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Modification and application of metal phthalocyanines in heterogeneous systems

  • Modern Problems of Physical Chemistry of Surfaces, Materials Science and Protection
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Abstract

This review discusses the main aspects of synthesis, structural modification, and practical application of an extremely important class of organic heterocyclic compounds, phthalocyanines and their metal complexes. The main attention is paid to application of phthalocyanines, in such promising areas as tribologically active systems, functional composite materials and coatings, and supramolecular chemistry.

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References

  1. Tsivadze, A.Yu., Usp. Khim., 2004, vol. 73, pp. 6–25.

    Google Scholar 

  2. Gorbunova, Y.G., Martynov, A.G., and Tsivadze, A.Y., in Handbook of Porphyrin Science, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., Singapore: World Scientific Publ., 2012, vol. 24, chap. 113, pp. 271–388.

    Article  Google Scholar 

  3. Martynov, A.G., Gorbunova, Y.G., and Tsivadze, A.Y., Russ. J. Inorg. Chem., 2014, vol. 59, no. 14, pp. 1635–1664.

    Article  Google Scholar 

  4. Gorbunova, Y.G., Tsivadze, A.Y., and Lapkina, L.A., J. Coord. Chem., 2003, vol. 56, pp. 1223–1232.

    Article  Google Scholar 

  5. Wöhrle, D., Schnurpfeil, G., Makarov, S.G., et al., Makrogeterotsikly, 2012, vol. 5, no. 3, pp. 191–202.

    Google Scholar 

  6. Herbst, W. and Hunger, K., Industrial Organic Pigments: Production, Properties, Applications, Weinheim Wiley-VCH, 2004.

    Book  Google Scholar 

  7. Zheltov, A.Ya. and Perevalov, V.P., Osnovy teorii tsvetnosti organicheskikh soedinenii (Theoretical Foundations of Organic Compounds’ Colority), Moscow Dmitry Mendeleev Univ. of Chemical Technology of Russia, 2012.

    Google Scholar 

  8. Nikol’skii, B.P., Spravochnik khimika (Handbook for Chemist), Moscow: Khimiya, 1966, vol. 1.

  9. Vadetskii, Yu.V., Neftegazovaya entsiklopediya (Oil and Gas Encyclopedia), Moscow: Moscow Aviation Inst. (National Research Univ.), All-Russian Research Inst. for the Organization, Management and Economics of the Oil and Gas Industry, 2003, vol. 2.

  10. Bazyakina, N.L., Extended Abstract of Cand. Sci. (Chem.) Dissertation, Nizhny Novgorod, 2006.

  11. Akhmadullina, A.G. and Akhmadullin, R.M., Khim. Tekhnol. Topl. Masel, 2008, vol. 44, no. 6, pp. 3–8.

    Google Scholar 

  12. Akhmadullina, A.G. and Akhmadullin, R.M., RF Patent 2529500, 2014.

  13. Akhmadullina, A.G., RF Patent 2110324, 1998.

  14. Belogorokhov, I.A., Doctoral Sci. (Phys.-Math.) Dissertation, Moscow Moscow State Univ., 2009.

    Google Scholar 

  15. Van Faassen, E. and Kerp, H., Sens. Actuators, B, 2003, vol. 88, pp. 329–333.

    Article  Google Scholar 

  16. Xie, D., Jiang, Y., Pan, W., Jiang, J., et al., Sens. Actuators, B, 2002, vol. 81, pp. 210–217.

    Article  Google Scholar 

  17. Xie, D., Pan, W., Jiang, Y.D., and Li, Y.R., Mater. Lett., 2003, vol. 57, pp. 2395–2398.

    Article  Google Scholar 

  18. Lam, M.K., Kwok, K.L., Tse, S.C., et al., Opt. Mater., 2006, vol. 28, pp. 709–713.

    Article  Google Scholar 

  19. Krasnovskii, L.A., Rodgers, M.A., Gal’pern, M.G., et al., Bioorg. Khim., 1990, vol. 16, no. 10, pp. 1413–1418.

    Google Scholar 

  20. Zakamov, V.R. and Leonov, E.S., Materialy 3-ei mezhdunarodnoi konferentsii “Khimiya tverdogo tela i sovremennye mikro-i nanotekhnologii” (Proc. 3rd Int. Conference “Chemistry of Solid State and Modern Microand Nanotechnologies”), Stavropol: North-Caucasus State Technical Univ., 2003, p. 212.

    Google Scholar 

  21. Il’chuk, G.A., Nikitin, S.E., Nikolaev, Yu.A., et al., Tech. Phys. Lett., 2004, vol. 30, pp. 967–969.

    Article  Google Scholar 

  22. Liu, L.C. and Hu, A.T., J. Porphyrins Phthalocyanines, 2003, vol. 7, no. 8, pp. 565–571.

    Article  Google Scholar 

  23. Beletskaya, I.P., Tyurin, V.S., Tsivadze, A.Yu., et al., Chem. Rev., 2009, vol. 109, no. 5, pp. 1659–1713.

    Article  Google Scholar 

  24. Mroz, P., Tegos, G., Gali, H., et al., Photochem. Photobiol. Sci., 2007, vol. 6, no. 11, pp. 1139–1149.

    Article  Google Scholar 

  25. Zhang, X.F., Xi, Q., and Zhao, J., J. Mater. Chem., 2010, vol. 20, no. 32, pp. 6726–6733.

    Article  Google Scholar 

  26. Phthalocyanines: Properties and Applications, Leznoff, C.C. and Lever, A.P.B., Eds., New York: VCH Publ.}}, 1996, vol. 4.

  27. Berezina, E.V., Doctoral Sci. (Eng.) Dissertation, Ivanovo, 2007.

    Google Scholar 

  28. Shaposhnikov, G.P., Kulinich, V.P., and Maizlish, V.E., Modifitsirovannye ftalotsianiny i ikh strukturnye analogi (Modified Phthalocyanines and their Structural Analogues), Koifman, O.I., Ed., Moscow Krasand, 2012.

  29. Balakirev, A.E., Extended Abstract of Cand. Sci. (Chem.) Dissertation, Ivanovo, 2001.

    Google Scholar 

  30. Sakamoto, K. and Ohno-Okumura, E., Materials, 2009, vol. 2, pp. 1127–1179.

    Article  Google Scholar 

  31. Baulin, V.E., Ovsyannikova, E.V., Kalashnikova, I.P., et al., Prot. Met. Phys. Chem. Surf., 2013, vol. 49, no. 1, pp. 5–31.

    Article  Google Scholar 

  32. Lutsenko, O.G., Shaposhnikov, G.P., Kulinich, V.P., and Lyubimtsev, A.V., Russ. J. Gen. Chem., 2004, vol. 74, no. 3, pp. 446–450.

    Article  Google Scholar 

  33. Kulinich, V.P., Shaposhnikov, G.P., and Badaukaite, R.A., Makrogeterotsikly, 2010, vol. 3, no. 1, pp. 23–29.

    Google Scholar 

  34. Shaposhnikov, G.P., Maizlish, V.E., and Kulinich, V.P., Russ. J. Gen. Chem., 2005, vol. 75, no. 9, pp. 1480–1488.

    Article  Google Scholar 

  35. Finikova, O.S., Cheprakov, A.V., Beletskaya, I.P., et al., J. Org. Chem., 2004, vol. 69, pp. 522–535.

    Article  Google Scholar 

  36. Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., and Abramov, I.G., Khim. Khim. Tekhnol., 2012, vol. 55, no. 12, pp. 13–25.

    Google Scholar 

  37. Stryapan, M.G., Efimova, S.V., Koifman, O.I., and Islyaikin, M.K., Makrogeterotsikly, 2010, vol. 3, no. 1, pp. 38–40.

    Google Scholar 

  38. Korzhenevskii, A.B., Efimova, S.V., and Koifman, O.I., Makrogeterotsikly, 2009, vol. 2, no. 2, pp. 103–113.

    Google Scholar 

  39. Troyanov, S.I., Lapkina, L.A., Larchenko, V.E., and Tsivadze, A.Yu., Dokl. Chem., 1999, vol. 367, nos. 4–6, p. 192.

    Google Scholar 

  40. Martynov, A.G., Gorbunova, Yu.G., Khrapova, I.G., et al., Russ. J. Inorg. Chem., 2002, vol. 47, no. 10, pp. 1479–1485.

    Google Scholar 

  41. Lapkina, L.A., Gorbunova, Yu.G., Larchenko, V.E., and Tsivadze, A.Yu., Russ. J. Inorg. Chem., 2003, vol. 48, no. 7, pp. 1053–1061.

    Google Scholar 

  42. Gorbunova, Yu.G., Lapkina, L.A., Martynov, A.G., et al., Russ. J. Coord. Chem., 2004, vol. 30, no. 4, pp. 245–251.

    Article  Google Scholar 

  43. Tolkacheva, E.O., Tsivadze, A.Yu., Bitiev, Sh.G., et al., Zh. Neorg. Khim., 1995, vol. 40, no. 6, p. 991.

    Google Scholar 

  44. Nefedova, I.V., Gorbunova, Yu.G., Sakharov, S.G., and Tsivadze, A.Yu., Russ. J. Inorg. Chem., 2005, vol. 50, no. 2, p. 165.

    Google Scholar 

  45. Lapkina, L.A., Sakharov, S.G., Konstantinov, N.Yu., et al., Russ. J. Inorg. Chem., 2007, vol. 52, no. 11, pp. 1758–1768.

    Article  Google Scholar 

  46. Martynov, A.G., Nefedova, I.V., Gorbunova, Yu.G., and Tsivadze, A.Yu., Mendeleev Commun., 2007, vol. 17, no. 1, p. 66.

    Article  Google Scholar 

  47. Martynov, A.G. and Gorbunova, Yu.G., Inorg. Chim. Acta, 2007, vol. 360, no. 1, pp. 122–130.

    Article  Google Scholar 

  48. Martynov, A.G., Zubareva, O.V., Gorbunova, Yu.G., et al., Eur. J. Inorg. Chem., 2007, no. 30, pp. 4800–4807.

    Article  Google Scholar 

  49. Martynov, A.G., Zubareva, O.V., Gorbunova, Yu.G., et al., Inorg. Chim. Acta, 2009, vol. 362, no. 11, p. 11.

    Article  Google Scholar 

  50. Nefedova, I.V., Gorbunova, Yu.G., Sakharov, S.G., and Tsivadze, A.Yu., Mendeleev Commun., 2006, vol. 16, no. 2, p. 67.

    Article  Google Scholar 

  51. Lapkina, L.A., Gorbunova, Yu.G., Nefedov, S.E., and Tsivadze, A.Yu., Russ. Chem. Bull., 2003, vol. 52, no. 7, p. 1633.

    Article  Google Scholar 

  52. Lapkina, L.A., Sakharov, S.G., Larchenko, V.E., et al., Russ. J. Inorg. Chem., 2007, vol. 52, no. 4, pp. 543–550.

    Article  Google Scholar 

  53. Martynov, A.G., Gorbunova, Y.G., and Tsivadze, A.Y., Dalton Trans., 2011, vol. 40, pp. 7165–7171.

    Article  Google Scholar 

  54. Tsivadze, A.Yu., Martynov, A.G., Polovkova, M.A., and Gorbunova, Yu.G., Russ. Chem. Bull., 2011, vol. 60, no. 11, pp. 2258–2262.

    Article  Google Scholar 

  55. Martynov, A.G. and Gorbunova, Yu.G., Polyhedron, 2010, vol. 13, no. 1, pp. 391–399.

    Article  Google Scholar 

  56. Birin, K.P., Gorbunova, Yu.G., and Tsivadze, A.Yu., Magn. Reson. Chem., 2010, vol. 48, no. 7, pp. 505–515.

    Article  Google Scholar 

  57. Gol’dshleger, N.F., Chernyak, A.V., Kalashnikova, I.P., et al., Russ. J. Gen. Chem., 2012, vol. 82, pp. 927–935.

    Article  Google Scholar 

  58. Gol’dshleger, N.F., Kalashnikova, I.P., Baulin, V.E., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, no. 4, pp. 471–477.

    Article  Google Scholar 

  59. Baulin, V.E., Ovsyannikova, E.V., Kalashnikova, I.P., et al., Prot. Met. Phys. Chem. Surf., 2013, vol. 49, no. 1, pp. 5–31.

    Article  Google Scholar 

  60. Lobanov, A.V., Gromova, G.A., Gorbunova, Yu.G., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2014, vol. 50, no. 5, pp. 570–577.

    Article  Google Scholar 

  61. Wen, Z.-Q., Feng, Y.-Q., Li, X.-G., et al., Dyes Pigm., 2011, vol. 92, no. 1, pp. 554–562.

    Article  Google Scholar 

  62. Bulychev, N., Confortini, O., Kopold, P., et al., Polymer, 2007, vol. 48, no. 9, pp. 2636–2643.

    Article  Google Scholar 

  63. Hou, X.-Y., Bian, S.-G., Chen, J.-F., and Le, Y., Opt. Mater., 2012, vol. 35, no. 2, pp. 201–204.

    Article  Google Scholar 

  64. Sis, H. and Birinci, M., Colloids Surf., A, 2014, vol. 455, pp. 58–66.

    Article  Google Scholar 

  65. Gol’dshleger, N.F., Baulin, V.E., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2014, vol. 50, no. 2, pp. 135–172.

    Article  Google Scholar 

  66. Shakhnovich, A. and Belmont, J., in The Chemistry of Inkjet Inks, Magdasi, S., Ed., Singapore: World Scientific Publ., 2010, p.101.

    Google Scholar 

  67. Tabayashi, I., Kawai, K., Inoue, S., et al., US Patent 6074467, 2000.

  68. Rodriguez-Parada, J.M. and Sheau-Hwa, M., EEC Patent 0915138, 1999.

  69. Carroll, J.B., Shakhnovich, A.I., and Williams, D.S., WIPO Patent 2007089859 A8, 2008.

  70. Shaohai, F., Changsen, D., Mingjun, Z., et al., Prog. Org. Coat., 2012, vol. 73, nos. 2–3, pp. 149–154.

    Article  Google Scholar 

  71. Yu, Y., Proc. NIP22: Int. Conference on Digital Printing Technologies, Denver, CO,2006, p. 197–200.

  72. Reipen, T., Plüg, C., and Weber, J., WIPO Patent 2007045311 A11, 2007.

  73. Bagai, S. and Topham, A., FRG Patent 2017040, 1970.

  74. Baebler, F., US Patent 6264733, 2001.

  75. Belmont, J.A., Johnson, J.E., and Adams, C.E., US Patent 5571311, 1996.

  76. Shakhnovich, A.I., Eur. Coat. J., 2006, no. 6, pp. 28–35.

    Google Scholar 

  77. Cepanec, I., Synthesis of Biaryls, Oxford Elsevier, 2004.

    Google Scholar 

  78. Zuev, K.V., Smrchek, V.A., Fedoseeva, M.S., et al., Khim. Prom-st. Segodnya, 2015, no. 8, pp. 24–30.

    Google Scholar 

  79. Dong, J., Corti, D.S., and Franses, E.I., Langmuir, 2010, vol. 26, no. 10, pp. 6995–7006.

    Article  Google Scholar 

  80. Lozzi, L., Santucci, S., La Rosa, S., et al., J. Chem. Phys., 2004, vol. 121, no. 4, pp. 1883–1889.

    Article  Google Scholar 

  81. Hiemenz, P.C. and Rajagopalan, R., Principles of Colloid and Surface Chemistry, New York Marcel Dekker, 1997.

    Book  Google Scholar 

  82. Hui, D., Nawaz, M., Morris, D.P., et al., J. Colloid Interface Sci., 2008, vol. 324, nos. 1–2, pp. 110–117.

    Article  Google Scholar 

  83. Zhao, Y., Ng, H., Hanson, E., et al., J. Chem. Theory Comput., 2010, vol. 6, no. 2, pp. 491–498.

    Article  Google Scholar 

  84. Klamann, D., Lubricants and Related Products: Synthesis, Properties, Applications, International Standards, New York Wiley-VCH, 1984.

    Google Scholar 

  85. Obel’nitskii, A.M., Egorushkin, E.A., Chernyavskii, Yu.N., et al., Toplivo, smazochnye materialy i okhlazhdayushchie zhidkosti. Uchebnik dlya vuzov (Fuel, Lubricants and Coolants. Student’s Book for Universities), Obel’nitskii, A.M., Ed., Moscow Poligran, 1997.

  86. Stepanov, B.I., Vvedenie v khimiyu i tekhnologiyu organicheskikh krasitelei (Introduction to Organic Pigments’ Chemistry and Technology), Moscow Khimiya, 1971.

    Google Scholar 

  87. Berezina, E.V., Cand. Sci. (Eng.) Dissertation, Ivanovo, 1992.

    Google Scholar 

  88. Godlevskii, V.A., Latyshev, V.N., Volkov, A.V., and Maurin, L.N., Trenie Iznos, 1995, vol. 16, no. 5, pp. 938–949.

    Google Scholar 

  89. Spravochnik po tribotekhnike. Smazochnye materialy, tekhnika smazki, opory skol’zheniya i kacheniya (Handbook on Triboengineering. Lubricants, Lubricants’ Technique, Sliding and Rolling Bearings), Khebda, M. and Chichinadze, A.B., Ed., Moscow: Mashinostroenie, 1990, vol. 2.

  90. Uspekhi khimii porfirinov (Progress in Porphyrins Chemistry), Golubchikov, O.A., Ed., St. Petersburg: Inst. of Chemistry of Saint-Petersburg State Univ. 2001, vol. 3, pp. 47–71.

  91. Berezina, E.V., Proizvodnye ftalotsianina kak prisadki k smazochnym kompozitsiyam (Phthalocyanines’ Derivatives as Additions to Lubricant Compositions), Ivanovo Ivanovo State Univ., 2007.

    Google Scholar 

  92. Berezina, E.V., Volkov, A.V., and Godlevskii, V.A., J. Frict. Wear, 2007, vol. 28, no. 1, pp. 2–11.

    Article  Google Scholar 

  93. Berezina, E.V., Godlevskii, V.A., and Fomichev, D.S., RF Patent 2361905, 2009.

  94. Butkene, R.V. and Motskute, D.V., Gal’vanotekh. Obrab. Poverkhn., 1993, vol. 11, no. 6, pp. 11–15.

    Google Scholar 

  95. Grilikhes, S.Ya. and Tikhonov, K.I., Elektroliticheskie i khimicheskie pokrytiya. Teoriya i praktika (Electrolytic and Chemical Coatings. Theory and Practice), Leningrad Khimiya, 1990.

    Google Scholar 

  96. Blestyashchie elektroliticheskie pokrytiya (Glossy Electrolytic Coatings), Matulis, Yu., Ed., Vilnus Mintis, 1969.

  97. Vyacheslavov, P.M., Elektroliticheskoe osazhdenie splavov (Electrolytic Deposition of Alloys), Leningrad Mashinostroenie, 1971.

    Google Scholar 

  98. Golubchikov, O.A., Larionov, A.V., Balmasov, A.V., and Semeikin, A.S., Makrogeterotsikly, 2014, vol. 7, no. 3, pp. 225–232.

    Google Scholar 

  99. Golubchikov, O.A., Larionov, A.V., Maizlish, V.E., and Balmasov, A.V., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2014, vol. 57, no. 12, pp. 60–62.

    Google Scholar 

  100. Saifullin, R.S., Zh. Vses. Khim. O-va im. D. I. Mendeleeva, 1980, vol. 25, no. 2, pp. 169–174.

    Google Scholar 

  101. Pietcher, D., J. Appl. Electrochem., 1984, vol. 14, no. 4, pp. 403–415.

    Article  Google Scholar 

  102. Saifullin, P.O., Khafizov, N.R., Khrushcheva, I.K., et al., in Teoriya i praktika gal’vanopokrytii iz kolloidnykh sistem i netoksichnykh elektrolitov (Galvanic Coatings of Colloid Systems and Non-Toxic Electrolytes: Theory and Practice), Novocherkassk: Nauchnaya Shkola, 1984, pp. 83–85.

    Google Scholar 

  103. Khafizov, N.R., Saifullin, P.O., and Kostyuchko, T.P., Kataliticheski aktivnaya poverkhnost’, poluchennaya khimicheskim i elektrokhimicheskim vosstanovleniem metallov (Catalytically Active Surface Generated by Means of Metals’ Chemical and Electrochemical Reduction), Available from ONIITEKHIM, Cherkassy, no. 373-khp88.

  104. Saifullin, R.S., Akulova, L.I., Vozdvizhenskii, G.S., and Ivanov, A.F., Met. Sci. Heat Treat., 1972, vol. 14, no. 1, pp. 77–79.

    Article  Google Scholar 

  105. Gerenrot, Yu.E., Gegel’, T.L., and Landis, B.V., Elektrokhimiya, 1973, vol. 9, no. 2, pp. 204–206.

    Google Scholar 

  106. Khafizov, N.R. and Saifullin, R.S., in Prikladnaya elektrokhimiya (Applied Electrochemistry), Kazan: Kazan State Chemical Technological Inst., 1988, pp. 120–125.

    Google Scholar 

  107. Khafizov, N.R. and Saifullin, P.O., Trudy 9-oi Vsesoyuznoi nauchno-tekhnicheskoi konferentsii po elektrokhimicheskim tekhnologiyam “Gal’vanotekhnika-87” (Proc. 9th All-Union Scientific and Technical Conference on Electrochemical Technologies “Galvanic Engineering-87”), Kazan, 1987, pp. 16–17.

    Google Scholar 

  108. Khafizov, N.R., Saifullin, R.S, and Kazaeva, N.V., Trudy konferentsii “Fiziko-khimicheskie metody issledovaniya v oblasti khimii, fiziki, biologii, meditsiny i narodnom khozyaistve” (Proc. Conference “Physical and Chemical Methods for Investigating in the Fields of Chemistry, Physics, Biology, Medicine and Economy”), Kazan: Kazan State Chemical Technological Inst., 1987, pp. 66.

    Google Scholar 

  109. Khafizov, N.R. and Saifullin, R.S., Trudy 2-oi mezhdunarodnoi nauchno-tekhnicheskoi konferentsii po aktual’nym problemam khimii i khimicheskoi tekhnologii “Khimiya-99” (Proc. 2nd Int. Scientific and Technical Conference on Topical Problems on Chemistry and Chemical Technology “Chemistry-99”), Ivanovo, 1999, pp. 75.

    Google Scholar 

  110. Khafizov, N.R., Cand. Sci. (Chem.) Dissertation, Kazan, 1999.

    Google Scholar 

  111. Saifullin, R.S., Neorganicheskie kompozitsionnye materialy (Inorganic Composite Materials), Moscow Khimiya, 1983.

    Google Scholar 

  112. Masilela, N. and Nyokong, T., Dyes Pigm., 2010, vol. 84, no. 3, pp. 242–248.

    Article  Google Scholar 

  113. Liu, L.C. and Hu, A.T., J. Porphyrins Phthalocyanines, 2003, vol. 7, no. 8, pp. 565–571.

    Article  Google Scholar 

  114. Yao, Y.Y., Chen, W.X., Zhao, B.Y., and Lue, S.S., Chin. J. Polym. Sci., 2006, vol. 24, no. 5, pp. 441–448.

    Article  Google Scholar 

  115. Opris, D.M., Nüesch, F., Löwe, C., et al., Chem. Mater., 2008, vol. 20, no. 21, pp. 6889–6896.

    Article  Google Scholar 

  116. Kussovski, V., Mantareva, V., Angelov, I., et al., FEMS Microbiol. Letts., 2009, vol. 294, no. 2, pp. 133–140.

    Article  Google Scholar 

  117. Li, H., Jensen, T.J., Fronczek, F.R., and Vicente, M.G.H., J. Med. Chem., 2008, vol. 51, no. 3, pp. 502–511.

    Article  Google Scholar 

  118. Strassert, C.A., Dicelio, L.E., and Awruch, J., Synthesis, 2006, no. 5, pp. 799–802.

    Google Scholar 

  119. Dumoulin, F., Durmus, M., Ahsen, V., and Nyokong, T., Coord. Chem. Rev., 2010, vol. 254, nos. 23–24, pp. 2792–2847.

    Article  Google Scholar 

  120. Biyiklioglu, Z., Durmus, M., and Kantekin, H., J. Photochem. Photobiol., A, 2011, vol. 222, no. 1, pp. 87–96.

    Article  Google Scholar 

  121. Esenpinar, A.A., Durmus, M., and Bulut, M., Spectrochim. Acta, Part A, 2011, vol. 81, no. 1, pp. 690–697.

    Article  Google Scholar 

  122. Durmus, M., Biyiklioglu, Z., and Kantekin, H., Synth. Met., 2009, vol. 159, nos. 15–16, pp. 1563–1571.

    Article  Google Scholar 

  123. Durmus, M., Yaman, H., Göl, C., et al., Dyes Pigm., 2011, vol. 91, no. 2, pp. 153–163.

    Article  Google Scholar 

  124. Varela, H., Bruno, R.L., and Torresi, R.M., Polymer, 2003, vol. 44, no. 18, pp. 5369–5379.

    Article  Google Scholar 

  125. Yilmaz, I., Arslan, S., Guney, S., and Becerik, I., Electrochim. Acta, 2007, vol. 52, no. 24, pp. 6611–6621.

    Article  Google Scholar 

  126. Damos, F.S., Luz, R.C.S., Tanaka, A.A., and Kubota, L.T., J. Electroanal. Chem., 2006, vol. 589, no. 1, pp. 70–81.

    Article  Google Scholar 

  127. Andreev, V.N., Ovsyannikova, E.V., and Alpatova, N.M., Russ. J. Electrochem., 2010, vol. 46, no. 9, pp. 1056–1062.

    Article  Google Scholar 

  128. Aslamazova, T.R., Kotenev, V.A., Zolotarevskii, V.I., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, no. 5, pp. 572–577.

    Article  Google Scholar 

  129. Zilbermann, I., Hayon, J., Katchlski, T., et al., Inorg. Chim. Acta, 2000, vol. 305, no. 1, pp. 53–60.

    Article  Google Scholar 

  130. Kadish, K.M., Nakanishi, T., Gürek, A., et al., J. Phys. Chem. B, 2001, vol. 105, no. 40, pp. 9817–9821.

    Article  Google Scholar 

  131. Nakanishi, T., Yilmaz, I., Nakashima, N., and Kadish, K.M., J. Phys. Chem. B, 2003, vol. 107, no. 20, pp. 12789–12796.

    Article  Google Scholar 

  132. Gorbunova, Yu.G., Enakieva, Yu.Yu., Demina, L.I., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, no. 4, pp. 441–446.

    Article  Google Scholar 

  133. Birin, K.P., Gorbunova, Yu.G., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, no. 4, pp. 417–423.

    Article  Google Scholar 

  134. Andryushkevich, S.O., Birin, K.P., Gorbunova, Yu.G., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, no. 4, pp. 494–502.

    Article  Google Scholar 

  135. Decher, G. and Hong, J.D., Makromol. Chem. Macromol. Symp., 1991, vol. 46, no. 1, pp. 321–327.

    Article  Google Scholar 

  136. Lvov, Y., Decher, G., and Möhwald, H., Langmuir, 1993, vol. 9, no. 2, pp. 481–486.

    Article  Google Scholar 

  137. Decher, G., Lvov, Y., and Schmitt, J., Thin Solid Films, 1994, vol. 244, nos. 1–2, pp. 772–777.

    Article  Google Scholar 

  138. Decher, G., Science, 1997, vol. 277, no. 5330, pp. 1232–1237.

    Article  Google Scholar 

  139. Crespillo, F.N., Zucolotto, V., Oliveira, O.N., and Nart, F.C., Int. J. Electrochem. Sci., 2006, vol. 1, pp. 151–159.

    Google Scholar 

  140. Birin, K.P., Kamarova, K.A., Gorbunova, Yu.G., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2013, vol. 49, no. 2, pp. 173–180.

    Article  Google Scholar 

  141. Tolkacheva, E.O., Tsivadze, A.Yu., and Bitiev, Sh.G., Zh. Neorg. Khim., 1993, vol. 38, no. 10, p. 1694.

    Google Scholar 

  142. Dvorkin, V.I., Gorbunova, Yu.G., Zhilov, V.I., et al., J. Anal. Chem., 2002, vol. 57, no. 6, pp. 552–556.

    Article  Google Scholar 

  143. Vannikov, A.V., Grishina, A.D., Gorbunova, Yu.G., et al., Dokl. Phys. Chem., 2005, vol. 403, no. 2, pp. 137–141.

    Article  Google Scholar 

  144. Vannikov, A.V., Grishina, A.D., Gorbunova, Yu.G., et al., Russ. J. Phys. Chem. A, 2006, vol. 80, no. 3, pp. 453–460.

    Article  Google Scholar 

  145. Grishina, A.D., Konnov, F.Yu., Gorbunova, Yu.G., et al., Russ. J. Phys. Chem. A, 2007, vol. 81, no. 6, pp. 982–989.

    Article  Google Scholar 

  146. Grishina, A.D., Gorbunova, Yu.G., Enakieva, Yu.Yu., et al., High Energy Chem., 2008, vol. 42, no. 4, pp. 297–304.

    Article  Google Scholar 

  147. Grishina, A.D., Gorbunova, Yu.G., Zolotarevsky, V.I., et al., J. Porphyrins Phthalocyanines, 2009, vol. 13, no. 1, p. 92.

    Article  Google Scholar 

  148. Vannikov, A.V., Grishina, A.D., Gorbunova, Y.G., et al., Polym. Sci., Ser. A, 2011, vol. 53, pp. 1069–1075.

    Article  Google Scholar 

  149. Vannikov, A.V., Grishina, A.D., Gorbunova, Yu.G., et al., High Energy Chem., 2014, vol. 48, no. 2, pp. 97–103.

    Article  Google Scholar 

  150. Grishina, A.D., Gorbunova, Yu.G., Krivenko, T.V., et al., Prot. Met. Phys. Chem. Surf., 2014, vol. 50, no. 4, pp. 472–479.

    Article  Google Scholar 

  151. Vannikov, A.V., Grishina, A.D., Gorbunova, Yu.G., et al., High Energy Chem., 2015, vol. 49, no 1, pp. 36–43.

    Article  Google Scholar 

  152. Vannikov, A.V., Gorbunova, Yu.G., Grishina, A.D., and Tsivadze, A.Yu., Prot. Met. Phys. Chem. Surf., 2013, vol. 49, no. 1, pp. 57–65.

    Article  Google Scholar 

  153. Selektor, S.L., Shokurov, A.V., Arslanov, V.V., et al., Russ. J. Electrochem., 2012, vol. 48, no. 2, pp. 218–234.

    Article  Google Scholar 

  154. Selektor, S.L., Sheinina, L.S., Shokurov, A.V., et al., Prot. Met. Phys. Chem. Surf., 2011, vol. 47, no. 4, pp. 447–456.

    Article  Google Scholar 

  155. Gorbunova, Yu.G., Kalashnikova, I.P., Rodriquez-Mendez, M.L., et al., Langmuir, 2001, vol. 17, pp. 5004–5010.

    Article  Google Scholar 

  156. Rodriquez-Mendez, M., Gorbunova, Yu.G., and de Saja, J.A., Langmuir, 2002, vol. 18, pp. 9560–9565.

    Article  Google Scholar 

  157. Selector, S.L., Arslanov, V.V., Gorbunova, Yu.G., et al., J. Porphyrins Phthalocyanines, 2008, vol. 12, no. 11, p. 1154.

    Article  Google Scholar 

  158. Selektor, S.L., Shokurov, A.V., Raitman, O.A., et al., Colloid J., 2012, vol. 74, no. 3, pp. 334–345.

    Article  Google Scholar 

  159. Selektor, S.L., Shokurov, A.V., Arslanov, V.V., et al., J. Phys. Chem. C, 2014, vol. 118, no. 8, pp. 4250–4258.

    Article  Google Scholar 

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Original Russian Text © V.P. Perevalov, E.G. Vinokurov, K.V. Zuev, E.A. Vasilenko, A.Yu. Tsivadze, 2017, published in Fizikokhimiya Poverkhnosti i Zashchita Materialov, 2017, Vol. 53, No. 2, pp. 115–131.

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Perevalov, V.P., Vinokurov, E.G., Zuev, K.V. et al. Modification and application of metal phthalocyanines in heterogeneous systems. Prot Met Phys Chem Surf 53, 199–214 (2017). https://doi.org/10.1134/S2070205117020186

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