A dicyanoisophorone-based highly sensitive and selective near-infrared fluorescent probe for sensing thiophenol in water samples and living cells. (October 2020)

• Record Type: Journal Article
• Authors: Zhang, Yintang; Hao, Yuanqiang; Ma, Xiaohua; Chen, Shu; Xu, Maotian
• Is Part Of: Environmental pollution. Volume 265(2020)Part B
• Publication Date: 2020-10
• Subjects: Fluorescent probe -- Thiophenol -- Near-infrared -- Dicyanoisophorone -- Large Stokes shift; Pollution -- Periodicals; Pollution -- Environmental aspects -- Periodicals; Environmental Pollution -- Periodicals; Pollution -- Périodiques; Pollution -- Aspect de l'environnement -- Périodiques; Pollution -- Effets physiologiques -- Périodiques; Pollution; Pollution -- Environmental aspects; Periodicals; Electronic journals; 363.73
• DOI: 10.1016/j.envpol.2020.114958
• Languages: English
• ISSNs: 0269-7491

Abstract

Abstract: Thiophenol (PhSH) is an important sulfhydryl compound in organic synthesis, but it is also a volatile environmental pollutant with high toxicity to organisms. Herein, we reported a novel near-infrared (NIR) probe (1 ) for turn-on fluorescence detection of PhSH. The probe was prepared by coupling 2, 4-dinitrophenyl (DNP) to a dicyanoisophorone-based fluorophore (2 ). PhSH can specifically perform a nucleophilic aromatic substitution on probe 1 and result in the release of fluorophore 2, thus achieving a turn-on fluorescence response (λem = 693 nm). A dramatic color change from red (λabs = 525 nm) to blue (λabs = 668 nm) was also observed. This fluorescent assay displayed a large Stokes shift (∼133 nm) and a high sensitivity for PhSH, as well as a low detection limit (34 nM). Moreover, probe 1 was successfully applied to monitor PhSH in real water samples and image PhSH in living cells. Graphical abstract: Image 1 Highlights: A novel trun-on near-infrared fluorescent probe (1 ) was developed for thiophenol. Probe 1 exhibited excellent sensitivity and selectivity for thiophenol. Probe 1 displayed a large Stokes shift (133 nm) for NIR sensing thiophenol. Probe 1 was applied for monitoring thiophenol in water samples and in live cells.