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<p>In this paper, a D-π-A fluorescent probe, (<i>E</i>)-2-(5,5-dimethyl-3-(2-(2,3,6,7-tetrahydro-1<i>H</i>,5<i>H</i>-pyrido[3,2,1-<i>ij</i>]quinolin-9-yl)vinyl)cyclohex-2-en-1-ylidene)malononitrile (<b>DFP</b>) was synthesized via the condensation of dicyanoisophorone and 9-formyljulolidine. The structure was characterized by NMR and ESI-HR-MS, and the structure optimization and energy level analysis were carried out by density functional theory (DFT) calculation. Additionally, its metal ion recognition performance was assessed by UV–vis absorption spectroscopy and fluorescence spectroscopy. The results showed that the probe could specifically recognize Fe<sup>3+</sup> in CH<sub>3</sub>OH/H<sub>2</sub>O (1:1, <i>v/v</i>, pH = 7.2) buffer system. Upon the addition of Fe<sup>3+</sup>, the probe solution changed from blue-purple to colorless, accompanied by a significant fluorescence quenching of over 90%, exhibiting high selectivity without obvious interference from other metal ions. Job’s plot and ESI–MS titration experiments revealed a 1:1 stoichiometry for the complex between the probe and Fe<sup>3+</sup>, with a binding constant of 1.4 × 10<sup>4</sup>&#xa0;M<sup>−1</sup>. Furthermore, the probe exhibited a low detection limit of 0.33&#xa0;µM for Fe<sup>3+</sup>, and the optimal pH range for the response was 5–9. In terms of practicality, the probe has been successfully used for visual detection of test paper and imaging of Fe<sup>3+</sup> in living cells.</p>

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Synthesis of Fluorescent Probe with D-π-A Structure and its Application in Dual-channel Recognition of Fe3+

  • 期刊论文

  • 发表日期：

    2026年7月22日

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  • Junli Shi,
  • Chenwei Fu,
  • Shengling Li,
  • Guo Cheng,
  • Shijia Lei,
  • Qian Wang,
  • Yihuan Cao,
  • Ziyu Zhang,
  • Duanlin Cao

摘要

In this paper, a D-π-A fluorescent probe, (E)-2-(5,5-dimethyl-3-(2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)cyclohex-2-en-1-ylidene)malononitrile (DFP) was synthesized via the condensation of dicyanoisophorone and 9-formyljulolidine. The structure was characterized by NMR and ESI-HR-MS, and the structure optimization and energy level analysis were carried out by density functional theory (DFT) calculation. Additionally, its metal ion recognition performance was assessed by UV–vis absorption spectroscopy and fluorescence spectroscopy. The results showed that the probe could specifically recognize Fe3+ in CH3OH/H2O (1:1, v/v, pH = 7.2) buffer system. Upon the addition of Fe3+, the probe solution changed from blue-purple to colorless, accompanied by a significant fluorescence quenching of over 90%, exhibiting high selectivity without obvious interference from other metal ions. Job’s plot and ESI–MS titration experiments revealed a 1:1 stoichiometry for the complex between the probe and Fe3+, with a binding constant of 1.4 × 104 M−1. Furthermore, the probe exhibited a low detection limit of 0.33 µM for Fe3+, and the optimal pH range for the response was 5–9. In terms of practicality, the probe has been successfully used for visual detection of test paper and imaging of Fe3+ in living cells.