Synthesis and post-polymerization modification of poly(arylene ether sulfone)s containing pendant sulfonamide groups

Abstract

A series of poly (arylene ether sulfone) (PAE) copolymers with pendant alkenes was synthesized by nucleophilic aromatic substitution polymerization using benzenesulfonamides as comonomers. The substitution pattern of leaving groups on the monomer (e.g., ortho/ortho, ortho/para, and meta/meta) was varied in order to investigate its effect on the properties of the resulting polymer. The polymers were subsequently modified using thiol-ene chemistry to probe the effect of side-chain structure on polymer properties. We found that the thermal properties of the modified polymers depend on the choice of sulfonamide regioisomer. Copolymers with the ortho/meta and meta/meta benzenesulfonamides were insensitive to the functional group added by the thiol-ene reaction, while the properties of materials made with other substitution patterns varied considerably based on the identity of the functional group installed. The resulting materials were all completely amorphous and exhibited thermal stability dependent on the benzenesulfonamide regioisomer employed, with an onset of weight loss ranging from 372 to 496 °C and 392–524 °C for the un- and thiol-modified polymers, respectively.