Low molecular weight organogelators derived from threefold symmetric tricarbamates

Abstract

A group of new low molecular weight organogelators based on threefold symmetric tricarbamate were synthesized and characterized. The tricarbamates with long alkyl chains were able to gelate a wide range of polar and nonpolar organic solvents such as acetonitrile and cyclohexane, generally at concentrations lower than 20g/L. The best organogel formation was obtained using a threefold symmetric tricarbamate in n-dodecane, in which a sufficiently transparent gel was formed at the critical gelation concentration 1g/L. Intermolecular hydrogen bonding by the tricarbamate in a nonpolar solvent benzene-d6 was indicated by 1H NMR spectra. Its maximum UV absorption was 11nm higher in chloroform than in n-dodecane, and this red shift indicated increased conjugation between the benzene core and the carbamate substituents, which confirmed a change in its conformation from nonpolar to polar solvent. The self-assembling behavior of the tricarbamate in dilute solutions was investigated by TEM. Fiber-like networks were observed in a large range of solution concentrations.