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A ratiometric fluorescent probe for rapid detection of extremely acidic and alkaline pH in aqueous solution

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Intracellular pH has a significant influence on cell metabolism and various physiological activities. Therefore, there is an urgent need for a chemical sensor with excellent performance for intracellular pH-sensitive detection, which is extremely helpful for further understanding of related physiological and pathological processes. In this work, a ratiometric fluorescent probe, (1-(pyren-1-yl)-3-(pyridine-3-yl)-acrylketone (PPAK), was synthesized by the condensation reaction of 1-acetylpyrene and 3-pyridinecarboxaldehyde. PPAK has been used to detect extremely acidic and extremely alkaline pH in aqueous solutions. The recognition mechanism of PPAK depended on the protonation of the pyridine groups under acidic conditions and the attack of hydroxyl toward the carbonyl group to break down the conjugated structure under alkaline conditions, respectively. PPAK also exhibited favorable properties including outstanding photostability, excellent selectivity, rapid response and large stokes shift (166 nm). Finally, the results of E. coli cells imaging demonstrated its applicability in monitoring the pH changes in living cells.

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The work was supported by the National Natural Science Foundation of China (No. 21472118, 21672131), Natural Science Foundation of Shanxi Province of China (No. 201701D121018), Talents Support Program of Shanxi Province (No. 2014401), Shanxi Province Outstanding Youth Fund (No. 2014021002), the Program for the Top Young and Middle-aged Innovative Talents of Higher Learning Institutions of Shanxi (No. 2013802).

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Correspondence to Jian-Bin Chao or Fang-Jun Huo.

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Chao, JB., Duan, YX., Zhang, YB. et al. A ratiometric fluorescent probe for rapid detection of extremely acidic and alkaline pH in aqueous solution. Chem. Pap. 75, 3317–3326 (2021).

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