A process in which macrocycles are synthesized under thermodynamic conditions from the alkyne metathesis-enabled depolymerization of arylene ethynylene polymers is described. Carbazolylethynylene homopolymers having N-alkyl or triethylene glycol monomethyl ether side chains were synthesized from the requisite 3,6-diiodocarbazole and 3,6-diethynylcarbazole using standard Sonogashira coupling conditions. Access to the desired diyne polymer was accomplished using Hay conditions for the oxidative coupling of terminal alkynes. Diethynylcarbazole was treated with Cu-TMEDA under aerobic conditions and the the presence of low molecular weight material was found. Diyne polymer was then subjected to standard alkyne metathesis conditions. The GPC trace of the crude reaction mixture shows conversion to lower molecular weight polymer and a monodisperse peak eluting near 29 mL.

Original languageEnglish (US)
Pages (from-to)3685-3687
Number of pages3
Issue number10
StatePublished - May 24 2011

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry


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