Pentagon-Fused Hollow Fullerene in C78 Family Retrieved by Chlorination

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• 作者：Yuan-Zhi Tan ; Jia Li ; Ting Zhou ; Yu-Qi Feng ; Shui-Chao Lin ; Xin Lu ; Zhuang-Ping Zhan ; Su-Yuan Xie ; Rong-Bin Huang ; Lan-Sun Zheng
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：September 15, 2010
• 年：2010
• 卷：132
• 期：36
• 页码：12648-12652
• 全文大小：234K
• 年卷期：v.132,no.36(September 15, 2010)
• ISSN：1520-5126

文摘

C₇₈ is one of the most widely investigated higher fullerenes. Among its huge isomer family, only one non-IPR (IPR = isolated pentagon ring) cage, the C₂-symmetric ^#22010C₇₈, was previously stabilized by endohedral derivatization. Here we report a new C₁-symmetric non-IPR hollow isomer, ^#23863C₇₈, which was captured as ^#23863C₇₈Cl₈ and then subjected to a regioselective substitution reaction with benzyl hydroperoxide to form ^#23863C₇₈(OOCH₂C₆H₅)Cl₇. The structural connectivity of ^#23863C₇₈, which contains a pair of fused pentagons, was confirmed by single-crystal X-ray diffraction analysis of the ^#23863C₇₈(OOCH₂C₆H₅)Cl₇ molecule, which shares the same fullerene core with ^#23863C₇₈Cl₈; 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.