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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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Detalles Bibliográficos
Autores principales: Huang, Xiao, Yang, Li, Emanuelsson, Rikard, Bergquist, Jonas, Strømme, Maria, Sjödin, Martin, Gogoll, Adolf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238539/
https://www.ncbi.nlm.nih.gov/pubmed/28144339
http://dx.doi.org/10.3762/bjoc.12.265
Descripción
Sumario: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.