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


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.

SUBMITTER: Boufflet P 

PROVIDER: S-EPMC5408564 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Pentafluorobenzene end-group as a versatile handle for <i>para</i> fluoro "click" functionalization of polythiophenes.

Boufflet Pierre P   Casey Abby A   Xia Yiren Y   Stavrinou Paul N PN   Heeney Martin M  

Chemical science 20161215 3


A convenient method of introducing pentafluorobenzene (PFB) as a single end-group in polythiophene derivatives is reported <i>via in situ</i> 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 s  ...[more]

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