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An Interlocked Figure-of-Eight Molecular Shuttle.

Authors
  • Gauthier, Maxime1
  • Fournel-Marotte, Karine1
  • Clavel, Caroline1
  • Waelès, Philip1
  • Laurent, Philippe1
  • Coutrot, Frédéric1
  • 1 Supramolecular Machines and Architectures Team, IBMM, Univ Montpellier, CNRS, ENSCM, Montpellier, France. , (France)
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Oct 26, 2023
Volume
62
Issue
44
Identifiers
DOI: 10.1002/anie.202310643
PMID: 37594476
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

Here is reported the synthesis and characterization of an interlocked figure-of-eight rotaxane molecular shuttle from a dibenzo-24-crown-8 (DB24C8) derivative. This latter bears two molecular chains, whose extremities are able to react together by click chemistry. One of the two substituting chain holds an ammonium function aimed at driving the self-entanglement through the complexation of the DB24C8 moiety. In the targeted figure-of-eight rotaxane, shuttling of the DB24C8 along the threaded axle from the best ammonium station to the weaker binding site triazolium was performed through deprotonation or deprotonation-then-carbamoylation of the ammonium. This way, two discrete co-conformational states were obtained, in which the folding and size of the two loops could be changed. © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

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