Abstract: | Developing hierarchical supramolecular structures is important for better understanding of various biological functions and possibly generating new materials for biomedical applications. Herein, we report the first examples of functional vesicles derived from cationic spherical organic molecules ( C1 ‐ C3 ) which were readily synthesized by reacting a C3‐symmetric tris‐benzimmidazole derivative (possessing a 1,3,5‐ethyl substituted aromatic core) with 1,3,5‐substituted tris‐bromomethyl benzene derivatives. Vesicle formation by C1 ‐ C3 was probed by high‐resolution microscopy (TEM and AFM), dynamic light scattering (DLS) and fluorescence microscopic imaging of calcein‐loaded vesicles. One of the vesicles Vesicle(C3) ] displayed the ability to load the anticancer drug doxorubicin ( DOX ). The drug was subsequently released from DOX@Vesicle(C3) in a stimuli‐responsive manner in presence of the well‐known vesicle destroyer Triton X‐100 , as revealed by in vitro cell migration assay carried out on a highly aggressive human breast cancer cell line ( MDA‐MB‐231 ). |