10.1016/S0040-4020(02)00828-1
The research aims to construct novel π-electronic systems by synthesizing and characterizing porphyrins with phenylenediamine pendant groups in a dimensionally oriented manner. The study explores the structural and electronic characteristics of these porphyrins, which depend on their atropisomers (aaaa and abab). Key chemicals used include pyrrole, 2-(ethoxycarbonylmethoxy)naphthalenecarbaldehyde for the porphyrin scaffold, and phenylenediamine for the redox-active pendant groups. The researchers employed various techniques such as 1H NMR, FT-IR, and MS for structural elucidation, absorption and fluorescence spectroscopy for electronic environment investigation, and electrochemistry for studying redox behavior. The findings reveal that the phenylenediamine pendant groups significantly influence the electronic properties of the porphyrins, leading to almost complete quenching of the porphyrin fluorescence emission and distinct redox potentials. The study concludes that these π-conjugated systems, with their unique electronic characteristics, hold potential for applications in photocatalysis and other photoreactive electron transfer systems.