A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

Xiao Huang, Li Yang, Rikard Emanuelsson, Jonas Bergquist, Maria Strømme, Martin Sjödin, Adolf Gogoll

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A new versatile polythiophene building block, 3-(3,4-ethylenedioxythiophene)prop-1-yne (pyEDOT) (3), is prepared from glycidol in four steps in 28% overall yield. pyEDOT features an ethynyl group on its ethylenedioxy bridge, allowing further functionalization by alkyne chemistry. Its usefulness is demonstrated by a series of functionalized polythiophene derivatives that were obtained by pre- and post-electropolymerization transformations, provided by the synthetic ease of the Sonogashira coupling and click chemistry.

Original languageEnglish
Pages (from-to)2682-2688
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume12
DOIs
Publication statusPublished - 2016 Dec 9
Externally publishedYes

Fingerprint

glycidol
Alkynes
Electropolymerization
Functional groups
Derivatives
polythiophene
3,4-ethylenedioxythiophene

Keywords

  • Electropolymerization
  • Functional polymers
  • Polythiophene
  • Sonogashira coupling
  • Thiophene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Huang, X., Yang, L., Emanuelsson, R., Bergquist, J., Strømme, M., Sjödin, M., & Gogoll, A. (2016). A versatile route to polythiophenes with functional pendant groups using alkyne chemistry. Beilstein Journal of Organic Chemistry, 12, 2682-2688. https://doi.org/10.3762/bjoc.12.265

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry. / Huang, Xiao; Yang, Li; Emanuelsson, Rikard; Bergquist, Jonas; Strømme, Maria; Sjödin, Martin; Gogoll, Adolf.

In: Beilstein Journal of Organic Chemistry, Vol. 12, 09.12.2016, p. 2682-2688.

Research output: Contribution to journalArticle

Huang, X, Yang, L, Emanuelsson, R, Bergquist, J, Strømme, M, Sjödin, M & Gogoll, A 2016, 'A versatile route to polythiophenes with functional pendant groups using alkyne chemistry', Beilstein Journal of Organic Chemistry, vol. 12, pp. 2682-2688. https://doi.org/10.3762/bjoc.12.265
Huang, Xiao ; Yang, Li ; Emanuelsson, Rikard ; Bergquist, Jonas ; Strømme, Maria ; Sjödin, Martin ; Gogoll, Adolf. / A versatile route to polythiophenes with functional pendant groups using alkyne chemistry. In: Beilstein Journal of Organic Chemistry. 2016 ; Vol. 12. pp. 2682-2688.
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