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

•Synthesis and characterization of peripherally tetra-substituted metallophthalocyanines.•Highly solubility in organic solvents.•The electrochemical properties of the zinc(II), cobalt(II) phthalocyanines.

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, 1H NMR, 13C 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.

Graphical abstractSynthesis and characterization of peripherally tetra-substituted metallophthalocyanines. Highly solubility in organic solvents. The electrochemical properties of the zinc(II), copper(II) and cobalt(II) phthalocyanines.Figure optionsDownload full-size imageDownload as PowerPoint slide