Multicomponent Diversity-Oriented Access to Boronic-Acid-Derived Pyrrolide Salicyl-Hydrazone Fluorophores with Strong Solid-State Emission

Fluorescent molecular platforms are highly sought after for their applications in biology and optoelectronics but face challenges with solid-state emission quenching. To address this, bulky substituents or aggregation-induced emission luminogens to restrict intramolecular motion are used to enhance the brightness. Here, we have successfully engineered a novel class of boron complexed pyrrolide salicyl-hydrazone fluorophores named BPSHY. These dyes were synthesized through a diversity-oriented condensation of pyrrole and salicylaldehyde derivatives combined with various aromatic boronic acids. The resulting 3D structures, owing to bulky boron axially substituted aryl groups, impart excellent solubility in a variety of solvents. Significantly, the BPSHY dyes exhibit strong absorption in the visible region and remarkably large Stokes shifts. Crucially, they demonstrate intense emission in aqueous solutions due to aggregation-induced emission effects. In solid-states, these dyes achieve high quantum yields, reaching up to 58%. Further expanding their utility, we developed two new BPSHY probes: one incorporating morpholine and another containing triphenylphosphine salt. Both of them are found to specifically label subcellular organelles such as lysosomes and mitochondria within live cells. Notably, these probes demonstrate exceptional staining efficacy and two-photon fluorescence feature. This highlights the considerable promise of BPSHY fluorophores for monitoring and visualizing the dynamic transformations of organelles.