Synthesis of non-peripherally tetra-substituted copper(ii) phthalocyanines: Characterization, optical and surface properties, fabrication and photo-electrical properties of a photosensitive diode

Abstract

This study describes the synthesis and characterization of a non-peripherally tetra-substituted copper(ii) phthalocyanine bearing 4-(trifluoromethoxy)phenol groups. Some spectroscopic techniques such as FT-IR, 1H-NMR, 13C-NMR, MALDI-TOF, SEM and UV-vis were used to characterize the compounds. The novel molecule of 3-(4-(trifluoromethoxy) phenoxy) phthalonitrile (1) was confirmed and its molecular structure and supra-molecular dynamics were revealed by the analysis of single crystal X-ray diffraction measurements. Ligand (1) and its copper(ii) phthalocyanine (2) were theoretically examined via HF and B3LYP, M06-2X methods by using the 3-21G, 6-31G and sdd basis sets. The calculated values of IR, NMR and UV-Vis spectra for ligand (1) and its copper(ii) phthalocyanine (2) were compared with the experimentally obtained values. The absorbance and reflectance spectra, optical band gaps, refractive indices, and the optical and electrical conductivities of compound (2) for different concentrations were investigated in detail. We fabricated a photosensitive diode and investigated its photo-electrical properties under dark and light conditions. © 2019 The Royal Society of Chemistry.