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

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry
• Materials Science

Background:

• Functional self-assemblies, like lipid vesicles and DNA helices, are fundamental to natural life.
• Developing self-assembly methods for functional organic particles is a key goal in supramolecular chemistry.

Purpose of the Study:

• To explore the self-assembly potential of a novel twisted macrocyclic host (MH).
• To investigate the formation of organic micro/nanoparticles from a macrocyclic host derived from an achiral precursor.

Main Methods:

• Synthesis of a twisted macrocyclic host (MH) via Schiff base reaction.
• Observation and characterization of self-assembled core-shell organic micro/nanospheres.
• Single-crystal X-ray diffraction analysis to elucidate structural and interaction mechanisms.

Main Results:

• Discovery of enantiomeric conformers from the macrocyclic host (MH).
• Direct precipitation of stable, core-shell-based organic micro/nanospheres with high yield.
• Identification of C-H···π interactions as crucial for the self-assembly of enantiomeric forms.

Conclusions:

• The macrocyclic host (MH) can undergo enantiomeric self-assembly to form complex core-shell structures.
• C-H···π interactions play a significant role in directing the solid-state self-assembly of these organic particles.
• This work offers a new pathway for creating functional organic micro/nanomaterials through supramolecular self-assembly.