Photo and redox-responsive vesicles assembled from Bola-type superamphiphiles

Abstract

Superamphiphiles are considered as a promising approach for fabricating stimuli-responsive materials. Sensitivity to more than one stimulus can improve the system's versatile performance. In this study, we proposed a facile dual-responsive vesicle constructed from Bola-type superamphiphiles. An azobenzene dimer linked by a disulfide bond was synthesized. As the guest molecule, the azobenzene dimer can be included into the β-cyclodextrin's cavity from both ends to form a novel Bola-type superamphiphile, which can further assemble into a vesicular structure in aqueous solution. The vesicles were characterized by transmission electron microscopy (TEM) and dynamic light scattering (DLS). The formation mechanism of the vesicular structure was suggested based on the NMR, Fourier transform infrared spectroscopy (FT-IR) and X-ray diffraction (XRD) results. The photo and redox responsiveness of the vesicles was studied. The vesicles were found able to carry mitomycin C (MMC) and the drug-release can be greatly promoted upon UV irradiation or reduction.