Microwave-Assisted Synthesis of Phthalocyanine Zinc Complexes Derived from Aminotricyanobiphenyl-Based Azo Dyes

Galina A. Selivanova,^a@ Evgeny V. Amosov,^a Vladimir G. Vasil¢ev,^a Evgeny A. Lukyanets,^b Evgeny V. Tretyakov,^a and Vitalij D. Shteingarts^a^†

^aN.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia

^bResearch Institute of Organic Intermediates and Dyes, 123995 Moscow, Russia

^@Corresponding author E-mail: galseliv@nioch.nsc.ru

DOI: 10.6060/mhc151192s

Macroheterocycles 2016 9(1) 80-88

Several new azo compounds were obtained by coupling 2,3’,4’-tricyanodiphenyl-4-diazonium bisulfate with β-naphthol, 3-hydroxy-2-naphthoic and salicylic acids, aniline, 2-toluidine, 2,6-xylidine, and N,N-dibutylaniline. New zinc complexes of tetra-4-[2-cyano-4-(2-hydroxy-1-naphthyldiazenyl)phenyl]phthalocyanine and tetra-4-[2-cyano-4-(4-dibutylaminophenyldiazenyl)phenyl]-phthalocyanine were obtained in 84 % and 67 % yields by condensation of the corresponding azo compounds in the presence of zinc acetate under microwave assistance. This method was also succesfully applied for the preparation of known zinc complexes based on 4-substituted 2,3’,4’-tricyanodiphenyls with enhanced yields.

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Microwave-Assisted Synthesis of Phthalocyanine Zinc Complexes Derived from Aminotricyanobiphenyl-Based Azo Dyes

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