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

Patra, Dhananjaya; Lee, Jaehyuk; Dey, Somnath; Lee, Jongbok; Kalin, Alexander J.; Putta, Anjaneyulu; Fei, Zhuping; McCarthy-Ward, Thomas; Bazzi, Hassan S.; Fang, Lei; Heeney, Martin; Yoon, Myung-Han; Al-Hashimi, Mohammed

MACROMOLECULES

2018

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.