Novel cobalt (II), zinc (II) phthalocyanines bearing discrete substituents: Synthesis, characterization, aggregation behavior, electrochemical properties and antioxidant activity

Abstract

A new phthalonitrile derivative bearing 3,4,5-trimethoxybenzyloxy and chloro-substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of phthalonitrile derivative in dimethylsulfoxide (DMSO) gave the metallophthalocyanines. Novel Co(II), Zn(II) phthalocyanines (Pcs) were obtained from the reaction 4-[(3,4,5- trimethoxybenzyloxy]-5-chlorophthalonitrile and metal salts. The novel compounds have been characterized by using elemental analysis, UV-Vis, FTIR, 1H-NMR spectral data. The aggregation behaviors of Co(II), Zn(II) Pcs were also investigated. These metallophthalocyanines do not show any aggregation behavior between 1.2 × 10−5 and 4.0 × 10−6Mconcentration range in DMF. The antioxidant activities of Pcs were investigated antioxidant assays such as free radical scavenging ability of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and ferrous ion chelating ability. Furthermore, the redox properties of the Pcs complexes were investigated by using cyclic voltammetry.