Lewis-Acid-Catalyzed BODIPY Boron Functionalization Using Trimethylsilyl Nucleophiles

Guanyu Zhang, Louisiana State University
Maodie Wang, Louisiana State University
Frank R. Fronczek, Louisiana State University
Kevin M. Smith, Louisiana State University
M. Graça H. Vicente, Louisiana State University

Abstract

Copyright © 2018 American Chemical Society. A novel and straightforward strategy for boron functionalization in boron dipyrromethenes (BODIPYs) is developed. In particular, this synthetic strategy provides new possibilities for the synthesis of sp 2 N-substituted (B-NCS and -NCO), benzotriazole- and trifluoroacetamide-substituted BODIPYs that were hitherto unknown. These new BODIPYs display an array of highly desirable photophysical properties (0.04 < φ f < 0.86), paving the road for further investigations in material applications.