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 either phenyl or naphthyl boronic acid.  The thermal properties of both polymers were evaluated via GPC, DSC and TGA. The iodo polymer possessed a glass transition temperature, Tg, of 133 C while the corresponding phenyl derivative displayed a slight decrease in Tg to 131 C.  The much bulkier naphthyl derivative provided a significantly higher Tg of 150 C.

Facile synthesis of functionalized poly (arylene ether sulfone)s

243rd National Meeting (2012)

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