Graduate Student Tyler Jones

"Successes Toward the Advancement of Bridged BODIPY Compounds and Discoveries Aiding Super Resolution Microscopy"

Super-resolution microscopy functions based on the ability of a chromophore to be photoactivatable. Thus, the engineering of molecules to possess these photoactivatable groups that can switch between light and dark states is advantageous towards the advancement of super-resolution microscopy. Boron dipyrromethene (BODIPY) is one of the most studied dyes due to its strong UV absorbance and sharp fluorescence peaks with high quantum yields. BODIPY has also been shown to be extremely versatile, with extensive research being undertaken with a large variety of substituent groups. Among these strategies, one approach is the formation of covalently bonded dimers. Previous synthetic methods for BODIPY oligomers require the use of strong oxidizers in the presence of protecting groups. Recent studies show that the synthesis can be carried out via a one-pot CuI-mediated radical homocoupling reaction, producing bridged BODIPY oligomers through a single electron transfer(1). From this, photochemical properties have been explored to compare the monomer to oligomeric BODIPY in both steady-state and both polar and nonpolar solvents using a combination of resonance Raman spectroscopy (RR), time-dependent density functional theory (TD-DFT) and ultrafast laser spectroscopy(2). Along with these interesting breakthroughs, BODIPY oligomers have gained much interest because of their near-infrared (NIR) absorption properties, proving useful in super-resolution imaging techniques such as single-molecule localization microscopy (SMLM)(3). This talk aims to shed light on the use of Bridged BODIPY oligomers and their relevance towards the advancement of these fluorescent dyes.

1. Gong, Q.; Cheng, K.; Wu, Q.; Li, W.; Yu, C.; Jiao, L.; Hao, E., One-Pot Access to Ethylene-Bridged BODIPY Dimers and Trimers through Single-Electron Transfer Chemistry. The Journal of Organic Chemistry 2021, 86 (21), 15761-15767.
2. Sandoval, J. S.; Gong, Q.; Jiao, L.; McCamant, D. W., Stimulated Resonance Raman and Excited-State Dynamics in an Excitonically Coupled Bodipy Dimer: A Test for TD-DFT and the Polarizable Continuum Model. The Journal of Physical Chemistry A 2023, 127 (34), 7156-7167.
3. Gong, Q.; Zhang, X.; Li, W.; Guo, X.; Wu, Q.; Yu, C.; Jiao, L.; Xiao, Y.; Hao, E., Long-Wavelength Photoconvertible Dimeric BODIPYs for Super-Resolution Single-Molecule Localization Imaging in Near-Infrared Emission. Journal of the American Chemical Society 2022, 144 (48), 21992-21999.