Synthesis and characterization of novel poly(aryl ether)s via nitro displacement reaction

Abstract

Two dinitro monomers with trufluoromethyl groups which activate the nitro leaving group at ortho position were synthesized. One is 3,3``-bis(trifluoromethyl)-4,4``-dinitrobiiphenyl(DNBP) and the other is 3,3``-bis(trifluoromethyl)-4,4``-dinitro phenylsulfone(DNPS). DNBP was prepared from 5-bromo-2-nitrobenzotrifluoride with copper powder via Ullmann coupling reaction. Novel poly(arylene oxide)s and poly (aryelene sulfide)s were prepared from DNBP and various aromatic diols and dithiols via nitro displacement reaction in mild condition. Some of the synthesized poly (arylene oxide)s and the poly(arylene sulfide)s showed high intrinsic viscosity and formed tough transparent film. They were stable up to 450℃. The doubly activated dinitro monomer(DNPS) was synthesized from 5-chloro-2-nitrobenzotrifluoride with 2 steps. Polymerization of DNPS with dihydroxy or dithiol comonomers produced poly (aryl ether sulfone)s and poly(aryl thioether sulfone)s with low molecular weigh.