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-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.