Pentagon-fused hollow fullerene in C78 family retrieved by chlorination.
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.
Tan
Yuan-Zhi
YZ
State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Li
Jia
J
Zhou
Ting
T
Feng
Yu-Qi
YQ
Lin
Shui-Chao
SC
Lu
Xin
X
Zhan
Zhuang-Ping
ZP
Xie
Su-Yuan
SY
Huang
Rong-Bin
RB
Zheng
Lan-Sun
LS
D002712:Chlorides / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D008958:Models, Molecular; D016062:Porosity
D002712:Chlorides; D037741:Fullerenes