Unsymmetrically Extended Polyfused Aromatics Embedding Coronene and Perylene Frameworks: Syntheses and Properties

Area of Science:

• Organic Chemistry
• Materials Science
• Condensed Matter Physics

Background:

• Polyfused aromatic hydrocarbons are crucial building blocks for organic electronic materials due to their extended pi-conjugation.
• Developing new synthetic routes to access complex polycyclic aromatic structures is essential for advancing organic semiconductor performance.
• Coronene and perylene derivatives are of particular interest for their unique electronic and photophysical properties.

Purpose of the Study:

• To synthesize a novel series of polyfused aromatic compounds incorporating coronene and perylene units.
• To investigate the structure-property relationships of these new materials as potential organic semiconductors.
• To evaluate the charge transport characteristics of the synthesized compounds.

Main Methods:

• Utilized a modified Ramirez-Corey-Fuchs reaction as the key synthetic step.
• Employed controlled reaction conditions to achieve both six-membered (annulation) and five-membered ring formations.
• Characterized the synthesized polyfused aromatics and measured their field-effect mobility.

Main Results:

• Successfully constructed a series of polyfused aromatics containing coronene and perylene frameworks.
• Achieved a range of extensively conjugated aromatic systems through controlled annulation strategies.
• One derivative, dibenzo[a,d]coronene, exhibited a significant p-type field-effect mobility of 0.42-0.64 cm²/V·s.

Conclusions:

• The modified Ramirez-Corey-Fuchs reaction is effective for constructing complex polyfused aromatic systems.
• The synthesized dibenzo[a,d]coronene derivative shows excellent potential as a p-type organic semiconductor.
• These findings open new avenues for designing high-performance organic electronic materials.