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Bisporphyrins with Bischlorin Features Obtained by Direct Anodic Coupling of Porphyrins
Author(s) -
Ruhlmann Laurent,
Gross Maurice,
Giraudeau Alain
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200304924
Subject(s) - phosphonium , porphyrin , chromophore , delocalized electron , monomer , photochemistry , chemistry , tetraphenylporphyrin , electrochemistry , redox , chlorin , inorganic chemistry , polymer chemistry , organic chemistry , polymer , electrode
The proximity of two or more porphyrin or chlorin‐like structures has been shown to be crucial in numerous biological processes, such as electron transfers. The one‐pot electrochemical synthesis of a dimeric tetraphenylporphyrin with one 1,2‐(diphenylphosphonium)benzene as a spacer and of its porphyrin‐monomer precursor are reported. These new compounds have been characterized by 1 H and 31 P NMR, ESR, and UV‐visible spectroscopy and microanalysis. Electrochemical data are reported, and the redox behavior is analyzed for the monomers and the dimers. Important interactions between the two chromophores and a phosphonium–phosphonium interaction have been observed. UV‐visible and 1 H NMR data along with electrochemical behavior suggest that the positive charge carried by the two phosphonium units is in part delocalized onto the π system of the porphyrins, this gives an unexpected bis‐porphyrin with bischlorin spectroscopic features.