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Unidirectional molecular motor on a gold surface

Naturevolume 437pages13371340 (2005) | Download Citation

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Abstract

Molecules capable of mimicking the function of a wide range of mechanical devices have been fabricated, with motors that can induce mechanical movement attracting particular attention1,2. Such molecular motors convert light or chemical energy into directional rotary or linear motion2,3,4,5,6,7,8,9,10, and are usually prepared and operated in solution. But if they are to be used as nanomachines that can do useful work, it seems essential to construct systems that can function on a surface, like a recently reported linear artificial muscle11. Surface-mounted rotors have been realized and limited directionality in their motion predicted12,13. Here we demonstrate that a light-driven molecular motor capable of repetitive unidirectional rotation14 can be mounted on the surface of gold nanoparticles. The motor design14 uses a chiral helical alkene with an upper half that serves as a propeller and is connected through a carbon–carbon double bond (the rotation axis) to a lower half that serves as a stator. The stator carries two thiol-functionalized ‘legs’, which then bind the entire motor molecule to a gold surface. NMR spectroscopy reveals that two photo-induced cis-trans isomerizations of the central double bond, each followed by a thermal helix inversion to prevent reverse rotation, induce a full and unidirectional 360° rotation of the propeller with respect to the surface-mounted lower half of the system.

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References

  1. 1

    Balzani, V., Venturi, M. & Credi, A. Molecular Devices and Machines—A Journey into the Nanoworld (Wiley-VCH, Weinheim, 2003)

  2. 2

    van Delden, R. A., ter Wiel, M. K. J., Koumura, N. & Feringa, B. L. in Molecular Motors (ed. Schliwa, M.) Ch. 23, 559–577 (Wiley-VCH, Weinheim, 2003)

  3. 3

    Koumura, N., Zijlstra, R. W. J., van Delden, R. A., Harada, N. & Feringa, B. L. Light-driven monodirectional molecular rotor. Nature 401, 152–155 (1999)

  4. 4

    Kelly, T. R., De Silva, H. & Silva, R. A. Unidirectional rotary motion in a molecular system. Nature 401, 150–152 (1999)

  5. 5

    Leigh, D. A., Wong, J. K. Y., Dehez, F. & Zerbetto, F. Unidirectional rotation in a mechanically interlocked molecular rotor. Nature 424, 174–179 (2003)

  6. 6

    Anelli, P. L., Spencer, N. & Stoddart, J. F. A molecular shuttle. J. Am. Chem. Soc. 113, 5131–5133 (1991)

  7. 7

    Sherman, W. B. & Seeman, N. C. A precisely controlled DNA biped walking device. Nano Lett. 4, 1203–1207 (2004)

  8. 8

    Sauvage, J.-P. (ed.) Molecular Machines and Motors (Structure and Bonding, Vol. 99, Springer, Berlin, 2001)

  9. 9

    van Delden, R. A., Koumura, N., Harada, N. & Feringa, B. L. Unidirectional rotary motion in a liquid crystalline environment; colour tuning by a molecular motor. Proc. Natl Acad. Sci. USA 99, 4945–4949 (2002)

  10. 10

    Koumura, N., Geertsema, E. M., van Gelder, M. B., Meetsma, A. & Feringa, B. L. Second generation light-driven molecular motors. Unidirectional rotation controlled by a single stereogenic center with near-perfect photoequilibria and acceleration of the speed of rotation by structural modification. J. Am. Chem. Soc. 124, 5037–5051 (2002)

  11. 11

    Liu, Y. et al. Linear artificial muscles. J. Am. Chem. Soc. 127, 9745–9759 (2005)

  12. 12

    Zheng, X. et al. Dipolar and nonpolar altitudinal molecular rotors mounted on an Au(111) surface. J. Am. Chem. Soc. 126, 4540–4542 (2004)

  13. 13

    Kottas, G. S., Clarke, L. I. & Horinek, D. Michl, J. Artificial molecular rotors. Chem. Rev. 105, 1281–1376 (2005)

  14. 14

    Koumura, N., Geertsema, E. M., Meetsma, A. & Feringa, B. L. Light-driven molecular rotor: unidirectional rotation controlled by a single stereogenic center. J. Am. Chem. Soc. 122, 12005–12006 (2000)

  15. 15

    Noji, H., Yasuda, R., Yoshida, M. & Kinosita, K. Direct observation of the rotation of F1-ATPase. Nature 386, 299–302 (1997)

  16. 16

    George Thomas, K. & Kamat, P. V. Chromophore-functionalised gold nanoparticles. Acc. Chem. Res. 36, 888–898 (2003)

  17. 17

    Manna, A. et al. Optimised photoisomerisation on gold nanoparticles capped by unsymmetrical azobenzene disulfides. Chem. Mater. 15, 20–28 (2003)

  18. 18

    Long, B., Nikitin, K. & Fitzmaurice, D. Assembly of an electronically switchable rotaxane on the surface of a titanium dioxide nanoparticle. J. Am. Chem. Soc. 125, 15490–15498 (2003)

  19. 19

    Brust, M., Walker, M., Behell, D., Schiffrin, D. J. & Whyman, R. J. Synthesis of thiol-derivatised gold nanoparticles in a 2-phase liquid-liquid system. Chem. Soc. Chem. Comm., 801–802 (1994)

  20. 20

    Lide, D. R. (ed.) CRC Handbook of Chemistry and Physics 2003–2004 84th edn 4–59 (CRC Press, Boca Raton, 2003)

  21. 21

    Ullman, A. Formation and structure of self-assembled monolayers. Chem. Rev. 96, 1533–1554 (1996)

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Acknowledgements

We thank C. R. van den Brom for performing the TEM measurements described, A. Meetsma for X-ray analysis and J. G. McGarvey for access to Raman facilities. Financial support from the Netherlands Organisation for Scientific Research (NWO-CW), the Materials Science Centre, and the University of Groningen is acknowledged. J.V. thanks the Departamento de Educación, Universidades e Investigación del Gobierno Vasco, for a postdoctoral fellowship.

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  1. Department of Organic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands

    • Richard A. van Delden
    • , Matthijs K. J. ter Wiel
    • , Michael M. Pollard
    • , Javier Vicario
    • , Nagatoshi Koumura
    •  & Ben L. Feringa

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Reprints and permissions information is available at npg.nature.com/reprintsandpermissions. The authors declare no competing financial interests.

Corresponding author

Correspondence to Ben L. Feringa.

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    This file contains Supplementary Methods, Supplementary Figures, Supplementary Tables and Supplementary Discussion. (PDF 1429 kb)

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https://doi.org/10.1038/nature04127

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