NDLI: Bistable or Oscillating State Depending on Station and Temperature in Three-Station Glycorotaxane Molecular Machines

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Bistable or Oscillating State Depending on Station and Temperature in Three-Station Glycorotaxane Molecular Machines

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Coutrot, Frédéric Romuald, Camille Busseron, Eric
Description	Author Affiliation: Busseron E ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-Universités Montpellier 2 et 1, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8, rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.)
Abstract	High-yield, straightforward synthesis of two- and three-station [2]rotaxane molecular machines based on an anilinium, a triazolium, and a mono- or disubstituted pyridinium amide station is reported. In the case of the pH-sensitive two-station molecular machines, large-amplitude movement of the macrocycle occurred. However, the presence of an intermediate third station led, after deprotonation of the anilinium station, and depending on the substitution of the pyridinium amide, either to exclusive localization of the macrocycle around the triazolium station or to oscillatory shuttling of the macrocycle between the triazolium and monosubstituted pyridinium amide station. Variable-temperature $^{1}H NMR$ investigation of the oscillating system was performed in $CD_{2}Cl_{2}.$ The exchange between the two stations proved to be fast on the NMR timescale for all considered temperatures (298–193 K). Interestingly, decreasing the temperature displaced the equilibrium between the two translational isomers until a unique location of the macrocycle around the monosubstituted pyridinium amide station was reached. Thermodynamic constants K were evaluated at each temperature: the thermodynamic parameters ΔH and ΔS were extracted from a Van′t Hoff plot, and provided the Gibbs energy ΔG. Arrhenius and Eyring plots afforded kinetic parameters, namely, energies of activation $E_{a},$ enthalpies of activation $ΔH^{≠},$ and entropies of activation $ΔS^{≠}.$ The ΔG values deduced from kinetic parameters match very well with the ΔG values determined from thermodynamic parameters. In addition, whereas signal coalescence of pyridinium hydrogen atoms located next to the amide bond was observed at 205 K in the oscillating rotaxane and at 203 K in the two-station rotaxane with a unique location of the macrocycle around the pyridinium amide, no separation of $^{1}H NMR$ signals of the considered hydrogen atoms was seen in the corresponding nonencapsulated thread. It is suggested that the macrocycle acts as a molecular brake for the rotation of the pyridinium–amide bond when it interacts by hydrogen bonding with both the amide NH and the pyridinium hydrogen atoms at the same time.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	33
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-09-03
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Rotaxanes Chemistry Aniline Compounds Magnetic Resonance Spectroscopy Models, Molecular Pyridinium Compounds Chemical Synthesis Stereoisomerism Structure-Activity Relationship Temperature Thermodynamics Triazoles Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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