Induction of Chirality in an Achiral Monolayer at
the Liquid/Solid Interface by a Supramolecular Chiral Auxiliary
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Abstract
An achiral oligo(<i>p</i>-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