Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu111

Meike Stöhr; Serpil Boz; Michael Schär; Manh-Thuong Nguyen; Carlo A Pignedoli; Daniele Passerone; W Bernd Schweizer; Carlo Thilgen; Thomas A Jung; François Diederich

doi:10.1002/anie.201102627

Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu111

Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9982-6. doi: 10.1002/anie.201102627. Epub 2011 Sep 12.

Authors

Meike Stöhr¹, Serpil Boz, Michael Schär, Manh-Thuong Nguyen, Carlo A Pignedoli, Daniele Passerone, W Bernd Schweizer, Carlo Thilgen, Thomas A Jung, François Diederich

Affiliation

¹ Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh, The Netherlands. m.a.stohr@rug.nl

PMID: 21913288
DOI: 10.1002/anie.201102627

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.