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

36 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)

Access to Document

10.1002/anie.201411242

Fingerprint Dive into the research topics of 'Fused corrole dimers interconvert between nonaromatic and aromatic states through two-electron redox reactions'. Together they form a unique fingerprint.

Cite this

@article{1bd3c53b411642ecb6e79a68d3f92455,

title = "Fused corrole dimers interconvert between nonaromatic and aromatic states through two-electron redox reactions",

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.",

author = "Shota Ooi and Takayuki Tanaka and Park, {Kyu Hyung} and Sangsu Lee and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2015",

month = mar,

day = "2",

doi = "10.1002/anie.201411242",

language = "English",

volume = "54",

pages = "3107--3111",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "10",

}

TY - JOUR

T1 - Fused corrole dimers interconvert between nonaromatic and aromatic states through two-electron redox reactions

AU - Ooi, Shota

AU - Tanaka, Takayuki

AU - Park, Kyu Hyung

AU - Lee, Sangsu

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2015/3/2

Y1 - 2015/3/2

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85027925652&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027925652&partnerID=8YFLogxK

U2 - 10.1002/anie.201411242

DO - 10.1002/anie.201411242

M3 - Article

AN - SCOPUS:85027925652

VL - 54

SP - 3107

EP - 3111

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 10

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Cite this