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

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Authors
Saura-Sanmartin, Adrian ; Martinez-Cuezva, Alberto ; Pastor Vivero, Aurelia ; Bautista, Delia ; Berná Cánovas, José
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Publisher
Royal Society of Chemistry
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DOI
10.1039/C8OB02234H
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Description
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 in both solution and 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 examined.
Citation
Organic & Biomolecular Chemistry 2018, 16 (38) , 6980-6987.
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