A water-soluble naphthalenediimide-containing hexacationic cage

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis
• Materials Science

Background:

• Naphthalenediimide (NDI) derivatives are known for their electronic properties.
• Designing water-soluble host molecules is crucial for biological and environmental applications.
• Efficient synthesis of complex molecular architectures remains a challenge.

Purpose of the Study:

• To synthesize a novel water-soluble cage incorporating multiple NDI units.
• To investigate the host-guest chemistry of the synthesized cage in aqueous and solid states.
• To explore the potential of the cage for accommodating different types of guests, including linear species.

Main Methods:

• One-pot synthesis of the NDI-based cage.
• Simultaneous formation of six irreversible C-N bonds via SN2 reaction.
• Spectroscopic and crystallographic characterization of the cage and its complexes.
• Host-guest interaction studies in aqueous solution and solid state.

Main Results:

• A water-soluble cage with three NDI units was successfully synthesized in a single step without purification.
• The cage demonstrated the ability to bind various π-electron rich guests peripherally in water.
• The cage formed inclusion complexes with linear guests like triiodide (I3-) and iodine (I2) in solution.
• The cage exhibited iodine vapor absorption capabilities in the solid state.

Conclusions:

• The developed one-pot synthetic strategy provides an efficient route to complex NDI-based cages.
• The water-soluble NDI cage exhibits versatile host-guest properties, accommodating diverse guests.
• The cage shows potential for applications in sensing, separation, or delivery of specific molecules, particularly iodine species.