Synthesis of bis-(benzhydryloxy) substituted axially silicon(IV) phthalocyanine: investigation of photophysical, photochemical, and computational electronic properties

Synthesis of axially disubstituted silicon(IV) phthalocyanine bearing benzhydryloxy groups obtained by reaction of SiPcCl₂ with diphenylmethanol is reported. Characterization of the compound was performed by ¹H and ¹³C NMR, UV–Vis, mass spectrometry, and FT-IR spectroscopy. Photophysical and photochemical properties were investigated. Fluorescence spectra measurements were performed in DMSO as solvent. A preferred chemical method was used to determine the amount of singlet oxygen production. Optimizations were calculated for the single-molecule Si-Pc with the 6–311 G (d, p) basis set at the B3LYP and B3PW91 levels of density functional theory (DFT). The charge transfer (or) charge delocalization between intramolecular donor–acceptor groups was determined by NBO analysis. Furthermore, molecular electrostatic potential, Fukui functions, electrophilic and nucleophilic character maps were calculated. The electronic structure and energy parameters of the investigated compound were determined to be ΔE_calc = 2.19 eV by DFT calculation and ΔE_opt = 1.84 by experimental UV spectrum.