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*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

44 Citaten (Scopus)
250 Downloads (Pure)

Samenvatting

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.

Originele taal-2English
Pagina's (van-tot)15270-15273
Aantal pagina's4
TijdschriftJournal of the American Chemical Society
Volume135
Nummer van het tijdschrift41
DOI's
StatusPublished - 16-okt-2013

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