Self-Assembly of a Rosin-Derived Glycosylated Surfactant into Chiral Wormlike Micelles with Unusual Viscoelasticity

The development of supramolecular systems from renewable forestry resources holds considerable significance. In this study, a glycosylated surfactant (R-8-Glu) was synthesized from rosin. Its rigid dehydroabietic skeleton and the polyhydroxylated glucosyl headgroup drove the formation of elongated wormlike micelles, conferring remarkable viscoelasticity. Rheological measurements revealed that the zero-shear viscosity exhibited two distinct concentration-scaling regimes with exponents of 8.2 and 28.8, significantly surpassing predictions from classical polymer models. Cryo-TEM illustrated a concentration-dependent transformation from spherical to wormlike micelles with cross-sectional diameters of 5-6 nm, while circular dichroism spectroscopy demonstrated the emergence of right-handed supramolecular chirality during the one-dimensional micellar growth. ¹H-¹H 2D NOESY NMR indicated that hydrophobic packing of the rosin skeleton and amide interactions cooperatively drove the self-assembly. This work highlights rosin-based surfactants as sustainable building blocks for viscoelastic and chiral soft materials in food, cosmetic, and biomedical applications.