Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 742–750 | Cite as

Synthesis and Properties of Tetra-4-{[(1,1'-biphenyl)-4-yl]oxy}phthalocyanines and Their Sulfonic Acid Derivatives

  • T. V. Tikhomirova
  • A. A. Peledina
  • V. E. Maizlish
  • A. S. Vashurin
  • G. P. Shaposhnikov


The template condensation of 4-{[(1,1'-biphenyl)-4-yl]oxy}phthalonitrile with cobalt, copper, and magnesium acetate resulted in the synthesis of metal phthalocyanines. Sulfochlorination of the latter followed by hydrolysis gave the corresponding sulfonic acid derivatives. The spectral characteristics and chemical properties of the synthesized compounds were studied.


metal phthalocyanines template synthesis sulfonic acids thermooxidative degradation 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.



The work was performed under the State contract with the Ministry of Education and Science of the Russian Federation (no. 4.1929.2017.4.6) and the President of the Russian Federation (project no. MK- 161.2017.3), using the equipment of the Center for Collective Use, Ivanovo State University of Chemical Technology.


  1. 1.
    Shaposhnikov, G.P., Kulinich, V.P., and Maizlish, V.E., Modifitsirovannye ftalocianiny i ikh strukturnye analogi (Modified Phthalocyanines and Their Structural Analogs), Moscow: KRASAND, 2012.Google Scholar
  2. 2.
    The Porphyrin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., New York: Academic, 2003, vol. 15.Google Scholar
  3. 3.
    Kudrik, E.V., Makarov, S.V., Ageeva, E.S., and Dereven’kov, I.A., Macroheterocycles, 2009, vol. 2, no. 1, p. 69.CrossRefGoogle Scholar
  4. 4.
    Çetinkaya, M., Pişkin, M., Altun, S., Odabaş, Z., and Durmus, M., J. Photochem. Photobiol. A, 2017, vol. 335, p. 17. doi 10.1016/j.jphotochem.2016.11.009CrossRefGoogle Scholar
  5. 5.
    Kuznetsova, N.A. and Kaliya, O.L., Macroheterocycles, 2015, vol. 8, no. 1, p. 8. doi 10.6060/mhc141243kCrossRefGoogle Scholar
  6. 6.
    Vashurin, A.S., Filippova, A.A., Znoyko, S.A., Voronina, A.A., Lefedova, O.V. Kuzmin, I.A., Maizlish, V.E., and Koifman, O.I., J. Porphyrins Phthalocyanines, 2015. vol. 19, no. 8, p. 983. doi 10.1142/S10884246144501028CrossRefGoogle Scholar
  7. 7.
    Xu, H.-N., Chen, H.-J., Zheng, B.-Y., Zheng, Y.-Q., Ke, M.-R., and Huang, J.-D., Ultrason. Sonochem., 2015, vol. 22, p. 125. doi 10.1016/j.ultsonch.2014.05.019CrossRefPubMedGoogle Scholar
  8. 8.
    Kantar, C., Akal, H., Kaya, B., Islamoglu, F., Turk, M., and Sasmaz, S., J. Org. Chem., 2015, vol. 783, p. 28. doi 10.1016/j.jorganchem.2014.12.042CrossRefGoogle Scholar
  9. 9.
    Tsunoda, T., Tanaka, A., Mase, T., and Sakamoto, S., Heterocycles, 2004, vol. 63, no. 5, p. 1113. doi 10.3987/COM-04-10025CrossRefGoogle Scholar
  10. 10.
    Ohkanda, J., Buckner, F.S., Lockman, J.W., Yokoyama, K., Carrico, D., Eastman, R., de Luca-Fradley, K., Davies, W., Croft, S.L., Voorhis, W.C.V., Gelb, M.H., Sebti, S.M., and Hamilton, A.D., J. Med. Chem., 2004, vol. 47, no. 2, p. 4463. doi 10.1021/jm030236oCrossRefGoogle Scholar
  11. 11.
    Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., Akopova, O.B., Bumbina, N.V., Usoltseva, N.V., and Abramov, I.G., Russ. J. Gen. Chem., 2014, vol. 84, no. 4, p. 708. doi 10.1134/S1070363214040185CrossRefGoogle Scholar
  12. 12.
    US Patent 20080004391, 2007.Google Scholar
  13. 13.
    Jiang, Z., Ou, Z., Chen, N., Wang, J., Huang, J., Shao, J., and Kadish, K.M., J. Porphyrins Phthalocyanines, 2005, vol. 9, no. 5, p. 352. doi 10.1142/S1088424605000447CrossRefGoogle Scholar
  14. 14.
    Arslanoğlu, Y., Sevim, A.M., Hamuryudan, E., and Gül, A., Dyes Pigments, 2006. vol. 68. p. 129. doi 10.1016/j.dyepig.2005.01.019CrossRefGoogle Scholar
  15. 15.
    Wei. J., Li, X., Xiao, Ch., and Lu, F., Vibrat. Spectrosc., 2017, vol. 92, p. 105. doi 10.1016/j.vibspec.2017.06.002CrossRefGoogle Scholar
  16. 16.
    Berezin, B.D. and Berezin, D.B., Khromofornye sistemy makrotsiklov i lineinykh molekul (Chromophoric Systems of Macrocycles and Linear Molecules), Moscow: URSS, 2013.Google Scholar
  17. 17.
    Berezin, B.D. and Berezin, D.B., Kurs sovremennoi organicheskoi khimii (Textbook on Modern Organic Chemistry), Moscow: Vysshaya Shkola, 1999.Google Scholar
  18. 18.
    Morrison, R.T. and Boyd, R.N., Organic Chemistry, Boston: Allyn and Bacon, 1973, 3rd ed.Google Scholar
  19. 19.
    Znoiko, S.A., Akopova, O.B., Bumbina, N.V., Maizlish, V.E., Shaposhnikov, G.P., and Usol’tseva, N.V., Macroheterocycles, 2014, vol. 7, no. 3, p. 287. doi 10.6060/mhc140930zCrossRefGoogle Scholar
  20. 20.
    Kulinich, V.P., Shaposhnikov, G.P., and Badaukaite, R.A., Makrogeterotsikly, 2010, vol. 3, no. 1, p. 23.Google Scholar
  21. 21.
    Kulinich, V.P., Badaukaite, R.A., Tikhomirova, T.V., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2013, vol. 83, no. 4, p. 744. doi 10.1134/S1070363213040233CrossRefGoogle Scholar
  22. 22.
    Terenin, A.R., Fotonika molekul krasitelei i rodstvennykh soedinenii (Photonics of Molecules of Dyes and Related), Leningrad: Nauka, 1967.Google Scholar
  23. 23.
    Vashurin, A.S., Russ. Chem. Bull., 2017, no. 9, p. 220. doi 10.1007/s11172-016-1572-zGoogle Scholar
  24. 24.
    Gessner, P.K. and Gessner, T., Disulfiram and its Metabolite, Diethyldithiocarbamate, Amsterdam: Springer, 1992. doi 10.1007/978-94-011-2328-0.CrossRefGoogle Scholar
  25. 25.
    Victoriano, L.I., Coord. Chem. Rev., 2000, vol. 196, p. 383. doi 10.1016/S0010-8545(99)00221-0CrossRefGoogle Scholar
  26. 26.
    Borisenkova, S.A., Petroleum Chem., 1991, vol. 31, no. 3, p. 391.Google Scholar
  27. 27.
    Filippova, A., Vashurin, A., Znoyko, S., Kuzmin, I., Razumov, M., Chernova, A., Shaposhnikov, G., and Koifman, O., J. Mol. Struct., 2017, vol. 1149, p. 17. doi 10.1016/j.molstruc.2017.07.086CrossRefGoogle Scholar
  28. 28.
    Tyapochkin, E.M. and Kozliak, E.I., J. Mol. Catal. A, 2005, vol. 242, p. 1. doi 10.1016/j.molcata.2005.07.008CrossRefGoogle Scholar
  29. 29.
    Vashurin, A.S., Pukhovskaya, S.G., Semeikin, A.S., and Golubchikov, O.A., Makrogeterotsikly, 2012, vol. 5, no. 1, p. 72. doi 10.6060/mhc2012.111251vGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • T. V. Tikhomirova
    • 1
  • A. A. Peledina
    • 1
  • V. E. Maizlish
    • 1
  • A. S. Vashurin
    • 1
    • 2
  • G. P. Shaposhnikov
    • 1
  1. 1.Research Institute of Macroheterocyclic ChemistryIvanovo State University of Chemical TechnologyIvanovoRussia
  2. 2.Kazan Federal UniversityKazan, TatarstanRussia

Personalised recommendations