Pentafluorobenzene end-group as a versatile handle for para fluoro "click" functionalization of polythiophenes
File(s)
Published version
Author(s)
Boufflet, P
Casey, A
Xia, Y
Stavrinou, PN
Heeney, M
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.
Date Issued
2016-12-15
Date Acceptance
2016-12-06
Citation
Chemical Science, 2016, 8 (3), pp.2215-2225
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.
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000395906900068&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
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