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A Porphyrin with Two Coordination Sites: The Biquinoline Ligand as a New Potential External Chelate
Author(s) -
Jeandon Christophe,
Ruppert Romain
Publication year - 2011
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.201100413
Subject(s) - porphyrin , chemistry , ring (chemistry) , intramolecular force , nitrene , ligand (biochemistry) , nitro , yield (engineering) , photochemistry , stereochemistry , medicinal chemistry , catalysis , organic chemistry , biochemistry , receptor , alkyl , materials science , metallurgy
Abstract A highly symmetrical doubly fused porphyrin was obtained after two successive intramolecular cyclizations.1 The first supplementary ring was closed by using the Cadogan reaction, involving the generation of an intermediate nitrene from the starting nitro function. By trying to use the same methodology for the second ring closure, we found that the Cadogan reaction could be used but that cyclization yields remained low. We showed, by taking into account unusual mass spectroscopy results, that the cyclization of the nitro functionality with the neighboring meso ‐phenyl took place in the absence of the oxygen abstracting phosphite used by Cadogan. The bis‐biquinolino‐fused porphyrin, bearing an internal and an external coordination site, was obtained in very good yield and showed strong absorbance between 700 and 800 nm.