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

• Published in: Journal of the American Chemical Society 2016-08, Vol.138 (32), p.10184-10190
• Main Authors: Meng, Dong, Fu, Huiting, Xiao, Chengyi, Meng, Xiangyi, Winands, Thorsten, Ma, Wei, Wei, Wei, Fan, Bingbing, Huo, Lijun, Doltsinis, Nikos L, Li, Yan, Sun, Yanming, Wang, Zhaohui
• Format: Article
• Language: English
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/jacs.6b04368

Two kinds of conjugated C 3-symmetric perylene dyes, namely, triperylene hexaimides (TPH) and selenium-annulated triperylene hexaimides (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 diffraction 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 π–π 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···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.