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meso – meso ‐Linked Diarylamine‐Fused Porphyrin Dimers
Author(s) -
Fukui Norihito,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2016
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.201604301
Subject(s) - porphyrin , dimer , diphenylamine , chemistry , photochemistry , intramolecular force , borylation , stereochemistry , organic chemistry , alkyl , aryl
A meso – meso ‐linked diphenylamine‐fused porphyrin dimer and its methoxy‐substituted analogue were synthesized from a meso – meso ‐linked porphyrin dimer by a reaction sequence involving Ir‐catalyzed β‐selective borylation, iodination, meso ‐chlorination, and S N Ar reactions with diarylamines followed by electron‐transfer‐mediated intramolecular double C−H/C−I coupling. While these dimers commonly display characteristic split Soret bands and small oxidation potentials, they produced different products upon oxidation with tris(4‐bromophenyl)aminium hexachloroantimonate. Namely, the diphenylamine‐fused porphyrin dimer was converted into a dicationic closed‐shell quinonoidal dimer, while the methoxy‐substituted dimer gave a meso – meso , β‐β doubly linked porphyrin dimer.