Enhanced Hypsochromic Shifts, Quantum Yield, and π-π Interactions in a meso,β-Heteroaryl-Fused BODIPY

Ning Zhao, Louisiana State University
Sunting Xuan, Louisiana State University
Frank R. Fronczek, Louisiana State University
Kevin M. Smith, Louisiana State University
M. Graça H. Vicente, Louisiana State University

Abstract

© 2017 American Chemical Society. We report the synthesis and investigation of an unprecedented 8-heteroaryl-fused BODIPY 4. This compound exhibits enhanced π-π stacking in the solid state, unusually large blue-shifts in the absorbance and emission spectra, and higher fluorescence quantum yield than its unfused precursor; DFT calculations suggest a small energy gap for 4 and strong electronic communication between the 8-OPh and the BODIPY core.