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一种新型β-二酮二氟硼衍生荧光探针的开发与应用,用于灵敏检测 HS。

Development and application of a novel β-diketone difluoroboron-derivatized fluorescent probe for sensitively detecting HS.

机构信息

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Nov 15;281:121609. doi: 10.1016/j.saa.2022.121609. Epub 2022 Jul 9.

DOI:10.1016/j.saa.2022.121609
PMID:35839692
Abstract

Hydrogen sulfide{Wang, 2018 #4}{Wang, 2018 #4}{Zhong, 2020 #9} (HS) is a poisonous and harmful gas molecule. Certain concentrations of HS{Liu, 2021 #8} can irritate the eyes, respiratory system, and central nervous system of human beings. Therefore, it was an urgent need for highly selective, anti-interference, and sensitive detection technology for hydrogen sulfide. Herein, a novel "turn-on" fluorescent probe 1-(2-(6,6-dimethylbicyclo[3.1.1]heptyl-2-ene-2-yl))-9-(4-(dimethylaminophenyl))non-1,6,8-triene-3,5-dione boron difluoride complex (MCBF) was designed and synthesized for detecting HS sensitively. MCBF displayed a remarkable fluorescence enhancement response to HS with a large Stokes shift of 220 nm. The sensitive detection of MCBF towards HS owned good selectivity, fast response time (6 min), excellent photostability, and low detection limit (0.44 μM). The sensing mechanism of MCBF towards HS was well confirmed by HRMS analysis, H NMR titration, and density functional theory (DFT) calculations. What's more, probe MCBF was successfully applied to detect the contained HS in red wine, which showed the potential practicability of MCBF in real samples analysis.

摘要

硫化氢(Wang, 2018 #4;Wang, 2018 #4;Zhong, 2020 #9)是一种有毒有害的气体分子。一定浓度的硫化氢(Liu, 2021 #8)会刺激人类的眼睛、呼吸系统和中枢神经系统。因此,人们迫切需要对硫化氢进行高选择性、抗干扰、灵敏的检测技术。在此,设计并合成了一种新型的“开启”型荧光探针 1-(2-(6,6-二甲基双环[3.1.1]庚-2-烯-2-基))-9-(4-(二甲氨基)苯基))-1,6,8-壬三烯-3,5-二酮硼酸二氟复合物(MCBF),用于灵敏检测 HS。MCBF 对 HS 表现出显著的荧光增强响应,Stokes 位移为 220nm。MCBF 对 HS 的灵敏检测具有良好的选择性、快速的响应时间(6 分钟)、优异的光稳定性和低检测限(0.44μM)。通过高分辨质谱分析、H NMR 滴定和密度泛函理论(DFT)计算,很好地证实了 MCBF 对 HS 的传感机制。此外,探针 MCBF 成功应用于红酒中 HS 的检测,表明 MCBF 在实际样品分析中具有潜在的实用性。

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引用本文的文献

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Molecules. 2024 Aug 22;29(16):3973. doi: 10.3390/molecules29163973.
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Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species.基于活性的荧光探针用于硫化氢及相关反应性硫物种。
Chem Rev. 2024 Apr 10;124(7):4124-4257. doi: 10.1021/acs.chemrev.3c00683. Epub 2024 Mar 21.