Synthesis and properties of unsymmetrical porphyrins possessing an isonicotinic acid moiety and phenyl, methoxyphenyl, or chlorophenyl groups

Abstract

The isonicotinic acid containing porphyrin compounds 5-{4-[3-(4-pyridylcarbonyloxy)propoxy]phenyl}-10,15,20-triphenylporphyrin, 5-{4-[3-(4-pyridylcarbonyloxy)propoxy]phenyl}-10,15,20-tri(4-methoxyphenyl)porphyrin, and 5-{4-[3-(4-pyridylcarbonyloxy)propoxy]phenyl}-10,15,20-tri(4-chlorophenyl)porphyrin are prepared and characterized by 1H NMR, 13C NMR, MS, elemental analysis, IR, and UV-Vis. In addition, their spectroscopic properties are investigated through using the Raman spectroscopy, fluorescence, and surface photovoltage measurements. The influence of different substituents on Raman spectra is small, but their impact on the fluorescence spectra and surface photovoltage measurements is significant. Molecular dynamic simulations and UV-Vis diffuse-reflectance spectra show that these porphyrin compounds are potential semiconductor materials.