Supramolecular organization and chiral resolution of p-terphenyl-m-dicarbonitrile on the AG(111) surface

Matthias Marschall, Joachim Reichert, Knud Seufert, Willi Auwärter, Florian Klappenberger, Alexander Weber-Bargioni, Svetlana Klyatskaya, Giorgio Zoppellaro, Alexei Nefedov, Thomas Strunskus, Christof Wöll, Mario Ruben, Johannes V. Barth

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

The supramolecular organization and layer formation of the non-linear, prochiral molecule [1, 1′4′,1″]-terphenyl-3,3′-dicarbonitrile adsorbed on the Ag(111) surface is investigated by scanning tunneling microscopy (STM) and near-edge X-ray absorption fine-structure spectroscopy (NEXAFS). Upon two-dimensional confinement the molecules are deconvoluted in three stereoisomers, that is, two mirror-symmetric trans- and one cis-species. STM measurements reveal large and regular islands following room temperature deposition, whereby NEXAFS confirms a flat adsorption geometry with the electronic p-system parallel to the surface plane. The ordering within the expressed supramolecular arrays reflects a substrate templating effect, steric constraints and the operation of weak lateral interactions mainly originating from the carbonitrile endgroups. High-resolution data at room temperature reveal enantiormorphic characteristics of the molecular packing schemes in different domains of the arrays, indicative of chiral resolution during the 2D molecular self-assembly process. At submonolayer coverage supramolecular islands coexist with a disordered fluid phase of highly mobile molecules. Following thermal quenching (down to 6 K) we find extended supramolecular ribbons stabilised again by attractive and directional noncovalent interactions, the formation of which reflects a chiral resolution of trans-species.

Original languageEnglish
Pages (from-to)1446-1451
Number of pages6
JournalChemPhysChem
Volume11
Issue number7
DOIs
StatePublished - 17 May 2010

Keywords

  • Adsorption
  • Enantiomorphism
  • Noncovalent interactions
  • Self-assembly
  • Supramolecular chemistry

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