Synthesis of water-soluble poly(p-phenyleneethynylene) in neat water under aerobic conditions via Suzuki-Miyaura polycondensation using a diborylethyne synthon.

We report the synthesis, structure, and characterization of a novel ethyne synthon, 1,2-bis(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)ethyne (B2C2). We demonstrate the utility of B2C2 in the Suzuki-Miyaura polycondensation reaction, synthesizing a water-soluble poly(p-phenyleneethynylene) from [2,5-diiodo-1,4-bis(3-propoxy-sulfonicacid)benzene] sodium salt in neat water under an aerobic atmosphere.