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

Chemical Science
Pierre BouffletMartin Heeney

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.

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Citations

Nov 13, 2018·Physical Chemistry Chemical Physics : PCCP·Mads P Sulbaek AndersenOle John Nielsen
Sep 30, 2020·Macromolecular Rapid Communications·Tieshuai ZhaoCaglar Remzi Becer
Jun 14, 2019·Chemistry : a European Journal·Federica CavalliLeonie Barner
Dec 29, 2020·Chemical Communications : Chem Comm·Simon LudwanowskiAndreas Walther
Mar 16, 2021·Advanced Science·Simon LudwanowskiAndreas Walther
Sep 13, 2017·The Journal of Organic Chemistry·Jiandong WangNorio Shibata
Jan 13, 2018·ACS Applied Materials & Interfaces·Chi ZhangFude Feng

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Methods Mentioned

BETA
FRET
Nuclear Magnetic Resonance
NMR
biosensing

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