An ESIPT-based fluorescent probe for the detection of phosgene in the solution and gas phases

Cuiyan Wu; Hai Xu; Yaqian Li; Ruihua Xie; Peijuan Li; Xiao Pang; Zile Zhou; Biao Gu; Haitao Li; Youyu Zhang

doi:10.1016/j.talanta.2019.03.003

An ESIPT-based fluorescent probe for the detection of phosgene in the solution and gas phases

Talanta. 2019 Aug 1:200:78-83. doi: 10.1016/j.talanta.2019.03.003. Epub 2019 Mar 2.

Authors

Cuiyan Wu¹, Hai Xu¹, Yaqian Li¹, Ruihua Xie¹, Peijuan Li², Xiao Pang¹, Zile Zhou¹, Biao Gu³, Haitao Li⁴, Youyu Zhang¹

Affiliations

¹ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China.
² Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China; Key Laboratory of Functional Organometallic Materials of College of Hunan Province, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, PR China.
³ Key Laboratory of Functional Organometallic Materials of College of Hunan Province, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, PR China.
⁴ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China. Electronic address: haitao-li@hunnu.edu.cn.

PMID: 31036228
DOI: 10.1016/j.talanta.2019.03.003

Abstract

Phosgene is a highly toxic gas that poses a serious threat to public health and safety. Herein, we describe the preparation of a ratiometric fluorescence probe (Pi) bearing hydroxyl and imidazole moieties as recognition sites, and employ it for the excited-state intramolecular proton transfer-based (ESIPT-based) detection of phosgene. It is the first time that hydroxyl and imidazole have been exploited as recognition sites for phosgene. In the presence of phosgene, Pi undergoes sequential nucleophilic substitution and cyclization reactions that facilitate a rapid response, high selectivity, and excellent sensitivity (detection limit = 0.14 μM). The sensing mechanism was verified by ¹H NMR spectroscopy and high-resolution mass spectrometry. Furthermore, we fabricated a fluorescent test strip (FTS-Pi) for the detection of phosgene in the gas phase that undergoes a fluorescence color change, from green to blue, under 365 nm UV light in the presence of phosgene, which is easily observed with the naked eye.

Keywords: Detection; Fluorescent probe; Fluorescent test strip; Phosgene; Ratiometric.