Induction of chirality in an achiral monolayer at the liquid/solid interface by a supramolecular chiral auxiliary.
An achiral oligo(p-phenylene vinylene) derivative with a ureido-triazine hydrogen bonding unit self-assembles into rows of hydrogen bonded dimers at the liquid/solid interface. Scanning tunneling microscopy reveals the formation of chiral domains, but overall, the surface remains racemic. Addition of a chiral auxiliary which is able to interact with the dimers through hydrogen bonding, showed that global organizational chirality could be achieved since a majority of the domains show the same handedness. After removing the chiral auxiliary with a volatile solvent, the global organizational chirality could be trapped, revealing a memory effect. With this straightforward supramolecular approach, we were able to create a chiral surface with preferred handedness composed of achiral molecules at the air/solid interface.
Department of Chemistry, Division of Molecular Imaging and Photonics, KU Leuven-University of Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
Inge
I
De Cat
Zongxia
Z
Guo
Subi J
SJ
George
E W
EW
Meijer
Albertus P H J
AP
Schenning
Steven
S
De Feyter