具有前所未有的加成模式的四官能化和六官能化[60]富勒烯衍生物的区域选择性电合成。
Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns.
作者信息
Liu Kai-Qing, Wang Jun-Jie, Yan Xing-Xing, Niu Chuang, Wang Guan-Wu
机构信息
Hefei National Laboratory for Physical Sciences at Microscale , CAS Key Laboratory of Soft Matter Chemistry , iChEM (Collaborative Innovation Center of Chemistry for Energy Materials) , Center for Excellence in Molecular Synthesis of CAS , Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , P. R. China . Email: gwang@.ustc.edu.cn.
State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou , Gansu 730000 , P. R. China.
出版信息
Chem Sci. 2019 Nov 20;11(2):384-388. doi: 10.1039/c9sc02131k. eCollection 2020 Jan 14.
The efficient and regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns has been achieved. The tetra-functionalized [60]fullerene derivative with an intriguing 1,2,4,17-addition pattern is regioselectively obtained by cyclization reaction of the dianionic species generated electrochemically from a [60]fulleroindoline with 1,2-bis(bromomethyl)benzene at 0 °C, and can be converted to the more stable 1,2,3,4-adduct at 25 °C. Furthermore, the hexa-functionalized [60]fullerene derivative with the 1,2,3,4,9,10-addition pattern displaying a unique ""-shaped configuration can be synthesized by protonation of the electrochemically generated dianion of the obtained tetra-functionalized 1,2,4,17-adduct. The structures of the tetra- and hexa-functionalized products have been determined by spectroscopic data and single-crystal X-ray analysis.
已经实现了具有前所未有的加成模式的四官能化和六官能化[60]富勒烯衍生物的高效区域选择性电合成。通过在0℃下，由[60]富勒吲哚啉电化学产生的双阴离子物种与1,2-双（溴甲基）苯进行环化反应，区域选择性地获得具有有趣的1,2,4,17-加成模式的四官能化[60]富勒烯衍生物，并且在25℃下可将其转化为更稳定的1,2,3,4-加合物。此外，通过对所获得的四官能化1,2,4,17-加合物的电化学产生的双阴离子进行质子化，可以合成具有独特“Ω”形构型的1,2,3,4,9,10-加成模式的六官能化[60]富勒烯衍生物。通过光谱数据和单晶X射线分析确定了四官能化和六官能化产物的结构。
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