Structures, spectral and electrochemical properties of N-(Naphth-2-ylmethyl)-appended porphyrinogens

Alkylation of 5,10,15,20-tetrakis(3,5-di-tert-butyl-4-oxo-2,5cyclohexadienylidene)porphyrinogen at its macrocyclic nitrogen atoms results in four multiply N-substituted products, which were isolated and characterized. The electrochemical and spectroelectrochemical properties of these compounds were determined. Molecular structures of the N-alkylated compounds are influenced strongly by intermolecular pi-pi stacking interaction between naphthyl groups leading to formation of dimers or stacked arrays of the macrocycle depending on multiplicity of substituents. The redox and spectral properties of the compounds are related to the increasing multiplicity of N-substitution. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)