Tailoring diradicaloid properties of expanded isophlorinoids with systematic core-modification.

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Expanded isophlorins are macrocyclic compounds with unique electronic properties.
• Tuning the diradicaloid character is crucial for developing novel functional materials.

Purpose of the Study:

• To synthesize and characterize 38π core-modified aromatic expanded isophlorins with eight heterocyclic rings.
• To investigate the relationship between structural modifications, aromaticity, and diradicaloid character.
• To explore the conformational diversity of these macrocycles.

Main Methods:

• Systematic structural modification of the isophlorin core.
• Synthesis of novel heterocyclic expanded isophlorins.
• Spectroscopic and computational analyses to determine structural and electronic properties.

Main Results:

• Successfully synthesized 38π core-modified aromatic expanded isophlorins featuring eight heterocyclic rings.
• Demonstrated significant structural diversity, including planar and non-planar conformations, influenced by heteroatom linkage.
• Established a correlation between structural variations, altered aromaticity, and the magnitude of diradical character.

Conclusions:

• Core-modified aromatic expanded isophlorins offer a versatile platform for engineering diradicaloid character.
• Conformational flexibility and tunable electronic properties are key features of these macrocycles.
• The findings provide insights into the design of novel organic materials with tailored electronic and magnetic properties.