Letter | Published:

Spatial periodicity in molecular switching

Nature Nanotechnology volume 3, pages 649653 (2008) | Download Citation

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Abstract

The ultimate miniaturization of future devices will require the use of functional molecules at the nanoscale and their integration into larger architectures1,2. Switches represent a prototype of such functional molecules because they exhibit characteristic states of different physical/chemical properties, which can be addressed reversibly3. Recently, various switching entities have been studied and switching of single molecules on surfaces has been demonstrated4,5,6,7,8,9,10,11,12,13. However, for functional molecules to be used in a future device, it will be necessary to selectively address individual molecules, preferentially in an ordered pattern. Here, we show that azobenzene derivatives in the trans form, adsorbed in a homogeneous two-dimensional layer, can be collectively switched with spatial selectivity, thus forming a periodic pattern of cis isomers. We find that the probability of a molecule switching is not equally distributed, but is strongly dependent on both the surrounding molecules and the supporting surface, which precisely determine the switching capability of each individual molecule. Consequently, exactly the same lattices of cis isomers are created in repeated erasing and re-switching cycles. Our results demonstrate a conceptually new approach to spatially addressing single functional molecules.

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References

  1. 1.

    , & Electronics using hybrid-molecular and mono-molecular devices. Nature 408, 541–548 (2000).

  2. 2.

    & Molecular electronics. Physics Today 56, 43–49 (2003).

  3. 3.

    Molecular Switches (Wiley-VCH, Weinheim, 2001).

  4. 4.

    et al. Conformational molecular switch of the azobenzene molecule: A scanning tunnelling microscopy study. Phys. Rev. Lett. 96, 156106 (2006).

  5. 5.

    , , , & Reversible cis-trans isomerization of a single azobenzene molecule. Angew. Chem. Int. Ed. 45, 603–606 (2006).

  6. 6.

    et al. Electric field-induced isomerization of azobenzene by STM. J. Am. Chem. Soc. 128, 14446–14447 (2006).

  7. 7.

    , , , & Reversible switching of tetra-tert-butyl-azobenzene on a Au(111) surface induced by light and thermal activation. Chem. Phys. Lett. 444, 85–90 (2007).

  8. 8.

    et al. Reversible photomechanical switching of individual engineered molecules at a metallic surface. Phys. Rev. Lett. 99, 038301 (2007).

  9. 9.

    et al. Cooperative light-induced molecular movements of highly ordered azobenzene self-assembled monolayers. Proc. Natl Acad. Sci. 104, 9937–9942 (2007).

  10. 10.

    , , & A single molecule view of bistilbene photoisomerization on a surface using scanning tunnelling microscopy. J. Am. Chem. Soc. 127, 10788–10789 (2005).

  11. 11.

    et al. Reversible conductance switching of single diarylethenes on a gold surface. Adv. Mater. 18, 1397–1400 (2006).

  12. 12.

    , & Current-induced hydrogen tautomerization and conductance switching of naphthalocyanine molecules. Science 317, 1203–1206 (2007).

  13. 13.

    et al. Adsorption and switching properties of azobenzene derivatives on different noble metal surfaces; Au(111), Cu(111) and Au(100). J. Phys. Chem. C 112, 10509–10514 (2008).

  14. 14.

    The effect of structure upon the reactions of organic compounds. Benzene derivatives. J. Am. Chem. Soc. 59, 96–103 (1937).

  15. 15.

    , , & Scanning tunnelling microscopy observations on the reconstructed Au(111) surface: Atomic structure, long-range superstructure, rotational domains and surface defects. Phys. Rev. B 42, 9307–9318 (1990).

  16. 16.

    et al. Supramolecular self-assembly and selective step decoration on the Au(111) surface. Europhys. Lett. 56, 254–260 (2001).

  17. 17.

    , , & Scanning tunnelling microscopy observation of an electronic superlattice at the surface of clean gold. Phys. Rev. Lett. 80, 1469–1472 (1998).

  18. 18.

    , , & Functionalizing hydrogen-bonded surface networks with self-assembled monolayers. Nature 454, 618–621 (2008).

  19. 19.

    A simple low-temperature ultrahigh-vacuum STM capable of atomic manipulation. Rev. Sci. Instrum. 67, 2960–2965 (1996).

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Acknowledgements

The authors thank K.-H. Rieder, J.I. Pascual and M. Wolf for careful reading of the manuscript. Financial support was provided by the German Research Foundation (DFG) through the SFB 658 (projects A1 and B8) and through contract no. GR 2697/1-2. C.D. thanks the Fondazione CRTrieste for financial support. This research was funded by the Progetto D4 (European Social Fund, Regione Friuli Venezia Giulia and Italian Ministry of Welfare).

Author information

Affiliations

  1. Department of Experimental Physics, Freie Universität Berlin, Arnimallee 14, 14195 Berlin, Germany

    • Carlo Dri
    •  & Leonhard Grill
  2. Department of Physics and CENMAT, University of Trieste, 34127 Trieste, Italy

    • Carlo Dri
  3. CNR-INFM Laboratorio TASC, Area Science Park, S.S. 14 Km 163.5, 34012 Basovizza-Trieste, Italy

    • Carlo Dri
  4. Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany

    • Maike V. Peters
    • , Jutta Schwarz
    •  & Stefan Hecht

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Contributions

S.H. and L.G. conceived the experiments. C.D. and L.G. performed the experiments and analysed the data. M.V.P., J.S. and S.H. synthesized the molecules. L.G. wrote the paper. C.D., S.H. and L.G. discussed the results and commented on the manuscript.

Corresponding authors

Correspondence to Stefan Hecht or Leonhard Grill.

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DOI

https://doi.org/10.1038/nnano.2008.269

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