CN112442357B - Double-reaction-site fluorescent probe - Google Patents
Double-reaction-site fluorescent probe Download PDFInfo
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- CN112442357B CN112442357B CN201910825870.5A CN201910825870A CN112442357B CN 112442357 B CN112442357 B CN 112442357B CN 201910825870 A CN201910825870 A CN 201910825870A CN 112442357 B CN112442357 B CN 112442357B
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The invention discloses a double-reaction-site fluorescent probe, which has the following specific chemical structural formula:
Description
Technical Field
The invention relates to a double-reaction-site fluorescent probe and application thereof in detection of mercury ions and hydrazine.
Background
Mercury is widely present in the food chain and in the ecological environment. Mercury salts with good water solubility are highly toxic and can cause brain and liver damage after inhalation, contact or misuse. Mercury ion (Hg)2+) Can be converted into methyl mercury and dimethyl mercury, the methyl mercury is more toxic than mercury ions and is easy to be absorbed by human body, and it is a disease of methyl mercury poisoning. At present, the analytical methods for detecting mercury mainly comprise inductively coupled plasma mass spectrometry, dithizone colorimetry, cold atomic absorption spectrometry, atomic fluorescence spectrometry, inductively coupled plasma emission spectrometry and the like.
Hydrazine (N)2H4) Is a strong reducing agent and plays an important role in agriculture, pharmacy and military industry. Hydrazine is a water-soluble compound, easily causes water pollution, and poses a threat to the safety of drinking water and agricultural products such as fruits and vegetables. N is a radical of2H4Can be absorbed by lung and skin of human body, and has high toxicity, mutagenicity and carcinogenicity to human health.
The organic small-molecule fluorescent probe detection method has the advantages of high detection speed, high sensitivity, simplicity and convenience in operation and the like, so that the method draws high attention of researchers, develops a bifunctional fluorescent probe for measuring the content of mercury ions and hydrazine, and has important research significance.
Disclosure of Invention
The invention aims to provide a double-reaction-site fluorescent probe which is suitable for detecting mercury ions and hydrazine in water.
More particularly, the present invention relates to a dual reaction site fluorescent probe, which is represented by the following formula:
drawings
FIG. 1 shows the fluorescence intensity of the fluorescent probe (10. mu.M) of the present invention in a dimethylsulfoxide/water (v/v ═ 1: 3) solution with the addition of mercury ions at different concentrations. Embedding a graph: concentration of mercury ions.
FIG. 2 is a standard curve of fluorescence intensity of the fluorescent probe of the present invention (10. mu.M) in a dimethylsulfoxide/water (v/v ═ 1: 3) solution as a function of mercury ion concentration.
FIG. 3 shows the change in fluorescence intensity of the fluorescent probe of the present invention (10. mu.M) in a solution of dimethyl sulfoxide/pH 7.4 buffer (1: 3 v/v) with the addition of hydrazine at various concentrations. Embedding a graph: the concentration of hydrazine.
FIG. 4 is a standard curve of fluorescence intensity of the fluorescent probe of the present invention (10. mu.M) in a dimethyl sulfoxide/pH 7.4 buffer solution (v/v ═ 1: 3) as a function of hydrazine concentration.
FIG. 5 shows the color change of the fluorescent probe test paper after the fluorescent probe test paper is soaked in mercury ion solutions (0, 1, 5, 10, 50 μ M) with different concentrations under a 365nm ultraviolet lamp.
FIG. 6 shows the color change of the fluorescent probe test paper after the fluorescent probe test paper of the present invention is dipped in hydrazine solution (0, 1, 5, 10, 50 μ M) with different concentrations under 365nm ultraviolet lamp.
Detailed Description
EXAMPLE 1 preparation of Dual reaction site fluorescent probes
The synthetic route is shown as the following formula:
compound 1(0.50g, 2.90mmol), compound 2(0.75g, 4.36mmol) were dissolved in dichloromethane (15mL), added to a 100mL three-necked flask, N-diisopropylethylamine (0.75mL) was added dropwise with stirring, stirred at room temperature for 5 hours, and isolated by column chromatography to give compound 3 as a white solid.
The product is characterized by nuclear magnetic hydrogen spectrum and nuclear magnetic carbon spectrum.
1H NMR(300MHz，DMSO)，δ(ppm)：10.18(s，1H)，8.67(s，1H)，8.33(d，J＝9.0Hz，1H)，8.15(d，J＝8.5Hz，1H)，8.07-7.93(m，2H)，7.69(dd，J＝8.9，2.4Hz，1H)，7.55(dd，J＝10.8，4.9Hz，2H)，7.39(dd，J＝7.6，4.4Hz，3H).13C NMR(75MHz，DMSO)：δ(ppm)：194.50，193.35，153.65，153.35，136.97，134.64，134.63，132.20，131.31，130.44，129.41，127.56，123.90，123.14，122.21，119.82.
EXAMPLE 2 preparation of fluorescent Probe test paper
The filter paper is cut into square test paper with the size of 1cm multiplied by 1cm, and the square test paper is soaked in 1mM of the fluorescent probe solution (DMSO solvent) to obtain the fluorescent probe test paper.
The change of the fluorescence intensity of the fluorescent probe of the invention along with the mercury ions is shown in figure 1, a standard curve of the fluorescence intensity of the fluorescent probe (10 mu M) along with the change of the mercury ion concentration can be made according to the change, the standard curve is shown in figure 2, and the fluorescent probe of the invention can be used for the quantitative detection of the mercury ions through the establishment of the standard curve. The fluorescence intensity of the fluorescent probe of the invention along with the change of hydrazine is shown in figure 3, a standard curve of the fluorescence intensity of the fluorescent probe (10 mu M) along with the change of hydrazine concentration can be made according to the change, the standard curve is shown in figure 4, and the fluorescent probe of the invention can be used for the quantitative detection of hydrazine through the establishment of the standard curve.
Mercury ions and hydrazine with different concentrations are dripped on the test paper, and the color change of the test paper is shown in figures 5 and 6. After the fluorescent probe test paper provided by the invention reacts with mercury ions with different concentrations, the color change of the test paper is shown in fig. 5, and the fluorescent probe test paper gradually changes from colorless to light blue along with the increase of the concentration of the mercury ions. After the fluorescent probe test paper of the invention reacts with hydrazine with different concentrations, the color change of the test paper is shown in figure 6, and the fluorescent probe test paper of the invention gradually changes from colorless to dark blue along with the increase of the hydrazine concentration. The fluorescent probe can be used for qualitative and semi-quantitative detection of mercury ions and hydrazine.
Claims (1)
1. A double-reaction-site fluorescent probe has a specific chemical structural formula as follows:
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910825870.5A CN112442357B (en) | 2019-09-03 | 2019-09-03 | Double-reaction-site fluorescent probe |
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| CN201910825870.5A CN112442357B (en) | 2019-09-03 | 2019-09-03 | Double-reaction-site fluorescent probe |
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| CN112442357B true CN112442357B (en) | 2022-05-17 |
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| CN115745899B (en) * | 2022-10-31 | 2024-03-12 | 郑州师范学院 | Mercury (II) fluorescent probe, preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107298664A (en) * | 2017-07-11 | 2017-10-27 | 济南大学 | A kind of colorimetric fluorescence probe for analyzing mercury ion, preparation method and application |
| CN107337654A (en) * | 2017-07-11 | 2017-11-10 | 济南大学 | A kind of fluorescence probe for analyzing mercury ion, preparation method and application |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107298664A (en) * | 2017-07-11 | 2017-10-27 | 济南大学 | A kind of colorimetric fluorescence probe for analyzing mercury ion, preparation method and application |
| CN107337654A (en) * | 2017-07-11 | 2017-11-10 | 济南大学 | A kind of fluorescence probe for analyzing mercury ion, preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| A fluorescent probe for hydrazine and its in vivo applications;Liangliang Xiao等;《RSC Advances》;20140829;第4卷;41807-41811 * |
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