Palladium-Catalyzed Polycondensation for the Synthesis of Poly(Aryl)Sulfides

Abstract

The palladium-catalyzed CS cross coupling reaction is investigated as a novel efficient tool for the synthesis of poly(phenyl)sulfide derivatives. The reaction proceeds through the polycondensation of dibromo arenes with a H₂ S-surrogate to yield poly(aryl)sulfides. The reaction is generalized by the synthesis of so-far-unprecedented poly(2,5-thiophene)sulfide. Number average molecular weights (M_sss ) of up to 3780 and 1770 g mol^-1 for poly(phenyl)sulfide and poly(thiophene)sulfide are achieved with degrees of polymerization (DP_n ) of 10 and 7, respectively. A mechanism for the new polycondensation reaction is suggested.

Keywords: cross-coupling; organometallic catalysts; polycondensation; polysulfides.