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Issue 13, 2019
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Twisted intramolecular charge transfer and aggregation-enhanced emission characteristics based quinoxaline luminogen: photophysical properties and a turn-on fluorescent probe for glutathione

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Abstract

Developing solid and aggregate state emitters with large Stokes shifts has long been a significant challenge in the detection and bioimaging fields. In this study, a novel quinoxaline-based luminogen (QUPY) with twisted intramolecular charge transfer (TICT) and aggregation-enhanced emission (AEE) characteristics has been designed and synthesized. Its pyridine salt derivative (QUPY-S) was also AEE-active and could be utilized as a fluorescent “turn-on” probe for the specific detection of glutathione (GSH). The cleavage of dinitrophenyl ether from QUPY-S by GSH generated AEE-active and less water-soluble QUPY, which exhibited a “turn-on” fluorescence response at around 516 nm. This reaction-based probe showed a large Stokes shift (131 nm), low detection limit (434 nM), fast response time, and low toxicity. QUPY-S was successfully applied for the detection of GSH in bovine serum samples with recoveries ranging from 91.9% to 100.7%. Additionally, QUPY-S could detect GSH in HeLa cells by confocal laser scanning microscopy.

Graphical abstract: Twisted intramolecular charge transfer and aggregation-enhanced emission characteristics based quinoxaline luminogen: photophysical properties and a turn-on fluorescent probe for glutathione

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Publication details

The article was received on 24 Oct 2018, accepted on 25 Jan 2019 and first published on 28 Jan 2019


Article type: Paper
DOI: 10.1039/C8TC05360J
Citation: J. Mater. Chem. C, 2019,7, 3779-3786

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    Twisted intramolecular charge transfer and aggregation-enhanced emission characteristics based quinoxaline luminogen: photophysical properties and a turn-on fluorescent probe for glutathione

    M. Cui, W. Li, L. Wang, L. Gong, H. Tang and D. Cao, J. Mater. Chem. C, 2019, 7, 3779
    DOI: 10.1039/C8TC05360J

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