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The delicate balance between H-bonding and van der Waals interactionsdetermine the stability,structure and chirality of many molecular andsupramolecular aggregates weakly adsorbed on solid surfaces.Yet the inherentcomplexity of these systems makes their experimental study at the molecularlevel very challenging.Small alcohols adsorbed on metal surfaces have become auseful model system to gain fundamental insight into the interplay of suchmolecule-surface and molecule-molecule interactions.Here, through a combinationof scanning tunneling microscopy and density functional theory,we compare andcontrast the adsorption and self-assembly of a range of small alcohols frommethanol to butanol on Au(111).We find that that longer chained alcohols preferto form zigzag chains held together by extended H-bonded networks betweenadjacent molecules.When alcohols bind to a metal surface datively via one ofthe two lone electron pairs of the oxygen atom they become chiral.Therefore,thechain structures are formed by a H-bonded network between adjacent moleculeswith alternating adsorbed chirality.These chain structures accommodate longeralkyl tails through larger unit cells, while the position of the hydroxyl groupwithin the alcohol molecule can produce denser unit cells that maximizeintermolecular interactions.Interestingly,when intrinsic chirality isintroduced into the molecule as in the case of 2-butanol the assembly changescompletely and square packing structures with chiral pockets are observed. Thisis rationalized by the fact that the intrinsic chirality of the moleculedirects the chirality of the adsorbed hydroxyl group meaning that heterochiralchain structures cannot form.Overall this study provides a general frameworkfor understanding the effect of simple alcohol molecular adstructures onH-bonded aggregates and paves the way for rationalizing 2D chiralsupramolecular assembly.

Chirality at two-dimensional surfaces: A perspective from small molecule alcohol assembly on Au(111)