Letter | Published:

Light-driven monodirectional molecular rotor

Nature volume 401, pages 152155 (09 September 1999) | Download Citation



Attempts to fabricate mechanical devices on the molecular level1,2 have yielded analogues of rotors3, gears4, switches5, shuttles6,7, turnstiles8 and ratchets9. Molecular motors, however, have not yet been made, even though they are common in biological systems10. Rotary motion as such has been induced in interlocked systems11,12,13 and directly visualized for single molecules14, but the controlled conversion of energy into unidirectional rotary motion has remained difficult to achieve. Here we report repetitive, monodirectional rotation around a central carbon–carbon double bond in a chiral, helical alkene, with each 360° rotation involving four discrete isomerization steps activated by ultraviolet light or a change in the temperature of the system. We find that axial chirality and the presence of two chiral centres are essential for the observed monodirectional behaviour of the molecular motor. Two light-induced cis-trans isomerizations are each associated with a 180° rotation around the carbon–carbon double bond and are each followed by thermally controlled helicity inversions, which effectively block reverse rotation and thus ensure that the four individual steps add up to one full rotation in one direction only. As the energy barriers of the helicity inversion steps can be adjusted by structural modifications, chiral alkenes based on our system may find use as basic components for ‘molecular machinery’ driven by light.

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  1. 1.

    in Miniaturization (ed. Gilbert, H. D.) (Reinhold, New York, 1961).

  2. 2.

    Nanosystems: Molecular Machinery, Manufacturing and Computation (Wiley, New York, 1992).

  3. 3.

    et al. Toward a switchable molecular rotor. J. Org. Chem. 62, 4943–4948 (1997).

  4. 4.

    & Concerted rotation in a tertiary aromatic amide: towards a simple molecular gear. Angew. Chem. Int. Edn Engl. 37, 1937–1939 (1998).

  5. 5.

    , , & Dynamic control and amplification of molecular chirality by circularly polarized light. Science 273, 1686–1688 (1996).

  6. 6.

    , , & A chemically and electrochemically switchable molecular shuttle. Nature 369, 133–136 (1994).

  7. 7.

    et al. Acid-base controllable molecular shuttles. J. Am. Chem. Soc. 120, 11932–11942 (1998).

  8. 8.

    & Design and synthesis of a “molecular turnstile”. J. Am. Chem. Soc. 117, 10662–10671 (1995).

  9. 9.

    , & In search of molecular ratchets. Angew. Chem. Int. Edn Engl. 36, 1866–1868 (1997).

  10. 10.

    , , & Directed observation of the rotation of F1-ATPase. Nature 386, 299–302 (1997).

  11. 11.

    , & Molecular machines. Acc. Chem. Res. 31, 405–414 (1998).

  12. 12.

    Transition metal-containing rotaxanes and catenanes in motion: toward molecular machines and motors. Acc. Chem. Res. 31, 611–619 (1998).

  13. 13.

    et al. Rotaxanes incorporating two different coordinating units in their thread: synthesis and electrochemically and photochemically induced molecular motions. J. Am. Chem. Soc. 121, 4397–4408 (1999).

  14. 14.

    et al. Rotation of a single molecule within a supramolecular bearing. Science 281, 531–533 (1998).

  15. 15.

    , & Chemistry of unique chiral olefins. 3. Synthesis and absolute stereochemistry of trans- and cis-1,1′,2,2′,3,3′,4,4′-octahydro-3,3′-dimethyl-4,4′-biphenanthrylidenes. J. Am. Chem. Soc. 119, 7256–7264 (1997).

  16. 16.

    & Photochemistry and absolute stereochemistry of unique chiral olefins, trans- and cis-1,1′,2,2′,3,3′,4,4′-octahydro-3,3′-dimethyl-4,4′-biphenanthrylidenes. Chem. Lett. 1151–1152 (1998).

  17. 17.

    Tilting at windmills? The second law survives. Angew. Chem. Int Edn Engl. 37, 909–910 (1998).

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Financial support from the Netherlands Organisation for Scientific Research (NWO-STW) to B.L.F. is acknowledged.

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

    • Nagatoshi Koumura
    • , Robert W. J. Zijlstra
    • , Richard A. van Delden
    •  & Ben L. Feringa
  2. †Institute for Chemical Reaction Science, Tohoku University, 2-1-1 Katahira, Aoba, Sendai 980-8577, Japan

    • Nagatoshi Koumura
    •  & Nobuyuki Harada


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Correspondence to Ben L. Feringa.

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