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 CC 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。