New chalcone-substituted metallophthalocyanines: Synthesis, characterization, and investigation of their properties

Abstract

The synthesis of novel metallophthalocyanines (M = Zn, Mg, and Co) derived from (E)-3-(3-bromophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one and (E)-3-(3-fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one is achieved. These complexes and the synthesized novel phthalonitrile derivatives are characterized by FTIR, 1H NMR, 13C NMR, UV-Vis, mass spectrometry, and elemental analysis. The aggregation properties of the metallophthalocyanines ZnPc, MgPc, and CoPc are investigated in different solvents and at different concentrations in dimethyl formamide. The electrochemical behavior is also investigated. The cyclic voltammograms give one oxidation reaction for all the bromo-derived metallophthalocyanines and one reduction reaction for all the fluoro-derived metallophthalocyanines. Fe3+, Cd2+, Hg2+, Cu2+, Ni2+, and Co2+ ions are titrated fluorometrically with the phthalocyanines. The bromo- and fluoro-substituted phthalocyanine compounds show different effects on the metal ion titrations.