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.
Liu
Yong
Y
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.
Liu
Xuejun
X
Warmuth
Ralf
R
D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D015394:Molecular Structure; D053769:Nanocapsules / Q000737:chemistry*; D010316:Particle Size; D012015:Reference Standards; D013816:Thermodynamics
C525254:1,3,5-tris(p-aminophenyl)benzene; D001555:Benzene Derivatives; D007097:Imines; D047028:Macrocyclic Compounds; D053769:Nanocapsules