水溶性萘酰亚胺类荧光探针对Fe3+和$\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的特异性检测

师春甜; 余美; 吴爱斌; 罗江雄; 黎小军; 王宁晨; 舒文明; 余维初

doi:10.6023/cjoc202204032

有机化学 >

2022 , Vol. 42 >Issue 9: 2806 - 2813

DOI: https://doi.org/10.6023/cjoc202204032

研究论文

水溶性萘酰亚胺类荧光探针对Fe³⁺和$\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的特异性检测

师春甜 ,
余美 ,
吴爱斌 ,
罗江雄 ,
黎小军 ,
王宁晨 ,
舒文明 ,
余维初

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a 长江大学化学与环境工程学院湖北荆州 434023
b 长江大学非常规油气协同创新中心湖北荆州 434023
c 湖南大学机械与运载工程学院长沙 410082

收稿日期: 2022-04-13

修回日期: 2022-06-02

网络出版日期: 2022-07-21

基金资助

国家科技重大专项基金(2017ZX05049-003-007); 国家自然科学基金(21801022)

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A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$

Chuntian Shi ,
Mei Yu ,
Aibin Wu ,
Jiangxiong Luo ,
Xiaojun Li ,
Ningchen Wang ,
Wenming Shu ,
Weichu Yu

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a School of Chemistry and Environmental Engineering, Yangtze University, Jingzhou, Hubei 434023
b Unconventional Oil and Gas Collaborative Innovation Center, Yangtze University, Jingzhou, Hubei 434023
c College of Mechanical and Vehicle Engineering, Hunan University, Changsha 410082

* Corresponding authors. E-mail: abwu@yangtzeu.edu.cn;

yuweichu@126.com

Received date: 2022-04-13

Revised date: 2022-06-02

Online published: 2022-07-21

Supported by

National Science and Technology Major Project of China(2017ZX05049-003-007); National Natural Science Foundation of China(21801022)

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摘要

合成了一种能选择性识别Fe³⁺和 $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的探针N-(2-(2-(2-羟基乙氧基)乙基)-1,3-二氧基-2,3-二氢-1H-苯并[de]异喹啉-6-基)呋喃-2-甲酰胺(1), 这是首个基于萘酰亚胺检测 $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的小分子探针. pH滴定表明, 分子内电荷转移(intramolecular charge transfer, ICT)效应增强引起的光谱红移是酰胺负离子形成的结果, 还研究了探针1在CH₃CN/N-2-羟乙基哌嗪-N'-2-乙磺酸(HEPES)缓冲溶液中对Fe³⁺和 $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的选择性、浓度滴定、时间依赖性、猝灭常数、检测限和识别机理等. 研究表明, Fe³⁺和 $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$通过内滤效应(IFE)快速猝灭探针1的荧光, 猝灭在30 s后恒定, 猝灭常数分别为6.14×10³和6.55×10³ L•mol^–1; 探针1对Fe³⁺和 $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的检测限分别为1.62和1.56 μmol/L; 水样中Fe³⁺和 $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的测定结果表明, 探针1可以作为一种在实际应用中的潜在检测工具.

关键词： 荧光探针; $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$; Fe³⁺; 萘酰亚胺; 内滤效应

本文引用格式

师春甜 , 余美 , 吴爱斌 , 罗江雄 , 黎小军 , 王宁晨 , 舒文明 , 余维初 . 水溶性萘酰亚胺类荧光探针对Fe³⁺和$\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的特异性检测[J]. 有机化学, 2022 , 42(9) : 2806 -2813 . DOI: 10.6023/cjoc202204032

Abstract

N-(2-(2-(2-Hydroxyethoxy)ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)furan-2-carboxamide (1) that can selectively recognize Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ was synthesized, which was the first small molecule probe based on naphthalimide to detect $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$. The pH titration showed that the spectral red shift caused by the enhancement of intramolecular charge transfer (ICT) effect was as a result of formation of amide anion. Besides, the selectivity, concentration titration, time dependence, quenching constant, detection limit and recognition mechanism of probe 1 to Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ were also studied in CH₃CN/N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid (HEPES) buffer solution. The results showed that Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ could rapidly quenched the fluorescence of probe 1 through the inner filter effect. The quenching effects remained constant after 30 s, and the quenching constants were 6.14×10³ and 6.55×10³ L•mol^–1, respectively. The detection limits of probe 1 for Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ were 1.62 and 1.56 μmol/L, respectively. The determination of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ in water samples made it clear that probe 1 could be used as a potential detection tool in practical application.

Key words： fluorescent probe; $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$; Fe³⁺; naphthalimide; inner filter effect

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