Peripherally 1,2-dinaphthyl ethanediol substituted phthalocyanine complexes: synthesis, characterization, aggregation, and application in benzyl alcohol oxidation at room temperature

Abstract

In this study, the synthesis of a novel 1,2-dinaphthyl ethanediol substituted phthalonitrile (2) together withtetra-substituted zinc(II) phthalocyanine (Pc) (3) and cobalt(II) Pc (4) bearing 1,2-dinaphthyl ethanediol at peripheral positions was described. The aggregation behaviors of metallophthalocyanines 3 and 4 in solution were investigated by carrying out Beer–Lambert experiments at different concentrations. In addition, the catalytic activity of new cobalt(II) Pc 4 was investigated for benzyl alcohol oxidation. Benzyl alcohol was converted to benzaldehyde using cobalt(II) Pc 4 as a catalyst by a conversion of 99% with selectivity of 100% at room temperature in 1 h. Several spectroscopic techniques such as FT-IR, UV-Vis, 1 H and 13 C NMR, and MALDI-TOF MS were used for the characterization of the newly synthesized compounds.