SiIV incorporation into a [28]hexaphyrin that triggered formation of möbius aromatic molecules

Shin Ichiro Ishida, Takayuki Tanaka, Jong Min Lim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Incorporation of SiIV into an expanded porphyrin has been achieved for the first time. Treatment of [28]hexaphyrin 1 with CH 3SiCl3 and N,N-diisopropylethylamine gave SiIV complex 2 and its N-fused product 4 that both have Möbius aromatic nature. In both complexes, the coordinated Si atom is satisfied in a typical trigonal bipyramidal coordination. SiIV incorporation induces conformational rigidification and redshifted absorption profiles due to σ-π conjugation between the Si atom and hexaphyrin macrocycle. Tamao-Fleming oxidation of 2 with H2O2 gave β-hydroxy [28]hexaphyrin 5, which exists as a ruffled rectangular shape in the solid state, yet it has been revealed to exist predominantly as a twisted Möbius aromatic conformer in CH2Cl2.

Original languageEnglish
Pages (from-to)8274-8278
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number27
DOIs
Publication statusPublished - 2014 Jul 1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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