Chirality transfer in 1D self-assemblies: Influence of H-bonding vs metal coordination between dicyano[7]helicene enantiomers

Aneliia Shchyrba, Manh Thuong Nguyen, Christian Wäckerlin, Susanne Martens, Sylwia Nowakowska, Toni Ivas, Jesse Roose, Thomas Nijs, Serpil Boz, Michael Schar, Meike Stöhr, Carlo A. Pignedoli, Carlo Thilgen, François Diederich, Daniele Passerone, Thomas A. Jung

Research output: Contribution to journalArticle

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 1D self-assembly.

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

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Scanning Tunnelling Microscopy
Photoelectron Spectroscopy
Enantiomers
Chirality
Self assembly
Metals
Binding Sites
Scanning tunneling microscopy
Binding sites
Adsorbates
Adsorbents
Density functional theory
X ray photoelectron spectroscopy
Molecules
Substrates
Experiments

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Shchyrba, A., Nguyen, M. T., Wäckerlin, C., Martens, S., Nowakowska, S., Ivas, T., ... Jung, T. A. (2013). Chirality transfer in 1D self-assemblies: Influence of H-bonding vs metal coordination between dicyano[7]helicene enantiomers. Journal of the American Chemical Society, 135(41), 15270-15273. https://doi.org/10.1021/ja407315f

Chirality transfer in 1D self-assemblies : Influence of H-bonding vs metal coordination between dicyano[7]helicene enantiomers. / Shchyrba, Aneliia; Nguyen, Manh Thuong; Wäckerlin, Christian; Martens, Susanne; Nowakowska, Sylwia; Ivas, Toni; Roose, Jesse; Nijs, Thomas; Boz, Serpil; Schar, Michael; Stöhr, Meike; Pignedoli, Carlo A.; Thilgen, Carlo; Diederich, François; Passerone, Daniele; Jung, Thomas A.

In: Journal of the American Chemical Society, Vol. 135, No. 41, 16.10.2013, p. 15270-15273.

Research output: Contribution to journalArticle

Shchyrba, A, Nguyen, MT, Wäckerlin, C, Martens, S, Nowakowska, S, Ivas, T, Roose, J, Nijs, T, Boz, S, Schar, M, Stöhr, M, Pignedoli, CA, Thilgen, C, Diederich, F, Passerone, D & Jung, TA 2013, 'Chirality transfer in 1D self-assemblies: Influence of H-bonding vs metal coordination between dicyano[7]helicene enantiomers', Journal of the American Chemical Society, vol. 135, no. 41, pp. 15270-15273. https://doi.org/10.1021/ja407315f
Shchyrba, Aneliia ; Nguyen, Manh Thuong ; Wäckerlin, Christian ; Martens, Susanne ; Nowakowska, Sylwia ; Ivas, Toni ; Roose, Jesse ; Nijs, Thomas ; Boz, Serpil ; Schar, Michael ; Stöhr, Meike ; Pignedoli, Carlo A. ; Thilgen, Carlo ; Diederich, François ; Passerone, Daniele ; Jung, Thomas A. / Chirality transfer in 1D self-assemblies : Influence of H-bonding vs metal coordination between dicyano[7]helicene enantiomers. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 41. pp. 15270-15273.
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AU - Roose, Jesse

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AU - Schar, Michael

AU - Stöhr, Meike

AU - Pignedoli, Carlo A.

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