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Fused Corrole Dimers Interconvert between Nonaromatic and Aromatic States through Two‐Electron Redox Reactions
Author(s) -
Ooi Shota,
Tanaka Takayuki,
Park Kyu Hyung,
Lee Sangsu,
Kim Dongho,
Osuka Atsuhiro
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201411242
Subject(s) - corrole , dimer , chemistry , photochemistry , excited state , absorption spectroscopy , absorption (acoustics) , redox , crystallography , organic chemistry , materials science , physics , quantum mechanics , nuclear physics , composite material
A singly linked corrole dimer was synthesized by condensation of a dipyrromethane‐1‐carbinol with 1,1,2,2‐tetrapyrroethane. Oxidation of the dimer gave doubly linked corrole dimers 9 and 10 as the first examples of fused corrole dimers involving a meso–meso linkage. Dimers 9 and 10 exhibit characteristic 1 H NMR spectra, absorption spectra, excited‐state dynamics, and two‐photon absorption (TPA) values, which indicate the nonaromatic nature of 9 and the aromatic nature of 10 . Interestingly, 9 is fairly stable despite its unusual 2H‐corrole structure, which has been ascribed to the presence of two direct connections between the individual corrole units.