一种荧光增强型甲醛荧光探针的合成及其性能研究

doi:10.6023/cjoc202110012

有机化学 ›› 2022, Vol. 42 ›› Issue (4): 1163-1169.DOI: 10.6023/cjoc202110012 上一篇下一篇

研究论文

一种荧光增强型甲醛荧光探针的合成及其性能研究

卢辉旭, 唐永和, 周红梅, 林伟英^*()

广西大学化学化工学院广西电化学能源材料重点实验室广西大学光功能材料与化学生物学研究院有色金属及材料加工新技术教育部重点实验室广西有色金属及特色材料加工重点实验室南宁 530004

收稿日期:2021-10-10 修回日期:2021-12-06 发布日期:2021-12-22
通讯作者: 林伟英
基金资助:
国家自然科学基金(21672083); 国家自然科学基金(21877048); 国家自然科学基金(22077048); 国家自然科学基金(22104019); 广西省自然科学基金(2021GXNSFDA075003); 广西省自然科学基金(2019GXNSFBA245068); 广西省自然科学基金(AD21220061); 广西大学启动基金(A3040051003)

Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe

Huixu Lu, Yonghe Tang, Hongmei Zhou, Weiying Lin()

Guangxi Key Laboratory of Electrochemical Energy Materials, Institute of Optical Materials and Chemical Biology,MOE Key Laboratory of New Processing Technology for Nonferrous Metals and Materials, Guangxi Key Laboratory of Processing for Non-ferrous Metals and Featured Materials, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004

Received:2021-10-10 Revised:2021-12-06 Published:2021-12-22
Contact: Weiying Lin
Supported by:
National Natural Science Foundation of China(21672083); National Natural Science Foundation of China(21877048); National Natural Science Foundation of China(22077048); National Natural Science Foundation of China(22104019); Natural Science Foundation of Guangxi Province(2021GXNSFDA075003); Natural Science Foundation of Guangxi Province(2019GXNSFBA245068); Natural Science Foundation of Guangxi Province(AD21220061); Startup Fund of Guangxi University(A3040051003)

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摘要/Abstract

甲醛(FA)对环境和人们的身体健康息息相关, 例如曝露在环境中的FA被人体吸收后, 轻则会引起头痛、喉咙发炎等不适, 重则会损害人体重要器官进而引发诸如白血病、阿尔兹海默症等疾病. 针对环境中FA的快速检测, 开发了一个荧光增强性的FA探针HSU-FA. 该探针选用萘酰亚胺染料作为荧光平台, 以肼基基团作为识别FA的位点, 通过肼基基团与羰基缩合成腙的反应达到识别FA的效果. 通过测试条件优化得出, 在乙酸含量为30%测试条件下探针HSU-FA对FA的识别效果最佳. 通过紫外-可见吸收光谱可知, 在FA的作用下探针的吸收光谱发生显著增强现象. 通过荧光光谱测试得出, 该探针对FA具有突出的识别能力和响应速度. 此外, 该探针具有较强的抗光漂白能力, 能够在溶液状态下稳定存在. 在溶液中该探针与FA相互作用可以展示出不同的荧光强度, 显示出了较强的浓度依赖性. 更重要的是, 利用无纺布制备的FA检测卡实现了环境中FA的快速检测.

关键词: 甲醛, 荧光探针, 环境检测, 萘酰亚胺, 肼基

Formaldehyde (FA) is closely related to the environment and people’s health. For example, when FA is absorbed by the human body after exposure to the environment, it will cause discomfort such as headache and throat inflammation, or damage the vital organs of the human body and then cause diseases such as leukemia and Alzheimer's disease. For the rapid detection of FA in the environment, a fluorescent enhanced FA probe HSU-FA was developed. The probe uses naphthalimide dye as the fluorescent platform and hydrazine group as the site of FA recognition. The FA recognition effect is achieved by the condensation reaction between hydrazine group and carbonyl group condensation to form hydrazone. According to the optimization of test conditions, under the test condition of 30% acetic acid content, the probe HSU-FA has the best identification effect on FA. According to the UV-vis absorption spectrum, the absorption spectrum of the probe was significantly enhanced under the action of FA. The fluorescence spectrum test shows that the probe has outstanding recognition ability and response speed to FA. In addition, the probe has a strong resistance to photobleaching and can be stable in solution. The interaction between the probe and FA in solution showed different fluorescence intensities, showing a strong concentration dependence. More importantly, the rapid detection of FA in the environment by using the FA detection card prepared from non-woven fabrics was realized.

Key words: formaldehyde, fluorescent probe, environmental detection, naphthalimide, hydrazine moiety

引用此文

卢辉旭, 唐永和, 周红梅, 林伟英. 一种荧光增强型甲醛荧光探针的合成及其性能研究[J]. 有机化学, 2022, 42(4): 1163-1169.

Huixu Lu, Yonghe Tang, Hongmei Zhou, Weiying Lin. Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1163-1169.

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图/表 7

图式1. 探针HSU-FA与甲醛作用机理

Scheme 1. Mechanism of reaction between HSU-FA probe and FA

图1. 不同浓度FA (0~8×10–4 mol•L–1)与1.0×10–5 mol•L–1 探针HSU-FA作用后在波长523 nm处的荧光信号强度值曲线

Figure 1. Fluorescence signal intensity curves at 523 nm after the interaction of different concentrations of FA (0~8×10–4 mol•L–1) and 1.0×10–5 mol•L–1 probe HSU-FA The test system is acetonitrile solution with 30% acetic acid; λex=440 nm; slit=10/10 nm

图2. 探针HSU-FA与FA作用后在523 nm处的荧光强度随时间的变化

Figure 2. Time-dependent fluorescence intensity of probe HSU- FA at 523 nm treated with FA

图3. 各种分析物与探针HSU-FA作用后的荧光强度对比图. 测试条件为λex=440 nm, 狭缝宽度10/10 nm

Figure 3. Comparison diagram of the fluorescence intensity of the above analytes with the probe HSU-FA. The test conditions: λex=440 nm, slit=10/10 nm The analytes from 1~26 are methylglyoxal, Sodium pyruvate, CuI, MnCl2, NaF, NaH2PO4, NaHS, NaSCN, NaSO4, CuSO4, CaCl2, CdCl2, CoCl2, MgCl2, NiCl2, ZnCl2, FeCl2, tert-butyl hydroperoxide, chloral hydrate, AgNO3, NaBr, NaS2, NaHSO3, sodium nitroprusside, acetaldehyde, glyoxal

图4. 0~800 μmol•L–1的FA溶液分别与1.0×10–5 mol•L–1的探针HSU-FA在含30%乙酸的乙腈溶液中作用的结果

Figure 4. Results of the interaction of 0~800 μmol•L–1 FA solution and 1.0×10–5 mol•L–1 probe HSU-FA in acetonitrile solution with 30% acetic acid, respectively

图5. 用不同浓度的FA溶液挥发后与浸泡过探针溶液的无纺布条分别作用, 使用共聚焦成像系统拍摄的荧光图

Figure 5. Fluorescence images taken by confocal scanning system after volatilizing FA solution with different concentrations and acting on non-woven strips soaked in probe solution, respectively (A1~A10) 0, 5.0×10–2, 1.0×10–1, 1.5×10–1, 2.0×10–1, 2.5×10–1, 3.0×10–1, 3.5×10–1, 4.0×10–1, 4.5×10–1 mol•L–1; (B) the liner relationship curve

. 图示2 探针HSU-FA的合成路线

Scheme 2. Synthesis route of probe HSU-FA

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一种荧光增强型甲醛荧光探针的合成及其性能研究

Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe

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