Poly(ether ether sulfone)s and sulfonated poly(ether ether sulfone)s derived from functionalized 1,1-diphenylethylene derivatives

Symmetrically disubstituted 1,1-diphenylethylene derivatives, 1,1-bis[4-(t-butyldimethylsiloxy)phenyl]ethylene and 1,1-bis(4-hydroxyphenyl)ethylene, were prepared by new synthesis methods and employed as functionalized monomers in the preparation of new poly(ether ether sulfone) derivatives, with the introduction of the 1,1-diphenylethylene unit along the polymer backbone. A series of parent 1,1-diphenylethylene based poly(ether ether sulfone)s were prepared via (a) the cesium fluoride catalysed polycondensation reactions of dihalogenated diaryl sulfones with silylated bisphenols and (b) the base catalysed aromatic nucleophilic substitution polycondensation reaction between aromatic dihalogenated diaryl sulfones with bisphenols. The post-polymerization sulfonation reaction via the thiol-ene addition reaction of the poly(ether ether sulfone) precursor containing the 1,1-diphenylethylene unit along the backbone, with sodium 3-mercapto-1-propane sulfonate, afforded well-defined sulfonated poly(ether ether sulfone), with the alkyl sulfonate group introduced pendant to the polymer backbone. The organic compounds and different polymer derivatives were characterized by standard chromatography, spectroscopy, spectrometry, thermal analyses, microscopy and X-ray diffraction measurements. (c) 2016 Society of Chemical Industry