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Symmetry breakdown of 4,4″-diamino-p-terphenyl on a Cu(111) surface by lattice mismatch

Author

Listed:
  • Qigang Zhong

    (Soochow University)

  • Daniel Ebeling

    (Justus-Liebig University)

  • Jalmar Tschakert

    (Justus-Liebig University)

  • Yixuan Gao

    (Institute of Physics & University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Deliang Bao

    (Institute of Physics & University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Shixuan Du

    (Institute of Physics & University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Chen Li

    (Dongguan University of Technology)

  • Lifeng Chi

    (Soochow University)

  • André Schirmeisen

    (Justus-Liebig University)

Abstract

Site-selective functionalization of only one of two identical chemical groups within one molecule is highly challenging, which hinders the production of complex organic macromolecules. Here we demonstrate that adsorption of 4,4″-diamino-p-terphenyl on a metal surface leads to a dissymmetric binding affinity. With low temperature atomic force microscopy, using CO-tip functionalization, we reveal the asymmetric adsorption geometries of 4,4″-diamino-p-terphenyl on Cu(111), while on Au(111) the symmetry is retained. This symmetry breaking on Cu(111) is caused by a lattice mismatch and interactions with the subsurface atomic layer. The dissymmetry results in a change of the binding affinity of one of the amine groups, leading to a non-stationary behavior under the influence of the scanning tip. Finally, we exploit this dissymmetric binding affinity for on-surface self-assembly with 4,4″-diamino-p-terphenyl for side-preferential attachment of 2-triphenylenecarbaldehyde. Our findings provide a new route towards surface-induced dissymmetric activation of a symmetric compound.

Suggested Citation

  • Qigang Zhong & Daniel Ebeling & Jalmar Tschakert & Yixuan Gao & Deliang Bao & Shixuan Du & Chen Li & Lifeng Chi & André Schirmeisen, 2018. "Symmetry breakdown of 4,4″-diamino-p-terphenyl on a Cu(111) surface by lattice mismatch," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05719-y
    DOI: 10.1038/s41467-018-05719-y
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