Organic core–shell-shaped micro/nanoparticles from twisted macrocycles in Schiff base reaction

Abstract

Functional self-assemblies derived from noncovalent interactions such as lipid vesicles and DNA chiral double helices are a typical feature of natural life activity. Because of this phenomenon, a self-assembly approach for various functional organic particles is a desirable objective in supramolecular chemistry. Here, we report the discovery of enantiomeric conformers from a twisted macrocyclic host (MH), which was obtained from an achiral precursor by Schiff base reaction. Further studies suggest that a series of unexpected and stable core–shell-based organic micro/nanospheres can be directly precipitated from a simple reaction solution with high yield. A single-crystal X-ray diffraction analysis of MH revealed that the unusual C–H⋯π interaction triggered self-assembly of the enantiomeric forms in the solid state plays an important role in the formation of the core–shell-shaped organic particles.