Skip to main content
SpringerLink
Log in

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

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  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/S1070363217070209

    Article  CAS  Google Scholar 

  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. 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/B405868B

    Google Scholar 

  4. Kimura, M., Nakada, K., Yamaguchi, Y., Hanabusa, K., Shirai, H., and Kobayashi, N., Chem. Commun., 1997, no. 13, p. 1215. doi 10.1039/A701263B

    Article  Google Scholar 

  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/C3CC47714B

    Article  CAS  Google Scholar 

  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/s11172-006-0372-2

    Article  CAS  Google Scholar 

  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/S108842461750002X

    Article  CAS  Google Scholar 

  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/S1070363214010204

    Article  CAS  Google Scholar 

  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.2014.05.019

    Article  CAS  PubMed  Google Scholar 

  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/S1070363217120544

    Article  CAS  Google Scholar 

  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/S1070363207010215

    Article  CAS  Google Scholar 

  12. Photosensitizers in Medicine, Environment, and Security, Nyokong, T. and Ahsen, V., Eds., Dordrecht: Springer, 2012.

    Google Scholar 

  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.200801778

    Article  CAS  PubMed  Google Scholar 

  14. Kimura, M., Tohata, Y., Ikeuchia, T., and Mori, Sh., RSC Adv., 2015, vol. 5, p. 82292. doi 10.1039/C5RA16610A

    Article  CAS  Google Scholar 

  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/S1088424614501028

    Article  CAS  Google Scholar 

  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.

  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. Barut, B., Sofuoğlu, A., Biyiklioglu, Z., and Özel, A., Dalton Trans., 2016, vol. 45, p. 14301. doi 10.1039/C6DT02720B

    Article  CAS  PubMed  Google Scholar 

  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/mhc140480z

    Article  CAS  Google Scholar 

  20. Abramov, I.G., Smirnov, A.V., Plakhtinskii, V.V., and Krasovskaya, G.G., Mendeleev Commun., 2002, vol. 2, p. 72. doi 10.1070/MC2002v012n02ABEH001538

    Google Scholar 

  21. Pretsch, E., Bullmann, F., and Affolter, C., Structural Determination of Organic Compounds. Tables of Spectral Data, Berlin: Springer, 2006.

    Google Scholar 

  22. Thorn, G.D. and Ludwig, R., The Dithiocarbamates and Related Compounds, Amsterdam: Elsevier, 1981.

    Google Scholar 

  23. Gessner, P.K. and Gessner, T., Disulfiram and Its Metabolite, Diethyldithiocarbamate, Amsterdam: Springer, 1992. doi 10.1007/978-94-011-2328-0

    Book  Google Scholar 

  24. Victoriano, L.I., Coord. Chem. Rev., 2000, vol. 196, p. 383. doi 10.1016/S0010-8545(99)00221-0

    Article  CAS  Google Scholar 

  25. Borisenkova, S.A., Petroleum Chem., vol. 31, no. 3, p. 391.

  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/JSC160105048V

    Article  CAS  Google Scholar 

  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.2005.07.008

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

  1. Research Institute of Macroheterocyclic Chemistry, Ivanovo State, University of Chemical Technology, pr. Sheremetevskii 7, Ivanovo, 15300, Russia

    S. A. Znoiko, I. A. Kuz’min, T. V. Tikhomirova, N. N. Smirnov, V. E. Maizlish, A. S. Vashurin & G. P. Shaposhnikov

  2. Kazan Federal University, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008, Russia

    A. S. Vashurin

Authors
  1. S. A. Znoiko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. A. Kuz’min
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. V. Tikhomirova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. N. Smirnov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. E. Maizlish
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. S. Vashurin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. P. Shaposhnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Znoiko.

Additional information

Original Russian Text © S.A. Znoiko, I.A. Kuz’min, T.V. Tikhomirova, N.N. Smirnov, V.E. Maizlish, A.S. Vashurin, G.P. Shaposhnikov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 4, pp. 672–678.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Znoiko, S.A., Kuz’min, I.A., Tikhomirova, T.V. et al. Nucleophilic Substitution in 4-Bromo-5-nitrophthalodinitrile: XVI.1 4-(1H-Benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy/sulfanyl]- phthalonitriles and Cobalt Phthalocyanines Thereof. Russ J Gen Chem 88, 751–757 (2018). https://doi.org/10.1134/S1070363218040205

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218040205

Keywords

Search

Navigation