Eleven bis-ureas have been synthesized, and some of their properties are reported. Several of these compounds form supramolecular polymers in organic solvents. The self-association is shown by FTIR spectroscopy to display cooperativity at two levels. The first level of cooperativity is due to the synergistic association of the two urea functions of a single molecule. The second level of cooperativity is revealed by the fact that the formation of dimers is less favored than that of long oligomers.

A low molecular weight bisurea in nonpolar solvents is shown to self-assemble by hydrogen bonding into two distinct high molecular weight structures. At low temperature and high concentration, the most stable structure is a thick cylindrical assembly, responsible for the very high viscosity of the solution. At higher temperature or lower concentration, the thick filaments disappear in favor of thinner filaments, leading to a lower viscosity. The reversible transition occurs over a temperature range of 5 degrees C only, showing that it is highly cooperative. The structural switch can also be triggered by changing the nature of the solvent or the composition in the case of a mixture of two bisureas. The high cooperativity and the tunability of this transition are useful for the design of responsive materials.