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

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) (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 d...

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Main Authors: Xiao Huang, Li Yang, Rikard Emanuelsson, Jonas Bergquist, Maria Strømme, Martin Sjödin, Adolf Gogoll
Format: Article
Language:English
Published: Beilstein-Institut 2016-12-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
electropolymerization
functional polymers
polythiophene
Sonogashira coupling
thiophene
Online Access:https://doi.org/10.3762/bjoc.12.265
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spelling doaj-d1ef51677b954f0389e5e30ca0a0d3142021-04-02T07:13:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-12-011212682268810.3762/bjoc.12.2651860-5397-12-265A versatile route to polythiophenes with functional pendant groups using alkyne chemistryXiao Huang0Li Yang1Rikard Emanuelsson2Jonas Bergquist3Maria Strømme4Martin Sjödin5Adolf Gogoll6Department of Chemistry - BMC, Uppsala University, Box 576, 751 23 Uppsala, SwedenNanotechnology and Functional Materials, Department of Engineering Sciences, Uppsala University, Box 534, 751 21 Uppsala, SwedenNanotechnology and Functional Materials, Department of Engineering Sciences, Uppsala University, Box 534, 751 21 Uppsala, SwedenDepartment of Chemistry - BMC, Uppsala University, Box 576, 751 23 Uppsala, SwedenNanotechnology and Functional Materials, Department of Engineering Sciences, Uppsala University, Box 534, 751 21 Uppsala, SwedenNanotechnology and Functional Materials, Department of Engineering Sciences, Uppsala University, Box 534, 751 21 Uppsala, SwedenDepartment of Chemistry - BMC, Uppsala University, Box 576, 751 23 Uppsala, SwedenA 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.https://doi.org/10.3762/bjoc.12.265electropolymerizationfunctional polymerspolythiopheneSonogashira couplingthiophene
collection DOAJ
language English
format Article
sources DOAJ
author Xiao Huang
Li Yang
Rikard Emanuelsson
Jonas Bergquist
Maria Strømme
Martin Sjödin
Adolf Gogoll
spellingShingle Xiao Huang
Li Yang
Rikard Emanuelsson
Jonas Bergquist
Maria Strømme
Martin Sjödin
Adolf Gogoll
A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
Beilstein Journal of Organic Chemistry
electropolymerization
functional polymers
polythiophene
Sonogashira coupling
thiophene
author_facet Xiao Huang
Li Yang
Rikard Emanuelsson
Jonas Bergquist
Maria Strømme
Martin Sjödin
Adolf Gogoll
author_sort Xiao Huang
title A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
title_short A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
title_full A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
title_fullStr A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
title_full_unstemmed A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
title_sort versatile route to polythiophenes with functional pendant groups using alkyne chemistry
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2016-12-01
description 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.
topic electropolymerization
functional polymers
polythiophene
Sonogashira coupling
thiophene
url https://doi.org/10.3762/bjoc.12.265
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