Chalcogen Bridged Thieno- and Selenopheno[2,3- d:5,4- d′]bisthiazole and Their Diketopyrrolopyrrole Based Low-Bandgap Copolymers

We report the synthesis and characterization of four novel small bandgap copolymers incorporating the electron-deficient thieno[2,3-d:5,4-d′]bisthiazole and selenopheno[2,3-d:5,4-d′]bisthiazole building blocks with a series of electron-deficient diketopyrrolopyrole units. The four resultant copolymers were synthesized via palladium Stille cross-coupling reaction, and their optical, thermal stability, electrochemical, and field-effect charge transport properties were investigated. All copolymers showed low optical bandgaps (1.53-1.56 eV); in addition, X-ray diffraction on solution-cast films revealed that the selenium-containing copolymers exhibit higher crystallinity compared to their thiophene counterparts.