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Updated: Dec 26, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented
Kai-Qing Liu1, Jun-Jie Wang1, Xing-Xing Yan1
1Hefei 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 .
Abstract:
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.
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