Improving the gelation properties of 3,5-diaminobenzoate-based organogelators in aromatic solvents with additional aromatic-containing pendants

A family of 3,5-diaminobenzoate derivatives containing different Cbz-protected alpha- or beta-amino side pendant chains and different aromatic-containing ester functionalities was prepared. It was found that the additional aromatic rings in the Cbz- and aromatic-containing ester moieties significantly improved the gelation properties of the resulting organogelators in aromatic solvents. Infrared and circular dichroism spectroscopy revealed that both H-bonding and pi-pi aromatic stacking interactions were the main driving forces for gelation. (c) 2006 Elsevier Ltd. All rights reserved.