Dynamic covalent surfactants

ORGN 282

Christophe B Minkenberg, C.B.Minkenberg@tudelft.nl1, Jan H. van Esch, j.h.vanesch@tudelft.nl2, and Louw Florusse, l.florusse@tudelft.nl1. (1) Department of Applied Sciences, Self-assembling systems, Delft University of Technology, Julianalaan 136, Delft, 2628BL, Netherlands, (2) Self-assembling systems, Delft Chem Tech, Technical University of Delft, Julianalaan, 136, Delft, 2628BL, Netherlands
Size and shape control through triggered self-assembly remains a major challenge in supramolecular chemistry. However, in self-assembling systems solely based on non-covalent interactions (scheme 1a), the thermodynamic and kinetic stability are strongly correlated, and it is inherently difficult to control them independent. It is our aim to develop and study new dynamic assemblies, which allow the independent control of thermodynamic and kinetic stability. To this extend, we synthesized two non-amphiphilic building blocks, which form surfactants in water by the formation of a dynamic covalent bond. These in situ formed surfactants form micelles above their critical micel concentration (cmc) (scheme 1b). We found a significant increase in micellization cooperativity by increasing the tail length of the surfactant. These surfactants also show a thermo reversible micellization, making them promising candidates for dynamic combinatorial libraries and temperature triggered encapsulation applications, respectively.