Yang Yu-Dong, Zhang Qian, Jin Xingchen, Chau Calvin V, Yang Jian, Henkelman Graeme, Chi Xiaodong, Gong Han-Yuan, Hooley Richard J, Sessler Jonathan L
Department of Chemistry, The University of Texas at Austin, 1105 East 24th Street, Stop A5300, Austin, TX, 78712-1224, USA.
State Key Laboratory of Materials Processing and Die & Mold Technology, School of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan, 430074, China.
Angew Chem Int Ed Engl. 2025 May;64(19):e202501245. doi: 10.1002/anie.202501245. Epub 2025 Mar 23.
Mounting concerns regarding per-/poly-fluoroalkyl substances (PFAS) on human health are focusing attention on trace-level PFAS detection in aqueous environments. Here, we report a readily prepared small molecule, 2,6-bis(3,5-diethyl-1H-pyrrol-2-yl)pyridine (receptor 1), that displays high binding affinities (logK = 4.9-6.2) and produces a strong "turn-on" emission response when exposed to representative PFAS in hexanes. The hydrophobic nature of 1, and its strong affinity for various PFAS, allowed hexanes solutions of 1 to be used as "turn-on" emission sensors for dilute aqueous solutions of long-chain (≥C) PFAS under acidic conditions (pH 2) by liquid-phase extraction (LPE). In the case of perfluorooctanoic acid (PFOA), the response was rapid (under 10 min) and sensitive. Limits of detection (LOD) as low as 250 ppt were readily achievable by direct naked-eye observation. LOD as low as 40 and 100 ppt, respectively, could be reached for deionized and tap water solutions of PFOA using a smartphone color-scanning application. Little change in the sensitivity was seen in the presence of a range of inorganic and organic species that could act as potential interferants. Support for the present findings came from UV-vis absorbance, fluorescence, H/F NMR spectroscopic analyses, density functional theory calculations, and single-crystal X-ray diffraction analyses.
人们对全氟/多氟烷基物质（PFAS）对人类健康的担忧日益增加，这使得人们将注意力集中在水环境中痕量PFAS的检测上。在此，我们报道了一种易于制备的小分子，2,6-双（3,5-二乙基-1H-吡咯-2-基）吡啶（受体1），它表现出高结合亲和力（logK = 4.9 - 6.2），并且在己烷中暴露于代表性PFAS时会产生强烈的“开启”发射响应。1的疏水性及其对各种PFAS的强亲和力，使得1的己烷溶液能够通过液相萃取（LPE）在酸性条件（pH 2）下用作长链（≥C）PFAS稀水溶液的“开启”发射传感器。对于全氟辛酸（PFOA），响应迅速（在10分钟内）且灵敏。通过直接肉眼观察很容易实现低至250 ppt的检测限。使用智能手机颜色扫描应用程序，PFOA的去离子水溶液和自来水溶液的检测限分别低至40和100 ppt。在存在一系列可能作为潜在干扰物的无机和有机物种的情况下，灵敏度几乎没有变化。紫外可见吸收、荧光、H/F NMR光谱分析、密度泛函理论计算和单晶X射线衍射分析为当前的研究结果提供了支持。
