Meta-positioning of Carbonitrile Functional Groups Induces Interfacial Egde-On Phase of Oligophenyl Derivatives

  • chair:

    Marschall, M. / Reichert, J. / Diller, K. / Klyatskaya, S. / Ruben, M. / Nefedov, A. / Wöll, C. / Kantorovich, L. / Klappenberger, F. / Barth, J. (2014)
  • place:

    Journal of Physical Chemistry C 118 (2014), 5, 2622-2633
  • Date: 2014

  • Marschall, M. / Reichert, J. / Diller, K. / Klyatskaya, S. / Ruben, M. / Nefedov, A. / Wöll, C. / Kantorovich, L. / Klappenberger, F. / Barth, J. (2014): „Meta-prositioning of Carbonitrile Functional Groups Induces Interfacial Egde-On Phase of Oligophenyl Derivatives“. In: Journal of Physical Chemistry C 118 (2014), 5, 2622-2633

Abstract

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We present a combined systematic experimental and theoretical study of the supramolecular organization of a carbonitrile-functionalized oligophenyl on Cu(111) and Ag(111) showing multiple self-assembled structures including a novel edge-on phase at room temperature. We were able to follow the coverage dependent assemblies by means of scanning tunneling microscopy, near-edge X-ray absorption-fine-structure spectroscopy, and X-ray photoelectron spectroscopy and supported the analysis of the experimental results by density functional theory calculations.

With increasing coverage the molecular orientation of the building blocks changes from nearly coplanar with the substrate to upright standing. With this reorientation, the stabilizing forces behind the respective bonding motives change from noncovalent molecule–molecule attraction governed by the polar functional groups to metal–organic coordination toward the substrate combined with intermolecular π–π interaction.