Arylene ethynylene macrocycles with intramolecular π-π stacking

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Macrocyclic compounds offer unique structural and electronic properties.
• Aromatic interactions play a crucial role in molecular self-assembly.
• Discotic molecules are known to exhibit liquid crystalline behavior.

Purpose of the Study:

• To synthesize novel arylene ethynylene macrocycles incorporating anthrylene and naphthylene units.
• To investigate the intramolecular interactions within these macrocycles.
• To explore the potential liquid crystalline properties of the synthesized compounds.

Main Methods:

• Synthesis of arylene ethynylene macrocycles.
• Nuclear Magnetic Resonance (NMR) spectroscopy to analyze molecular structure and interactions.
• Density Functional Theory (DFT) calculations to model and support structural findings.

Main Results:

• Successful synthesis of anthrylene and naphthylene-containing macrocycles.
• Observation of significant upfield shifts in NMR spectra, indicating intramolecular π-π stacking.
• DFT calculations confirmed the proposed intramolecular stacking motif.
• The anthrylene-containing macrocycle exhibited a liquid-crystal phase.

Conclusions:

• Arylene ethynylene macrocycles can adopt conformations with intramolecular π-π stacking.
• The discotic shape of the anthrylene macrocycle is responsible for its liquid crystalline behavior.
• These findings contribute to the design of novel functional organic materials.