Fused corrole dimers interconvert between nonaromatic and aromatic states through two-electron redox reactions

Shota Ooi; Takayuki Tanaka; Kyu Hyung Park; Sangsu Lee; Dongho Kim; Atsuhiro Osuka

doi:10.1002/anie.201411242

Fused corrole dimers interconvert between nonaromatic and aromatic states through two-electron redox reactions

Shota Ooi, Takayuki Tanaka, Kyu Hyung Park, Sangsu Lee, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

Abstract

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 ¹H 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.

Original language	English
Pages (from-to)	3107-3111
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	10
DOIs	https://doi.org/10.1002/anie.201411242
Publication status	Published - 2015 Mar 2

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/anie.201411242

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abstract = "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 1H 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.",

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AU - Ooi, Shota

AU - Tanaka, Takayuki

AU - Park, Kyu Hyung

AU - Lee, Sangsu

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2015/3/2

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AB - 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 1H 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.

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Fused corrole dimers interconvert between nonaromatic and aromatic states through two-electron redox reactions

Abstract

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