Ring size affects the kinetic and thermodynamic formation of [2]rotaxanes featuring an unsymmetric bis-crown ether component

Masaya Naito; Takaaki Fujino; Shinya Tajima; Shinobu Miyagawa; Kazuyuki Yoshida; Hajime Inoue; Hiroaki Takagawa; Tsuneomi Kawasaki; Yuji Tokunaga

doi:10.1039/C9QM00441F

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Ring size affects the kinetic and thermodynamic formation of [2]rotaxanes featuring an unsymmetric bis-crown ether component†

Masaya Naito,

^a Takaaki Fujino,^a Shinya Tajima,^a Shinobu Miyagawa,^a Kazuyuki Yoshida,^b Hajime Inoue,^b Hiroaki Takagawa,^b Tsuneomi Kawasaki

^c and Yuji Tokunaga

*^a

Author affiliations

* Corresponding authors

^a Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
E-mail: tokunaga@u-fukui.ac.jp

^b Forensic Science Laboratory, Fukui Prefectural Police H.Q., Ohte, Fukui 910-8515, Japan

^c Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

Bridging of a [2]pseudorotaxane formed from an unsymmetric mono-crown ether and an ammonium salt has provided two types of [2]rotaxanes, with the axle component positioned within a large (4L) and small (4S) ring, respectively. ¹H NMR spectroscopy has revealed that 4L is the kinetically favored [2]rotaxane, whereas 4S is thermodynamically favored at low temperature.

This article is part of the themed collection: Mechanical Bond and Dynamic Covalent Bond

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Article information

DOI: https://doi.org/10.1039/C9QM00441F
Article type: Research Article
Submitted: 06 ⵢⵓⵍ 2019
Accepted: 09 ⴽⵜⵓ 2019
First published: 11 ⴽⵜⵓ 2019

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Mater. Chem. Front., 2019,3, 2702-2706

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Ring size affects the kinetic and thermodynamic formation of [2]rotaxanes featuring an unsymmetric bis-crown ether component

M. Naito, T. Fujino, S. Tajima, S. Miyagawa, K. Yoshida, H. Inoue, H. Takagawa, T. Kawasaki and Y. Tokunaga, Mater. Chem. Front., 2019, 3, 2702 DOI: 10.1039/C9QM00441F

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Materials Chemistry Frontiers

Ring size affects the kinetic and thermodynamic formation of [2]rotaxanes featuring an unsymmetric bis-crown ether component†

Abstract

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Ring size affects the kinetic and thermodynamic formation of [2]rotaxanes featuring an unsymmetric bis-crown ether component

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