A novel bisphenol monomer with grafting capability and the resulting poly(arylene ether sulfone)s

A new bisphenol monomer, 1,1-bis(4-hydroxyphenyl)-1-(4-(4-fluorophenyl)thio)phenyl-2,2,2-trifluoroethane (3FBPT), containing a masked grafting site was readily synthesized in high yield in two reaction steps. A conventional aromatic nucleophilic substitution (SNAr) was used for copolymerization of this monomer with difluorodiphenyl sulfone and hexafluorobisphenol A, which gave high molecular weight linear poly(arylene ether sulfone)s containing 4-fluorophenyl sulfide pendant groups. After oxidation to convert the sulfide to sulfone, the para fluorine on the pendant group becomes activated for further SNAr reaction for the introduction of other functionality onto the pendant side chains such as sulfonated species for fuel cell applications. All the polymers are thoroughly characterized by H-1, F-19, and C-13 NMR spectroscopy. Thermal analysis study shows that these polymers have T(g)s between 180 and 230 degrees C according to the monomer ratio and have excellent thermal stability up to 500 degrees C.