Dynamic Imine Chemistry at Complex Double Emulsion Interfaces

Interfacial chemistry provides an opportunity to control dynamic materials. By harnessing the dynamic covalent nature of imine bonds, emulsions are generated in situ, predictably manipulated, and ultimately destroyed along liquid-liquid and emulsion-solid interfaces through simple perturbation of the imine equilibria. We report the rapid production of surfactants and double emulsions through spontaneous in situ imine formation at the liquid-liquid interface of oil/water. Complex double emulsions with imine surfactants are stable to neutral and basic conditions and display dynamic behavior with acid-catalyzed hydrolysis and imine exchange. We demonstrate the potential of in situ imine surfactant formation to generate complex surfactants with biomolecules (i.e., antibodies) for biosensing applications. Furthermore, imine formation at the emulsion-solid interface offers a triggered payload release mechanism. Our results illustrate how simple, dynamic interfacial imine formation can translate changes in bonding to macroscopic outputs.