Department of Chemistry, The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo, 113-0033, Japan.
JST, ERATO, Isobe Degenerate π-Integration Project, Hongo 7-3-1, Bunkyo-ku, Tokyo, 113-0033, Japan.
Nat Commun. 2018 Sep 17;9(1):3779. doi: 10.1038/s41467-018-06270-6.
The hydrogen bond is undoubtedly one of the most important non-covalent interactions. Among the several types of the hydrogen bonds, the CH-π interaction is a relatively new notion that is being recognised in chemistry and biology. Although the CH-π hydrogen bond and conventional hydrogen bonds share common features such as directionality, this weak interaction has played a secondary role in molecular recognition. In this study, we have devised a host-guest complex that is assembled solely by the CH-π hydrogen bonds. Multivalent interactions of a bowl-shaped hydrocarbon with its peripheral hydrogen atoms are made possible via CH-π hydrogen bonds by adopting a tubular hydrocarbon as a host for their enthalpy-driven complexation. Concyclic arrays of weak hydrogen bonds further allow dynamic rotational motions of the guest in the host. Solid-state analysis with crystallographic and spectroscopic methods reveal a single-axis rotation of the bowl in the tube.
氢键无疑是最重要的非共价相互作用之一。在几种氢键中，CH-π 相互作用是一个相对较新的概念，在化学和生物学中得到了认可。尽管 CH-π 氢键与传统氢键具有共同的方向性等特征，但这种弱相互作用在分子识别中一直处于次要地位。在这项研究中，我们设计了一种仅由 CH-π 氢键组装的主体-客体复合物。通过采用管状碳氢化合物作为主体，碗状碳氢化合物与其外围氢原子之间的多价相互作用可以通过 CH-π 氢键来实现，从而使其发生焓驱动的络合。弱氢键的共环排列进一步允许客体在主体中进行动态旋转运动。晶体学和光谱学方法的固态分析表明，碗在管中的单轴旋转。
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