Oligomers and soluble polymers incorporating conjugated alpha-oligothiophene units bridged by sulfide and sulfone groups are reported. The oligomers and polymers are characterized by solution H-1 NMR spectroscopy, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, gel permeation chromatography, and photo physical methods. The energies of the frontier orbitals, the physical properties, and the optical absorption and emission of these oligomers and polymers were found to be dependent on the oxidation state of the bridging sulfur.