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Bisulfite recognition properties of two benzothiazole inner salt compounds
Journal of Photochemistry and Photobiology A: Chemistry ( IF 4.1 ) Pub Date : 2020-06-30 , DOI: 10.1016/j.jphotochem.2020.112739
Zhipeng Li , Yilin Zhu , Xiangshuo Gong , Yixin Zhang , Miaomiao Xing , Shuyue Ma , Ruifang Guan , Duxia Cao , Zhiqiang Liu

Two fluorescent probes based on benzothiazole inner salt structure for detecting bisulfite, 2-{2-[4-(N,N-diethylamino)-phenyl]vinyl}-N-(3-sulfonatepropyl)-benzothiazole, inner salt (1) and 2-{2-[4-(N,N-diethylamino)-2-hydroxyl-phenyl]vinyl}-N-(3-sulfonatepropyl)-benzothiazole, inner salt (2), have been developed. The probes can specifically recognize bisulfite (HSO3) in HEPES-DMSO mixed solution (VHEPES:VDMSO = 1:9) with low detection limits (1, 75.6 nM; 2. 23.4 nM) and fast response rate (<60 s). The sensing mechanism investigation by 1H NMR titration indicates that HSO3 attacks to Cdouble bondC double bond by nucleophilic addition reaction, which results in broken conjugated structure and quenched red fluorescence. Probe 2 with hydroxyl substituent group has higher sensitivity for HSO3 than probe 1, which is believed to be due to the synergistic effect from hydroxyl coordinating with HSO3. The probes also can be used to the determination of bisulfite in food products and real-water samples.



中文翻译:

两种苯并噻唑内盐化合物的亚硫酸氢盐识别特性

两种基于苯并噻唑内盐结构的荧光探针,用于检测亚硫酸氢盐,2- {2- [4-(N,N-二乙氨基)-苯基]乙烯基} -N-(3-磺酸基丙基)-苯并噻唑,内盐(1)和已经开发了2- {2- [4-(N,N-二乙氨基)-2-羟基-苯基]乙烯基} -N-(3-磺酸基丙基)-苯并噻唑,内盐(2)。探针可以特异地识别亚硫酸氢盐(HSO 3 - )在HEPES-DMSO混合溶液(V HEPES:V DMSO  = 1:9)具有低检测限(1,75.6纳米; 2 23.4纳米。)和快速响应速率(<60 s)。传感机制的研究1个1 H NMR滴定表明,HSO 3 -至C攻击双键通过亲核加成反应C双键,其结果在打破共轭结构和淬灭红色荧光。探头2具有羟基取代基团具有用于HSO更高的灵敏度3 -比探针1,这被认为是由于从与羟基HSO协调的协同效应3 - 。该探针还可用于测定食品和实际水样品中的亚硫酸氢盐。

更新日期:2020-06-30
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