Highly selective near-infrared fluorescent probe with large Stokes shift and sensitivity for H2S detection in water, foodstuff and imaging in living cells. (December 2022)

• Record Type: Journal Article
• Authors: Xie, Ling; Fan, Tingting; Yao, Ruihong; Mu, Yanqun; Wang, Renjie; Fan, Congbin; Pu, Shouzhi
• Is Part Of: Dyes and pigments. Volume 208(2023)
• Publication Date: 2022-12
• Subjects: Benzothiadiazole -- Near-infrared (NIR) fluorescence -- Hydrogen sulfide -- Living cells imaging; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2022.110828
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Hydrogen sulfide (H2 S) is an endogenous gas signaling molecule that plays an indispensable role in human physiological processes and is of great significance for sensitivity detection in environmental and foodstuff applications. Herein, a novel near-infrared (NIR) fluorescent probe based on 4-(5-(7-(thiophen-2-yl)benzo[c] [1, 2, 5]thiadiazol-4-yl)thiophen-2-yl)phenol) (D-A-D structure) and 2, 4-dinitrobenzenesulfonyl chloride were successfully synthesized. The fluorescent probe 4-(5-(7-(thiophen-2-yl)benzo[c] [1, 2, 5]thiadiazol-4-yl)thiophen-2-yl)phenyl 2, 4-dinitrobenzenesulfonate (TTPD ) could selectively response to H2 S by releasing a D-A-D group as fluorescence enhancing system, which performed NIR "turn-on" fluorescence (652 nm) in acetonitrile solution, triggering by the cleavage of sulfonamide group. The fluorescent probe detected H2 S with the excellent characteristics of fluorescence intensity emission change, high selectivity, outstanding anti-interference performance, large Stokes shift (192 nm), and low limit of detection (LOD) (LOD = 62.1 nM). What's more, this probe not only served as a tool for monitoring H2 S in food quality and diverse water samples with good recovery rates, but also it showed low toxicity and an outstanding capability in cell imaging. Graphical abstract: Image 1 This paper describes a "turn-on" fluorescence probe TTPD for the sensitive and selective detection of hydrogen sulfide (H2 S). The mechanism of H2 S detection is based on the nucleophilic feature of H2 S leading to cleavage of 2, 4-dinitrobenzenesulfonyl groups, which perform large stokes shift (192 nm), near-infrared (NIR) emission wavelength (λem = 652 nm) and low detection limit (62.1 nM). Moreover, the reaction between TTPD and H2 S can be detected in a fluorescence color assay, and the fluorescent color of the reaction mixture changes from weak orange to bright orange obviously. In addition, this study demonstrates the potential of novel developed fluorescent probes TTPD could H2 S imaging in Hela cells and detect H2 S in environmental water samples and foodstuff. Highlights: The novel fluorescence probe TTPD containing D-A-D conjugation system for determination of H2 S was raised. TTPD showed large Stokes shift, NIR fluorescence, high sensitivity, and wonderful anti-interference after adding H2 S. TTPD was successfully applied for imaging exogenous and endogenous H2 S in Hela cells and tracking foodstuff freshness.