Soluble polyacetylene derivatives by chain-growth polymerization of dienes

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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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

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Polyacetylenes
Polymers
Polymerization
Derivatives
Energy gap
Electronic properties
Organic solvents
Solubility
Monomers
Molecular weight
Fabrication

ASJC Scopus subject areas

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

Cite this

Soluble polyacetylene derivatives by chain-growth polymerization of dienes. / Luo, Kai; Kim, Sung Jin; Cartwright, Alexander N.; Rzayev, Javid.

In: Macromolecules, Vol. 44, No. 12, 28.06.2011, p. 4665-4671.

Research output: Contribution to journalArticle

Luo, Kai ; Kim, Sung Jin ; Cartwright, Alexander N. ; Rzayev, Javid. / Soluble polyacetylene derivatives by chain-growth polymerization of dienes. In: Macromolecules. 2011 ; Vol. 44, No. 12. pp. 4665-4671.
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