The synthesis and electrochemical characterization of new metallophthalocyanines containing 4-aminoantipyrine moieties on peripherally positions

Abstract

The electrochemical characterization and synthetic procedures of novel metallophthalocyanines (Co, Cu and Mn) 5, 6 and 7 fused eight N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-4-methylbenzenesulfonamide groups connected to ethylmercapto arms on peripherally positions were reported in this work. The metal complexes 5, 6 and 7 were prepared by a tetramerization reaction of the phthalonitrile derivative 4 with corresponding metal salts and materials. The characterization of new products was made by a combination of elemental analysis, FT–IR, MALDI–TOF mass spectral data, UV–Vis, 1H NMR and 13C NMR. Electrochemical characterization of metallophthalocyanines was determined by using cyclic voltammetry (CV) and square wave voltammetry (SWV) techniques. Copper(II) phthalocyanine showed Pc based electron transfer processes because of redox inactive metal center. On the other hand, MnIII and CoII metal ions behave as redox active cations in the core of the phthalocyanines. Therefore, MnIIIClPc and CoIIPc gave metal and ligand based reduction reactions as expected.