Chiral molecular glass: Synthesis and characterization of enantiomerically pure thiophene-based [7]helicene

Makoto Miyasaka, Andrzej Rajca, Maren Pink, Suchada Rajca

Research output: Contribution to journalArticle

65 Scopus citations

Abstract

Synthesis of thiophene-based [7]helicenes, which are functionalized for both design of organic chiral glasses with strong chiroptical properties and for further homologation to higher [n]helicenes, is reported. The key synthetic transformations are kinetic resolution of the intermediate diketone and the annelation step forming the center benzene ring by means of an intramolecular McMurry reaction. Based upon X-ray crystallographic determinations of the absolute configurations for (+)-enantiomers of the diketone and the [7]helicene, stereochemical correlation between the (R) axial chirality of the diketone and the (M) helical chirality of the [7]helicene is established. One such enantiopure trimethylsilyl-substituted [7]helicene possesses enchanced chiroptical properties and forms a chiral molecular glass.

Original languageEnglish (US)
Pages (from-to)6531-6539
Number of pages9
JournalChemistry - A European Journal
Volume10
Issue number24
DOIs
StatePublished - Dec 3 2004

Keywords

  • Chirality
  • Helical structures
  • Heterocycles
  • Kinetic resolution
  • Molecular glass
  • Oligothiophenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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