Ligand protonation leads to highly fluorescent boronium cations.

ABSTRACT: Fluorophores that respond to external stimuli, such as changes in pH, have utility in bio-imaging and sensing applications. Almost all pH-responsive fluorophores rely on complex syntheses and the use of pH-responsive functional groups that are peripheral to the fluorophore framework. In this work, pH-responsive boron-containing heterocycles based on tridentate acyl pyridylhydrazone ligands were prepared. These non-emissive heterocycles were synthesized in three steps from inexpensive, commercially available reagents without the use of chromatography or air-sensitive reagents. Treatment with acid resulted in protonation of the boron-bound methylamine donor and efficient blue photoluminescence. Experimental and computational analysis revealed that protonation changed the geometric structure

SUBMITTER: Watson AER 

PROVIDER: S-EPMC11701515 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature