Abstract
Phthalonitriles substituted with o-hydroxybenzoic, o-aminobenzoic, and o-mercaptobenzoic acids moieties were synthesized by nucleophilic substitution of bromine in 4-bromophthalonitrile and of nitro group in 4-nitrophthalonitrile. Template condensation of these phthalonitriles with metal acetates gave the corresponding phthalocyanines. Metal-free phthalocyanines were synthesized by dissociation of the magnesium complexes of the substituted phthalocyanines in a sulfuric acid medium. Treatment of the resultant phthalocyanines with sodium ethoxide in ethanol yielded sodium salts of the carboxylic acids. The spectral properties of the compounds synthesized were examined.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Shaposhnikov, G.P., Maizlish, V.E., and Kulinich, V.P., Modifitsirovannye ftalotsianiny i ikh strukturnye analogi (Modified Phthalocyanines and Their Structural Analogs), Moscow: Krasand, 2012.
The Porphyrin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., San Diego: Academic, Elsevier Science (United States), 2003, vol. 15.
Vorozhtsov, G.N., Kazachkina, N.I., Luzhkov, Yu.M., Kuznetsova, N.A., Luk’yanets, E.A., Mikhalenko, S.A., Pecherskikh, E.V., Solov’eva, L.I., Chissov, V.I., and Yakubovskaya, R.I., RF Patent 2193563, 2002.
Butenin, A.V., Vorozhtsov, G.N., Zolotavkina, Yu.B., Kaliya, O.L., Kogan, B.Ya., Luzhkov, Yu.M., Pankratov, A.A., Chissov, V.I., and Yakubovskaya, R.I., RF Patent 2376999, 2009.
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 https://doi.org/10.1134/S1070363217120544
Maizlish, V.E., Martynyuk, T.A., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2014, vol. 84, no. 1, p. 131. doi https://doi.org/10.1134/S1070363214010204
Thiel, W. and Mayer, R., J. Prakt. Chem., 1986, vol. 328, no. 4, p. 497.
Shishkina, O.V., Maizlish, V.E., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 1997, vol. 67, no. 5, p. 789.
Abramov, I.G., Doctoral (Chem.) Dissertation, Yaroslavl, 2003.
Shein, S.M., Doctoral (Chem.) Dissertation, Novosibirsk, 1970.
Dyer, J.R., Applications of Absorption Spectroscopy of Organic Compounds, New Jersey: Prentice-Hall, 1965.
Uspekhi khimii porfirinov (Advances in Porphyrin Chemistry), Golubchikov, O.A., Ed., St. Petersburg: Inst. Khimii Sankt-Petersb. Gos. Univ., 1997.
Sidorov, A.N. and Kotlyar, I.P., Opt. Spektrosk., 1961, vol. 11, no. 2, p. 175.
Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrins and Phthalocyanine), Moscow: Nauka, 1978.
Vul’fson, S.V., Lebedev, O.L., and Luk’yanets, E.A., Zh. Prikl. Spektrosk., 1972, vol. 17, no. 5, p. 903.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Russian Text © The Author(s), 2017, published in Rossiiskii Khimicheskii Zhurnal, 2017, Vol. 61, No. 1, pp. 67–76.
Funding
This study was financially supported by the Ministry of Education and Science of the Russian Federation (project no. 4.1929.2017/4.6).
Conflict of Interest
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Kuznetsova, D.A., Tikhomirova, T.V., Maizlish, V.E. et al. Tetrasubstituted Phthalocyanines with Benzoic Acids Moieties. Russ J Gen Chem 89, 1297–1306 (2019). https://doi.org/10.1134/S1070363219060264
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363219060264