The synthesis and electrochemistry of novel, symmetrical, octasubstituted phthalocyanines

In this study, the preparation of new phthalocyanines with eight dialkylaminophenoxy or trialkylaminophenoxy substituents on periphery of the phthalocyanines was achieved by the cyclotetramerization of 1,2-dicyano-4,5-bis[3-(diethylamino)phenoxy]benzene (2). All of the synthesized compounds have been characterized by using elemental analysis, UV-vis, FT-IR, H-1 NMR and MS spectroscopic data. Aggregation behaviors of phthalocyanines were investigated in different solvents. The electrochemistry and in situ spectroelectrochemical properties of neutral and electrogenerated complexes were also characterized. All complexes coated on the working electrodes with electropolymerization process, which is a desired property for the functional materials for their practical applications. Dialkylamine groups on the substituents cause to electropolymerization of the complexes on the working electrode. Number of the substituents and the metal center of the complexes alter the character of the electropolymerization processes. (C) 2013 Elsevier B.V. All rights reserved.