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Unidirectional rotation in a mechanically interlocked molecular rotor

Nature volume 424, pages 174–179 (2003)Cite this article

Abstract

Molecular motor proteins are ubiquitous in nature1 and have inspired attempts to create artificial machines2 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° intramolecular rotation around a single bond3,4; another is a molecule capable of repetitive unimolecular rotation driven by multiple and successive isomerization of its central double bond5,6,7,8. 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]catenanes9 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 sites10,11,12. 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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Figure 1: Stimuli-induced sequential movement of a macrocycle between three different binding sites in a [2]catenane.
Figure 2: Ring-closing reactions to form macrocycle E,E-2, [2]catenane E,E-1 and [3]catenane E,E-3.
Figure 3: Structural characterization of E,E-1-3 and model compounds.
Figure 4: Structural characterization of photoisomerized macrocycles and catenanes Z,E-1-3 and Z,Z-1-3.
Figure 5: Stimuli-induced unidirectional rotation in a four-station [3]catenane, 3.

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Acknowledgements

We thank E. M. Perez for developing the catalytic Br2 reaction conditions and P. J. Nash for several of the model [2]rotaxanes. This work was carried out through the support of the RTN network EMMMA and the FET MechMol. D.A.L. is an EPSRC Advanced Research Fellow.

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Authors and Affiliations

  1. School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, EH9 3JJ, Edinburgh, UK

    David A. Leigh & Jenny K. Y. Wong

  2. Dipartimento di Chimica ‘G. Ciamician’, Universita degli Studi di Bologna, via F. Selmi 2, 40126, Bologna, Italy

    François Dehez & Francesco Zerbetto

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  1. David A. Leigh
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Correspondence to David A. Leigh.

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Leigh, D., Wong, J., Dehez, F. et al. Unidirectional rotation in a mechanically interlocked molecular rotor. Nature 424, 174–179 (2003). https://doi.org/10.1038/nature01758

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