Photophysical, photochemical and DNA binding studies of prepared phthalocyanines

Abstract

In this study, three phthalocyanine derivatives (M = Zn, Co, and metal-free) were synthesized using the corresponding ligand 4-(2-(4-(tert-butyl)phenoxy)ethoxy)phthalonitrile 2 in peripheral position, which was prepared from the reaction of 4-nitrophthalonitrile with 2-(4-(tert-butyl)phenoxy)ethan-1-ol 1. Metallophthalocyanine (MPc) and Metal-free phthalocyanine (H2Pc) derivatives, which have soluble groups in peripheral positions were synthesized. They are have high soluble in organic solvents depending on the appropriate position such as (tetrahydrofuran (THF), chloroform (CHCl3), methylene chloride (DCM), acetone (ACE), Dimethyl formamide (DMF), and dimethylsulphoxide (DMSO))....etc. The structures of Metallophthalocyanine (MPc) and Metal-free phthalocyanine (H2Pc) compounds 3a, 3b, and 3c were characterized using UV-vis spectroscopy, infrared (FT-IR) spectroscopy, and MALDI-TOF MS. Additionally, DNA binding, metal chelating effect assay, and DPPH [2, 2-diphenyl-1-picrylhydrazyl hydrate] radical scavenging assay of MPcs H2Pc were investigated. In the interaction between Pc and CT-DNA the intrinsic binding constant (Kb) calculation was gave. Although the phthalocyanine compounds (3a, 3b and 3c) shoved low iron-containing iron chelating properties compared to EDTA, they can be said to have high metal chelating properties at the specified concentrations for this phthalocyanines. The DPPH radical scavenging activity of Pcs was elucidated according to the estimation of their in vitro antioxidant activities. (C) 2019 Elsevier Ltd. All rights reserved.