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Updated: Jun 10, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Pentagon-fused hollow fullerene in C78 family retrieved by chlorination
Yuan-Zhi Tan1, Jia Li, Ting Zhou
1State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Abstract:
C(78) is one of the most widely investigated higher fullerenes. Among its huge isomer family, only one non-IPR (IPR = isolated pentagon ring) cage, the C(2)-symmetric (#22010)C(78), was previously stabilized by endohedral derivatization. Here we report a new C(1)-symmetric non-IPR hollow isomer, (#23863)C(78), which was captured as (#23863)C(78)Cl(8) and then subjected to a regioselective substitution reaction with benzyl hydroperoxide to form (#23863)C(78)(OOCH(2)C(6)H(5))Cl(7). The structural connectivity of (#23863)C(78), which contains a pair of fused pentagons, was confirmed by single-crystal X-ray diffraction analysis of the (#23863)C(78)(OOCH(2)C(6)H(5))Cl(7) molecule, which shares the same fullerene core with (#23863)C(78)Cl(8); support for the structure is provided by comparable IR measurements and computation. Theoretical studies suggest that the differences in C-Cl bond length, intermediate stability, and steric effects of the involved molecules account for the chemical regioselectivity of the substitution reaction.
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