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

A new versatile polythiophene building block, 3-(3,4-ethylenedioxythiophene)prop-1-yne (pyEDOT) ( ), 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 d...

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Published inBeilstein journal of organic chemistry Vol. 12; no. 1; pp. 2682 - 2688
Main Authors Huang, Xiao, Yang, Li, Emanuelsson, Rikard, Bergquist, Jonas, Strømme, Maria, Sjödin, Martin, Gogoll, Adolf
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 09.12.2016
Beilstein-Institut
Subjects
Acids
Carbon
Chemistry
electropolymerization
Engineering Science with specialization in Nanotechnology and Functional Materials
Full Research Paper
functional polymers
Polymerization
Polymers
polythiophene
Sonogashira coupling
Teknisk fysik med inriktning mot nanoteknologi och funktionella material
thiophene
Sonogashira coupling
electropolymerization
functional polymers
polythiophene
thiophene
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Summary:A new versatile polythiophene building block, 3-(3,4-ethylenedioxythiophene)prop-1-yne (pyEDOT) ( ), 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.
Bibliography:ObjectType-Article-1
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ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.265