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Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon

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Abstract

Nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by benzene- and alkanethiols in the presence of a base was studied at different reactant ratios. The substitution is characterized by complete regioselectivity: the chlorine atom in position 4 of tetrachlorophthalonitrile is replaced first; next follows replacement of the 5-chlorine atom. The reactions of tetrachlorophthalonitrile with nucleophiles at ratios of 1:2 and 1:4 lead to the formation of the corresponding 3,6-dichloro-4,5-bis[phenyl(alkyl)sulfanyl]- and tetrakis[phenyl(alkyl)sulfanyl]phthalonitriles. The latter were converted into metal complexes of [phenyl-(alkyl)sulfanyl]-substituted phthalocyanines which absorb in the red and near-IR regions of the electronic spectra.

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Authors and Affiliations

  1. Research Institute of Organic Intermediates and Dyes, ul. Bol’shaya Sadovaya 1/4, Moscow, 123995, Russia

    K. A. Volkov, V. M. Negrimovskii & E. A. Luk’yanets

  2. Mendeleev Russian University of Chemical Technology, Moscow, Russia

    G. V. Avramenko

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  1. K. A. Volkov
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  2. G. V. Avramenko
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  3. V. M. Negrimovskii
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  4. E. A. Luk’yanets
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Original Russian Text © K.A. Volkov, G.V. Avramenko, V.M. Negrimovskii, E.A. Luk’yanets, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 6, pp. 1022–1030.

For communication XLII, see [1].

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Volkov, K.A., Avramenko, G.V., Negrimovskii, V.M. et al. Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon. Russ J Gen Chem 77, 1108–1116 (2007). https://doi.org/10.1134/S107036320706028X

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  • DOI: https://doi.org/10.1134/S107036320706028X

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