Light-driven exchange between extended and contracted lasso-like isomers of a bistable [1]rotaxane

Organic & Biomolecular Chemistry
Adrian Saura-SanmartinJosé Berná

Abstract

The synthesis of a set of benzylic amide [1]rotaxanes via a self-templating clipping approach is described. This methodology supposes the 1 + 1 coupling of isophthaloyl dichloride with an acyclic diamine precursor incorporating a templating arm. The structure of the threaded compounds was determined both in solution and in the solid state. The conversion into the corresponding unthreaded isomers, also obtained by deslipping of [2]rotaxane models, was evaluated in competitive and non-competitive hydrogen-bonding solvents. The switch of the extended and contracted lasso-like isomers of a bistable [1]rotaxane by an olefin isomerization promoted by UV light irradiation was also accomplished and their ring positional integrity was examined.

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Citations

May 13, 2020·Chemical Society Reviews·Arturo Blanco-GómezMarcos D García
Feb 23, 2021·Angewandte Chemie·Adrian Saura-SanmartinJose Berna
Jul 11, 2020·Journal of the American Chemical Society·Adrian Saura-SanmartinJose Berna
Sep 18, 2021·Chemical Reviews·Romain CostilBen L Feringa
Nov 5, 2021·Chemical Communications : Chem Comm·Chih-Wei ChuChristoph A Schalley
Dec 10, 2021·Chemical Communications : Chem Comm·Adrian Saura-SanmartinJose Berna
Nov 26, 2021·Chemistry : a European Journal·Xu-Sheng DuChuan-Feng Chen

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Methods Mentioned

BETA
X-ray
amidation
thermal treatment

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