An evaluation of the relationship between two- and three-dimensional packing in self-organised monolayers and bulk crystals of amphiphilic 2,2′:6′,2"-terpyridines

2,2': 6',2 ''-Terpyridine (tpy) ligands with pendant octadecyloxy, 4-octyloxyphenyl or 4-octadecyloxyphenyl substituents at the 4'-position have been prepared and structurally characterised. Monolayers of the compounds have been prepared on highly oriented pyrolytic graphite (HOPG) and investigated by STM. The monolayer structure corresponds to the bulk crystal structure if the latter contains planar sheets. The tpy ligands are prochiral and form homochiral domains within the monolayer, providing a spectacular visual representation of the symmetry-breaking concomitant with the formation of a monolayer.