NDLI: Pentafluorobenzene end-group as a versatile handle for <i>para</i> fluoro “click” functionalization of polythiophenes

Content Provider	Royal Society of Chemistry (RSC)
Author	Xia, Yiren Boufflet, Pierre Heeney, Martin Casey, Abby Stavrinou, Paul N.
Copyright Year	2017
Abstract	A convenient method of introducing pentafluorobenzene (PFB) as a single end-group in polythiophene derivatives is reported via in situ quenching of the polymerization. We demonstrate that the PFB-group is a particularly useful end-group due to its ability to undergo fast nucleophilic aromatic substitutions. Using this molecular handle, we are able to quantitatively tether a variety of common nucleophiles to the polythiophene backbone. The mild conditions required for the reaction allows sensitive functional moieties, such as biotin or a cross-linkable trimethoxysilane, to be introduced as end-groups. The high yield enabled the formation of a diblock rod-coil polymer from equimolar reactants under transition metal-free conditions at room temperature. We further demonstrate that water soluble polythiophenes end-capped with PFB can be prepared via the hydrolysis of an ester precursor, and that such polymers are amenable to functionalization under aqueous conditions.
Starting Page	2215
Ending Page	2225
Page Count	11
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	8
Issue Number	3
Journal	Chemical Science
DOI	10.1039/c6sc04427a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	End-group Hydrolysis Ester Polythiophene Polymerization Polymer Biotin Pentafluorobenzene
Content Type	Text
Resource Type	Article
Subject	Chemistry

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