Aromaticity Competition in Differentially Fused Borepin-Containing Polycyclic Aromatics

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Polycyclic aromatic hydrocarbons (PAHs) are extensively studied for their electronic and optical properties.
• Borepin, a heterocyclic aromatic compound, offers unique structural and electronic characteristics.
• Incorporating borepin into PAHs presents opportunities for novel molecular architectures and functionalities.

Purpose of the Study:

• To synthesize and characterize novel borepin-based polycyclic aromatics with varying arene fusions.
• To investigate the aromaticity and electronic properties of these new compounds.
• To compare the properties of newly synthesized borepins with existing literature compounds.

Main Methods:

• Streamlined Ti-mediated alkyne reduction for Z-olefin formation.
• Direct lithiation and borepin ring formation.
• Crystallographic, magnetic, and computational analyses.

Main Results:

• Successful synthesis of borepin-based polycyclic aromatics with two different arene fusions.
• Characterization revealed insights into the aromaticity of novel, differentially fused [b,f]borepins.
• Evaluation of properties for borepin motifs integrated into larger polycyclic systems.

Conclusions:

• The developed synthetic route provides access to diverse borepin-based PAHs.
• The study elucidates the interplay of aromaticity in fused ring systems containing borepins.
• These findings contribute to the understanding of novel aromatic systems and their potential applications.