Design, synthesis and photophysical studies of BODIPY-o, m, p-phenylenediamine-based probes: Insights into their responsiveness under different pH conditions

Abstract

In this paper, a series of novel phenylenediamine-fluoroboron pyrrole fluorescent derivatives were prepared which have distinct responsiveness under different hydrogen ion concentration (pH) conditions. It is noticed that the products showed excellent fluorescence properties in different solvents, especially in tetrahydrofuran and dichloromethane, with the most prominent fluorescence intensity, while the fluorescence in methanol, acetonitrile, and dimethyl sulfoxide was weaker. Responsiveness under different hydrogen ion concentration conditions in aqueous solutions were also observed, where the fluorescence intensity is quenching when the pH is 4.0. With regard to cells imaging investigation, the products showed the prominent fluorescence in HeLa cells. Further acidic cell imaging results showed that under acidic conditions made of formic acid or acetic acid, the intracellular fluorescence of the compounds was clustered around the cells and intensive enough different from without acidity control group. Especially, the compounds have unique fluorescence in acidic environment and has great potential and research value as acidic probes.