We report the stannylation of a benzocarborano[2,1-b:3,4-b′]dithiophene monomer and its polymerization by Stille polycondensation with solubilized cyclopentadithiophene and diketopyrrolopyrrole derivatives. The physical, material, and optoelectronic properties of the resultant conjugated copolymers are reported, demonstrating that benzocarboranodithiophene acts as a mildly electron-withdrawing monomer.