Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Light-driven monodirectional molecular rotor

Nature volume 401, pages 152–155 (1999)Cite this article

Abstract

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.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Figure 1: Photochemical and thermal isomerization processes of (P,P)-trans-1.
Figure 2: Ultraviolet–visible spectra (hexane solvent).
Figure 3: Circular dichroism (CD) spectra system in each of four stages of switching (see text).

Similar content being viewed by others

References

  1. Feynman,R. P. in Miniaturization (ed. Gilbert, H. D.) (Reinhold, New York, 1961).

    Google Scholar 

  2. Drexler,K. E. Nanosystems: Molecular Machinery, Manufacturing and Computation (Wiley, New York, 1992).

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Huck,N. P. M., Jager,W. F., de Lange,B. & Feringa,B. L. Dynamic control and amplification of molecular chirality by circularly polarized light. Science 273, 1686–1688 (1996).

    Article  ADS  CAS  Google Scholar 

  6. Bissell,S. A., Córdova,E., Kaifer,A. E. & Stoddart,J. F. A chemically and electrochemically switchable molecular shuttle. Nature 369, 133–136 (1994).

    Article  ADS  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Bedard,T. C. & Moore,J. S. Design and synthesis of a “molecular turnstile”. J. Am. Chem. Soc. 117, 10662–10671 (1995).

    Article  CAS  Google Scholar 

  9. Kelly,T. R., Tellitu,I. & Sestelo,J. P. In search of molecular ratchets. Angew. Chem. Int. Edn Engl. 36, 1866–1868 (1997).

    Article  CAS  Google Scholar 

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

    Article  ADS  CAS  PubMed  Google Scholar 

  11. Balzani,V., Gómez-López,M. & Stoddard,J. F. Molecular machines. Acc. Chem. Res. 31, 405–414 (1998).

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  13. Armaroli,N. 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).

    Article  CAS  Google Scholar 

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

    Article  ADS  CAS  PubMed  Google Scholar 

  15. Harada,N., Koumura,N. & Feringa,B. L. 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).

    Article  CAS  Google Scholar 

  16. Koumura,N. & Harada,N. 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. Davis,A. P. Tilting at windmills? The second law survives. Angew. Chem. Int Edn Engl. 37, 909–910 (1998).

    Article  ADS  CAS  Google Scholar 

Download references

Acknowledgements

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

Author information

Authors and Affiliations

  1. Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, AG Groningen, 9747, 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, 980-8577, Sendai, Japan

    Nagatoshi Koumura & Nobuyuki Harada

Authors
  1. Nagatoshi Koumura
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Robert W. J. Zijlstra
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Richard A. van Delden
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nobuyuki Harada
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ben L. Feringa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ben L. Feringa.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koumura, N., Zijlstra, R., van Delden, R. et al. Light-driven monodirectional molecular rotor. Nature 401, 152–155 (1999). https://doi.org/10.1038/43646

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1038/43646

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing