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J Am Chem Soc. 2003 Nov 5;125(44):13360-1.

Chiroptical switching in a bistable molecular shuttle.

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School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK.


Although various methods for switching the positions of macrocycles in bistable rotaxane-based molecular shuttles have been developed, exploiting such movements to trigger property changes has thus far received little attention. Here we describe one of the first examples of a property change achieved through a controlled large-amplitude translational motion in a rotaxane; a novel type of chiroptical switch is described, in which light-induced translation of the macrocycle along the thread of a [2]rotaxane produces a strong induced circular dichroism (ICD) response only when the macrocycle is hydrogen-bonded to a chiral peptide station.


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