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Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 751–757 | Cite as

Nucleophilic Substitution in 4-Bromo-5-nitrophthalodinitrile: XVI.1 4-(1H-Benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy/sulfanyl]- phthalonitriles and Cobalt Phthalocyanines Thereof

  • S. A. Znoiko
  • I. A. Kuz’min
  • T. V. Tikhomirova
  • N. N. Smirnov
  • V. E. Maizlish
  • A. S. Vashurin
  • G. P. Shaposhnikov
Article
  • 9 Downloads

Abstract

A method of synthesis of 4-(1H-benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy]- and -5-[(4-carboxyphenyl) sulfanyl]phthalonitriles starting with 4-bromo-5-nitrophthalonitriles was developed. The synthesized phthalonitriles were used to prepare cobalt tetra-4-(1H-benzotriazol-1-yl)-tetra-5-[(4-carboxyphenyl)oxy/sulfanyl]phthalocyanines. The spectral and catalytic properties of the resulting octasubstituted phthalocyanines were studied.

Keywords

4-bromo-5-nitrophthalodinitrile cobalt phthalocyanine octasubstituted phthalocyanines phthalonitriles 

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Notes

Acknowledgments

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 with partial financial support of 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.

References

  1. 1.
    Znoiko, S.A., Golovashova, E.S., Potekhina, O.V., Berezin, D.B., Serova, M.A., Maizlish, V.E., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2017, vol. 87, no. 7, p. 1562. doi 10.1134/S1070363217070209CrossRefGoogle Scholar
  2. 2.
    Shaposhnikov, G.P., Kulinich, V.P., and Maizlish, V.E., Modifitsirovannye ftalotsianiny i ikh strukturnye analogi (Modified Phthalocyanines and Their Structural Analogs), Koifman, O.I., Ed., Moscow: KRASAND, 2012.Google Scholar
  3. 3.
    Choi, Ch.-F., Tsang, P.-T., Huang, J.-D., Cha, E.Y.M., Ko, W.-H., Fong, W.-P., and Ng, D.K.P., Chem. Commun., 2004, p. 2236. doi 10.1039/B405868BGoogle Scholar
  4. 4.
    Kimura, M., Nakada, K., Yamaguchi, Y., Hanabusa, K., Shirai, H., and Kobayashi, N., Chem. Commun., 1997, no. 13, p. 1215. doi 10.1039/A701263BCrossRefGoogle Scholar
  5. 5.
    Ikeuchi, T., Nomoto, H., Masaki, N., Griffith, M.J., Mori, Sh., and Kimura, M., Chem. Commun., 2014, vol. 50, p. 1941. doi 10.1039/C3CC47714BCrossRefGoogle Scholar
  6. 6.
    Kudrik, E.V., Maizlish, V.E., Tararykina, T.V., Shaposhnikov, G.P., Smirnova, A.I., and Usol’tseva, N.V., Russ. Chem. Bull., 2006, vol. 55, no. 6, p. 1028. doi 10.1007/s11172-006-0372-2CrossRefGoogle Scholar
  7. 7.
    Vashurin, A., Maizlish, V., Kuzmin, I., Znoyko, S., Morozova, A., Razumov, M., and Koifman, O., J. Porphyrins Phthalocyanines, 2017, vol. 21, no. 1, p. 37. doi 10.1142/S108842461750002XCrossRefGoogle Scholar
  8. 8.
    Maizlish, V.E., Martynyuk, T.A., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2014, vol. 84, no. 1, p. 131. doi 10.1134/S1070363214010204CrossRefGoogle Scholar
  9. 9.
    Xu, H.-N., Chen, H.-J., Zheng, B.-Y., Zheng, Y.-Q., Ke, M.-R., and Huang, J.-D., Ultrason. Sonochem., 2015, vol. 22, no. 1, p. 125. doi 10.1016/j.ultsonch.2014.05.019CrossRefGoogle Scholar
  10. 10.
    Morozova, A.P., Znoiko, S.A., Vashurin, A.S., Zav’yalov, A.V., Maizlish, V.E., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2017, vol. 87, no. 12, p. 3063. doi 10.1134/S1070363217120544CrossRefGoogle Scholar
  11. 11.
    Shaposhnikov, G.P., Maizlish, V.E., and Kulinich, V.P., Russ. J. Gen. Chem., 2007, vol. 77, no. 1, p. 138. doi 10.1134/S1070363207010215CrossRefGoogle Scholar
  12. 12.
    Photosensitizers in Medicine, Environment, and Security, Nyokong, T. and Ahsen, V., Eds., Dordrecht: Springer, 2012.Google Scholar
  13. 13.
    Cid, J.-J., García-Iglesias, M., Yum, J.-H., Forneli, A., Albero, J., Martínez-Ferrero, E., Vázquez, P., Grätzel, M., Nazeeruddin, M.K.., Palomares, E., and Torres, T., Chem. Eur. J., 2009, vol. 15, no. 20, p. 5130. doi 10.1002/chem.200801778CrossRefGoogle Scholar
  14. 14.
    Kimura, M., Tohata, Y., Ikeuchia, T., and Mori, Sh., RSC Adv., 2015, vol. 5, p. 82292. doi 10.1039/C5RA16610ACrossRefGoogle Scholar
  15. 15.
    Vashurin, A., Maizlish, V., Pukhovskaya, Sv., Voronina, A., Kuzmin, I., Futerman, N., Golubchikov, O., and Koifman, O., J. Porphyrins Phthalocyanines, 2015, vol. 19, p. 573. doi 10.1142/S1088424614501028CrossRefGoogle Scholar
  16. 16.
    Maizlish, V.E, Papakhin, A.A., Shaposhnikov, G.P., Kuzmina, E.L., and Petrov, O.A., RF Patent 2463324, 2012; Byull. Izobret., 2012, no. 26.Google Scholar
  17. 17.
    Morozova, A.P., Znoiko, S.A., Vashurin, A.S., Zav’yalov, A.V., Maizlish, V.E., and Shaposhnikov, G.P., Ross. Khim. Zh., 2016, vol. 60, no. 2, p. 80.Google Scholar
  18. 18.
    Barut, B., Sofuoğlu, A., Biyiklioglu, Z., and Özel, A., Dalton Trans., 2016, vol. 45, p. 14301. doi 10.1039/C6DT02720BCrossRefGoogle Scholar
  19. 19.
    Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., Zubkova, O.N., and Savinova, A.I., Macroheterocycles, 2014, vol. 7, no. 4, p. 425. doi 10.6060/mhc140480zCrossRefGoogle Scholar
  20. 20.
    Abramov, I.G., Smirnov, A.V., Plakhtinskii, V.V., and Krasovskaya, G.G., Mendeleev Commun., 2002, vol. 2, p. 72. doi 10.1070/MC2002v012n02ABEH001538Google Scholar
  21. 21.
    Pretsch, E., Bullmann, F., and Affolter, C., Structural Determination of Organic Compounds. Tables of Spectral Data, Berlin: Springer, 2006.Google Scholar
  22. 22.
    Thorn, G.D. and Ludwig, R., The Dithiocarbamates and Related Compounds, Amsterdam: Elsevier, 1981.Google Scholar
  23. 23.
    Gessner, P.K. and Gessner, T., Disulfiram and Its Metabolite, Diethyldithiocarbamate, Amsterdam: Springer, 1992. doi 10.1007/978-94-011-2328-0CrossRefGoogle Scholar
  24. 24.
    Victoriano, L.I., Coord. Chem. Rev., 2000, vol. 196, p. 383. doi 10.1016/S0010-8545(99)00221-0CrossRefGoogle Scholar
  25. 25.
    Borisenkova, S.A., Petroleum Chem., vol. 31, no. 3, p. 391.Google Scholar
  26. 26.
    Vashurin, A.S., Kuzmin, I.A., Mayzlish, V., Razumov, M., Golubchikov, O., and Koifman, O., J. Serb. Chem. Soc., 2016, vol. 81, no. 9, p. 1025. doi 10.2298/JSC160105048VCrossRefGoogle Scholar
  27. 27.
    Tyapochkin, E.M. and Kozliak, E.I., J. Mol. Catal. A, 2005, vol. 242, nos. 1–2, p. 1. doi 10.1016/j.molcata.2005.07.008CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • S. A. Znoiko
    • 1
  • I. A. Kuz’min
    • 1
  • T. V. Tikhomirova
    • 1
  • N. N. Smirnov
    • 1
  • V. E. Maizlish
    • 1
  • A. S. Vashurin
    • 1
    • 2
  • G. P. Shaposhnikov
    • 1
  1. 1.Research Institute of Macroheterocyclic Chemistry, Ivanovo StateUniversity of Chemical TechnologyIvanovoRussia
  2. 2.Kazan Federal University, ul. Kremlevskaya 18TatarstanRussia

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