Effect of Fluorination of 2,1,3-Benzothiadiazole

The 4,7-dithieno-2,1,3-benzothiadiazole (DTBT) moiety and its fluorinated counterpart are important π-conjugated building blocks in the field of organic electronics. Here we present a combined experimental and theoretical investigation into fundamental properties relating to these two molecular entities and discuss the potential impact on extended π-conjugated materials and their electronic properties. While the fluorinated derivative, in the solid state, packs with a cofacial overlap smaller than that of DTBT, we report experimental evidence of stronger optical absorption as well as stronger intra- and intermolecular contacts upon fluorination.