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The Synergistic Mechanisms of AIE, ESIPT and ICT in the α-cyanostilbene-based Derivative: A Red-fluorescence Probe With a Large Stokes’ Shift for Copper (II) Ion Determination and Reversible Response to Amine/acid Vapor

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Abstract

Herein, α-cyanostilbene-based luminogen with an electron donor-π-electron acceptor (D-π-A) architecture was formylated into the salicylaldehyde-analogue luminogen, followed by the Schiff base reaction with phenylamine, a red-emitting luminogen was elaborately designed and successfully synthesized in a high yield of 89%. Its well-defined structure was confirmed by FT-IR, MALDI-TOF-MS, HR-MS and 1H/13C NMR technologies. Based on the synergistic mechanisms of aggregation-induced emission (AIE), excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT), it enjoyed a red-fluorescence emission at 627 nm in THF/water mixtures (fw = 95%) and was used as a probe. Moreover, the TLC-based test strips loaded with the probe not only exhibited the reversible fluorescence response to amine/acid vapor but also showed sensitive and selective fluorescence response towards Cu2+. Furthermore, the fluorescence titration experiment between the probe and Cu2+ in THF/water mixtures (fw = 95%, pH = 7.4) revealed that the detection limit was 1.18 × 10-7 M and the binding constant was 1.59 × 105. Job’s plot experiment and HR-MS analysis revealed the 2:1 binding stoichiometry of the probe with Cu2+. The method enabled real-time assessment for Cu2+ in real water samples. This study could offer insightful opinions on the development of long-wavelength emissive luminogens based on α-cyanostilbene.

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Acknowledgements

We are grateful for the financial support from the Undergraduate Innovation Program in Neijiang Normal University (No. X2022054 and No. X2022269).

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This work was financially supported by the Undergraduate Innovation Program in Neijiang Normal University (No. X2022054 and No. X2022269).

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

    Meihui Chen, Yongchun Chen, Min Zhong, Donghong Xie, Chuan Wang, Xiaorui Ren, Shizhou Huang, Jia Xu & Mingguang Zhu

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  2. Yongchun Chen
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Contributions

Meihui Chen: Conceptualization, Investigation, Writing - original draft. Yongchun Chen: Investigation. Min Zhong: Investigation. Donghong Xie: Investigation. Chuan Wang: Investigation. Xiaorui Ren: Investigation. Shizhou Huang: Investigation. Jia Xu: Investigation. Mingguang Zhu: Conceptualization, Methodology, Writing - original draft, Writing - review & editing.

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Chen, M., Chen, Y., Zhong, M. et al. The Synergistic Mechanisms of AIE, ESIPT and ICT in the α-cyanostilbene-based Derivative: A Red-fluorescence Probe With a Large Stokes’ Shift for Copper (II) Ion Determination and Reversible Response to Amine/acid Vapor. J Fluoresc 34, 1075–1090 (2024). https://doi.org/10.1007/s10895-023-03341-w

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