Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Oct 26;62(44):e202310643.
doi: 10.1002/anie.202310643. Epub 2023 Aug 28.

An Interlocked Figure-of-Eight Molecular Shuttle

Maxime Gauthier  1 , Karine Fournel-Marotte  1 , Caroline Clavel  1 , Philip Waelès  1 , Philippe Laurent  1 , Frédéric Coutrot  1
Affiliations

An Interlocked Figure-of-Eight Molecular Shuttle

Maxime Gauthier et al. Angew Chem Int Ed Engl. .

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.

Keywords: Dibenzo-24-Crown-8; Figure of 8; Mechanical Bond; Molecular Shuttle; Rotaxane.

PubMed Disclaimer

References

    1. The term “supramolecular” was introduced for the first time in 1978, see: J.-M. Lehn, Pure Appl. Chem. 1978, 50, 871-892. J.-M. Lehn shared the Nobel Prize in Chemistry in 1987 with D. J. Cram and C. Pedersen.
    1. C. O. Dietrich-Buchecker, J.-P. Sauvage, J.-P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098.
    1. None
    1. C. Bruns, J. F. Stoddart, The Nature of the Mechanical Bond: From Molecules to Machines, Wiley, Hoboken, 2017;
    1. S. F. M. van Dongen, S. Cantekin, J. A. A. W. Elemans, A. E. Rowan, R. J. M. Nolte, Chem. Soc. Rev. 2014, 43, 99-122;

LinkOut - more resources