An Interlocked Figure‐of‐Eight Molecular Shuttle

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 h...

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Bibliographic Details
Published in:Angewandte Chemie 2023-10, Vol.135 (44)
Main Authors: Gauthier, Maxime, Fournel‐Marotte, Karine, Clavel, Caroline, Waelès, Philip, Laurent, Philippe, Coutrot, Frédéric
Format: Article
Language:English
Subjects:
Ammonium
Binding sites
Chemical synthesis
Chemistry
Entanglement
Extremities
Molecular chains
Rotaxanes
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Summary: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.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202310643