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A novel ratiometric and reversible fluorescent probe based on naphthalimide for the detection of Al3+ and pH with excellent selectivity

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Abstract

A novel ratiometric and reversible fluorescent probe, (E)-2-butyl-6-hydroxy-5-(((2-(methylthio)phenyl)imino)methyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (denoted as probe L), based on naphthalimide and displaying excellent selectivity and hydrophilicity was designed and synthesized in order to be able to quickly identify Al3+. As the concentration of Al3+ was increased, the probe L emission peak gradually shifted to a lower wavelength (i.e., blue shifted) under single-wavelength excitation. And under UV light, a change in the fluorescence from green to blue was detected by the naked eye. The sensing mechanism was indicated to involve intramolecular charge transfer (ICT). The binding mode of L-Al3+ was investigated by performing Job-plot and density functional theory (DFT) calculations. Probe L also showed a pH-response behavior: when the pH was increased from 8 to 10, the fluorescence intensity of the probe gradually increased, with a particularly good linear relationship. In addition, bioimaging investigations indicated that probe L is membrane permeable and that it can be used to identify Al3+ in zebrafish and HeLa cells.

Graphical abstract: A novel ratiometric and reversible fluorescent probe based on naphthalimide for the detection of Al3+ and pH with excellent selectivity

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Supplementary files

Article information


Submitted
20 Dec 2019
Accepted
18 Jan 2020
First published
21 Jan 2020

New J. Chem., 2020, Advance Article
Article type
Paper

A novel ratiometric and reversible fluorescent probe based on naphthalimide for the detection of Al3+ and pH with excellent selectivity

Z. Li, W. Chen, L. Dong, Y. Song, R. Li, Q. Li, D. Qu, H. Zhang, Q. Yang and Y. Li, New J. Chem., 2020, Advance Article , DOI: 10.1039/C9NJ06309A

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