Remarkable stabilization of self-assembled organogels by polymerization

In recent years a number of low molecular weight organic compounds have been found to be effective gelators for organic solvents. They have in common that in organic solution they self-assemble into elongated fiber-like structures through highly specific intermolecular interactions. These fibers in turn form a three-dimensional network encapsulating the solvent. The welldefined molecular arrangement within the fibers offers ample opportunity for the development of functional gels. Large open network structures with, for instance, recognition sites or electron conducting groups open new possibilities in areas such as catalysis, sensor technology, and materials science. However, organogels commonly suffer from instability, for instance, due to crystallization or lack of mechanical robustness. Furthermore, despite major achievements in supramolecular chemistry to achieve controlled self-assembly of organic molecules, until now most low molecular weight gelators have been found by serendipity rather then by design. Very recently, Hanabusa and co-workers and our group succeeded in the systematic design of novel gelators for organic solvents by exploiting the selfassembling properties of urea groups. Here we report a novel polymerizable organogelator for organic solvents, based on (1R,2R)-trans-1,2-bis(ureido)cyclohexane, and the formation of highly stable organogels. These systems differ from macromolecular gels in that the monomeric compound already forms gels through aggregation by extensive hydrogen-bond formation.