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α-Cyanostilbene-based Molecule with the Synergistical Mechanisms of AIE, ESIPT and TICT: A New Schiff Base Probe for Selective Detection of Fe3+ and Reversible Response to HCl/NH3 Vapor

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Abstract

We designed and synthesized a new Schiff base probe, which incorporated the salicylaldehyde-analogue α-cyanostilbene and benzophenone hydrazone by the imine linkage. Its chemical structure was verified by FT-IR, MALDI-TOF-MS, HR-MS and 1H/13C NMR technologies. It could exhibit a red fluorescence based on the synergistical effects of aggregation-induce emission (AIE), excited-state intramolecular proton transfer (ESIPT) and twisted intramolecular charge-transfer (TICT) in the aggregation or solid states. Interestingly, the TLC-based test strip loaded with the target compound showed the reversible fluorescence response to amine/acid vapor and on-site visual fluorescence quenching response to Fe3+. In THF/water mixtures (fw = 90%, 10 µM, pH = 7.4), the detection limit (DL) and the binding constant (Ka) of the developed probe towards Fe3+ were evaluated as 5.50 × 10− 8 M and 1.69 × 105, respectively. The developed probe was successfully applied for the detection of Fe3+ with practical, reliable, and satisfying results.

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Acknowledgements

We are grateful for the financial support from the Scientific Research Program in Neijiang Normal University (No. X20B0047), the Undergraduate Innovation Program in Neijiang Normal University (No. X2022054).

Funding

The study was supported by the Scientific Research Program in Neijiang Normal University (No. X20B0047), the Undergraduate Innovation Program in Neijiang Normal University (No. X2022054).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang, 641100, P. R. China

    Meihui Chen, Wenrong Chen, Qing Zhu, Liping Yang, Xiazhong Zhang, Donghong Xie, Jianqiang Chen, Yuanbin Wu, Yuping Zhu & Mingguang Zhu

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  1. Meihui Chen
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  2. Wenrong Chen
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  3. Qing Zhu
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Contributions

Meihui Chen: Conceptualization, Investigation, Writing-original draft. Wenrong Chen: Investigation. Qing Zhu: Investigation. Liping Yang: Investigation. Xiazhong Zhang: Investigation. Donghong Xie: Investigation. Jianqiang Chen: Investigation. Yuanbin Wu: Investigation. Yuping Zhu: Investigation. Mingguang Zhu: Conceptualization, Methodology, Writing-original draft, Writing-review & editing.

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Correspondence to Jianqiang Chen or Mingguang Zhu.

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Chen, M., Chen, W., Zhu, Q. et al. α-Cyanostilbene-based Molecule with the Synergistical Mechanisms of AIE, ESIPT and TICT: A New Schiff Base Probe for Selective Detection of Fe3+ and Reversible Response to HCl/NH3 Vapor. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03609-9

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