An “On–Off” AIE-Based Lock-and-Key Fluorescent Probe System for Detection of Fentanyl/Norfentanyl

The misuse of fentanyl poses significant social risks, and accurately and swiftly detecting fentanyl in field settings presents a considerable challenge. Herein, we have designed and synthesized a fluorescent probe TP-CF<sub>3</sub>-COOH, which is composed of carboxyl- and trifluoromethy...

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Bibliographic Details
Main Authors: Jing Sun, Junge Zhi, Li Zhang, Yan Qi, Jiefang Sun, Yushen Jin, Jie Yin, Kai Yao, Bing Shao
Format: Article
Language:English
Published: MDPI AG 2025-04-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/30/9/1985
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Summary:The misuse of fentanyl poses significant social risks, and accurately and swiftly detecting fentanyl in field settings presents a considerable challenge. Herein, we have designed and synthesized a fluorescent probe TP-CF<sub>3</sub>-COOH, which is composed of carboxyl- and trifluoromethyl-binding center tetraphenyl butadiene. The unique centrosymmetric configuration of the TP-CF<sub>3</sub>-COOH probe allows for the construction of a fluorescence “on–off” mechanism recognition platform by spatially matching fentanyl and its metabolite norfentanyl. Importantly, this study reveals that the interaction of fentanyl or norfentanyl with TP-CF<sub>3</sub>-COOH results in spontaneous self-assembly, generating a three-dimensional complex sphere that is smaller than the two-dimensional sheet fluorescence probe. This self-assembly process results in the quenching of fluorescence. Theoretical calculations demonstrate that this process is accompanied by intermolecular through-space charge transfer during self-assembly, leading to a blue shift in emission wavelength. As a result, the TP-CF<sub>3</sub>-COOH fluorescent probe enables the quantitative detection of fentanyl/norfentanyl within a range of 1 × 10<sup>−2</sup>–1 × 10<sup>3 </sup>μg/L, with limits of detection of 2 × 10<sup>−4 </sup>μg/L and 3 × 10<sup>−4 </sup>μg/L, respectively. This cost-effective, rapid, and sensitive fluorescent probe holds great potential for the onsite screening and detection of fentanyl and its analogues.
ISSN:1420-3049