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Molecules 2017, 22(11), 2017; doi:10.3390/molecules22112017

How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?

Supramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, Université Montpellier, ENSCM, Case Courrier 1706, Bâtiment Chimie (17), 3ème étage, Faculté des Sciences, Place Eugène Bataillon, 34095 Montpellier CEDEX 5, France
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Received: 3 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
(This article belongs to the Special Issue Interlocked Molecules, Molecular Machines, Motors and Muscles)
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Abstract

Interlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of interactions for crown ethers, the very straightforwardly obtained amide motif has more rarely been envisaged as molecular station. In this article, we report the use of secondary and tertiary amide moieties as efficient secondary molecular station in pH-sensitive molecular shuttles. Depending on the N-substitution of the amide station, and on deprotonation or deprotonation-carbamoylation, the actuation of the molecular machinery differs accordingly to very distinct interactions between the axle and the DB24C8. View Full-Text
Keywords: molecular machine; rotaxane; amide; ammonium; amine; dibenzo-24-crown-8; template molecular machine; rotaxane; amide; ammonium; amine; dibenzo-24-crown-8; template
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Riss-Yaw, B.; Morin, J.; Clavel, C.; Coutrot, F. How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? Molecules 2017, 22, 2017.

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