Fused Bis-Benzothiadiazoles as Electron Acceptors

Fused bis-benzothiadiazoles with different molecular geometries, namely, linear benzoquinone-fused bis(benzothiadiazole) (Q-BBT) and V-shaped sulfone-fused bis(benzothiadiazole) (S-BBT), were synthesized. Single crystal analysis of Q-BBT and S-BBT revealed profoundly distinct packing modes, which must be ascribed to the different molecular shapes. Experimental and theoretical studies indicated that both compounds give rise to electron-accepting materials. This work thus also contributes to the diversity of electron acceptors based on bis-benzothiadiazole moieties and highlights the important role of molecular shape for the solid-state packing of organic conjugated materials.