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Volume 30
Issue 9
10.3390/molecules30091985
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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

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

by
Jing Sun
1,2,
Junge Zhi
3,
Li Zhang
4,
Yan Qi
2,
Jiefang Sun
2,
Yushen Jin
2,
Jie Yin
2,
Kai Yao
1,2,* and
Bing Shao
1,2,*
1
National Key Laboratory of Veterinary Public Health Security, College of Veterinary Medicine, China Agricultural University, Beijing 100193, China
2
Beijing Key Laboratory of Diagnostic and Traceability Technologies for Food Poisoning, Beijing Center for Disease Prevention and Control, Beijing 100013, China
3
School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488, China
4
College of Science, China Agricultural University, Beijing 100193, China
*
Authors to whom correspondence should be addressed.
Molecules 2025, 30(9), 1985; https://doi.org/10.3390/molecules30091985 (registering DOI)
Submission received: 20 March 2025 / Revised: 23 April 2025 / Accepted: 28 April 2025 / Published: 29 April 2025
Versions Notes

Abstract

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-CF3-COOH, which is composed of carboxyl- and trifluoromethyl-binding center tetraphenyl butadiene. The unique centrosymmetric configuration of the TP-CF3-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-CF3-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-CF3-COOH fluorescent probe enables the quantitative detection of fentanyl/norfentanyl within a range of 1 × 10−2–1 × 103 μg/L, with limits of detection of 2 × 10−4 μg/L and 3 × 10−4 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.
Keywords: fentanyl; aggregation-induced luminescence probe; self-assembly drive; spatial specific recognition; through-space charge transfer (TSCT) fentanyl; aggregation-induced luminescence probe; self-assembly drive; spatial specific recognition; through-space charge transfer (TSCT)

Share and Cite

MDPI and ACS Style

Sun, J.; Zhi, J.; Zhang, L.; Qi, Y.; Sun, J.; Jin, Y.; Yin, J.; Yao, K.; Shao, B. An “On–Off” AIE-Based Lock-and-Key Fluorescent Probe System for Detection of Fentanyl/Norfentanyl. Molecules 2025, 30, 1985. https://doi.org/10.3390/molecules30091985

AMA Style

Sun J, Zhi J, Zhang L, Qi Y, Sun J, Jin Y, Yin J, Yao K, Shao B. An “On–Off” AIE-Based Lock-and-Key Fluorescent Probe System for Detection of Fentanyl/Norfentanyl. Molecules. 2025; 30(9):1985. https://doi.org/10.3390/molecules30091985

Chicago/Turabian Style

Sun, Jing, Junge Zhi, Li Zhang, Yan Qi, Jiefang Sun, Yushen Jin, Jie Yin, Kai Yao, and Bing Shao. 2025. "An “On–Off” AIE-Based Lock-and-Key Fluorescent Probe System for Detection of Fentanyl/Norfentanyl" Molecules 30, no. 9: 1985. https://doi.org/10.3390/molecules30091985

APA Style

Sun, J., Zhi, J., Zhang, L., Qi, Y., Sun, J., Jin, Y., Yin, J., Yao, K., & Shao, B. (2025). An “On–Off” AIE-Based Lock-and-Key Fluorescent Probe System for Detection of Fentanyl/Norfentanyl. Molecules, 30(9), 1985. https://doi.org/10.3390/molecules30091985

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