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      Regulation of Macrocycle Shuttling Rates in [2]Rotaxanes by Amino‐Acid Speed Bumps in Organic–Aqueous Solvent Mixtures

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          A molecular information ratchet.

          Motor proteins and other biological machines are highly efficient at converting energy into directed motion and driving chemical systems away from thermodynamic equilibrium. But even though these biological structures have inspired the design of many molecules that mimic aspects of their behaviour, artificial nanomachine systems operate almost exclusively by moving towards thermodynamic equilibrium, not away from it. Here we show that information about the location of a macrocycle in a rotaxane-a molecular ring threaded onto a molecular axle-can be used, on the input of light energy, to alter the kinetics of the shuttling of the macrocycle between two compartments on the axle. For an ensemble of such molecular machines, the macrocycle distribution is directionally driven away from its equilibrium value without ever changing the relative binding affinities of the ring for the different parts of the axle. The selective transport of particles between two compartments by brownian motion in this way bears similarities to the hypothetical task performed without an energy input by a 'demon' in Maxwell's famous thought experiment. Our observations demonstrate that synthetic molecular machines can operate by an information ratchet mechanism, in which knowledge of a particle's position is used to control its transport away from equilibrium.
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            Unidirectional rotation in a mechanically interlocked molecular rotor.

            Molecular motor proteins are ubiquitous in nature and have inspired attempts to create artificial machines that mimic their ability to produce controlled motion on the molecular level. A recent example of an artificial molecular rotor is a molecule undergoing a unidirectional 120 degrees intramolecular rotation around a single bond; another is a molecule capable of repetitive unimolecular rotation driven by multiple and successive isomerization of its central double bond. Here we show that sequential and unidirectional rotation can also be induced in mechanically interlocked assemblies comprised of one or two small rings moving around one larger ring. The small rings in these [2]- and [3]catenanes move in discrete steps between different binding sites located on the larger ring, with the movement driven by light, heat or chemical stimuli that change the relative affinity of the small rings for the different binding sites. We find that the small ring in the [2]catenane moves with high positional integrity but without control over its direction of motion, while the two rings in the [3]catenane mutually block each other's movement to ensure an overall stimuli-induced unidirectional motion around the larger ring.
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              Mechanically Interlocked Molecules (MIMs)-Molecular Shuttles, Switches, and Machines (Nobel Lecture)

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                Author and article information

                Contributors
                (View ORCID Profile)
                (View ORCID Profile)
                Journal
                European Journal of Organic Chemistry
                Eur. J. Org. Chem.
                Wiley
                1434-193X
                1099-0690
                September 30 2020
                August 18 2020
                September 30 2020
                : 2020
                : 36
                : 5820-5827
                Affiliations
                [1 ]Institut des Sciences Moléculaires, CNRS UMR 5255 University of Bordeaux 33405 Talence France
                [2 ]IRAMAT, CNRS UMR 5060, Maison de l'Archéologie Université Bordeaux Montaigne 33607 Pessac France
                Article
                10.1002/ejoc.202000997
                dca0beae-0868-4e3a-8605-12db8552bcf0
                © 2020

                http://onlinelibrary.wiley.com/termsAndConditions#vor

                http://doi.wiley.com/10.1002/tdm_license_1.1


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