Electronic-Optical Properties of Tetraphenylporphyrin Derivatives Containing Amino Acid Fragments

Abstract— The complexing properties of 5-{4′-[2-amino-3-(4-hydroxyphenyl)propanamidophenyl]}-10,15,20-triphenylporphine, 5-{4′-[N-(tert-butoxycarbonyl)-2-amino-3-(4-hydroxyphenyl)propanamidophenyl]}-10,15,20-triphenylporphine, 5-(4′-{N-(tert-butoxycarbonyl)-2-amino-3-[4-(tert-butoxycarbonyloxy)phenyl]propanamidophenyl})-10,15,20-triphenylporphine, and 5-{4′-[2-amino-3-(4-hydroxyphenyl)propanamidophenyl]}-10,15,20-tris(4-methylphenyl)porphine toward Zn²⁺ in acetonitrile at 298–318 K were studied by spectrophotometry. Substituents in the meso-phenyl fragments of the macrocycle were found to affect the spectral and coordination properties of the analyzed compounds. The previously studied 5-(4′-aminophenyl)-10,15,20-triphenylporphine was used as reference. The energies of formation of the protonated forms of the studied ligands, obtained by quantum-chemical calculations, showed good correlation with the experimental values.