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Applied Physics A

, Volume 93, Issue 2, pp 247–252 | Cite as

Formation and manipulation of discrete supramolecular azobenzene assemblies

  • Sofia Selvanathan
  • Maike V. Peters
  • Jutta Schwarz
  • Stefan HechtEmail author
  • Leonhard GrillEmail author
Article

Abstract

Azobenzene derivatives were deposited onto a Au(111) surface and studied by scanning tunneling microscopy. The symmetry of the parent azobenzene was broken by introducing tert-butyl groups which are known to decouple the molecular core from the substrate, on the one end, and carboxylic acid groups which direct and stabilize the supramolecular assembly structure on the surface by intermolecular hydrogen bonding, on the other end. As a consequence of the interacting COOH groups, the molecules assemble on the surface either in extended, polymeric chains and/or in discrete, hexameric rosettes. The high stability of the rosette structure is proven experimentally by controlled lateral displacement on the surface without breaking the non-covalent interactions. Although switching attempts were not successful, the approach herein should facilitate the construction of well-defined multi-switch arrays.

PACS

68.37.Ef 72.80.Le 81.07.-b 82.37.Gk 85.65.+h 

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Supplementary material

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References

  1. 1.
    L. Grill, M. Dyer, L. Lafferentz, M. Persson, M.V. Peters, S. Hecht, Nat. Nanotechnol. 2, 687 (2007) ADSCrossRefGoogle Scholar
  2. 2.
    S. Weigelt, C. Busse, C. Bombis, M.M. Knudsen, K.V. Gothelf, T. Strunskus, C. Wöll, M. Dahlbom, B. Hammer, E. Laegsgaard, F. Besenbacher, T.R. Linderoth, Angew. Chem. Int. Ed. 46, 1 (2007) CrossRefGoogle Scholar
  3. 3.
    M. Stöhr, M. Wahl, C.H. Galka, T. Riehm, T.A. Jung, L.H. Gade, Angew. Chem. Int. Ed. 44, 7394 (2005) CrossRefGoogle Scholar
  4. 4.
    D.L. Keeling, N.S. Oxtoby, C. Wilson, M.J. Humphry, N.R. Champness, P.H. Beton, Nano Lett. 3, 9 (2003) ADSCrossRefGoogle Scholar
  5. 5.
    J.A. Theobald, N.S. Oxtoby, M.A. Phillips, N.R. Champness, P.H. Beton, Nature 424, 1029 (2003) ADSCrossRefGoogle Scholar
  6. 6.
    J.V. Barth, J. Weckesser, N. Lin, A. Dmitriev, K. Kern, Appl. Phys. A 76, 645 (2003) ADSCrossRefGoogle Scholar
  7. 7.
    J.V. Barth, J. Weckesser, C. Cai, P. Günter, L. Bürgi, O. Jeandupeux, K. Kern, Angew. Chem. Int. Ed. 39, 1230 (2000) CrossRefGoogle Scholar
  8. 8.
    R. Otero, M. Lukas, R.E.A. Kelly, W. Xu, E. Laegsgaard, I. Stensgaard, L.N. Kantorovich, F. Besenbacher, Science 319, 312 (2008) ADSCrossRefGoogle Scholar
  9. 9.
    G. Pawin, K.L. Wong, K.-Y. Kwon, L. Bartels, Science 313, 961 (2006) ADSCrossRefGoogle Scholar
  10. 10.
    J.V. Barth, G. Costantini, K. Kern, Nature 437, 671 (2005) ADSCrossRefGoogle Scholar
  11. 11.
    S. DeFeyter, F.C. DeSchryver, Chem. Soc. Rev. 32, 139 (2003) CrossRefGoogle Scholar
  12. 12.
    C. Joachim, J.K. Gimzewski, A. Aviram, Nature 408, 541 (2000) ADSCrossRefGoogle Scholar
  13. 13.
    B.L. Feringa, Molecular Switches (Wiley-VCH, Weinheim, 2001) CrossRefGoogle Scholar
  14. 14.
    V. Iancu, S.-W. Hla, Proc. Natl. Acad. Sci. 103, 13718 (2006) ADSCrossRefGoogle Scholar
  15. 15.
    Z.J. Donhauser, B.A. Mantooth, K.F. Kelly, L.A. Bumm, J.D. Monnell, J.J. Stapleton, D.W. Price Jr., A.M. Rawlett, D.L. Allara, J.M. Tour, P.S. Weiss, Science 292, 2303 (2001) CrossRefGoogle Scholar
  16. 16.
    F. Moresco, G. Meyer, K.-H. Rieder, H. Tang, A. Gourdon, C. Joachim, Phys. Rev. Lett. 86, 672 (2001) ADSCrossRefGoogle Scholar
  17. 17.
    P. Liljeroth, J. Repp, G. Meyer, Science 317, 1203 (2007) ADSCrossRefGoogle Scholar
  18. 18.
    H. Rau, Photochromism—Molecules and Systems (Elsevier, Amsterdam, 2003), p. 165 Google Scholar
  19. 19.
    C. Zhang, M.-H. Du, H.-P. Cheng, X.-G. Zhang, A.E. Roitberg, J.L. Krause, Phys. Rev. Lett. 92, 158301 (2004) ADSCrossRefGoogle Scholar
  20. 20.
    A. Kirakosian, M.J. Comstock, J. Cho, M.F. Crommie, Phys. Rev. B 71, 113409 (2005) ADSCrossRefGoogle Scholar
  21. 21.
    J.A. Miwa, S. Weigelt, H. Gersen, F. Besembacher, F. Rosei, T. Linderoth, J. Am. Chem. Soc. 128, 3164 (2006) CrossRefGoogle Scholar
  22. 22.
    B.Y. Choi, S.J. Kahng, S. Kim, H. Kim, H.W. Kim, Y.J. Song, J. Ihm, Y. Kuk, Phys. Rev. Lett. 96, 156106 (2006) ADSCrossRefGoogle Scholar
  23. 23.
    M. Alemani, M.V. Peters, S. Hecht, K.-H. Rieder, F. Moresco, L. Grill, J. Am. Chem. Soc. 128, 14446 (2006) CrossRefGoogle Scholar
  24. 24.
    S. Hagen, F. Leyssner, D. Nandi, M. Wolf, P. Tegeder, Chem. Phys. Lett. 444, 85 (2007) ADSCrossRefGoogle Scholar
  25. 25.
    M.J. Comstock, N. Levy, A. Kirakosian, J. Cho, F. Lauterwasser, J.H. Harvey, D.A. Strubbe, J.M.J. Frechet, D. Trauner, S.G. Louie, M.F. Crommie, Phys. Rev. Lett. 99, 038301 (2007) ADSCrossRefGoogle Scholar
  26. 26.
    J. Henzl, M. Mehlhorn, H. Gawronski, K.-H. Rieder, K. Morgenstern, Angew. Chem. Int. Ed. 45, 603 (2006) CrossRefGoogle Scholar
  27. 27.
    M. Alemani, S. Selvanathan, F. Moresco, K.-H. Rieder, F. Ample, C. Joachim, M.V. Peters, S. Hecht, L. Grill, J. Phys. Chem. C 112, 10509 (2008) Google Scholar
  28. 28.
    G. Pace, V. Ferri, C. Grave, M. Elbing, C. v. Hänisch, M. Zharnikov, M. Mayor, M.A. Rampi, P. Samori, Proc. Natl. Acad. Sci. 104, 9937 (2007) ADSCrossRefGoogle Scholar
  29. 29.
    J.V. Barth, Annu. Rev. Phys. Chem. 58, 375 (2007) ADSCrossRefGoogle Scholar
  30. 30.
    G. Meyer, Rev. Sci. Instrum. 67, 2960 (1996) ADSCrossRefGoogle Scholar
  31. 31.
    L. Grill, J. Phys.: Condens. Matter 20, 053001 (2008) ADSGoogle Scholar
  32. 32.
    L. Grill, K.-H. Rieder, F. Moresco, S. Stojkovic, A. Gourdon, C. Joachim, Nano Lett. 6, 2685 (2006) ADSCrossRefGoogle Scholar
  33. 33.
    G.M. Whitesides, E.E. Simanek, J.P. Mathias, C.T. Seto, D.N. Chin, M. Mammen, D.M. Gordon, Acc. Chem. Res. 28, 37 (1995) CrossRefGoogle Scholar
  34. 34.
    D. Payer, A. Comisso, A. Dmitriev, T. Strunskus, N. Lin, C. Wöll, A. DeVita, J.V. Barth, K. Kern, Chem. Eur. J. 13, 3900 (2007) CrossRefGoogle Scholar
  35. 35.
    L. Bartels, G. Meyer, K.-H. Rieder, Chem. Phys. Lett. 273, 371 (1997) ADSCrossRefGoogle Scholar
  36. 36.
    Supplementary material Google Scholar

Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  1. 1.Institut für ExperimentalphysikFreie Universität BerlinBerlinGermany
  2. 2.Department of ChemistryHumboldt-Universität zu BerlinBerlinGermany

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