Benzyl and tert-butyl carbamate derivatives of 1,ω-amino acids as simple yet efficient gelators

Article abstract of DOI:10.1016/j.tet.2007.03.126

We report the synthesis and a study of the gelation properties of a series of N-protected long-chain amino acids. Especially, benzyl and tert-butyl carbamate derivatives of 11-aminoundecanoic acid in their deprotonated form can gelate polar organic solvents and water at very low concentration (less than 5 mM). This is explained by the contribution of multiple forces-H-bond, van der Waals and ionic interactions-in the gel aggregate formation and stabilization, which is confirmed by the experimental data. Among the series of compounds investigated, only a dimer of 11-aminoundecanoic acid is capable of gelating toluene, which stems from the increased number of hydrogen bonding sites in the main aliphatic chain.