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N. V. Usol'tseva¹, А. I. Smirnova¹, А. V. Kazak¹, М. I. Kovaleva¹, N. Е. Galanin², G. P. Shaposhnikov², V. V. Bodnarchuk³, S. V. Yablonskii³

Author affiliations
¹Nanomaterials Research Institute, Ivanovo State University,
39 Ermak St., Ivanovo, 153025, Russia
E-mail: nv_usoltseva@mail.ru
²Research Institute of Macroheterocyclic compounds, Ivanovo State University of Chemistry and Technology,
7 Sheremetievsky Ave., Ivanovo, 153000, Russia
E-mail: nik-galanin@yandex.ru
³Shubnikov Institute of Crystallography of the Russian Academy of Sciences,
59 Leninsky prospect, Moscow, 119333, Russia

Abstract
Phthalocyanines with different quantity and ratio of donor and acceptor substituents in one molecule of the А₃В type were synthesized by means of the mixed condensation of 3,6-dihexadecyloxyphthalonitrile (component A) with 4,5-dichloro- or 3,4,5,6-tetrachlorophthalonitrile (component B). On the basis of the synthesized ligands the corresponding complexes with copper, zinc and indium were obtained. The spectral properties of the ligands and their metal complexes in chloroform solution were studied. It is shown that the position and intensity of the absorption bands depends on the metal complexing agent. The ligand and zinc complex of phthalocyanine with dichloronitrile fragment showed fluorescence properties, while among the analogues with tetrachloronitrile fragment only zinc complex fluoresces. Mesomorphic properties of the synthesized phthalocyanines were studied by optical polarization microscopy and differential scanning calorimetry. All the studied compounds, except indium complex, exhibit thermotropic mesophase, the type of which depends on the number of chlorine atoms introduced into the phthalocyanine molecule. Photoelectric properties of the individual ligand having dichlorophthalonitrile fragment and mixture of this ligand with fullerene (C₆₀) were investigated.

Keywords: mix-substituted phthalocyanines, metal complexes, synthesis, mesomorphism, absorption spectra, fluorescence, photoelectric properties