ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Jian-Bin Chao, Yue-Xiang Duan, Yong-Bin Zhang, Cai-Xia Yin, Ming-Gen Zhao, Jin-Yu Sun, and Fang-Jun Huo

Scientific Instrument Center, Shanxi University, Taiyuan, People’s Republic of China

E-mail: chao@sxu.edu.cn

Received: 16 July 2020  Accepted: 7 October 2020

Abstract:

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.

Keywords: PH probe; Ratiometric; Extreme acidity; Extreme alkaline; Imaging

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01572-4

Chemical Papers 75 (7) 3317–3326 (2021)