Cross-conjugated oligothiophenes derived from the (C2S) n helix: Asymmetric synthesis and structure of carbon-sulfur [11]helicene

Makoto Miyasaka, Andrzej Rajca, Maren Pink, Suchada Rajca

Research output: Contribution to journalArticle

126 Scopus citations

Abstract

(-)-Sparteine-mediated asymmetric synthesis of di-n-octyl-substituted carbon-sulfur [11]helicene, a helical (C2S)n β-undecathiophene, is described. The atom-efficient routes rely on one-step tri-annelation or two-step di- and mono-annelation to provide enantiomeric excess of (+)- or (-)-[11]helicene, respectively. X-ray structures for homologous [11] and [7]helicenes indicate similar helical curvatures. The optical band gap, Eg ≈ 3.5 eV, is estimated for the (C2S)n helix polymer, with onset of electron localization at n ≤ 7.

Original languageEnglish (US)
Pages (from-to)13806-13807
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number40
DOIs
StatePublished - Oct 12 2005

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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