Sep 17, 2018

Concyclic CH-π arrays for single-axis rotations of a bowl in a tube

Overview of the press release

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 recognized in chemistry and biology. Although the CH-π hydrogen bond shares common features, such as directionality, with conventional hydrogen bonds, this weak interaction has played a secondary role in molecular recognition. In this study, we devised a host-guest complex that was assembled solely by the CH-π hydrogen bonds. Multivalent interactions of a bowl-shaped hydrocarbon with its periphery hydrogen atoms were 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 allowed dynamic rotational motions of the guest in the host. Solid-state analysis with crystallographic and spectroscopic methods revealed an anomalous single-axis rotation of the bowl in the tube.


Figure: Pictured is a supramolecular complex of a bowl-shaped molecule entrapped in a tubular molecule, which is created from its crystal structure. In the solid state, the bowl guest rotates in the tube in a manner similar to a ball bearing. The weak CH-π hydrogen bonds are distributed in a concyclic arrangement and relayed for single-axis reorientations of the bowl.


Publication details

Journal Nature Communications
Title Concyclic CH-π arrays for single-axis rotations of a bowl in a tube
Authors Taisuke Matsuno, Masahiro Fujita, Kengo Fukunaga, Sota Sato & Hiroyuki Isobe*
DOI 10.1038/s41467-018-06270-6
Paper link

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