund, New J. Chem., 2005, 29, 881.CrossRefGoogle Scholar
  18. 18.
    E. N. Ushakov, S. P. Gromov, A. I. Vedernikov, E. V. Malysheva, A. A. Botsmanova, M. V. Alfimov, B. Eliasson, U. G. Edlund, J. K. Whitesell, M. A. Fox, J. Phys. Chem. A, 2002, 106, 2020.CrossRefGoogle Scholar
  19. 19.
    E. N. Ushakov, V. A. Nadtochenko, S. P. Gromov, A. I. Vedernikov, N. A. Lobova, M. V. Alfimov, F. E. Gostev, A. N. Petrukhin, O. M. Sarkisov, Chem. Phys., 2004, 298, 251.CrossRefGoogle Scholar
  20. 20.
    S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. S. Basok, Yu. A. Strelenko, M. V. Alfimov, J. A. K. Howard, New J. Chem., 2011, 35, 724.CrossRefGoogle Scholar
  21. 21.
    K. P. Butin, A. A. Moiseeva, S. P. Gromov, A. I. Vedernikov, A. A. Botsmanova, E. N. Ushakov, M. V. Alfimov, J. Electroanal. Chem., 2003, 547, 93.CrossRefGoogle Scholar
  22. 22.
    D. Oelkrug, A. Tompert, H. J. Egelhaaf, M. Hanack, E. Steinhuber, M. Hohloch, H. Meier, U. Stalmach, Synth. Met., 1996, 83, 231.CrossRefGoogle Scholar
  23. 23.
    B. J. Laughlin, T. L. Duniho, S. J. El Homsi, B. E. Levy, N. Deligonul, J. R. Gaffen, J. D. Protasiewicz, A. G. Tennyson, R. C. Smith, Org. Biomol. Chem., 2013, 11, 5425.CrossRefGoogle Scholar
  24. 24.
    K. Sandros, M. Sundahl, O. Wennerström, U. Norinder, J. Am. Chem. Soc., 1990, 112, 3082.CrossRefGoogle Scholar
  25. 25.
    E. Marri, F. Elisei, U. Mazzucato, D. Pannacci, A. Spalletti, J. Photochem. Photobiol. A, 2006, 177, 307.CrossRefGoogle Scholar
  26. 26.
    G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, R. H. Grubbs, J. Am. Chem. Soc., 1998, 120, 3641.CrossRefGoogle Scholar
  27. 27.
    M. Kim, D. R. Whang, J. Gierschnerb, S. Y. Park, J. Mater. Chem. C, 2015, 3, 231.CrossRefGoogle Scholar
  28. 28.
    M. Cavazzini, S. Quici, S. Orlandi, C. Sissa, F. Terenziani, A. Painelli, Tetrahedron, 2013, 69, 2827.CrossRefGoogle Scholar
  29. 29.
    A. Chaieb, A. Khoukh, R. Brown, J. Francois, C. DagronLartigau, Optical Materials, 2007, 30, 318.CrossRefGoogle Scholar
  30. 30.
    B. S. Kalanoor, P. B. Bisht, S. Annamalai, I. S. Aidhen, J. Luminescence, 2009, 129, 1094.CrossRefGoogle Scholar
  31. 31.
    J. Motoyoshiya, Z. Fengqiang, Y. Nishii, H. Aoyama, Spectrochim. Acta A, 2008, 69, 167.CrossRefGoogle Scholar
  32. 32.
    S. J. K. Pond, O. Tsutsumi, M. Rumi, O. Kwon, E. Zojer, J. L. Bredas, S. R. Marder, J. W. Perry, J. Am. Chem. Soc., 2004, 126, 9291.CrossRefGoogle Scholar
  33. 33.
    B. Strehmel, K. B. Henbest, A. M. Sarker, J. H. Malpert, D. Y. Chen, M. A. J. Rodgers, D. C. Neckers, J. Nanosci. Nanotech., 2001, 1, 107.CrossRefGoogle Scholar
  34. 34.
    W.-S. Xia, R. H. Schmehl, C.-J. Li, J. T. Mague, C.-P. Luo, D. M. Guldi, J. Phys. Chem. B, 2002, 106, 833.CrossRefGoogle Scholar
  35. 35.
    D. Schwöppe, H. Meier, J. Prakt. Chem., 2000, 342, 459.CrossRefGoogle Scholar
  36. 36.
    L. A. Fedorov, A. N. Ermakov, Spektroskopiya YaMR v neorganicheskom analize [NMR Spectroscopy in Inorganic Analysis], Nauka, Moscow, 1989, 245 pp. (in Russian).Google Scholar
  37. 37.
    A. I. Vedernikov, S. S. Basok, S. P. Gromov, L. G. Kuz’mina, V. G. Avakyan, N. A. Lobova, E. Yu. Kulygina, T. V. Titkov, Yu. A. Strelenko, E. I. Ivanov, J. A. K. Howard, M. V. Alfimov, Russ. J. Org. Chem. (Engl. Transl.), 2005, 41, 843 [Zh. Org. Khim., 2005, 864].CrossRefGoogle Scholar
  38. 38.
    P. Gans, A. Sabatini, A. Vacca, Talanta, 1996, 43, 1739.CrossRefGoogle Scholar
  39. 39.
    O. B. Stanislavskii, E. N. Ushakov, S. P. Gromov, O. A. Fedorova, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 1996, 45, 564 [Izv. Akad. Nauk, Ser. Khim., 1996, 605].CrossRefGoogle Scholar
  40. 40.
    S. P. Gromov, O. A. Fedorova, E. N. Ushakov, A. V. Buevich, I. I. Baskin, Y. V. Pershina, B. Eliasson, U. Edlund, M. V. Alfimov, J. Chem. Soc., Perkin Trans. 2, 1999, 1323.Google Scholar
  41. 41.
    R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev., 1991, 91, 1721.CrossRefGoogle Scholar
  42. 42.
    Ch. Mann, K. Barnes, Elektrokhimicheskie reaktsii v nevodnykh sistemakh [Electrochemical Reactions in Nonaqueous Systems], Khimiya, Moscow, 1974, 194 (in Russian).Google Scholar
  43. 43.
    Organicheskaya elektrokhimiya [Organic Electrochemistry], Eds M. Beiser, H. Lund, Khimiya, Moscow, 1988, 282 pp. (in Russian).Google Scholar
  44. 44.
    B. Fabre, P. Marrec, J. Simonet, J. Electroanal. Chem., 2000, 485, 94.CrossRefGoogle Scholar
  45. 45.
    F. Wada, H. Hirayama, H. Namiki, K. Kikukawa, T. Matsuda, Bull. Chem. Soc. Jpn, 1980, 53, 1473.CrossRefGoogle Scholar
  46. 46.
    E. A. Safonova, A. G. Martynov, V. I. Zolotarevskii, S. E. Nefedov, Y. G. Gorbunova, A. Yu. Tsivadze, Dalton Trans., 2015, 44, 1366.CrossRefGoogle Scholar
  47. 47.
    H. Shimakoshi, T. Inaoka, Y. Hisaeda, Tetrahedron Lett., 2003, 44, 6421.CrossRefGoogle Scholar
  48. 48.
    S. P. Gromov, O. A. Fedorova, A. I. Vedernikov, V. V. Samoshin, N. S. Zefirov, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 1995, 44, 116 [Izv. Akad. Nauk, Ser. Khim., 1995, 121].CrossRefGoogle Scholar
  49. 49.
    M. J. Plater, T. Jackson, Tetrahedron, 2003, 59, 4673.CrossRefGoogle Scholar
  50. 50.
    A. Heller, J. Chem. Phys., 1964, 40, 2839.CrossRefGoogle Scholar
  51. 51.
    A. E. Siegrist, P. Liechti, H. R. Meyer, K. Weber, Helv. Chim. Acta, 1969, 52, 2521.CrossRefGoogle Scholar
  52. 52.
    Y. M. Ha, H. J. Lee, D. Park, H. O. Jeong, J. Y. Park, Y. J. Park, K. J. Lee, J. Y. Lee, H. R. Moon, H. Y. Chung, Biol. Pharm. Bull., 2013, 36, 55.CrossRefGoogle Scholar
  53. 53.
    SAINT, Version 6.02A, Bruker AXS Inc. Madison, Wisconsin (USA), 2001.Google Scholar
  54. 54.
    SHELXTL-Plus, Version 5.10, Bruker AXS Inc., Madison, Wisconsin (USA), 1997.Google Scholar
  55. 55.
    O. V. Dolomanov, L. J. Bourhis, R. J Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr., 2009, 42, 339.CrossRefGoogle Scholar
  56. 56.
    J. P. Perdew, K. Burke, M. Ernzerhof, Phys.Rev. Lett., 1996, 77, 3865.CrossRefGoogle Scholar
  57. 57.
    D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.CrossRefGoogle Scholar
  58. 58.
    D. N. Laikov, Yu. A. Ustynyuk, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 820 [Izv. Akad. Nauk, Ser. Khim., 2005, 804].CrossRefGoogle Scholar
  59. 59.
    S. K. Wolff, T. Ziegler, J. Chem. Phys., 1998, 109, 895.CrossRefGoogle Scholar
  60. 60.
    S. N. Dmitrieva, N. I. Sidorenko, N. A. Kurchavov, A. I. Vedernikov, A. Ya. Freidzon, L. G. Kuz’mina, A. K. Buryak, T. M. Buslaeva, A. A. Bagatur’yants, Y. A. Strelenko, J. A. K. Howard, S. P. Gromov, Inorg. Chem., 2011, 50, 7500.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • A. I. Vedernikov
    • 1
  • V. N. Nuriev
    • 2
  • O. V. Fedorov
    • 3
  • A. A. Moiseeva
    • 2
  • N. A. Kurchavov
    • 1
  • L. G. Kuz’mina
    • 4
  • A. Ya. Freidzon
    • 1
    • 5
  • E. S. Pod’yacheva
    • 2
  • A. V. Medved’ko
    • 2
  • S. Z. Vatsadze
    • 2
  • S. P. Gromov
    • 1
    • 2
  1. 1.Center of PhotochemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  4. 4.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  5. 5.National Research Nuclear University “MEPhI”MoscowRussian Federation

Personalised recommendations