Internally 2,5-Thienylene-Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form

Takanori Soya; Hirotaka Mori; Yongseok Hong; Yun Hee Koo; Dongho Kim; Atsuhiro Osuka

doi:10.1002/anie.201700607

Internally 2,5-Thienylene-Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form

Takanori Soya, Hirotaka Mori, Yongseok Hong, Yun Hee Koo, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

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

20 Citations (Scopus)

Abstract

Internally 1,3-phenylene- and 2,5-thienylene-bridged [46]decaphyrins 2 and 3 have been synthesized. While 2 shows modest aromatic character derived from the global 46π-conjugated circuit, 3 displays larger aromatic character owing to the contribution of an (annuleno)annulene-type network consisting of two twisted Möbius aromatic thia[28]hexaphyrin segments in addition to the global 46π-network. Upon protonation, these [46]decaphyrins underwent large structural changes to acquire strong aromaticity. Protonated 3 has been revealed to take on a planar structure composed of fused two triangular thia[28]hexaphyrin segments.

Original language	English
Pages (from-to)	3232-3236
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	12
DOIs	https://doi.org/10.1002/anie.201700607
Publication status	Published - 2017 Mar 13

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© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/anie.201700607

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title = "Internally 2,5-Thienylene-Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of M{\"o}bius Aromatic Thia[28]hexaphyrins and Strong H{\"u}ckel Aromaticity of its Protonated Form",

abstract = "Internally 1,3-phenylene- and 2,5-thienylene-bridged [46]decaphyrins 2 and 3 have been synthesized. While 2 shows modest aromatic character derived from the global 46π-conjugated circuit, 3 displays larger aromatic character owing to the contribution of an (annuleno)annulene-type network consisting of two twisted M{\"o}bius aromatic thia[28]hexaphyrin segments in addition to the global 46π-network. Upon protonation, these [46]decaphyrins underwent large structural changes to acquire strong aromaticity. Protonated 3 has been revealed to take on a planar structure composed of fused two triangular thia[28]hexaphyrin segments.",

author = "Takanori Soya and Hirotaka Mori and Yongseok Hong and Koo, {Yun Hee} and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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month = mar,

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doi = "10.1002/anie.201700607",

language = "English",

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Internally 2,5-Thienylene-Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form. / Soya, Takanori; Mori, Hirotaka; Hong, Yongseok et al.
In: Angewandte Chemie - International Edition, Vol. 56, No. 12, 13.03.2017, p. 3232-3236.

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

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T1 - Internally 2,5-Thienylene-Bridged [46]Decaphyrin

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AU - Soya, Takanori

AU - Mori, Hirotaka

AU - Hong, Yongseok

AU - Koo, Yun Hee

AU - Kim, Dongho

AU - Osuka, Atsuhiro

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Internally 2,5-Thienylene-Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form

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