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

Nature Communications
Taisuke MatsunoHiroyuki Isobe

Abstract

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.

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Citations

Jan 29, 2019·Chemistry : a European Journal·Shinji Toyota, Eiji Tsurumaki
Jun 14, 2019·Angewandte Chemie·Youzhi Xu, Max von Delius
Nov 30, 2019·Chemistry, an Asian Journal·Taisuke MatsunoHiroyuki Isobe
Aug 25, 2019·Nature Communications·Shinya AdachiNaoya Kumagai
Oct 28, 2019·Frontiers in Chemistry·Dapeng LuPingwu Du
Feb 23, 2019·Chemical Communications : Chem Comm·Yu-Dong Yang, Han-Yuan Gong
Dec 15, 2018·Angewandte Chemie·Zhe SunHiroyuki Isobe
Sep 28, 2020·Angewandte Chemie·Hironori MatsukiKenji Kobayashi
Mar 12, 2021·Nature Communications·Taisuke MatsunoHiroyuki Isobe
Mar 23, 2021·Angewandte Chemie·Junting WangJunzhi Liu
Apr 23, 2021·Angewandte Chemie·Niklas GrabickiOliver Dumele
Aug 27, 2021·Nature Communications·Taisuke MatsunoHiroyuki Isobe
Nov 13, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Javid Ahmad MallaPinaki Talukdar

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Methods Mentioned

BETA
isothermal titration calorimetry
NMR
BSSE
X-ray

Software Mentioned

ORIGIN
SHELXL
SIMU
LC
COOT
NMR
DFIX
SQUEEZE
XG
BLYP

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