Double headed alkyl triazole glycosides – alternatives for APGs with increased hydrophilicity part 1: synthesis and physicochemical properties

Abstract An economically viable route towards doubled headed alkyl triazole glycoside surfactants (ATG) is reported. The approach applies common industrial precursors leading to reasonable product yields. The interface-dominating hydrophilic domain favors curved assemblies over lamellar analogs, thereby enhancing the water solubility of the surfactants. In terms of assembly behavior, the double headed ATG matched corresponding chain analogs of alkyl polyglucosides (APG), thereby implying a compensation of the triazols’ hydrophobic effect by the parallel head groups. Likewise, the foaming behavior matched ATG analogs, suggesting comparable application potential. Differing emulsion behavior of Y-shape ATGs suggests π-stacking cohesion between triazoles with C 3 -spacer, whereas a shorter C 2 linker prevents these, leading to better emulsion stability, reflected in substantially smaller droplet size for oil-in-water.