Chlorofullerenes featuring triple sequentially fused pentagons.
The triple sequentially fused pentagons (TSFP) motif is one of the basic subunits that could be used for constructing fullerenes, but it violates the isolated pentagon rule (IPR) and has not been found in carbon cages to date. The properties of TSFP-incorporating fullerenes are thus poorly explored both theoretically and experimentally. Reported herein are four chlorinated derivatives of three different fullerene cages, all with the TSFP motif. X-ray crystallographic analyses indicate that the molecular strain inherent to the pentagon adjacency of a TSFP is significantly relieved upon exohedral chlorination, leaving one of the four pentagon fusion sites unsaturated and rendering the present derivatives chiral. This unique reactivity, in stark contrast to that of previously reported non-IPR fullerenes containing double fused pentagons or triple directly fused pentagons, can be rationalized by density functional theory calculations, and are expected to stimulate further studies of these new members of the fullerene family, both theoretically and experimentally.
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
Yuan-Zhi
YZ
Tan
Jia
J
Li
Feng
F
Zhu
Xiao
X
Han
Wen-Sheng
WS
Jiang
Rong-Bin
RB
Huang
Zhiping
Z
Zheng
Zhuo-Zhen
ZZ
Qian
Rui-Ting
RT
Chen
Zhao-Jiang
ZJ
Liao
Su-Yuan
SY
Xie
Xin
X
Lu
Lan-Sun
LS
Zheng