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Issue 3, 2017
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Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

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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.

Graphical abstract: Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

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Publication details

The article was received on 04 Oct 2016, accepted on 06 Dec 2016 and first published on 15 Dec 2016


Article type: Edge Article
DOI: 10.1039/C6SC04427A
Citation: Chem. Sci., 2017,8, 2215-2225
  • Open access: Creative Commons BY license
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    Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

    P. Boufflet, A. Casey, Y. Xia, P. N. Stavrinou and M. Heeney, Chem. Sci., 2017, 8, 2215
    DOI: 10.1039/C6SC04427A

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