Lewis-Acid-Catalyzed BODIPY Boron Functionalization Using Trimethylsilyl Nucleophiles

Area of Science:

• Organic Chemistry
• Materials Science
• Photophysics

Background:

• Boron dipyrromethenes (BODIPYs) are a class of fluorescent dyes with diverse applications.
• Functionalization of BODIPYs is crucial for tuning their properties.
• Previous synthetic strategies have limitations in accessing specific substitution patterns.

Purpose of the Study:

• To develop a novel and straightforward synthetic strategy for boron dipyrromethene (BODIPY) functionalization.
• To synthesize previously unknown BODIPY derivatives with specific N-substitutions.
• To explore the photophysical properties of these newly synthesized BODIPYs.

Main Methods:

• A novel synthetic strategy was employed for boron functionalization.
• The method allowed for the introduction of sp2 N-substituted groups (B-NCS and -NCO).
• Benzotriazole and trifluoroacetamide substituents were successfully incorporated.

Main Results:

• A straightforward strategy for boron functionalization of BODIPYs was successfully developed.
• Synthesis of novel sp2 N-substituted, benzotriazole-substituted, and trifluoroacetamide-substituted BODIPYs was achieved.
• The synthesized BODIPYs exhibited a wide range of desirable photophysical properties, with fluorescence quantum yields (Φf) ranging from 0.04 to 0.86.

Conclusions:

• The developed synthetic strategy offers new possibilities for BODIPY synthesis.
• The novel BODIPY derivatives possess tunable and desirable photophysical characteristics.
• These findings pave the way for the application of these BODIPYs in materials science.