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 journalArticlepeer-review

15 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 Mar 13

Bibliographical note

Funding Information:
The work at Kyoto was supported by JSPS KAKENHI Grant Numbers 25220802 and 16K13952. T.S. acknowledges a JSPS Fellowship for Young Scientists. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea. The quantum calculations of ACID were performed using the supercomputing resources of the Korea Institute of Science and Technology Information (KISTI).

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

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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