Synthesis, characterization and spectral properties of novel zinc phthalocyanines derived from C2 symmetric diol

Abstract

In this study, we described the syntheses of new zinc(II) phthalocyanine compounds derived from (1R,2R)-1,2-diphenyl-1,2-ethanediol units. The phthalonitrile precursors 3 and 4 were synthesized by the reaction of 4,5-dichlorophthalonitrile with (1R,2R)-1,2-diphenyl-1,2-ethanediol. The synthesis of zinc(II) phthalocyanine 5 and zinc(II) phthalocyanine polymer 6 by cyclotetramerization of corresponding phthalonitrile derivative were accomplished in the presence of Zn(CH3CO2)(2) in a Schlenk tube containing quinoline under nitrogen atmosphere. The zinc(II) phthalocyanine 5 showed enhanced solubility in various organic solvents. The aggregation behavior of phthalocyanines was investigated at different concentrations in different solvents. Both phthalocyanines were found to exist in non-aggregated form at concentrations between 10 x 10(-6) and 1 x 10(-6) mol dm(-3). As the concentration increased to 5 x 10(-5) mol dm(-3), a deviation from ideality was observed for both phthalocyanines. The novel compounds were characterized by a combination of elemental analysis and H-1 NMR, C-13 NMR, IR, UV-Vis and MS spectral data. (C) 2014 Elsevier B.V. All rights reserved.