Hydrobenzoin-based rigid chiral polymer

Anna Bieging, Li Xin Liao, Dominic V. McGrath

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


We prepared a rigid, chiral polymer (1) from optically active hydrobenzoin-based subunits. Nonracemic monomer units 6 and 8 were prepared by asymmetric dihydroxylation (AD) methodology and polymerization was carried out under Sonagashira coupling conditions. Polymer I was obtained in good yield with a molecular weight Mn = 5,100 (PDI = 2.3). Modeling suggests that polymer 1 could form a stable helical mainchain conformation in solution or the solid state. The chiroptical data of the polymer and a low-molecular weight model compound (9) are compared.

Original languageEnglish (US)
Pages (from-to)258-263
Number of pages6
Issue number2-3
StatePublished - 2002


  • Asymmetric dihydroxylation
  • Foldamer
  • Macromolecular asymmetry
  • Phenyl ethynylene
  • Polymer
  • Sonagashira coupling
  • Stilbene diol

ASJC Scopus subject areas

  • Drug Discovery
  • Analytical Chemistry
  • Spectroscopy
  • Catalysis
  • Pharmacology
  • Organic Chemistry


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