Soluble polyacetylene derivatives by chain-growth polymerization of dienes

Kai Luo, Sung Jin Kim, Alexander N. Cartwright, Javid Rzayev

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

A new method for the fabrication of soluble polyacetylene derivatives was developed based on bromination-dehydrobromination of bicyclic diene polymers. High molecular weight polymer precursors were synthesized by radical 1,4-polymerization of the corresponding dienes, which contained a bicyclo[2.2.2]octane skeleton. Polymer precursors with narrow molecular distributions were prepared by nitroxide-mediated polymerization of the bicyclic diene monomers. Regioselective elimination from the brominated polymer afforded a polyacetylene derivative contaning bicyclic substituents, which was readily soluble in common organic solvents. The polymer electronic bandgap, obtained by optical and electrochemical measurements, was in the range 1.4-1.7 eV. Low bandgap values were attributed to the conformational inflexibility of the bicyclic substituent forcing coplanar orientation of the backbone double bonds. Solid-state conductivity of the produced polymer in the undoped form was measured to be 1.5 × 10-5 S/m. This new synthetic method allows for the chain-growth production of polyacetylene derivatives that possess favorable electronic properties and superior solubility characteristics to pristine polyacetylene.

Original languageEnglish (US)
Pages (from-to)4665-4671
Number of pages7
JournalMacromolecules
Volume44
Issue number12
DOIs
StatePublished - Jun 28 2011

ASJC Scopus subject areas

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

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