Cyclohexanediamine Derivatives as Organogelators

Results of gelation tests are summarized in Table 2.12. The fluids to be gelled range from protic solvents to aprotic ones, from polar solvents to nonpolar ones, and from mineral oils to edible ones. It is obvious that both 80 and 81 are excellent organogelators whose gelation abilities are comparable to those of 68 and 69. For example, the amount of 80 necessary to gel one liter of acetonitrile, N,N-dimethylformamide, ethanol, ethyl acetate, tetrachloromethane, toluene and hexane are 5 g, 10 g, 33 g, 8 g, 23 g, 12 g and 6 g, respectively. This means that one molecule of 80 interacts with about 1800 molecules of acetonitrile, 600 molecules of A,A -dimethylformamide, 200 molecules of ethanol, 600 molecules of ethyl 

2 Macromolecular Organic Assemblies Table 2.12 Gelation test of 80 and 81 and minimum gel concentration necessary for gelation at 25°C  

The thermodynamic parameters for sol-to-gel transition in toluene were found by calculation to be A// = 65 kJ/mol, = -160 J/K mol suggesting that the enthalpic contribution is important for gelation. The AH value 65 kJ/mol is 

On the other hand, trioctadecyl-c/5-l,3,5-cyclohexanetricarboxamide (84), in which three C=0 groups are located at equatorial positions in the cyclohexane ring, is a good organogelator for nonpolar solvents, including hexane (1 g L ), cyclohexane (2 g L ), toluene (5 g L ), tetrachloromethane (5 g L ), benzene (3 g L ), chlorobenzene (3 g L ), tetrahydrofuran (9 g L ), pyridine (1 g L ), kerosene (1 g L ) and salad oil (2 g L ). The values in parentheses indicate minimum gel concentrations. 

---