Oxidizing-responsive vesicles made from “tadpole-like supramolecular amphiphiles” based on inclusion complexes between driving molecules and β-cyclodextrin

Abstract: Novel slender hydrophobic ferrocenyl molecules (1–9) synthesized by efficient one-pot method in global high yields having poor aqueous solubility are driving molecules in formation of inclusion complexes with β-CD to self-assemble into vesicles in water. These vesicles were observed by TEM and confirmed by DLS, SEM and AFM for the first time. According to the complex stoichiometry and stability constant by UV, the one-head and one-tail “tadpole-like supramolecular amphiphiles” based on these inclusion complexes between driving molecules and β-CD were firstly assumed to construct these vesicles. Effects of chain length in driving molecules on formation of vesicles were estimated for the first time. The response of these vesicles to an oxidizing agent was also discussed. This work promotes to establish complete theoretical system of “supramolecular amphiphiles” and paves the way to combine supramolecular host–guest chemistry and membrane chemistry for potentially functional applications such as biomaterials for the separation of bacteria. [Copyright &y& Elsevier]