Multicomponent Dynamic Covalent Assembly of a Rhombicuboctahedral Nanocapsule

Molecular container compounds have a range of potential applications in chemical and biological sciences, most notably as nanoreactors, drug delivery devices, and storage materials. We report a highly efficient dynamic covalent chemistry approach for the synthesis of covalent rhombicuboctahedral nanocapsule 1 from 14 square- and triangular-shaped molecular components. The nanocapsule is obtained in a one-pot reaction in high yield and high purity, and has a solvodynamic diameter of 3.9 nm. In our approach, six formyl cavitands and eight 1,3,5-tris(p-aminophenyl)benzene molecules are assembled into a molecular rhombicuboctahedron through twenty four newly formed dynamic imine bonds. Binding studies show that 1 encapsulates tetraalkylammonium salts in toluene. We also discuss the growth mechanism of this nanocapsule.