基于芳基糠醛功能化巴比妥酸衍生物识别和分离Hg 2+/Fe 3+的新型荧光传感器

doi:10.6023/cjoc201903053

有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2829-2834.DOI: 10.6023/cjoc201903053 上一篇下一篇

所属专题：荧光探针-生物传感合辑；有机超分子化学合辑

研究论文

基于芳基糠醛功能化巴比妥酸衍生物识别和分离Hg ²⁺/Fe ³⁺的新型荧光传感器

朱文博, 朱伟, 丁金东, 马小强, 姚红, 张有明, 林奇^*(), 魏太保^*()

西北师范大学化学化工学院生态环境相关高分子材料教育部重点实验室甘肃省高分子材料重点实验室兰州 730070

收稿日期:2019-03-24 修回日期:2019-05-13 发布日期:2019-06-06
通讯作者: 林奇,魏太保 E-mail:linqi2004@126.com;weitaibao@126.com
基金资助:
国家自然科学基金资助项目(21662031);国家自然科学基金资助项目(21661028);国家自然科学基金资助项目(21574104);国家自然科学基金资助项目(21262032)

A Novel Fluorescent Sensor Based on Aryl-furfural Functionalized Barbituric Acid for Recognition and Separation of Hg ²⁺/Fe ³⁺

Zhu Wenbo, Zhu Wei, Ding Jindong, Ma Xiaoqiang, Yao Hong, Zhang Youming, Lin Qi^*(), Wei Taibao^*()

Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering,Northwest Normal University, Lanzhou 730070

Received:2019-03-24 Revised:2019-05-13 Published:2019-06-06
Contact: Lin Qi,Wei Taibao E-mail:linqi2004@126.com;weitaibao@126.com
Supported by:
Project supported by the National Natural Science Foundation of China(21662031);Project supported by the National Natural Science Foundation of China(21661028);Project supported by the National Natural Science Foundation of China(21574104);Project supported by the National Natural Science Foundation of China(21262032)

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摘要/Abstract

合成了一种新型的基于5-(3-硝基苯基)-呋喃-2-甲醛功能化的巴比妥酸衍生物传感器QS. 通过 ¹H NMR, ¹³C NMR, MS等方法对QS进行了表征. QS的荧光光谱结果表明QS的二甲亚砜(DMSO)溶液在498 nm 有最大荧光发射, 在365 nm紫外灯下照射发出绿色荧光. QS对Hg ²⁺和Fe ³⁺的水溶液有不同的荧光检测能力, Hg ²⁺能使探针QS的荧光增强为橙色, Fe ³⁺使其荧光猝灭, 实现了实时检测. 传感器QS对Hg ²⁺和Fe ³⁺的荧光检测限分别为3.25×10 ^–8和4.0× 10 ^–8 mol?L ^–1. 根据Job曲线和质谱研究得到QS与汞离子和铁离子化学计量比均为1∶1, 提出了QS与Hg ²⁺和Fe ³⁺的可能结合模式. 加入$H_{2}PO_{4}^{-}$能使含有Fe ³⁺的QS溶液(QS-Fe)荧光恢复, 可用于Fe ³⁺的循环检测. 此外, 固体QS可从水溶液中吸附 Hg ²⁺和Fe ³⁺(吸附率分别为92.0%和91.8%), 具有较好的吸附能力.

关键词: 巴比妥酸衍生物, 荧光传感器, 铁离子, 汞离子, 离子吸附

A novel fluorescent sensor based on 5-(3-nitrophenyl)-furan-2-carbaldehyde functionalized barbituric acid derivative (QS) was successfully synthesized. QS was characterized by ¹H NMR, ¹³C NMR and MS. The maximum fluorescence emission wavelength of QS in dimethyl sulfoxide (DMSO) solution was determined to be 498 nm and green fluorescence was emitted under 365 nm ultraviolet lamp. QS showed different fluorescence identification ability for aqueous solution of Hg ²⁺ and Fe ³⁺. Hg ²⁺ can enhance the fluorescence of probe QS to orange, and Fe ³⁺ quenches its fluorescence, thus realizing real- time detection. The limits of detection of QS for Hg ²⁺ and Fe ³⁺ are 3.25×10 ^–8 and 4.0×10 ^–8 mol? L ^–1, respectively. The fluorescence measurements and MS studies suggest that the binding stoichiometry ratios of QS with Hg ²⁺ and Fe ³⁺ are recognized as 1∶1, respectively. The possible modes of QS with Hg ²⁺ and Fe ³⁺ are proposed. The addition of $H_{2}PO_{4}^{-}$ caused the fluorescence of QS-Fe recover, indicating that QS can be used for cyclic detection of Fe ³⁺. More importantly, the separation percentages of the solid QS for Hg ²⁺and Fe ³⁺ are 92.0% and 91.8% in aqueous solution, respectively, indicating that it has excellent ingestion capacity.

Key words: barbituric acid derivatives, fluorescence sensor, iron ion, mercury ion, ion absorption

引用此文

朱文博, 朱伟, 丁金东, 马小强, 姚红, 张有明, 林奇, 魏太保. 基于芳基糠醛功能化巴比妥酸衍生物识别和分离Hg ²⁺/Fe ³⁺的新型荧光传感器[J]. 有机化学, 2019, 39(10): 2829-2834.

Zhu Wenbo, Zhu Wei, Ding Jindong, Ma Xiaoqiang, Yao Hong, Zhang Youming, Lin Qi, Wei Taibao. A Novel Fluorescent Sensor Based on Aryl-furfural Functionalized Barbituric Acid for Recognition and Separation of Hg ²⁺/Fe ³⁺[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2829-2834.

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图/表 7

Scheme 1. Synthesis of the sensor QS

Figure 1. Fluorescence spectra of QS (1.0×10–4 mol?L–1) in DMSO with metal ions (Fe3+, Hg2+, Ni2+, Zn2+, Ca2+, Cu2+, Cr3+, Ba2+, Co2+, Ag+, Pb2+, Hg2+, Al3+ and Mg2+) in response to Hg2+ and Fe3+ (10 equiv.) upon excitation at 355 nm Inset: color change of QS with metal ions

Figure 2. Fluorescence emission data for QS (1.0×10–4 mol? L–1) with different perchlorate salts of cations (10 equiv.) and the previous mixture with (a) Hg2+ (10 equiv.) and (b) Fe3+ (10 equiv.) in DMSO solutions at room temperature (excitation wavelength=355 nm)

Figure 3. Fluorescence emission spectra of QS (0.1 mmol?L–1) excited at 355 nm with addition of increasing concentrations of (a) Hg2+ (0~11.0 equiv.) and (b) Fe3+ (0~5.5 equiv.) in DMSO solution Inset: a plot of fluorescence intensity depending on the concentration of (a) Hg2+ in the range from 0 to 11 equiv. and (b) Fe3+ in the range from 0 to 5.5 equiv.

Figure 4. Fluorescence emission spectra of QS-Fe (0.1 mmol? L–1) excited at 355 nm with addition of increasing concentrations of $H_{2}PO_{4}^{-}$ in DMSO solution Inset: fluorescence changes under 365 nm UV lamp

Figure 5. FT-IR spectra of powder QS and QS-Hg

Scheme 2. Proposed combination of QS with Hg2+ and Fe3+

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基于芳基糠醛功能化巴比妥酸衍生物识别和分离Hg ²⁺/Fe ³⁺的新型荧光传感器

A Novel Fluorescent Sensor Based on Aryl-furfural Functionalized Barbituric Acid for Recognition and Separation of Hg ²⁺/Fe ³⁺

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