By Chandrakant S. Desai, Hema J. Siriwardane

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Urea, thiourea and guanidinium groups have been incorporated into synthetic receptors and shown to bind with tetramethylammonium (TMA) acetate in dimethyl sulfoxide (DMSO), as detailed in Table 2. The binding af®nity of this bidentate interaction increases uniformly with the increasing acidity of the hydrogen-bond donor protons. Other groups have also exploited these simple motifs for the recognition of carboxylates (Fig. 14). Wilcox used ureas such as 18 to complex various anions including carboxylates [55].

25. 5 Other Hydrogen-Bonded Organogelators Surfactants such as sodium bis(2-ethylhexyl)sulfosuccinate (AOT) 47 were found to transform into organogelators by addition of suitable phenols in nonpolar solvents [78]. The authors suggest that hydrogen bonding may occur between the head group of AOT and the hydroxyl group of several phenol molecules. Furthermore, NMR investigations indicate that the phenol-AOT aggregates form stacked strands within the gel matrix (see Fig. 26). Hanabusa has studied small peptides with long alkyl substituents, for example 48, and found them to gel organic solvents at very low concentrations [79, 80].

Two families of sugar-based gelators. Substitution and conformation have a remarkable effect on the gelation abilities of these compounds Controlling Hydrogen Bonding 55 5 Non-Hydrogen-Bonded Organogelators The main focus of this chapter has been organogelators in which the key selfassembling interactions are well-de®ned hydrogen-bonding patterns. However, there are many other organogelators that do not use hydrogen bonding to organize the gel matrix. These include fatty acids, surfactants, anthracene and steroid derivatives [33].

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