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Reversing the direction in a light-driven rotary molecular motor

Nature Chemistry volume 3, pages 53–60 (2011)Cite this article

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Abstract

Biological rotary motors can alter their mechanical function by changing the direction of rotary motion. Achieving a similar reversal of direction of rotation in artificial molecular motors presents a fundamental stereochemical challenge: how to change from clockwise to anticlockwise motion without compromising the autonomous unidirectional rotary behaviour of the system. A new molecular motor with multilevel control of rotary motion is reported here, in which the direction of light-powered rotation can be reversed by base-catalysed epimerization. The key steps are deprotonation and reprotonation of the photochemically generated less-stable isomers during the 360° unidirectional rotary cycle, with complete inversion of the configuration at the stereogenic centre. The ability to change directionality is an essential step towards mechanical molecular systems with adaptive functional behaviour.

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Figure 1: Conceptual illustration of rotary motion in a molecular motor and the change from clockwise to anticlockwise rotation.
Figure 2: Design of a molecular motor for base-mediated epimerization.
Figure 3: Schematic representation of controlled clockwise and anticlockwise rotary cycles of molecular motor 1 using different triggers.
Figure 4: Synthesis of the reversible molecular motor 1.
Figure 5: Monitoring of photochemical and thermal behaviour of a reversible molecular motor.
Figure 6: Monitoring of the base-catalysed epimerization process.
Figure 7: Characterization of various stages of the full rotation cycle comprising photochemical, thermal and base-catalysed isomerization steps.

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Acknowledgements

We thank the Netherlands Organization for Scientific Research, the Zernike Institute for Advanced Materials, the European Research Council (advanced grant no: 227897) and the University of Groningen for financial support.

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  1. Michael M. Pollard: Deceased

Authors and Affiliations

  1. Centre for Systems Chemistry, Stratingh Institute for Chemistry and Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen, 9747AG, The Netherlands

    Nopporn Ruangsupapichat, Michael M. Pollard, Syuzanna R. Harutyunyan & Ben L. Feringa

  2. Department of Chemistry, York University, 4700 Keele Street, Toronto, M3J 1P3, Ontario, Canada

    Michael M. Pollard

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  1. Nopporn Ruangsupapichat
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Contributions

N.R. and M.M.P. carried out the experimental work. All the authors contributed to the design of the experiments, the analysis of the data and the writing of the paper.

Corresponding author

Correspondence to Ben L. Feringa.

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The authors declare no competing financial interests.

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Ruangsupapichat, N., Pollard, M., Harutyunyan, S. et al. Reversing the direction in a light-driven rotary molecular motor. Nature Chem 3, 53–60 (2011). https://doi.org/10.1038/nchem.872

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