Soluble, Chiral Polyacetylenes: Syntheses and Investigation of Their Solution Conformation

Jeffrey S. Moore, Christopher B. Gorman, Robert H. Grubbs

Research output: Contribution to journalArticlepeer-review

Abstract

Soluble and highly conjugated polyacetylene derivatives bearing chiral appendages have been synthesized and characterized. The backbone π → π* transition of these polymers showed substantial circular dichroism (CD). The magnitude of the CD for the polymers is characteristic of a disymmetric chromophore. Thus, the chiral side groups twist the main chain in predominantly one sense rather than just electronically perturbing that chromophore. The ellipticity observed for the polyacetylenes studied here, having an α-branched substituent on only one of every eight backbone atoms, is of the order of magnitude observed for previously studied chiral polyacetylenes that had α-branched substituents on every other backbone atom. This observation suggests that the chirality imparted to the backbone by the substituent is not greatly influenced by the proximity of neighboring substituents. Decreasing temperature had much more influence on the CD of the cis polymers than on the CD of the trans polymers in their respective π → π* regions. cis-Poly-RCOTs (where RCOT is substituted cyclooctatetraene) are much more conformationally flexible and may be helical, although the CD data do not provide conclusive evidence of this conformation.

Original languageEnglish (US)
Pages (from-to)1704-1712
Number of pages9
JournalJournal of the American Chemical Society
Volume113
Issue number5
DOIs
StatePublished - Feb 1 1991
Externally publishedYes

ASJC Scopus subject areas

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

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