Chirality Transfer in 1D Self-Assemblies: Influence of H-Bonding vs Metal Coordination between Dicyano[7]helicene Enantiomers

Aneliia Shchyrba, [No Value] Manh-Thuong Nguyen, Christian Waeckerlin, Susanne Martens, Sylwia Nowakowska, Toni Ivas, Jesse Roose, Thomas Nijs, Serpil Boz, Michael Schaer, Meike Stöhr, Carlo A. Pignedoli, Carlo Thilgen, Francois Diederich, Daniele Passerone, Thomas A. Jung*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

47 Citations (Scopus)
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Abstract

Chiral recognition as well as chirality transfer in supramolecular self-assembly and on-surface coordination is studied for the enantiopure 6,13-dicyano[7]helicene building block. It is remarkable that, with this helical molecule, both H-bonded chains and metal-coordinated chains can be formed on the same substrate, thereby allowing for a direct comparison of the chain bonding motifs and their effects on the self-assembly in experiment and theory. Conformational flexure and both adsorbate/adsorbent and intermolecular interactions can be identified as factors influencing the chiral recognition at the binding site. The observed H-bonded chains are chiral, however, the overall appearance of Cu-coordinated chains is no longer chiral. The study was performed via scanning tunneling microscopy, X-ray-photoelectron spectroscopy and density functional theory calculations. We show a significant influence of the molecular flexibility and the type of bonding motif on the chirality transfer in the ID self-assembly.

Original languageEnglish
Pages (from-to)15270-15273
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number41
DOIs
Publication statusPublished - 16-Oct-2013

Keywords

  • MOLECULAR CHIRALITY
  • SPONTANEOUS RESOLUTION
  • MONOLAYERS
  • SURFACE
  • HOMOCHIRALITY
  • INDUCTION
  • EXCESS
  • CYANO
  • ACID

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