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 journalArticlepeer-review

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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