Polycouplings of Alkynyl Bromides and Sulfonamides toward Poly(ynesulfonamide)s with Stable Csp–N Bonds

The development of new polymerization methodology is crucial for polymer materials. Alkyne polymerization based on versatile reactions of C≡C bonds have attracted much attention recently because they can produce a great diversity of polymer materials with unsaturated structures and potential semiconducting properties. Among that, the polymerizations between alkyne and amine/amide which afford nitrogen-substituted alkynes with the triple bonds strongly polarized by the nitrogen atoms are quite attractive but challenging. In this work, the polycoupling of alkynyl bromides and sulfonamides is reported as the first example to generate polymers with stable N–C≡C bonds in the polymer main chain. The polycoupling of various aromatic/aliphatic alkynyl bromides and sulfonamides can be carried out at mild condition in the presence of CuSO4·5H2O, 1,10-phenanthroline, and K2CO3 at 65 °C under nitrogen, affording poly(ynesulfonamide)s with high molecular weights (up to 22 000 g/mol) in high yields (up to 95%). Incorpo...