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Synthesis, Characterization, and Electronic Properties of Metalloporphyrins Annulated to Exocyclic Imidazole and Imidazolium Rings
Author(s) -
Lefebvre JeanFrançois,
Leclercq Dominique,
Gisselbrecht JeanPaul,
Richeter Sébastien
Publication year - 2010
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.200901310
Subject(s) - chemistry , imidazole , triethyl orthoformate , porphyrin , hexafluorophosphate , cyclic voltammetry , formic acid , medicinal chemistry , ring (chemistry) , electrochemistry , alkylation , organic chemistry , catalysis , ionic liquid , electrode
meso ‐Tetraarylporphyrin complexes (M = Ni, Cu, Zn, H 2 ) fused to an imidazole ring across two neighboring β‐pyrrolic positions were synthesized through a cyclization reaction between β,β′‐diaminoporphyrins and formic acid or trimethyl orthoformate under acidic conditions. Two synthetic procedures were used to obtain the corresponding porphyrin N , N′ ‐dimethylimidazolium salts derivatives: alkylation of the imidazole nitrogen atoms with iodomethane and the cyclization reaction between the porphyrin bearing two neighboring β‐ N ‐methyl groups and trimethyl orthoformate in the presence of ammonium hexafluorophosphate. The electrochemical properties of these porphyrins annulated to an imidazole/imidazolium ring have been investigated by cyclic and rotating disk voltammetry.