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Two new β-diketone-boron difluoride based near-infrared fluorescent probes 1 and 2 which exhibit polarity sensitivity have been designed and synthesized. Probes 1 and 2 are composed of a β-diketone-boron difluoride moiety as an acceptor unit, and a diethylamino group and a phenolic hydroxyl group as donor units. The long conjugate structures form a "donor–acceptor–donor" configuration, induce intramolecular charge transfer (ICT), and confer near-infrared fluorescence emission and excellent polarity sensitivity. The photophysical properties of these two probes were investigated in detail. Experimental data demonstrated that as the environmental polarity decreased, the fluorescence intensity of the probes increased obviously, accompanied by a blue-shift of the maximum emission wavelength. In addition, these two probes were photostable and solely sensitive to polarity without interference from viscosity, pH and common active species. Theoretical calculations indicated that probes 1 and 2 displayed lower energy gaps and faster non-radiative decay in polar solvents. Furthermore, probes 1 and 2 were utilized to quantitatively detect the polarity of a binary mixture through the satisfactory linear relationship between the fluorescence emission intensity ratios and the orientation polarizability of the mixed solvent. Additionally, probe 1 was successfully utilized to visualize the polarity distribution of live cells. Both of these probes are perfect candidates for studying polarity in vitro and even in live systems. [ABSTRACT FROM AUTHOR]

Mitochondria as essential organelles play critical roles in cellular metabolism. Mitochondrial pH is a vital parameter that directly affects the unique function of mitochondria. Herein, we present a new ratiometric fluorescent probe M-pH for monitoring the pH within the mitochondria. M-pH consists of a stable and large π-electron conjugated merocyanine system. The lipophilic cationic benzyl group will facilitate the accumulation of M-pH in mitochondria. The phenol unit is the recognition moiety, achieving the ratiometric sensing of pH changes. The experimental results indicate that M-pH displays ratiometric fluorescence response to different pH values. Meanwhile, M-pH shows negligible response to common species, and has high stability and low cytotoxicity. In biological experiments, M-pH can solely accumulate in mitochondria and visualize the pH changes during mitophagy and cell apoptosis. We thus believe that M-pH has great potential as a practical tool for real-time monitoring of pH changes of mitochondria, contributing to revealing the pathogenesis of mitochondrial pH associated diseases. [ABSTRACT FROM AUTHOR]