Control of Ambidextrous Gelation Properties by the Molecular Shape in Terms of Positional Isomers

Abstract

In contrast to numerous organogelators and hydrogelators reported so far ambidextrous gelators capable of gelating organic solvents and water are very limited. For the purpose of knowing the relationship between an efficient ambidextrous gelator and its molecular shape we have prepared amphiphiles consisting of a benzene ring to which a hydrophobic moiety and a hydrophilic moiety are connected via ortho, meta, and para positions. In glutamate-based amphiphilic compounds it has been found that ambidextrous gelation properties are completely different among structural isomers (positional isomers). The meta and para isomers exhibit ambidextrous gelation properties depending on the hydrophobic and the hydrophilic structures. On the contrary the ortho isomers yet prepared do not work as ambidextrous gelators.