Abstract
Novel water- and organic-soluble derivatives of octakis-4,5-(sulfanylphenyl)phthalocyanine and its magnesium and aluminum complexes were synthesized starting from 4,5-bis(phenylsulfanyl)phthalonitrile obtained by nucleophilic substitution of the bromine and nitro group in 4-bromo-5-nitrophthalonitrile. Spectral and luminescence characteristics of the newly synthesized compounds were studied.
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Znoiko, S.A., Serova, M.A., Uspenskaya, A.A., Zav’yalov, A.V., Maizlish, V.E., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2016, vol. 86, no. 11, p. 1859. doi 10.1134/S1070363216110165
Shaposhnikov, G.P., Kulinich, V.P., and Maizlish, V.E., Modifitsirovannye ftalotsianiny i ikh strukturnye analogi (Modified Phthalocyanines and Their Structural Analogs), Moscow URSS, 2012.
The Porphirin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., Boston, Academic, 2003. vol. 15.
Wöhrle, D., Schnurpfeil, G., Makarov, S.G., Kazarin A., and Suvorova, O.N., Macroheterocycles, 2012, vol. 5, no. 3, p. 191. doi 10.6060/mhc2012.120990w
Shaabani, A., Keshipour, S., Hamidzad, M., and Shaabani, Sh., J. Mol. Catal. A, 2014, p. 494. doi 10.1016/j.molcata.2014.09.003
Berezina, E.V., Proizvodnye phthalotsianina kak prisadki k smazochnym kompozitsiyam (Phthalocyanine Derivatives as Additives to Lubricating Compositions), Ivanovo Ivanovsk. Gos. Univ., 2007.
Bankole, O.M. and Nyokong, T., J. Coord. Chem., 2015, vol. 68, no. 20, p. 3727. doi 10.1080/00958972.2015.1077237
Makarov, V.I., Vasil’chenko, S.Yu., Ryabova, A.V., Konov, V.I., Shevchenko, E.N., Lukyanets, E.A., Ermakov, A.E., and Loschenov, V.B., Russ. J. Gen. Chem., 2015, vol. 85, no. 1, p. 338. doi 10.1134/S107036321501048X
Negrimovsky, V.M., Makarova, E.A., Mikhalenko, S.A., Solov’eva, L.I., Yuzhakova, O.A., Donyagina, V.F., Volkov, K.A., Komissarov, A.N., Shevchenko, E.N., Dudkin, S.V., Berezina, A.P., Lastovoy, A.P., and Lukyanets, E.A., Russ. J. Gen. Chem., 2015, vol. 85, no. 1, p. 240. doi 10.1134/S1070363215010417
Meerovich, I.G., Volkov, K.G., Meerovich, G.A., Luk’yanets, E.A., Negrimovskii, V.M., Loshchenov, V.B., Oborotova, N.A., and Baryshnikov, A.Yu., Ross. Bioterapevt. Zh., 2014, vol. 13, no. 3, p. 41.
Meerovich, I.G., Sanarova, E.V., Meerovich, G.A., Derkacheva, V.M., Volkov, K.A., Negrimovsky, V.M., Barkanova, S.V., Lukyanets, E.A., Oborotova, N.A., Smirnova, Z.S., Borisova, L.M., Lantsova, A.V., Polozkova, A.P., Orlova, O.L., Loschenov, V.B., Umnova, L.V., Baryshnikov, A.Yu., and Vorozhtsov, G.N., Russ. J. Gen. Chem., 2015, vol. 85, no. 1, p. 280. doi 10.1134/S1070363215010430
Volkov, K.A., Avramenko, G.V., Negrimovskii, V.M., and Luk’yanets, E.A., Russ. J. Gen. Chem., 2007, vol. 77, no. 6, p. 1108. doi 10.1134/S107036320706028X
Maevskii, S.V., Bykov, A.S., Gorokhov, V.V., and Rybachkov, V.V., Ross. Bioterapevt. Zh., 2008, vol. 7, no. 1, p. 21.
Bonnett, R., Chemical Aspects of Photodynamic Therapy, London VHC, 2000.
Methods in Molecular Biology. Photodynamic Therapy: Methods and Protocols, Gomer, C.J., Ed., New York: Springer, 2010, vol. 635, p. 155.
Shishkina, O.V., Maizlish, V.E., Shaposhnikov, G.P., Lubimtsev, A.V., Smirnov, R.P., and Baran’sky, A., Russ. J. Gen. Chem., 1997, vol. 67, no. 5, p. 793.
Abramov, I.G., Smirnov, A.V., Plakhtinskii, V.V., and Krasovskaya, G.G., Mendeleev Commun., 2002, vol. 2, p. 72. doi 10.1070/MC2002v012n02ABEH001538
Tau, P. and Nyokong, T., J. Porphyrins Phthalocyanines, 2006, vol. 10, no. 8, p. 1040. doi 10.1142/S1088424606000399
Koptyaev, A.I., Galanin, N.E., and Shaposhnikov, G.P., Macroheterocycles, 2015, vol. 8, no. 2, p. 156. doi 10.6060/mhc140925g
Berezin, B.D. and Berezin, D.B., Khromofornye sistemy makrotsiklov i lineinykh molekul (Chromophoric Systems of Macrocycles and Linear Molecules), Moscow URSS, 2013.
Rumyantseva, T.A., Efremova, M.V., Sizova, M.V., Shaposhnikov, G.P., Anan’eva, G.A., and Usol’tseva, N.V., Zhidk. Krist. Prakt. Ispol’z., 2012, no. 2, issue 40, p. 29.
Tuncel, S., Banimuslem, H.A.J., Durmus, M., Gürek, A.G., Ahsen, V., Basova, T.V., and Hassan, A.K., New J. Chem., 2012, vol. 36, p. 1665. doi 10.1039/C2NJ40247E
Uspekhi khimii porfirinov (Advances in Porphyrin Chemistry), Golubchikov, O.A., Ed., St. Petersburg: NII Khimii S.-Peterburg. Gos. Univ., 2001, vol. 3, p. 191.
Shukhto, O.V., Solodukhin, T.N., Startseva, O.M., Khudyaeva, I.S., Belykh, D.V., Kustov, A.V., Romanenko, Yu.V., and Berezin, D.B., Vestn. Tadzhiksk. Nats. Univ. Ser. Estestv. Nauk, 2016, vol. 1/4, no. 216, p. 127.
Gurinovich, G.P., Sevchenko, A.A., and Solov’ev, K.N., Spektroskopiya khlorofilla i rodstvennykh soedinenii (Spectroscopy of Chlorophyll and Related Compounds), Minsk Nauka i Tekhnika, 1968.
Parker, S.A., Photoluminescence of Solutions: With Applications to Photochemistry and Analytical Chemistry, Amsterdam Elsevier, 1968.
Dhami, S. and Phillips, D., J. Photochem. Photobiol. A, 1996, vol. 100, nos. 1–3, p. 77. doi 10.1016/S1010-6030 (96)04438-3
Sapunov, V.V., J. Appl. Spectrosc., 1990, vol. 67, no. 1, p. 22. doi 10.1007/BF02681415
Berezin, D.B., Makrotsiklicheskii effekt i strukturnaya khimiya porfirinov (Macrocyclic Effect and Structural Chemistry of Porphyrins), Moscow URSS, 2010.
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Original Russian Text © S.А. Znoiko, E.S. Golovashova, O.V. Potekhina, D.B. Berezin, M.А. Serova, V.E. Maizlish, G.P. Shaposhnikov, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 7, pp. 1169–1178.
For communication XIV, see [1].
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Znoiko, S.A., Golovashova, E.S., Potekhina, O.V. et al. Nucleophilic substitution in 4-bromo-5-nitrophthalodinitrile: XV. Synthesis of bis-4,5-(phenylsulfanyl)phthalonitrile, octakis-4,5-(phenylsulfanyl)phthalocyanines, and their sulfo and alkylsulfamoyl derivatives. Russ J Gen Chem 87, 1562–1571 (2017). https://doi.org/10.1134/S1070363217070209
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DOI: https://doi.org/10.1134/S1070363217070209