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A near-infrared fluorescent sensor with large Stokes shift for rapid and highly selective detection of thiophenols in water samples and living cells

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Abstract

The development of simple methods with high sensitivity and selectivity to differentiate toxic aromatic thiols (thiophenols) from aliphatic thiols (cysteine, homocysteine, and glutathione) and hydrogen sulfide (H2S) is of great significance. Herein, we report on the fabrication of a novel near-infrared (NIR) fluorescent sensor for rapid and highly selective detection of thiophenols through the photoinduced electron transfer (PET) mechanism. In the presence of the thiophenols, an obvious enhancement of NIR fluorescence at 658 nm could be visualized with the aid of nucleophilic aromatic substitution (SNAr) reaction. The sensor displays large Stokes shift (~ 227 nm), fast response time (< 30 s), high sensitivity (~ 8.3 nM), and good biocompatibility. Moreover, the as-prepared sensor possesses an excellent anti-interference feature even when other possible interferents exist (aliphatic thiols and H2S) and has been successfully utilized for thiophenol detection in both water samples and living cells.

Illustration of the sensor for thiophenol imaging in living cells

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Acknowledgements

We gratefully acknowledge financial support of the present work by NSFC (Project no. 21172065) and Hunan Provincial Natural Science Foundation of China (No. 2016JJ5005).

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Authors and Affiliations

  1. Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, China

    Rongjin Zeng, Qian Gao, Fenmin Cheng, Yunshan Yang, Peisheng Zhang, Shu Chen, Jian Chen & Yunfei Long

  2. Department of Stomatology, Xiangtan Central Hospital, Xiangtan, Hunan, 411201, China

    Heping Yang

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  1. Rongjin Zeng
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  2. Qian Gao
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Correspondence to Rongjin Zeng.

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Zeng, R., Gao, Q., Cheng, F. et al. A near-infrared fluorescent sensor with large Stokes shift for rapid and highly selective detection of thiophenols in water samples and living cells. Anal Bioanal Chem 410, 2001–2009 (2018). https://doi.org/10.1007/s00216-018-0867-3

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  • DOI: https://doi.org/10.1007/s00216-018-0867-3

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