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Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns†
Chemical Science ( IF 9.969 ) Pub Date : 2023-02-15 , DOI: 10.1039/c9sc02131k Kai-Qing Liu, Jun-Jie Wang, Xing-Xing Yan, Chuang Niu, Guan-Wu Wang
Chemical Science ( IF 9.969 ) Pub Date : 2023-02-15 , DOI: 10.1039/c9sc02131k Kai-Qing Liu, Jun-Jie Wang, Xing-Xing Yan, Chuang Niu, Guan-Wu Wang
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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 “S”-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.
更新日期：2020-01-06
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