Three-Bladed Rylene Propellers with Three-Dimensional Network Assembly for Organic Electronics

Two kinds of conjugated C-3-syrnmettic perylene dyes, namely, triperylene hexaimides (TPH) and selenium annulated triperylene hexairnides: (TPH-Se); are efficiently synthesized. Both TPH and TPH-Se have broad and strong absorption in the region 300-600 nm together with suitable LUMO levels of about -3.8 eV. Single-crystal X-ray difftaction studies show that TPH displays an extremely twisted three bladed propeller configuration and a unique 3D network assembly in which three PBI subunits in one TPH molecule have strong pi-pi intermolecular interactions with PBI subunits in neighboring molecules. The integration of selenophene to TPH endows TPH-Se with a More distorted propeller configuration and a more compact 3D network assembly due to the Se center dot center dot center dot O interactions. A single-crystal transistor confirms that both TPH and TPH-Se possess good electron-transport ability. TPH and TPH-Se acceptor-based solar cells show high power conversion efficiency of 8.28% and 9.28%, respectively, which mainly results from the combined properties of broad and strong absorption ability, appropriate LUMO level, desirable aggregation, high electron mobility, and good film morphology with the polymer donor.