4.6 Article

An Anionic Ring Locked into an Anionic Axle: A Metastable Rotaxane with Chemically Activated Electrostatic Stoppers

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 62, Pages 14042-14047

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201902735

Keywords

host-guest systems; metastable compounds; rotaxanes; self-assembly; supramolecular chemistry

Funding

  1. Conacyt [255979, 282202]

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The use of the electrostatic stoppers concept in the field of mechanically interlocked molecules is reported; these stoppers are chemically sensitive end groups on a linear guest molecule that allows for the conversion of a pseudo-rotaxane species into a rotaxane complex by a change in the medium acidity. The chemical stimulus causes the appearance of negative charges on both ends of the linear component, passing from cationic to anionic, and causing a significant ring-to-axle electrostatic repulsion. This phenomenon has two different and simultaneous effects: 1) destabilizes the complex as a consequence of confining an anionic ring into an anionic axle, and 2) increases the dissociation energy barrier, thus impeding ring extrusion. This newly formed metastable rotaxane species is resistant to solvent and temperature effects and performs as a two-state degenerated molecular shuttle in solution.

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