Phenolic‐Linked Alkyl Glycosides: Impact of Molecular Design on Surfactant Behavior

Following a recently reported new approach towards glycoside‐based surfactants, a series of phenol‐linked alkyl glucosides has been prepared. The new surfactants, which differed in the design of the hydrophilic and hydrophobic domains, were investigated on their potential for oil in water (O/W) and water in oil (W/O) applications. Previously reported high Krafft points for the surfactants could be significantly reduced by applying either a single branched hydrophobic domain or a parallel alignment of two hydrophilic head groups. Biantennary surfactants originating from bisalkylation of the phenolic linker, on the other hand, exhibited high Krafft points of previously investigated straight chain monoantennary alkyl phenol glycosides (APhGs). A rationale for the differing behavior of the two biantennary surfactant types can be found in packing constraints affecting π‐stacking interactions of the aromatic linker. The investigation underlines the need for structural packing constraints for effective phenolic surfactants in O/W‐systems.