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

Pierre Boufflet, Abby Casey, Yiren Xia, Paul N. Stavrinou, Martin Heeney

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


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.
Original languageEnglish (US)
Pages (from-to)2215-2225
Number of pages11
JournalChemical Science
Issue number3
StatePublished - Jan 1 2017
Externally publishedYes

Bibliographical note

Generated from Scopus record by KAUST IRTS on 2023-02-14

ASJC Scopus subject areas

  • General Chemistry


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