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Liu, Kai-Qing; Wang, Jun-Jie; Yan, Xing-Xing; Niu, Chuang; Wang, Guan-Wu
Chemical science (Cambridge), 01/2020, Volume: 11, Issue: 2Journal Article
The efficient and regioselective electrosynthesis of tetra- and hexa-functionalized 60fullerene derivatives with unprecedented addition patterns has been achieved. The tetra-functionalized 60fullerene derivative with an intriguing 1,2,4,17-addition pattern is regioselectively obtained by cyclization reaction of the dianionic species generated electrochemically from a 60fulleroindoline 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 60fullerene 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. The regioselective electrosynthesis of tetra- and hexa-functionalized 60fullerene derivatives with unprecedented 1,2,4,17-( cis -3) and 1,2,3,4,9,10-( S "-shaped) addition patterns is achieved.
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