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Iridium Complex of N‐Fused Bilatrienone: Oxidative Cleavage of N‐Fused Porphyrin Induced by Iridium‐Cyclooctadiene Complexation
Author(s) -
Abraham Jibin Alex,
Mori Shigeki,
Ishida Masatoshi,
Furuta Hiroyuki
Publication year - 2021
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.202100789
Subject(s) - iridium , tetrapyrrole , chemistry , photochemistry , porphyrin , cyclooctadiene , chromophore , metalation , moiety , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enzyme
Abstract N‐fused porphyrin (NFP) is a unique class of photostable near‐infrared dyes with an 18π aromatic tetrapyrrole macrocyclic skeleton containing a tri‐fused pentacyclic moiety. Here, the synthesis of an iridium complex of N‐fused bilatrienone is reported as the degradation product of Ir‐cyclooctadiene (cod)‐induced oxidative cleavage of NFP under aerobic conditions. Similar to the native bilin chromophores, the ring‐opened complex featured a broken π‐conjugation circuit and exhibited a broad visible absorption band. In contrast, metalation of NFP using an iridium(I)(cod) complex under an inert atmosphere resulted in the formation of a cod‐isomerized (κ 1 ,η 3 ‐C 8 H 12 )‐Ir complex.