The "Nitrogen Effect": Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in...

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry
• Physical Chemistry

Background:

• Observing weak intermolecular forces is challenging in polar protic solvents due to overwhelming solvent interactions.
• Formation of ternary assemblies of pure organic compounds in such solvents is particularly difficult.

Purpose of the Study:

• To overcome the challenges of observing weak intermolecular forces in polar protic solvents.
• To template the formation of a three-component halogen-bonded ternary assembly.
• To investigate the role of fused aromatic N-heterocycles and resorcinarene cavities in assembly formation.

Main Methods:

• Utilized fused aromatic N-heterocycles as binding components.
• Employed an open resorcinarene cavity as a templating agent.
• Conducted experiments in a polar protic solvent system.

Main Results:

• Successfully templated the formation of a three-component ternary assembly.
• Demonstrated the ability to observe weak intermolecular forces despite competitive solvent environment.
• Established a method for creating halogen-bonded ternary assemblies in challenging solvent conditions.

Conclusions:

• The binding of fused aromatic N-heterocycles within a resorcinarene cavity effectively templates ternary assemblies.
• This approach overcomes significant challenges posed by polar protic solvents for observing weak interactions.
• The study provides a novel strategy for constructing complex organic assemblies via halogen bonding.