Synthesis and evaluation of chiral β-amino acid-based low-molecular-weight organogelators possessing a methyl/trifluoromethyl side chain

Abstract

The synthesis and gelation properties of chiral β-amino acid-based low-molecular-weight organogelators, possessing methyl/trifluoromethyl side chains, are reported. The structure of the side chain and chirality were found to be important parameters affecting the gelation ability. The pure enantiomer of the trifluoromethylated β-amino acid displayed good gelation properties due to the formation of fibrillar networks, driven by enhanced amide hydrogen bonding. An investigation of the effects of the alkyl chain length showed that longer alkyl chain improved the gelation ability, yet the same supramolecular structure was observed in all, as well as an odd–even effect in both the melting points and T_g values.