Abstract
Stepwise nucleophilic substitution of bromine and nitro group in 4-bromo-5-nitrophthalodinitrile has led to a series of phthalonitriles containing benzotriazole and aryloxy fragments; basing on them, the mixed-substituted phthalocyanines have been prepared. The spectral properties of products have been studied. According to simulation of columnar mesomorphism only one of the products is not capable of mesomorphism characteristic of discotic mesogens; the result has been confirmed with the experiment.
Similar content being viewed by others
References
Znoiko, S.A., Kambolova, A.S., Maizlish, V.E., Shaposhnikov, G.P., Abramov, I.G., and Filimonov, S.N., Russ. J. Gen. Chem., 2009, vol. 79, no. 8, p. 1735.
Bazanov, M.I., Shishkina, O.V., Maizlish, V.E., Petrov, A.V., Shaposhnikov, G.P., Smirnov, R.P., and Gzheidzyak, A., Russ. J. Electrochem., 1998, vol. 34, no. 8, p. 818.
Bykova, V.V., Usol’tseva, N.V., Anan’eva, G.A., Shaposhnikov, G.P., and Maizlish, V.E., Izv. Akad. Nauk, Ser. Fiz., 1998, vol. 62, no. 8, p. 1647.
Wohrle, D., Schnurpfeil, G., Makarov, S.G., Kazarin, A., and Suvorova, O.N., Macroheterocycl., 2012, vol. 5, no. 3, p. 191.
Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., Abramov, I.G., and Voron’ko, M.V., Russ. J. Gen. Chem., 2007, vol. 7, no. 9, p. 1623.
Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., and Abramov, I.G., Izv. Vuzov, Ser. Khim. Khim. Tekhnol., 2012, vol. 55, no. 12, p. 13.
Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., Abramov, I.G., Anan’eva, G.A., Bykova, V.V., and Usol’tseva, N.V., Liquid. Cryst. and Their Appl., 2009, no. 1(27), p. 24.
Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrin and Phthalocyanine), Moscow: Nauka, 1978.
Vul’fson, S.V., Lebedev, O.L., and Luk’yanets, E.A., Zh. Prikl. Spektr., 1972, vol. 17, no. 5, p. 903.
Berardi, R., Cetschini, M., and Zannoni, C.A., J. Chem. Phys., 2003, vol. 119, no. 18, p. 9933.
Miglioli, I., Muccioli, L., Orlandi, S., Ricci, M., Berardi, R., and Zannoni, C., Theor. Chem. Acc., 2007, vol. 118, no. 1, p. 203.
Luk’yanov, I.Yu., Sotskii, V.V., Bykova, V.V., and Usol’tseva, N.V., Liquid. Cryst. and Their Appl., 2011, no. 3, p. 84.
Akopova, O.B., Doctoral (Chem.) Dissertation, Ivanovo, 2008.
Shestakova, R.G., Prosochkina, T.R., Tokunova, E.E., Tyurina, L.A., and Kantor, E.A., Russ. J. Gen. Chem., 2006, vol. 76, no. 4, p. 615.
Akopova, O.B., Bulavkova, M.G., Gruzdev, M.S., and Frolova, T.V., Russ. J. Gen. Chem., 2011, vol. 81, no. 4, p. 714.
Akopova, O.B., Zdanovich, S.A., Akopov, A.A., Kotovich, L.N., and Usol’tseva, N.V., Izv. Akad. Nauk, Ser. Fiz., 1997, vol. 61, no. 3, p. 624.
Bumbina, N.V., Luk’yanov, I.Yu., Akopova, O.B., and Usol’tseva, N.V., Liquid. Cryst. and Their Appl., 2012, no. 3(41), p. 31.
Znoyko, S.A., Maizlish, V.E., Shaposhnikov, G.P., Filimonov, S.N., and Abramov, I.G., J. Porphyrins Phthalocyanines, 2008, vol. 12, nos. 3–6, p. 798.
Znoiko, S.A., Maizlish, V.E., Shaposhnikov, G.P., Bykova, V.V., and Usol’tseva, N.V., Liquid. Cryst. and Their Appl., 2011, no. 4(38), p. 69.
Bumbina, N.V., Akopova, O.B., Znoiko, S.A., Usol’tseva, N.V., Krivova, A.V., Maizlish, V.E., and Shaposhnikov, G.P., Abstracts of Papers, Mezhdunar. nauch.-prakt. konf. “Sovremennye problemy i puti ikh resheniya v nauke, transporte, proizvodstve i obrazovanii-2012” (Int. Sci.-Pract. Conf. “Modern Problems and Their Decisions in Science, Transportation, Manufacturing, and Education-2012”), vol. 44, no. 4. Odessa: Chernomor’e, 2012, p. 64.
Shishkina, O.V., Maizlish, V.E., Shaposhnikov, G.P., Lyubimtsev, A.V., Smirnov, R.P., and Baran’ski, A., Zh. Obshch. Khim., 1997, vol. 67, no. 5, p. 812.
Abramov, I.G., Smirnov, A.V., and Plakhtinskii, V.V., Panorama sovremennoi khimii Rossii. Uspekhi v neftekhimicheskom sinteze polifunktsional’nykh aromaticheskikh soedinenii (Prospect of Modern Chemistry in Russia. Advances in Petrochemical Synthesis of Polyfunctional Aromatic Compounds), Moscow: Khimiya, 2005, p. 85.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © S.A. Znoiko, O.B. Akopova, N.V. Bumbina, N.V. Usoltseva, V.E. Maizlish, G.P. Shaposhnikov, I.G. Abramov, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 4, pp. 629–636.
For communication X, see [1].
Rights and permissions
About this article
Cite this article
Znoiko, S.A., Akopova, O.B., Bumbina, N.V. et al. Nucleophilic substitution in 4-bromo-5-nitrophthalodinitrile: XI. Preparation, properties, and prediction of mesomorphism in mixed-substituted phthalocyanines containing aryloxy and benzotriazole fragments. Russ J Gen Chem 84, 708–714 (2014). https://doi.org/10.1134/S1070363214040185
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363214040185