TY - JOUR
T1 - An “On–Off” AIE-Based Lock-and-Key Fluorescent Probe System for Detection of Fentanyl/Norfentanyl
AU - Sun, Jing
AU - Zhi, Junge
AU - Zhang, Li
AU - Qi, Yan
AU - Sun, Jiefang
AU - Jin, Yushen
AU - Yin, Jie
AU - Yao, Kai
AU - Shao, Bing
N1 - Publisher Copyright:
© 2025 by the authors.
PY - 2025/5
Y1 - 2025/5
N2 - 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.
AB - 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.
KW - aggregation-induced luminescence probe
KW - fentanyl
KW - self-assembly drive
KW - spatial specific recognition
KW - through-space charge transfer (TSCT)
UR - http://www.scopus.com/inward/record.url?scp=105004829823&partnerID=8YFLogxK
U2 - 10.3390/molecules30091985
DO - 10.3390/molecules30091985
M3 - Article
AN - SCOPUS:105004829823
SN - 1420-3049
VL - 30
JO - Molecules
JF - Molecules
IS - 9
M1 - 1985
ER -