School of Chemistry and Food Engineering, Key Laboratory of Road Structure and Material of Ministry of Transport, Changsha University of Science and Technology, Changsha, Hunan, 410114, China.
School of Hydraulic Engineering, Changsha University of Science and Technology, Changsha, Hunan, 410114, China.
J Fluoresc. 2021 May;31(3):755-761. doi: 10.1007/s10895-021-02702-7. Epub 2021 Mar 1.
SO and its derivatives are widely present in the environment and living organisms, endangering the environment and human health. Therefore, it is of great significance for the effective detection of sulfur dioxide (SO) and its hydrated derivatives (HSO /SO). In this study, based on the mechanism of intramolecular charge transfer (ICT), a water-soluble colorimetric fluorescent probe (E)-2-(4-acetamidostyryl)-3-(5-carboxypentyl)-1, 1-dimethyl-1H-benzo[e]indol-3-ium (ABI) for the detection of SO derivatives was successfully synthesized from p-acetaminobenzaldehyde by connecting the benzo[e]indoles cationic fluorophore containing highly activated methyl via C = C double bond, and the ABI structure was characterized by HRMS and H NMR, C NMR. Studies have shown that the ABI probe has some advantages such as good selectivity for SO derivatives, high sensitivity (detection limit LOD = 14.9 nM), and fast reaction rate. After adding HSO, the color of the probe solution changed from light yellow to colorless within 10 s, which provides a simple way to identify bisulfite with the naked eye. Studies on the effect of pH on the fluorescence performance of ABI showed that fluorescence performance of ABI was stable in the range of pH (7.0-10.26). Therefore, ABI is expected to become an effective tool for detecting SO derivatives in cells and organisms in the future.
SO 及其衍生物广泛存在于环境和生物体内,对环境和人类健康构成威胁。因此,有效检测二氧化硫(SO)及其水合衍生物(HSO / SO)具有重要意义。在本研究中,基于分子内电荷转移(ICT)机制,通过 C=C 双键将含有高活性甲基的苯并[e]吲哚阳离子荧光团连接到 p-乙酰苯甲醛上,成功合成了一种水溶性比色荧光探针(E)-2-(4-乙酰氨基苯乙烯基)-3-(5-羧戊基)-1,1-二甲基-1H-苯并[e]吲哚-3-鎓(ABI),用于检测 SO 衍生物,并通过高分辨率质谱(HRMS)和 1H NMR、13C NMR 对 ABI 结构进行了表征。研究表明,ABI 探针对 SO 衍生物具有一些优点,如良好的选择性、高灵敏度(检测限 LOD = 14.9 nM)和快速反应速率。加入 HSO 后,探针溶液的颜色在 10 秒内从浅黄色变为无色,这为肉眼识别亚硫酸盐提供了一种简单的方法。研究 pH 对 ABI 荧光性能的影响表明,ABI 的荧光性能在 pH(7.0-10.26)范围内稳定。因此,ABI 有望成为未来在细胞和生物体中检测 SO 衍生物的有效工具。