Direct observation of long-range chirality transfer in a self-assembled supramolecular monolayer at interface in situ

Abstract

Due to the interest in the origin of life and the need to synthesize new functional materials, the study of the origin of chirality has been given significant attention. The mechanism of chirality transfer at molecular and supramolecular levels remains underexplored. Herein, we study the mechanism of chirality transfer of N, N’-bis (octadecyl)-L-/D-(anthracene-9-carboxamide)-glutamic diamide (L-/D-GAn) supramolecular chiral self-assembled at the air/water interface by chiral sum-frequency generation vibrational spectroscopy (chiral SFG) and molecular dynamics (MD) simulations. We observe long-range chirality transfer in the systems. The chirality of Cα-H is transferred first to amide groups and then transferred to the anthracene unit, through intermolecular hydrogen bonds and π-π stacking to produce an antiparallel β-sheet-like structure, and finally it is transferred to the end of hydrophobic alkyl chains at the interface. These results are relevant for understanding the chirality origin in supramolecular systems and the rational design of supramolecular chiral materials.