Pentafluorobenzene end-group as a versatile handle for para fluoro "click" functionalization of polythiophenes

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Title: Pentafluorobenzene end-group as a versatile handle for para fluoro "click" functionalization of polythiophenes
Author(s): Boufflet, P
Casey, A
Xia, Y
Stavrinou, PN
Heeney, M
Item Type: Journal Article
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.
Publication Date: 15-Dec-2016
Date of Acceptance: 6-Dec-2016
URI: http://hdl.handle.net/10044/1/48722
DOI: https://dx.doi.org/10.1039/c6sc04427a
ISSN: 2041-6520
Publisher: Royal Society of Chemistry
Start Page: 2215
End Page: 2225
Journal / Book Title: Chemical Science
Volume: 8
Issue: 3
Copyright Statement: © 2017 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (https://creativecommons.org/licenses/by/3.0/). Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
THIOL-PARA-FLUORO
GRIGNARD METATHESIS POLYMERIZATION
CATALYST-TRANSFER POLYCONDENSATION
SELF-ASSEMBLED MONOLAYERS
CONJUGATED POLYMERS
MOLECULAR-WEIGHT
SOLAR-CELLS
REGIOREGULAR POLY(3-ALKYLTHIOPHENE)S
COPOLYMERS SYNTHESIS
BIOTIN TECHNOLOGY
Publication Status: Published
Open Access location: http://pubs.rsc.org/en/content/articlelanding/2017/sc/c6sc04427a#!divAbstract
Appears in Collections:Physics
Chemistry
Experimental Solid State
Faculty of Natural Sciences



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