Facile Synthesis of Functionalized poly (arylene ether sulfone) s

Abstract

The synthesis of poly (arylene ether) s, with a pendant aryl iodide was achieved via nucleophilic aromatic substitution, NAS of 3-iodo-3’,5’-difloro- diphenylsulfone, 1, with Bisphenol-A. Monomer 1 was prepared by the reaction of 3, 5- diflorodiphenylsulfone with N-Iodosuccinimide, NIS. Model reactions indicated that the iodo group was stable to NAS conditions. Both GC/MS analysis and NMR spectroscopy indicated quantitative displacement of the two fluorine atoms while the iodo group remained untouched. Furthermore, the introduction of the desired functional groups was achieved via the Pd (OAc) 2 catalyzed cross-coupling reaction with phenyl, naphthyl, and phenyl acetyl boronic acid. The thermal properties of the polymers were evaluated via GPC, DSC and TGA. The iodo polymer possessed a glass transition temperature, Tg, of 144 C while the corresponding phenyl derivative displayed a slight decrease in Tg to 131 C. The much bulkier naphthyl derivative provided a higher Tg of 150 C. The more polar acetyl derivative showed a much higher Tg of 165 C. All the polymers exhibited high Td5% values between 400 C and 500 C.