Encapsulation of Formaldehyde and Hydrogen Cyanide in an Open-Cage Fullerene
Encapsulation of Formaldehyde and Hydrogen Cyanide in an Open-Cage Fullerene
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DOI：
10.1002/chem.201601737
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发表时间：
2016-06-20
影响因子：
4.3
通讯作者：
Yeh, Wen-Yann
中科院分区：
文献类型：
--
作者：
Chen, Chi-Shian;Kuo, Ting-Shen;Yeh, Wen-Yann
C63NO2(Ph)(2)(Py)(1)与邻苯二胺和吡啶反应生成C63H4NO2(Ph)(2)(Py)(N2C6H4)(2)和H2O@2的混合物。化合物2是一种新的含20元杂环孔的开笼富勒烯，已通过核磁共振光谱、高分辨率质谱和x射线晶体学对其进行了充分的表征。2的椭圆孔沿长轴跨度为7.45埃，沿小轴跨度为5.62埃，其大小足以捕获水和小有机分子。因此，在氯苯中加热2和H2O@2与氰化氢和甲醛的混合物，分别得到HCN@2和H2CO@2。H-1核磁共振光谱显示，由于富勒烯笼的强屏蔽作用，内嵌物质（δ = -1.30至-11.30 ppm）发生了明显的上场偏移。
Reaction of C63NO2(Ph)(2)(Py) (1) with o-phenylenediamine and pyridine produces a mixture of C63H4NO2(Ph)(2)(Py)(N2C6H4) (2) and H2O@2. Compound 2 is a new open-cage fullerene containing a 20-membered heterocyclic orifice, which has been fully characterized by NMR spectroscopy, high-resolution mass spectrometry, and X-ray crystallography. The elliptical orifice of 2 spans 7.45 angstrom along the major axis and 5.62 angstrom along the minor axis, which is large enough to trap water and small organic molecules. Thus, heating a mixture of 2 and H2O@2 with hydrogen cyanide and formaldehyde in chlorobenzene affords HCN@2 and H2CO@2, respectively. The H-1 NMR spectroscopy reveals substantial upfield shifts for the endohedral species (delta = -1.30 to -11.30 ppm), owing to the strong shielding effect of the fullerene cage.