A Novel Bisphenol Monomer with Grafting Capability and the Resulting Poly(arylene ether sulfone)s

Abstract

A novel bisphenol monomer with grafting capability and the resulting poly(arylene ether sulfone)s Li, Z.; Ding, J.; Robertson, G.P.; Guiver, M.D. ABSTRACT: 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 (S N Ar) 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 S N Ar 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 1 H, 19 F, and 13 C NMR spectroscopy. Thermal analysis study shows that these polymers have T g s between 180 and 230°C according to the monomer ratio and have excellent thermal stability up to 500°C.

Preparation and characterization of crosslinked cellulose/sulfosuccinic acid membranes as proton conducting electrolytes

“…High cost, synthetic difficulty, toxic intermediates, loss of proton conductivity at high temperatures (>100°C), and high methanol crossover are serious drawback for practical applications in fuel cells. Therefore, there has been a great deal of research in the development of alternative proton conducting membranes to the perfluorinated membranes [14][15][16].…”

Synthesis and characterization of sulfonated poly(arylene ether)s with sulfoalkyl pendant groups for proton exchange membranes

“…They found that SPI with sulfonic groups introduced to flexible aliphatic side chains, the proton conduction activation energy (E a ) was smaller than that of SPI with sulfonic groups directly attached to main chain. Some studies about sulfonated poly(arylene ether)s with sulfonic groups introduced to side chains have been also reported in recent years [22][23][24][25][26][27][28]. Most of them were obtained by graft or post-sulfonation process to introduce sulfonated group to polymer side chain, while direct copolymerization method was seldom adopted due to the limitation of sulfonated monomers.…”

Low Water Swelling and High Proton Conducting Sulfonated Poly(arylene ether) with Pendant Sulfoalkyl Groups for Proton Exchange Membranes

“…sulfonated poly(arylene ether)s with sulfonic groups introduced onto side chains have also been reported in later years. [22][23][24][25][26][27][28][29] Most of the polymers were obtained by a graft or post-sulfonation process to introduce the sulfonated group to the polymer side chain. Compared to chemical grafting and post-sulfonation methods, the direct copolymerization method allows close control of the polymer structure, which includes the sulfonate content (SC) in the polymer.…”