电合成
电泳剂
化学
亲核细胞
三氟乙酸
戒指(化学)
晶体结构
电化学
结晶学
有机化学
催化作用
电极
物理化学
作者
Zheng‐Chun Yin,Mingjie Li,Cheng Niu,Weifeng Wang,Wen-Rui Liu,Qianwen Zhang,Guan‐Wu Wang
标识
DOI:10.1002/anie.202304321
摘要
Abstract Simultaneous electrochemical ring contraction and expansion reactions remain unexplored to date. Herein, the reductive electrosynthesis of heterocycle‐fused fulleroids from fullerotetrahydropyridazines and electrophiles in the presence of a trace amount of oxygen has been achieved with concurrent ring contraction and ring expansion. When trifluoroacetic acid and alkyl bromides are employed as electrophiles, heterocycle‐fused fulleroids with a 1,1,2,6‐configuration are regioselectively formed. In contrast, heterocycle‐fused fulleroids with a 1,1,4,6‐configuration are regioselectively produced as two separable stereoisomers if phthaloyl chloride is used as the electrophile. The reaction proceeds through multiple steps of electroreduction, heterocycle ring‐opening, oxygen oxidation, heterocycle contraction, fullerene cage expansion, and nucleophilic addition. The structures of these fulleroids have been determined by spectroscopic data and single‐crystal X‐ray diffraction analyses. The observed high regioselectivities have been rationalized by theoretical calculations. Representative fulleroids have been applied in organic solar cells as the third component and exhibit good performance.
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