Electrosynthesis of buckyballs with fused-ring systems from PCBM and its analogue

Wei-Feng Wang; Kai-Qing Liu; Chuang Niu; Yun-Shu Wang; Yang-Rong Yao; Zheng-Chun Yin; Muqing Chen; Shi-Qi Ye; Shangfeng Yang; Guan-Wu Wang

doi:10.1038/s41467-023-43774-2

Electrosynthesis of buckyballs with fused-ring systems from PCBM and its analogue

Nat Commun. 2023 Dec 5;14(1):8052. doi: 10.1038/s41467-023-43774-2.

Authors

Wei-Feng Wang¹, Kai-Qing Liu¹, Chuang Niu¹, Yun-Shu Wang², Yang-Rong Yao³, Zheng-Chun Yin¹, Muqing Chen^{3

4}, Shi-Qi Ye¹, Shangfeng Yang⁵, Guan-Wu Wang^{6

7}

Affiliations

¹ Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
² Hefei No. 1 High School, Hefei, Anhui, 230601, P. R. China.
³ Hefei National Research Center for Physical Sciences at the Microscale, CAS Key Laboratory of Materials for Energy Conversion, and Department of Materials Science and Engineering, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
⁴ School of Environment and Civil Engineering, Dongguan University of Technology, Dongguan, Guangdong, 523808, P. R. China.
⁵ Hefei National Research Center for Physical Sciences at the Microscale, CAS Key Laboratory of Materials for Energy Conversion, and Department of Materials Science and Engineering, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China. sfyang@ustc.edu.cn.
⁶ Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China. gwang@ustc.edu.cn.
⁷ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000, P. R. China. gwang@ustc.edu.cn.

Abstract

[6,6]-Phenyl-C₆₁-butyric acid methyl ester (PCBM), a star molecule in the fullerene field, has found wide applications in materials science. Herein, electrosynthesis of buckyballs with fused-ring systems has been achieved through radical α-C-H functionalization of the side-chain ester for both PCBM and its analogue, [6,6]-phenyl-C₆₁-propionic acid methyl ester (PCPM), in the presence of a trace amount of oxygen. Two classes of buckyballs with fused bi- and tricyclic carbocycles have been electrochemically synthesized. Furthermore, an unknown type of a bisfulleroid with two tethered [6,6]-open orifices can also be efficiently generated from PCPM. All three types of products have been confirmed by single-crystal X-ray crystallography. A representative intramolecularly annulated isomer of PCBM has been applied as an additive to inverted planar perovskite solar cells and boosted a significant enhancement of power conversion efficiency from 15.83% to 17.67%.