Synthesis of sulfonate ester and sulfonic acid-containing poly(arylene perfluorocyclobutane)s (PFCB) by direct copolymerization of a sulfonate ester-containing precursor

This paper reports the first synthesis of sulfonated poly(arylene perfluorocyclobutane)s by direct polycondensation of a new sulfonate ester-containing bis(trifluorovinylether) precursor and subsequent hydrolysis of the resulting polymers. The multi-step synthesis of a bis(trifluorovinylether) monom...

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Bibliographic Details
Published in:Polymer (Guilford) 2017-01, Vol.108, p.179-192
Main Authors: Marestin, Catherine, Thiry, Xavier, Rojo, Sergio, Chauveau, Edouard, Mercier, Regis
Format: Article
Language:English
Subjects:
Biphenyl
Chemical properties
Chemical Sciences
Chemical synthesis
Copolymerization
Copolymers
Esters
Hydrolysis
Material chemistry
Monomers
Physicochemical properties
Polymerization
Polymers
Precursors
Sulfonate ester bistrifluorovinyl ether
Sulfonated poly(arylene perfluorocyclobutane)
Sulfonates
Sulfonic acid
Sulfuric acid
Synthesis (chemistry)
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Summary:This paper reports the first synthesis of sulfonated poly(arylene perfluorocyclobutane)s by direct polycondensation of a new sulfonate ester-containing bis(trifluorovinylether) precursor and subsequent hydrolysis of the resulting polymers. The multi-step synthesis of a bis(trifluorovinylether) monomer bearing sulfonic acid groups protected as sulfonate esters (SE-TFVE) is described. Based on this precursor and 4,4′-bis(trifluorovinyloxy)biphenyl (4,4′-TFVE), sulfonate ester-containing poly(arylene perfluorocyclobutane) copolymers (SE-PFCB) were synthesized by 2π + 2π step-growth cyclopolymerization. Their thermal and physico-chemical properties were characterized. Free acid polymers (SA-PFCB) were subsequently obtained by hydrolysis of sulfonate ester groups. A preliminary evaluation of the proton conductive properties of these polymers is reported. [Display omitted] •Sulfonate ester-containing bistrifluorovinyl ether monomer synthesis.•Direct polycondensation of sulfonate ester-containing precursor.•Synthesis and characterization of sulfonated Poly(arylene perfluorocyclobutane)s.
ISSN:0032-3861
1873-2291
DOI:10.1016/j.polymer.2016.11.061