萘异硫氰酸酯修饰的水杨醛衍生物作为氟离子荧光探针的研究

引用本文: 邹颖怡, 冯锐鸿, 罗颖欣, 马明君, 朱璐瑶, 马立军. 萘异硫氰酸酯修饰的水杨醛衍生物作为氟离子荧光探针的研究[J]. 分析化学, 2022, 50(4): 574-584. doi: 10.19756/j.issn.0253-3820.210878 shu

Citation: ZOU Ying-yi, FENG Rui-hong, LUO Ying-xin, MA Ming-jun, ZHU Lu-yao, MA Li-jun. Study on Salicylaldehyde Derivatives Modified by Naphthalene Isothiocyanate as Fluorescent Probe for Fluoride Ion[J]. Chinese Journal of Analytical Chemistry, 2022, 50(4): 574-584. doi: 10.19756/j.issn.0253-3820.210878 shu

萘异硫氰酸酯修饰的水杨醛衍生物作为氟离子荧光探针的研究

华南师范大学化学学院, 广州 510006

通讯作者: 马立军,E-mail:mlj898021@scnu.edu.cn

基金项目:
广东省自然科学基金项目(No.2015A030313392)

广州市科技计划项目(No.2018J2200342)资助

摘要: 以萘异硫氰酸酯分别化学修饰水杨醛、4-(二乙氨基)水杨醛,合成了两种荧光分子(分子1和2),利用核磁共振和高分辨质谱技术对其结构进行了表征和确证。采用荧光光谱技术对这两种分子与常见阴离子的结合进行研究,结果表明,分子1和分子2均可选择性识别F^–,可作为检测F^–的荧光探针。探针1(分子1)对F^–表现出荧光增强型响应,当F^–浓度为20.0μmol/L时,探针1溶液的荧光强度增强了15倍。与探针1相对比,探针2(分子2)由于引入了二乙氨基团,对F^–显示出高选择性,并且具有比率型荧光识别特性。加入F^–可引起探针2在456 nm处荧光强度下降,同时在503 nm处出现新的荧光发射峰,并且强度逐渐增强。同时,采用探针1和2对F^–均具有较低的检出限,分别为0.35和0.68μmol/L。通过B-H方程计算出探针1和2与F^–的结合常数分别为3.8×10⁴和6.98×10³ L/mol,表明这两种探针与F^–具有较强的结合作用。通过核磁共振氢谱探究了探针1和2与F^–的结合模式,结果表明,两种探针对F^–的荧光识别机理均为分子内电荷转移(ICT)。利用两种探针制备得到的荧光试纸可对水体系和牙膏中的F^–进行快速的荧光检测,具有良好的实用性。

关键词:

English

Study on Salicylaldehyde Derivatives Modified by Naphthalene Isothiocyanate as Fluorescent Probe for Fluoride Ion

School of Chemistry, South China Normal University, Guangzhou 510006, China

Corresponding author: MA Li-jun, mlj898021@scnu.edu.cn

Received Date: 06 December 2021
Revised Date: 07 March 2022
Fund Project:
Supported by the Natural Science Foundation of Guangdong Province,China(No. 2015A030313392)

the Science and Technology Planning Project of Guangzhou,China(NO. 2018J2200342)

Abstract: Two fluorescent molecules(1 and 2) were synthesized by salicylaldehyde and 4-(diethylamino) salicylaldehyde with naphthalene isothiocyanate.Their structures were characterized by nuclear magnetic resonance(NMR) and mass spectrometry(MS).The results of UV-vis absorption spectra and fluorescence spectra showed that molecule 1 and molecule 2 had high sensitivity to fluoride ion(F^-) in DMSO solution, which could be used as fluorescence probes for F^- detection.Probe 1(molecule 1) showed fluorescence enhancement to F^-, and the fluorescence intensity increased by 15 times when F^-concentration was 20.0μmol/L.Compared to probe 1, probe 2(molecule 2) showed high selectivity ratio fluorescence recognition for F^- due to the presence of diethylamino group.The addition of F^-could cause decrease of fluorescence emission peak of probe 2 at 456 nm, while a new fluorescence emission peak appeared at 503 nm and gradually increased.Probes 1 and 2 had low detection limits of 0.35μmol/L and 0.68μmol/L toward F^-respectively.By the B-H equation, the constants of probe 1 and probe 2 to F^- were 3.8×10⁴ L/mol and 6.98×10³ L/mol, indicating that the two probes had strong binding affinity with F^-.In addition, the binding modes between probe 1 and probe 2 and F^-were investigated by ¹H NMR.The analysis of experimental results showed that the fluorescence recognition mechanism of both two probes was intramolecular charge transfer(ICT).Finally, the test papers prepared by the two probes were used for simple fluorescence detection of F^- in toothpaste solution, which proved their good practicability.

Key words:

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沈阳化工大学材料科学与工程学院沈阳 110142

萘异硫氰酸酯修饰的水杨醛衍生物作为氟离子荧光探针的研究

通讯作者: 马立军,E-mail:mlj898021@scnu.edu.cn

English

Study on Salicylaldehyde Derivatives Modified by Naphthalene Isothiocyanate as Fluorescent Probe for Fluoride Ion

Corresponding author: MA Li-jun, mlj898021@scnu.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

萘异硫氰酸酯修饰的水杨醛衍生物作为氟离子荧光探针的研究

通讯作者: 马立军,E-mail:mlj898021@scnu.edu.cn

English

Study on Salicylaldehyde Derivatives Modified by Naphthalene Isothiocyanate as Fluorescent Probe for Fluoride Ion

Corresponding author: MA Li-jun, mlj898021@scnu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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