Novel supramolecular coatings that make use of low-molecular weight ditopic monomers with guanine end groups are studied using fluid tapping AFM. These molecules assemble on highly oriented pyrolytic graphite (HOPG) from aqueous solutions to form nanosized banding structures whose sizes can be systematically tuned at the nanoscale by tailoring the molecular structure of the monomers. The nature of the self-assembly in these systems has been studied through a combination of the self-assembly of structural derivatives and molecular modeling. Furthermore, we introduce the concept of using these molecular assemblies as scaffolds to organize functional groups on the surface. As a first demonstration of this concept, scaffold monomers that contain a monomethyl triethyleneglycol branch were used to organize these "functional" units on a HOPG surface. These supramolecular grafted assemblies have been shown to be stable at biologically relevant temperatures and even have the ability to significantly reduce static platelet adhesion.