Self-organization of amphiphilic supermolecules consisted of complementary hydrogen bonds provide supramolecular assemblies of higher hierarchy, which are soluble in water or in organic media (mesoscopic supramolecular assemblies). When ammonium-derivatized cyanuric acids and dialkylmelamines were mixed in water, complementary hydrogen bond-mediated bilayer assembly were spontaneously formed. This “reconstitution” in water is achieved as a result of interplaying hydrophobic interaction and hydrogen bond formation. The hydrogen bond-mediated bilayers displayed unique bilayer characteristics as exemplified by dynamic aggregate separation process, which was observed for ternaly complimentary mixtures. On the other hand, an equimolar mixture of dialkyl-melamine and naphthalenediimide formed stable dispersions in cyclohexanes. Electron microscopy observations indicated the presence of flexible rods with a diameter of ca. 100Å, and is most probably composed of circularly hydrogen-bonded units of the two components. In addition, an equimolar mixtures of dialkyl-melamine and alkylated cyanuric acid provided linear hydrogen bond-mediated bilayer structures both in cyclohexanes and in chloroform, in which thermal phase transition characteristics were preserved in organic media.