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Title

Weinreb Amide, Ketone and Amine as Potential and Competitive Secondary Molecular Stations for Dibenzo‐[24]Crown‐8 in [2]Rotaxane Molecular Shuttles.

Authors

Gauthier, Maxime; Coutrot, Frédéric

Abstract

This paper reports the synthesis and study of new pH‐sensitive DB24C8‐based [2]rotaxane molecular shuttles that contain within their axle four potential sites of interaction for the DB24C8: ammonium, amine, Weinreb amide, and ketone. In the protonated state, the DB24C8 lay around the best ammonium site. After either deprotonation or deprotonation‐then‐carbamoylation of the ammonium, different localizations of the DB24C8 were seen, depending on both the number and nature of the secondary stations and steric restriction. Unexpectedly, the results indicated that the Weinreb amide was not a proper secondary molecular station for the DB24C8. Nevertheless, through its methoxy side chain, it slowed down the shuttling of the macrocycle along the threaded axle, thereby partitioning the [2]rotaxane into two translational isomers on the NMR timescale. The ketone was successfully used as a secondary molecular station, and its weak affinity for the DB24C8 was similar to that of a secondary amine.

Subjects

KETONES; AMINES; SECONDARY amines; PROTON transfer reactions; POLYCHLORINATED dibenzodioxins

Publication

Chemistry - A European Journal, 2021, Vol 27, Issue 70, p17576

ISSN

0947-6539

Publication type

Academic Journal

DOI

10.1002/chem.202103805

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