Synthesis and Structure–Property Relationships of Amphiphilic Organogelators

Abstract

A series of low-molecular-weight amphiphilic molecules was synthesized and investigated for their ability to gel organic solvents. These amphiphilic molecules are composed of a head-group moiety capable of forming intermolecular associations through hydrogen bonds and n-alkyl chains of various lengths. This paper describes the continuation of recently published work, in which this class of gelators was presented for the first time. Here, the focus addresses systematically three different structural variations of the head-group moiety: 1) the rigidity, 2) the type and strength of the hydrogen-bond-forming units, and 3) the reduction of the intermolecular interaction by incorporating a lateral substituent. The gelation behavior was investigated in p-xylene and in several polar solvents. The aim was to establish structure-property relationships and to provide organogelators capable of forming gels at low concentrations with adjustable sol-gel transition temperatures and good optical quality. For some individual compounds of the series this property profile was achieved. For the investigated solvents, with particular compounds, sol-gel transition temperatures above 100 degrees C with a reasonable concentration of gelator are obtainable.