Synthesis, characterization and electrochemistry of 1-phenoxypropan-2-yloxy substituted phthalocyanines

Abstract

4-(1-phenoxypropan-2-yloxy)phthalonitrile (3) and peripherally tetra 1-phenoxypropan-2-yloxy substituted zinc(II) (4), cobalt(II) (5) and copper(II) (6) phthalocyanine were prepared. Structural characterization of novel complexes was performed by spectrophotometric measurements. The determination of the redox active or redox inactive metal center effect on the electrochemistry, in-situ spectroelectrochemisty and electrocolorimetry of compounds were performed in dimethylformamide. The redox properties and mechanisms were examined by electrochemical measurements. The peripherally tetra substituted cobalt(II) phthalocyanine (5) showed both metal and ligand-based redox processes, while zinc(II) (4) and cobalt(II) phthalocyanines only displayed ligand-based redox processes. These results were confirmed by electrochemical and in-situ spectroelectrochemical measurements. Moreover, the semiconducting nature of the compounds were illuminated via electrochemical measurements. (C) 2020 Elsevier B.V. All rights reserved.