A novel rosin-based photoresponsive anionic amphiphile, sodium N-azophenyl maleopimaric acid imide carboxylate (AzoMPCOONa), has been successfully synthesized. Its molecular structure was characterized by 1H and 13C NMR and mass spectrometry (MS). The photoisomerization of AzoMPCOONa was evaluated by ultraviolet (UV)-visible spectrometry and 1H NMR. The structure of AzoMPCOONa could be converted between the trans and cis isomers by irradiation with UV/visible light. Importantly, a fascinating photoresponsive viscoelastic solution was prepared by mixing AzoMPCOONa and cetyltrimethylammonium bromide (CTAB). The properties of the photoresponsive viscoelastic solution were further investigated by rheology, circular dichroism (CD), and cryogenic transmission electron microscopy (cryo-TEM). Initially, the AzoMPCOONa/CTAB system was a gel-like solution composed of entangled wormlike micelles possessing the right-handed chiral structure. After UV irradiation for 10 min, the gel-like solution transformed into a slightly viscous solution, its zero-shear viscosity dramatically reduced by 2 orders of magnitude, and the aggregates were converted into rod-like micelles and spherical micelles. In addition, the right-handed chiral structure of the aggregates disappeared. These dramatic changes in the viscosity and the aggregate structure can be attributed to the photoisomerization of the azobenzene group in AzoMPCOONa, which led to changes in the molecular geometry and the packing parameter of the AzoMPCOONa/CTAB system. Interestingly, the right-handed chiral structure of wormlike micelles also is photoresponsive. The results reveal the superiority of forest resources for preparing viscoelastic solutions.
Keywords: biomass resource; chirality; photoresponsive; viscoelastic solution; wormlike micelles.