A Möbius aromatic [28]Hexaphyrin bearing a diethylamine group: A rigid but smooth conjugation circuit

Tomohiro Higashino, Takanori Soya, Woojae Kim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The reaction of [26]hexaphyrin with triethylamine in the presence of BF3 OEt2 and O2 furnished a diastereomeric mixture of a diethylamine-bearing [28]hexaphyrin as a rare example of a Möbius aromatic metal-free expanded porphyrin. The Möbius aromaticity of these molecules is large, as indicated by their large diatropic ring currents, which are even preserved at 100 C, owing to their internally multiply bridged robust structure with a smooth conjugation network. These molecules were reduced with NaBH4 to give an antiaromatic [28]hexaphyrin, and were oxidized with MnO2 to give aromatic [26]hexaphyrins, both through a Möbius-to-Hückel topology switch induced by a C-N bond cleavage.

Original languageEnglish
Pages (from-to)5456-5459
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number18
DOIs
Publication statusPublished - 2015 Apr 27

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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