How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?
Benjamin Riss-Yaw,
Justine Morin,
Caroline Clavel,
Frédéric Coutrot
Affiliations
Benjamin Riss-Yaw
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
Justine Morin
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
Caroline Clavel
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
Frédéric Coutrot
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
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.
