一种大斯托克斯位移的红光发射荧光探针选择性检测次氯酸
A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid
作者单位E-mail
白佳坤 山西师范大学化学与材料科学学院, 教育部磁性分子与磁信息材料重点实验室, 太原 030032 jiakun_bai@163.com 
徐婷 山西师范大学化学与材料科学学院, 教育部磁性分子与磁信息材料重点实验室, 太原 030032  
张璐 山西师范大学化学与材料科学学院, 教育部磁性分子与磁信息材料重点实验室, 太原 030032  
彭江 山西师范大学化学与材料科学学院, 教育部磁性分子与磁信息材料重点实验室, 太原 030032  
李宇强 中北大学化学与化工学院, 太原 030051 yuqiangli@nuc.edu.cn 
贾俊辉 山西师范大学化学与材料科学学院, 教育部磁性分子与磁信息材料重点实验室, 太原 030032 jiajunhui@sxnu.edu.cn 
摘要: 设计、合成了一种基于巴比妥酸衍生物的具有D-π-A结构的光学探针3。该探针能够作为一种高度灵敏和选择性的次氯酸指示剂,快速实现对次氯酸的比色和荧光信号(开-关)的双响应(约15 s)。推测的响应机制是ClO-与C=C之间发生了亲电加成和氧化裂解反应,导致探针的D-π-A结构遭到破坏,从而阻断了其分子内电荷转移(intramolecular charge transfer,ICT)进程。探针只需一步即可合成,同时具有红光发射(628 nm)和较大的斯托克斯位移(158 nm),检测限(limit of detection,LOD)低至14 nmol·L-1。此外,探针还表现出低细胞毒性,并成功应用于活细胞成像。
关键词: 大斯托克斯位移  次氯酸检测  比色荧光双响应  红光发射  细胞成像
基金项目: 山西省基础研究计划(No.20210302124075,202203021222040)、国家自然科学基金(No.221805175)和山西省科技成果转化引导专项(No.202104021301045)资助。
Abstract: An optical probe (3) with a donor-π-acceptor (D-π-A) structure for the detection of hypochlorous acid (HClO) was synthesized by a one-step reaction. It employed a barbituric acid derivative as the electron acceptor and 4-(dimethylamino)cinnamaldehyde as the electron donor. The probe exhibited high sensitivity and selectivity for the detection of HClO, rapidly responding with distinct colorimetric and fluorescent “on-off” signals (about 15 s). The probe displayed a linear relationship between fluorescence intensity and HClO concentration, with a low detection limit (LOD) of 14 nmol·L-1, which made it suitable for quantitative HClO detection. Moreover, the probe exhibited red light emission (628 nm) with a significant Stokes shift (158 nm) and good photostability, which provided advantages for its application in cell imaging. The proposed reaction mechanism, which was deduced from high-resolution mass spectrometry data, involved electrophilic addition and oxidative cleavage of the C=C bond by ClO-, which led to the disruption of the probe's D-π-A structure. Consequently, this effectively halted the intramolecular charge transfer (ICT) process of the probe. MTT cytotoxicity assays demonstrated minimal toxicity of the probe following 12, 24, and 48 h of incubation with HepG2 cells. The probe was successfully applied to living cell imaging and enabled the detection of HClO via fluorescence quenching within the living cellular milieu.
Keywords: large Stokes shift  hypochlorite detection  colorimetric and fluorescent dual-response  red-emitting  cell imaging
投稿时间:2024-01-01 修订日期:2024-04-05
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白佳坤,徐婷,张璐,彭江,李宇强,贾俊辉.一种大斯托克斯位移的红光发射荧光探针选择性检测次氯酸[J].无机化学学报,2024,40(6):1095-1104.
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