Synthesis of Cu-Porphyrazines by Annulated Diazepine Rings with Electrochemical, Conductance Activities and Computational Studies

Abstract

In this investigation, we synthesized novel Cu-porphyrazines annulated with diazepines moiteis, the diazepines rings were obtained via 1,4-cycloaddition reactions of chalcone derivatives 1a-d with 2,3-diaminomaleonitrile utilized ultrasonic energy as green source energy to afford the corresponding diazepine derivatives 4a-d. The formed diazepine was characterized by using data from proton and carbon NMR, fourier-transform infrared spectra and Mass spectrum. Furthermore, in one pot system, the diazepine compounds reacted with copper sulfate in the presence of DBU to give Cu-porphyrazines annulated with diazepines moieties. The prepared Cu-porphyrazine rings 5a-d were characterized using solid state NMR, analysed HSQC, FT-IR, and thermal gravimetrical analysis. The Cu-Porphyrazines and diazepine compounds underwent electrochemical behavior such as cyclic voltammetry and impedance spectroscopy to ensure presence of Cu atom in the core of cyclic diazepines rings and approved the oxidation and reduction of these Porphyrazines on the surface and ability of their reactivity. The electrical conductivity of new Cu-porphyrazines were measured. The obtained diazepines and Cu-porphyrazines were investigated through DFT/B3PW91/LANDZ2 basis set and the stability of these compounds was confirmed. Graphic Abstract: [Figure not available: see fulltext.]