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

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.

本研究报道了一种前所未有的8-杂芳基稠合氟化硼二吡咯（BODIPY）4的合成与性能研究。该化合物在固态下表现出增强的π-π堆积作用，其吸收光谱与发射光谱呈现出异常显著的蓝移现象，且相较于未稠合的前驱体，其荧光量子产率更高；密度泛函理论（DFT）计算结果表明，化合物4具有较小的能级间隙，且8-OPh与BODIPY母核之间存在强电子耦合作用。