Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111)

Meike Stöhr, Serpil Boz, Michael Schär, Manh Thuong Nguyen, Carlo A. Pignedoli, Daniele Passerone, W. Bernd Schweizer, Carlo Thilgen, Thomas A. Jung, Franãçois Diederich

Research output: Contribution to journalArticle

Abstract

Birds of a feather flock together: STM and DFT studies provide the first example of spontaneous chiral resolution of a helicene on a surface. Racemic 6,13-dicyano[7]helicene forms fully segregated domains of pure enantiomers (2D conglomerate) on Cu(111). The propensity of the system to optimize intermolecular CN⋯HC(Ar) hydrogen bonding and CN⋯CN dipolar interactions translates into chiral recognition with preferential assembly of homochiral molecules.

Original languageEnglish (US)
Pages (from-to)9982-9986
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number42
DOIs
StatePublished - Oct 10 2011
Externally publishedYes

Keywords

  • chirality
  • helicenes
  • scanning probe microscopy
  • spontaneous resolution
  • surface-confined self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Stöhr, M., Boz, S., Schär, M., Nguyen, M. T., Pignedoli, C. A., Passerone, D., Schweizer, W. B., Thilgen, C., Jung, T. A., & Diederich, F. (2011). Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111). Angewandte Chemie - International Edition, 50(42), 9982-9986. https://doi.org/10.1002/anie.201102627