Synthesis and electrochemistry of metallophthalocyanines bearing {4-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]phenoxy} groups

Abstract

In this study, metallophthalocyanines 4, 5, 6 was carried out by the cyclotetramerization of 4-{3-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]phenoxy}phthalonitrile 3. The synthesis of metallo derivatives [Zn(II), Co(II), Cu(II)] of phthalocyanines obtained from corresponding phthalonitrile derivative and in the presence of the anhydrous divalent metal salts (Zn(CH3COO)(2), CoCl2 and CuCl2) was described. These phthalocyanines showed good solubility in organic solvents such as chloroform, tetrahydrofuran, DMSO and DMF. The newly synthesized Pcs were verified by IR, H-1 NMR, C-13 NMR, UV-vis and MS spectral data. The electrochemical properties of the zinc(II), copper(II) and cobalt(II) phthalocyanines were investigated by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods. The cobalt complex showed a metal based reduction process, while zinc phthalocyanines were giving ligand based electron transfer processes. (C) 2013 Elsevier B. V. All rights reserved.