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

Research output: Contribution to journalArticle

11 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 languageEnglish
Pages (from-to)3232-3236
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number12
DOIs
Publication statusPublished - 2017 Jan 1

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Protonation
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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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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.",
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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; Koo, Yun Hee; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 56, No. 12, 01.01.2017, p. 3232-3236.

Research output: Contribution to journalArticle

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