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1 2017

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Mix-substituted phthalocyanines of a “push–pull”-type and their metal complexes as prospective nanostructured materials for optoelectronics

Usol'tseva N. V., Smirnova A. I., Kazak A. V., Giricheva N. I., Galanin N. E., Shaposhnikov G. P., Bodnarchuk V. V., Yablonskii S. V.

Opto-Electronics Review

2017

Vol. 25, No. 2

127--136

To study the influence of structural features of phthalocyanine (Pc) derivatives on their physico-chemical properties in bulk and thin films, 23 new phthalocyanines with different quantity and ratio of donor (alkyloxy-groups, in fragment “A”) and acceptor (Cl-, in fragment “B”) substituents in one molecule of the A3B, ABAB and AABB types with varied length of alkyloxy-substituents and their metal complexes were designed and synthesized. A comparative analysis of spectral, mesomorphic and photoelectric properties of these mix-substituted phthalocyanines of a “push–pull” type was performed. It was shown that non-peripheral substitution by alkyloxy-fragments in hetero-substituted Pcs (similar to homo-substituted Pc) leads to red-shifting of the Q-band into near-IR region. The intensity of photoluminescence, position of peaks and their splitting are strongly connected with chemical structure of Pcs and the type of solvent. In contrast to non-mesogenic octyloxy-Pc (A4) having alkyloxy-substituents in non-peripheral positions, 22 of 23 synthesized compounds possess columnar mesomorphism. The change of donor–acceptor ratio can influence the type of mesophase. A new approach to the creation of materials for optoelectronics is proposed and implemented, which includes design of compounds possessing vitrification from mesophase with maintenance of a columnar order, absorption in the near IR-region of the spectrum and good performance electrophysical characteristics simultaneously.