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

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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.

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

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Publication details

The article was received on 10 Sep 2018, accepted on 12 Sep 2018 and first published on 13 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02234H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Light-driven exchange between extended and contracted lasso-like isomers of a bistable [1]rotaxane

    A. Saura-Sanmartin, A. Martinez-Cuezva, A. Pastor, D. Bautista and J. Berna, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02234H

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