Understanding Enantioselective Interactions by Pulling Apart Molecular Rotor Complexes

Enantioselective interactions underpin many important phenomena from biological mechanisms to chemical catalysis. In this regard, there is great interest in understanding these effects at the molecular level. Surfaces provide a platform for these studies and aid in the long-term goal of designing heterogeneous enantiospecific interfaces. Herein we report a model system consisting of molecular rotors, one intrinsically chiral (propylene oxide) and one that becomes chiral when adsorbed on a surface (propene). Scanning tunneling microscopy (STM) measurements enable the chirality of each individual molecule to be directly visualized, and density functional theory based calculations are performed to rationalize the chiral time-averaged appearance of the molecular rotors. While there are no attractive intermolecular interactions between the molecular species themselves, when mixed together there is a strong preference for the formation of 1:1 heteromolecular pairs. We demonstrate that STM tip-induced molecular ...