Remote Chiral Communication in Coadsorber-Induced Enantioselective 2D Supramolecular Assembly at a Liquid/Solid Interface

 

Ting Chen, Shu-Ying Li, Dong Wang,* Man Yao, and Li-Jun Wan*

 

Angew. Chem. Int. Ed. Just Accepted Manuscript DOI: 10.1002/anie.201410927

 

Abstract: Remote chiral communication in 2D supramolecular assembly at a liquid/solid interface was investigated at the molecular level. The stereochemical information in a chiral coadsorber was transmitted over a flexible spacer with a length of up to five methylene groups to a 2D supramolecular assembly of achiral building blocks with the cooperation of specific hydrogen bonding between the chiral coadsorber and achiral building blocks and the confinement effect during 2D crystallization. When the position of the stereogenic center was changed with respect to the stereocontrolling moiety, an odd– even effect was found. A stereogenic center closer to the stereocontrolling moiety transmitted the stereochemical information to the 2D supramolecular assembly more reliably. This result is beneficial not only for mechanistic understanding of chiral communication in 2D supramolecular assembly on surfaces but also for the rational design of homochiral supramolecular assemblies on surfaces.