Indeno[2,1-c]fluorene Quasi[8]circulenes Through Intramolecular Cyclization

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Polycyclic aromatic hydrocarbons (PAHs) are crucial in chemical sciences.
• Quasi[8]circulenes and indenofluorenes (IFs) possess notable properties but haven't been combined.
• Integrating these structures presents synthetic challenges.

Purpose of the Study:

• To synthesize and characterize novel curved indeno[2,1-c]fluorene quasi[8]circulenes.
• To explore the integration of quasi[8]circulenes and IFs into a single molecular framework.
• To investigate the chiroptical, optoelectronic, and redox properties of these new compounds.

Main Methods:

• Intramolecular cyclization of a helicene diketone precursor.
• Regioselective triflation for orthogonal functionalization.
• Spectroscopic and electrochemical characterization of synthesized compounds.

Main Results:

• Successfully synthesized curved indeno[2,1-c]fluorene quasi[8]circulenes via a high-yielding cyclization.
• Demonstrated orthogonal functionalization capabilities.
• Observed multiple accessible redox states tunable by substituents.
• Reported unprecedented aggregation behavior and inherent chirality.

Conclusions:

• Developed an efficient synthetic route to novel quasi[8]circulene-IF hybrids.
• These compounds exhibit rich, tunable electronic and optical properties.
• The unique structures offer potential for advanced materials and molecular architectures.