Iodide-induced shuttling of a halogen- and hydrogen-bonding two-station rotaxane

Antonio Caballero; Laura Swan; Fabiola Zapata; Paul D Beer

doi:10.1002/anie.201407580

Iodide-induced shuttling of a halogen- and hydrogen-bonding two-station rotaxane

Angew Chem Int Ed Engl. 2014 Oct 27;53(44):11854-8. doi: 10.1002/anie.201407580. Epub 2014 Sep 11.

Authors

Antonio Caballero¹, Laura Swan, Fabiola Zapata, Paul D Beer

Affiliation

¹ Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA (UK).

PMID: 25213038
DOI: 10.1002/anie.201407580

Abstract

The first example of utilizing halogen-bonding anion recognition to facilitate molecular motion in an interlocked structure is described. A halogen-bonding and hydrogen-bonding bistable rotaxane is prepared and demonstrated to undergo shuttling of the macrocycle component from the hydrogen-bonding station to the halogen-bonding station upon iodide recognition. In contrast, chloride-anion binding reinforces the macrocycle to reside at the hydrogen-bonding station.

Keywords: anions; halogen bonding; molecular motion; rotaxanes; template synthesis.