Chiral surfaces can be created by the adsorption of intrinsically chiral molecules, with the handedness defined by the molecule [1-4]. Additionally, a second manifestation of chirality may arise due to the molecule-substrate interaction in the form of a chiral adsorption footprint. Thus, chiral surfaces may possess both handedness and ‘footedness’ [5-8]. How both these aspects unfold and express themselves in organized molecular layers is little understood. This talk will illustrate how the ordering of handedness and footedness within organised assemblies of amino-acids on a Cu(110) surface can be tracked at the single-molecule level. The complex behaviour observed can be understood on the basis of three simple generic rules . Using these rules, it is possible to generate every possible footprint and enantiomer arrangement that could be expressed by an amino-acid monolayer. A truly surprising level of complexity in chiral ordering behavior emerges, with a manifold of possible outputs, ranging from segregations of chirality into separate enantiopure assemblies, to ordered racemic compounds with heterochiral unit cells, to solid solutions where chirality is randomly distributed. This complexity in output can emerge at either the handed or the footed levels, leading to highly complex combinations and permutations.
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Chemical Communications, 52 (2016) 14075.