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Structures, Spectral and Electrochemical Properties of N ‐(Naphth‐2‐ylmethyl)‐Appended Porphyrinogens
Author(s) -
Hill Jonathan P.,
Schmitt Wolfgang,
McCarty Amy Lea,
Ariga Katsuhiko,
D’Souza Francis
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500257
Subject(s) - chemistry , electrochemistry , multiplicity (mathematics) , alkylation , stacking , intermolecular force , redox , spectral properties , stereochemistry , nitrogen atom , crystallography , molecule , computational chemistry , organic chemistry , electrode , group (periodic table) , mathematical analysis , mathematics , catalysis
Alkylation of 5,10,15,20‐tetrakis(3,5‐di‐ tert ‐butyl‐4‐oxo‐2,5‐cyclohexadienylidene)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 π‐π 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)