Transformation of Supramolecular Membranes to Vesicles Driven by Spontaneous Gradual Deprotonation on Membrane Surfaces

The various proteins and asymmetric lipid bilayers present in cell membranes form curvatures, resulting in structural transformations to generate vesicles. Fission and fusion processes between vesicles and cell membranes are reversible in living organisms. Although the transformation of a two-dimensional membrane to a three-dimensional vesicle structure is a common natural phenomenon, the lack of a detailed understanding at the molecular level limits the development of synthetic systems for functional materials. Herein, we report a supramolecular membrane system through donor–acceptor interactions using a π-deficient acceptor and π-rich donor as building blocks. The reduced electrostatic repulsion between ammonium cations and the spontaneously deprotonated neutral amino group induced anisotropic membrane curvature, resulting in membrane fission to form vesicles with a detailed understanding at the molecular level. Furthermore, the reversible transformation of vesicles to membranes upon changing the pH provides a novel synthetic system exhibiting both fission and fusion processes.