Russian Chemical Bulletin

, Volume 53, Issue 11, pp 2532–2541 | Cite as

Monolayers and Langmuir-Blodgett films of crown-substituted phthalocyanines

  • V. V. Arslanov
  • Yu. G. Gorbunova
  • S. L. Selektor
  • L. S. Sheinina
  • O. G. Tselykh
  • Yu. Yu. Enakieva
  • A. Yu. Tsivadze


Tetra-15-crown-5-phthalocyanine ligand and its ruthenium complex with axial CO and MeOH groups were synthesized. The properties of their monolayers and Langmuir-Blodgett films were studied. In the case of the ligand, monolayer films of molecular associates are formed. The compatibility of the ligand and stearic acid in a mixed binary monolayer was established. Stearic acid improves the ligand distribution over the water surface and results in the formation of monolayer associates immobilized in its matrix. The condensation effect of Na+ cations on the mixed monolayers was found. The ruthenium complex (R4Pc)Ru(MeOH)(CO) forms stable true monolayers. The macrocycle planes in stacking are inclined relatively to the normal to the subphase surface by an angle of 25°. The Langmuir-Blodgett films of the complex were established to have redox peaks. A high electrochemical stability of the Langmuir-Blodgett films and a high electroactivity of phthalocyanine rings were demonstrated. It was shown by impedance spectroscopy that the binding of Na+ and K+ ions by Langmuir-Blodgett films of the (R4Pc)Ru(MeOH)(CO) complex results in an increase in the impedance values in a region of medium frequencies by three and five times, respectively.

Key words

tetra-15-crown-5-phthalocyanine monolayers Langmuir-Blodgett films orientation of macrocycles electronic spectroscopy cyclic voltammetry impedance spectroscopy 


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  1. 1.
    A. Yu. Tsivadze, Usp. Khim., 2004, 73, 6 [Russ. Chem. Rev., 2004, 73 (Engl. Transl.)].Google Scholar
  2. 2.
    N. Kobayashi, Coord. Chem. Rev., 2002, 227, 129.CrossRefGoogle Scholar
  3. 3.
    Y. Matsuzawa and K. Ichimura, Langmuir, 2000, 16, 8390.CrossRefGoogle Scholar
  4. 4.
    M. J. Cook, A. J. Dunn, M. F. Daniel, R. C. O. Hart, R. M. Richardson, and S. J. Roser, Thin Solid Films, 1988, 159, 395.CrossRefGoogle Scholar
  5. 5.
    M. Hanack, A. Gul, A. Hirsch, B. K. Mandal, L. R. Subramanian, and E. Witke, Mol. Cryst. Liq. Cryst., 1990, 187, 365.Google Scholar
  6. 6.
    R. A. Hunn, S. K. Gupta, J. R. Fryer, and B. L. Eyres, Thin Solid Films, 1985, 134, 35.CrossRefGoogle Scholar
  7. 7.
    E. Brynda, I. Koropecky, L. Kalvoda, and S. Nespurek, Thin Solid Films, 1991, 199, 375.Google Scholar
  8. 8.
    G. G. Roberts, M. C. Petty, S. Baker, M. T. Fowler, and N. J. Thomas, Thin Solid Films, 1985, 123, 113.Google Scholar
  9. 9.
    N. B. McKeown, M. J. Cook, A. J. Thomson, K. J. Harrison, M. F. Daniel, R. M. Richardson, and S. J. Roser, Thin Solid Films, 1988, 159, 469.Google Scholar
  10. 10.
    P. Valerio and P.-A. Albouy, Thin Solid Films, 1996, 287, 237.Google Scholar
  11. 11.
    K. Ogawa, H. Yonehara, and E. Maekawa, Thin Solid Films, 1992, 210, 535.Google Scholar
  12. 12.
    S. Fouriaux, F. Armand, O. Araspin, A. Ruaudel-Teixier, E. M. Maya, P. Vazquez, and T. Torres, J. Phys. Chem., 1996, 100, 16985.Google Scholar
  13. 13.
    H.-Q. Xiang, K. Tanaka, A. Takahara, and T. Kajiyama, Chem. Lett., 2001, 536.Google Scholar
  14. 14.
    A. W. Snow and N. L. Jarvis, J. Am. Chem. Soc., 1984, 106, 4706.Google Scholar
  15. 15.
    E. J. Osburn, L.-K. Chau, S.-Y. Chen, N. Collins, D. F. O’Brien, and N. R. Armstrong, Langmuir, 1996, 12, 4784.Google Scholar
  16. 16.
    E. J. Osburn, A. Schmidt, L.-K. Chau, S.-Y. Chen, P. Smolenyak, N. R. Armstrong, and D. F. O’Brien, Adv. Mater., 1996, 8, 926.Google Scholar
  17. 17.
    T. Thami, C. Chassenieux, C. Fretighny, J.-P. Roger, and F. Steybe, J. Porphyrins Phthalocyanines, 2002, 6, 563.Google Scholar
  18. 18.
    Yu. G. Gorbunova, O. Yu. Komarova, S. V. Demin, S. V. Meshkov, and A. Yu. Tsivadze, Koord. Khim., 1997, 23, 553 [Russ. J. Coord. Chem., 1997, 23 (Engl. Transl.)].Google Scholar
  19. 19.
    V. Ahsen, E. Yilmazer, M. Ertas, and O. Bekaroglu, J. Chem. Soc., Dalton Trans., 1988, 2, 40.Google Scholar
  20. 20.
    Yu. Yu. Enakieva, Yu. G. Gorbunova, S. G. Sakharov, and A. Yu. Tsivadze, Zh. Neorg. Khim., 2002, 47, 1966 [Russ. J. Inorg. Chem., 2002, 47 (Engl. Transl.)].Google Scholar
  21. 21.
    P. Valerio and P.-A. Albouy, Thin Solid Films, 1996, 287, 237.Google Scholar
  22. 22.
    S. Palacin, P. Lesieur, I. Stefanelli, and A. Barraud, Thin Solid Films, 1988, 159, 83.CrossRefGoogle Scholar
  23. 23.
    S. Palacin, Adv. Colloid Interface Sci., 2000, 87, 165.CrossRefPubMedGoogle Scholar
  24. 24.
    H. Gruniger, D. Mobius, and H. Meyer, J. Chem. Phys., 1983, 79, 3701.CrossRefGoogle Scholar
  25. 25.
    P. E. Smolenyak, E. J. Osburn, S.-Y. Chen, L.-K. Chau, D. F. O’Brien, and N. R. Armstrong, Langmuir, 1997, 13, 6568.CrossRefGoogle Scholar
  26. 26.
    B. D. Berezin, Koordinatsionnye soedineniya porfirinov i ftalotsianina [Coordination Compounds of Porphyrins and Phthalocyanine], Nauka, Moscow, 1978, p. 68, 214 (in Russian).Google Scholar
  27. 27.
    C. C. Leznoff and A. B. P. Lever, Phthalocyanines. Properties and Applications, VCH Publishers, New York, 1989, 1993, 1996, V. 1–4.Google Scholar
  28. 28.
    N. Kobayashi and A. B. P. Lever, J. Am. Chem. Soc., 1987, 109, 4261.CrossRefGoogle Scholar
  29. 29.
    A. Ruaudel-Teixier, A. Barraud, B. Belbeoch, and M. Rouillay, Thin Solid Films, 1983, 99, 33CrossRefGoogle Scholar
  30. 30.
    H.-G. Liu, D.-J. Qian, X.-S. Feng, Q.-B. Xue, and K.-Z. Yang, Langmuir, 2000, 16, 5079.CrossRefGoogle Scholar
  31. 31.
    M. Burgchard, M. Schmelzer, S. Roth, P. Haisch, and M. Hanack, Langmuir, 1994, 10, 4265.CrossRefGoogle Scholar
  32. 32.
    M. I. Gobernado-Mitre, R. Aroca, and J. A. de Saja, Langmuir, 1993, 9, 2185.CrossRefGoogle Scholar
  33. 33.
    Y. Matsuzawa, T. Seki, and K. Ichimura, Thin Solid Films, 1997, 301, 162.CrossRefGoogle Scholar
  34. 34.
    Y. Gorbunova, M. L. Rodriguez-Mendez, I. P. Kalashnikova, L. G. Tomilova, and J. A. de Saja, Langmuir, 2001, 17, 5004.CrossRefGoogle Scholar
  35. 35.
    D. Dolphin, B. R. James, A. J. Murray, and J. R. Thornback, Can. J. Chem., 1980, 58, 1125.Google Scholar
  36. 36.
    O. E. Sielcken, M. M. van Tilborg, M. F. M. Roks, R. Hendriks, W. Drenth, and R. J. M. Nolte, J. Am. Chem. Soc., 1987, 109, 4261.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2004

Authors and Affiliations

  • V. V. Arslanov
    • 1
  • Yu. G. Gorbunova
    • 1
  • S. L. Selektor
    • 1
  • L. S. Sheinina
    • 1
  • O. G. Tselykh
    • 1
  • Yu. Yu. Enakieva
    • 1
  • A. Yu. Tsivadze
    • 1
  1. 1.Institute of Physical ChemistryRussian Academy of SciencesMoscowRussian Federation

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