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A dual-channel chemosensor based on rhodamine and BODIPY conjugated dyad for ratiometric detection of Hg2+ and fluorescence on–off recognition of Cu2+ in aqueous solution and living cells

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Abstract

A novel probe RB for discriminative detection of Hg2+ and Cu2+ constructed by rhodamine and BODIPY was designed and synthesized. Probe RB consists of three parts: BODIPY as the energy donor, rhodamine as the energy receptor, and thiosemicarbazide as the reacting site. Probe RB selectively binds with Hg2+ and Cu2+ ions in in EtOH/H2O (V/V = 1:1) among tested metal ions. Probe RB exhibited a fluorescence red shift from 513 to 593 nm for Hg2+ and a fluorescence quenching for Cu2+. The mechanism study showed that the fluorescence changes of probe RB after the addition of Hg2+ was due to oxadiazole formation when the thiosemicarbazide moiety was liberated by Hg2+-facilitated ring opening of the spirocyclic group, while Cu2+ not only opened the spirolactam ring, but also bonded to the opening product through 1:2 mode. It is worth noting that all these types of probes could only detect Hg2+ or Cu2+ through metal ions-facilitated ring opening of the spirocyclic group mechanism. To the best of our knowledge, probe RB was firstly reported to detect Hg2+ and Cu2+ discriminatively. Moreover, probe RB demonstrated excellent sensitivity toward Hg2+ (LOD 8.36 nM) and Cu2+ (LOD 0.16 μM), fast responsive time (within 30 s) and wide pH range (6.0–10.0 for Hg2+, 6.0–11 for Cu2+). This probe was further successfully applied to Hela cells and could easily discriminate Hg2+ and Cu2+ through double-channel imaging.

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Acknowledgements

Thanks for the support of Jianghan University Foundation (2021KJZX001).

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Correspondence to Dan Wen or Yanhua Yu.

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Ma, L., Xu, G., Deng, X. et al. A dual-channel chemosensor based on rhodamine and BODIPY conjugated dyad for ratiometric detection of Hg2+ and fluorescence on–off recognition of Cu2+ in aqueous solution and living cells. Chem. Pap. 77, 583–593 (2023). https://doi.org/10.1007/s11696-022-02504-6

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  • DOI: https://doi.org/10.1007/s11696-022-02504-6

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