Conformational Fixation of a Rectangular Antiaromatic [28]Hexaphyrin Using Rationally Installed Peripheral Straps

Tomoki Yoneda, Taeyeon Kim, Takanori Soya, Saburo Neya, Juwon Oh, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A rectangular [28]hexaphyrin bearing outer straps at the long side has been synthesized by SNAr reaction of [26]hexaphyrin with allyl alcohol, intramolecular olefin metathesis by using Hoveyda-Grubbs second-generation catalyst, and reduction with NaBH4. The peripheral straps enforce a rectangular conformation for the [28]hexaphyrin, which shows Hückel antiaromatic character, as confirmed by its planar X-ray structure, a strong paratropic ring current, characteristic UV/Vis/NIR absorption features, small electrochemical HOMO-LUMO gap, and very fast S1 decay.

Original languageEnglish
Pages (from-to)4413-4417
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number13
DOIs
Publication statusPublished - 2016 Mar 18

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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