Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe

doi:10.6023/cjoc202110012

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1163-1169.DOI: 10.6023/cjoc202110012 Previous Articles Next Articles

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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

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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Abstract

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

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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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Fig. & Tab. 7

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

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

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

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

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

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

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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