Synthesis, characterization, photophysicochemical properties and theoretical study of novel zinc phthalocyanine containing four tetrathia macrocycles

Abstract

In this work, Zn(II) phthalocyanine derivative (TTU-Pc) bearing 13-membered tetrathia macrocycles was synthesized, and the novel Zn(II) phthalocyanine derivative was fully characterized by elemental analysis and general spectroscopic methods such as MALDI-TOF mass, FT-IR, UV-vis and H-1-NMR. The synthesized phthalocyanine derivative has quite limited solubility in most of the common organic solvents. Fluorescence measurement was conducted for this Zn(II) phthalocyanine to estimate its fluorescence quantum yields. The singlet oxygen generation ability was also examined to investigate its photosensitizer properties. General trends were described for quantum yields of fluorescence, photodegradation and singlet oxygen quantum yields of this compound. The electrochemical properties of the molecule were investigated by cyclic voltammetry (CV) and square wave voltammetry (SWV). In addition, the lowest energy structure, the electronic structure and frontier molecular orbitals were calculated in DFT and the excitation spectrum was obtained by TDDFT calculations. We found that our computational and experimental results were in agreement.