CN111518093A - Fluorescent probe for detecting sulfide and preparation and application thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for detecting sulfide and preparation and application thereof, the fluorescent probe has high selectivity and can specifically identify sulfide in a solution; the anti-interference capability is strong, and the interference of other substances in the environment on the detection of the probe can be prevented; the sensitivity is high, and the method is suitable for detecting trace sulfides; the reaction is rapid, the color change is obvious, the synthesis is simple, the property is stable, and the application prospect is wide. The fluorescent probe can be obtained by simple chemical synthesis, and has low preparation cost and easy popularization.
Description
Technical Field
The invention relates to preparation of a small-molecule fluorescent dye in a chemical detection technology, in particular to a fluorescent probe for detecting sulfide based on near-infrared hemicyanine dye and a synthesis method thereof.
Background
The sulfide is one of important parameters representing the quality of water, is widely present in the environment, water and domestic industrial waste liquid, is toxic, and inhales hydrogen sulfide to cause cell hypoxia, so that the low concentration of the sulfide can cause discomfort, specifically manifested as eye stabbing pain, lacrimation, watery nasal discharge, sore throat, headache, dizziness, nausea and other symptoms, and therefore, the detection of the sulfide has important significance. The existing detection method for detecting sulfides in construction water adopts a sulfate weight method (GB 11899-89 determination weight method for water sulfate), the method has multiple steps, a water sample needs to be pretreated before measurement, ageing and precipitation even need to be carried out overnight, and the requirement on testers is high. The sulfur trioxide of construction materials such as cement, mineral powder, fly ash, coarse and fine aggregates and the like is also determined by complicated operation (GB/T176-.
Owing to the development of fluorescence imaging technology in these years, fluorescence imaging analysis has the advantages of high sensitivity, good selectivity, rapid response, simple operation and the like, basically does not damage biological samples, is used for detecting small molecules in organisms, is not used for detecting construction materials, and is easily influenced by interfering ions due to complex synthesis of a plurality of probes. Therefore, the development of the fluorescence-activated near-infrared fluorescence probe which has high selectivity, high sensitivity and good light stability and can rapidly detect the sulfide in real time has important practical value.
Disclosure of Invention
The invention aims to provide a near-infrared fluorescent probe capable of detecting sulfide in water and a preparation method and application thereof aiming at the problems in the prior art of the existing sulfide fluorescent probe.
The technical scheme of the invention is as follows:
a near-infrared fluorescent probe for detecting sulfide has the following structural general formula:
a preparation method of the sulfide near-infrared fluorescent probe comprises the following preparation processes:
the preparation method comprises the following specific steps:
1) heating the compound 1 and resorcinol in acetonitrile solution of potassium carbonate for reaction, separating and purifying to obtain a compound 2:
2) reacting the compound 2, 4-dinitrofluorobenzene and cesium carbonate in a dichloromethane solution, separating and purifying to obtain purple powder, namely a fluorescent probe 3 for detecting sulfide:
in the step (1), the mass ratio of the compound 1, the resorcinol and the potassium carbonate is 1:2: 2; the weight ratio of the compound 1, namely the heptamethine benzothiazole cyanine dye to the solvent acetonitrile is 1: 6-7; the weight ratio of the total weight of the potassium carbonate and the resorcinol to the solvent acetonitrile is 1: 14-15.
In the step (1), the heating temperature is 60 ℃, and the reaction time is 5 hours.
And (2) the separation and purification step in the step (1) is to carry out suction filtration on the reaction liquid, and the filtrate is subjected to reduced pressure distillation and concentration to obtain a crude product. Separating and purifying the crude product by column chromatography silica gel, wherein the volume ratio of the eluent is 100:1-5 of dichloromethane-methanol mixed solution.
In the step (2), the mass ratio of the compound 2, 4-dinitrofluorobenzene and cesium carbonate is 1:4: 1.
In the step (2), the reaction time is 12 h.
In the step (2), the separation and purification step is to concentrate the reaction solution under vacuum and reduce pressure and purify the reaction solution by column chromatography; the eluent is 100:1-5 of dichloromethane-methanol mixed solution.
An application of the near-infrared fluorescent probe in detecting sulfide. The probe can be used for quantitative detection of sulfide concentration in systems such as solution and the like.
In the above application, the excitation wavelength is 680nm, and the detection wavelength is 735 nm.
The invention has the advantages and beneficial effects that:
the invention designs and synthesizes a near-infrared fluorescent probe 3. The prepared probe can realize the rapid open type identification of the near infrared fluorescent signal of the selectivity and the sensitivity of the sulfide. The selectivity is high, and sulfides in the solution can be specifically identified; the anti-interference capability is strong, and the interference of other substances in the environment on the detection of the probe can be prevented; the sensitivity is high, and the method is suitable for detecting trace sulfides; the reaction is rapid, the color change is obvious, the synthesis is simple, the property is stable, and the application prospect is wide.
Drawings
FIG. 1 shows the structure of a fluorescent probe 3;
FIG. 2 is a graph of the fluorescence spectra of fluorescent probes with different analytes added, with the color change of the sulfide solution added in the inset;
FIG. 3 shows the change of the sulfide test strip.
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
The preparation route of example 1 and compound 2 is as follows:
the preparation method comprises the following specific steps:
dye 1(579mg, 1mmol), potassium carbonate (276mg, 2mmol) and resorcinol (220mg, 2mmol) were dissolved in acetonitrile (10mL) under argon atmosphere with stirring at room temperature, heated at 60 ℃ for 5 hours, and cooled to room temperature after completion of the reaction to obtain a reaction solution. And carrying out suction filtration on the reaction solution, and carrying out reduced pressure distillation and concentration on the filtrate to obtain a crude product. Separating and purifying the crude product by using column chromatography silica gel, wherein the volume ratio of eluent is 100:1-5 dichloromethane-methanol mixture to afford the desired product 2 as a dark blue solid in 81% yield.1H NMR(400MHz,DMSO-d6,ppm):8.27(1H),8.21(1H),8.04(1H),7.73(1H),7.61(1H),7.34(1H),7.25(1H),6.82(1H),6.77(1H),6.73(1H),4.74-4.68(2H),2.66-2.62(4H),1.80(2H),1.38(3H)；13C NMR(100MHz,DMSO-d6,ppm):169.66,161.51,158.41,154.28,142.60,141.49,131.64,129.39,129.17,127.53,127.32,126.03,124.28,115.75,114.49,114.14,112.35,105.07,102.36,43.43,28.97,24.78,20.56,13.91；HRMS(ESI):calcd.for C24H22NO2S+[M]+:388.1366,Found:388.1391。
The preparation route of example 2 and probe 3 is as follows:
the preparation method comprises the following specific steps:
compound 2(95mg, 0.2mmol) was weighed out and dissolved in dry dichloromethane (5mL), and after stirring for 5min with argon, 2, 4-dinitrofluorobenzene (94uL, 0.8mmol) and cesium carbonate (65mg, 0.2mmol) were added, the mixture was stirred at room temperature overnight. And (3) carrying out reduced pressure distillation and concentration on the reaction liquid to obtain a crude product, separating and purifying the crude product by using column chromatography silica gel, wherein the volume ratio of the eluent is 100:1-5 dichloromethane-methanol mixture to give the desired product 3 as a purple solid in 16% yield. m.p.190-192 ℃.1H NMR(400MHz,DMSO-d6,ppm):8.96(d,J＝2.8Hz,1H),8.53-8.50(m,1H),8.36-8.32(d,J＝14.8Hz,1H),8.24-8.23(d,J＝8.0Hz,1H),8.18-8.14(d,J＝8.8Hz,1H),7.81-7.77(m,1H),7.70-7.66(m,1H),7.60-7.59(d,J＝8.0Hz,1H),7.42-7.40(m,2H),7.24(s,1H),7.18-7.158(m,1H),7.05-7.02(d,J＝14.8Hz,1H),4.83-4.78(m,2H),2.70-2.67(m,4H),1.84-1.81(t,J＝4.6Hz,2H),1.42-1.39(t,J＝7.0Hz,3H)；13C NMR(100MHz,DMSO-d6,ppm):170.64,156.86,156.17,155.70,154.45,153.67,142.68,142.58,141.49,140.31,130.22,130.18,129.67,129.53,128.31,128.14,127.81,124.31,122.44,120.89,120.08,116.36,114.28,113.32,108.02,43.99,29.23,24.64,20.37,14.16.HRMS:(C30H24N3O6S+) M/z calculated value [ M]+554.1380 measured value [ M ]]+:554.1400.
Fluorescent detection application of probe 3:
the probe was formulated to a concentration of 5.0 × 10-3Storing the DMSO solution in mol/L in dark for later use. The detection method comprises the following steps:
1) selective detection of Probe 3
The probes were each prepared to 1 × 10 in phosphate buffered solution (containing 25% ethanol, 10mM, pH 7.4)-53mL of the solution to be detected in mol/L, and then respectively adding 1 × 10-4mol/L of different analytes (K)+，Na+Cu2+，Mg2+，Ca2+，Hg2+，Fe3+，F-，Cl-，Br-，I-，SO4 2-，SO3 2-，HSO3 -，HSO4 -，HCO3 -，H2PO4 -，P2O7 4-，ClO4 -，ClO-，OAc-，NO3 2-，NO2 -，H2O2，，Na2S, sodium citrate), excited at 680nm wavelength, the fluorescence emission spectra of each solution were tested and compared for fluorescence intensity at 735 nm. As can be seen from FIG. 2, only sodium sulfide can cause a significant change in fluorescence of the solution, while the fluorescence of the solution is not substantially changed when other small molecules are added, which means that the probe can specifically recognize sodium sulfide and is not substantially interfered.
2) Probe 3 for actual detection
A solution containing a trace amount of sodium sulfide is prepared and dripped on a probe test strip to observe the color change of the test strip, as shown in figure 3, the obvious change of purple color into blue color is observed on the test strip.
The above description is provided for further details of the present invention with reference to specific embodiments, and it should not be construed that the present invention is limited to these descriptions, and it is apparent to those skilled in the art that the present invention is applicable as a fluorescent probe to the novel fluorescent dye of the present invention, and the present invention is not limited to the fluorescent probe.
Claims (8)
1. A near-infrared fluorescent probe for detecting sulfide is characterized in that: structural formula (xvi):
2. a method for preparing a fluorescent probe according to claim 1, comprising the steps of:
1) heating the compound 1 and resorcinol in acetonitrile solution of potassium carbonate for reaction, separating and purifying to obtain a compound 2:
2) reacting the compound 2, 4-dinitrofluorobenzene and cesium carbonate in a dichloromethane solution, separating and purifying to obtain purple powder, namely a fluorescent probe 3 for detecting sulfide:
3. the method for preparing the near-infrared fluorescent probe for detecting the sulfide as claimed in claim 2, wherein in the step (1), the mass ratio of the compound 1, the resorcinol and the potassium carbonate is 1:2: 2; in the step (2), the mass ratio of the compound 2, 4-dinitrofluorobenzene and cesium carbonate is 1:4: 1.
4. The near-infrared fluorescent probe for detecting sulfide as claimed in claim 2, wherein in the step (1), the heating temperature is 60 ℃, and the reaction time is 5 h; in the step (2), the reaction time is 12 h.
5. The near-infrared fluorescent probe for detecting sulfide as claimed in claim 2, wherein in the step (1), the separation and purification step is to concentrate the reaction solution under vacuum to a crude product and purify the crude product by column chromatography; the eluent is dichloromethane-methanol mixed solution with the volume ratio of 100: 1-5.
6. The near-infrared fluorescent probe for detecting sulfide as claimed in claim 2, wherein in the step (2), the separation and purification step is to concentrate the reaction solution under vacuum to a crude product and purify the crude product by column chromatography; the eluent is dichloromethane-methanol mixed solution with the volume ratio of 100: 1-5.
7. Use of a fluorescent probe according to claim 1 for detecting a sulfide in water.
8. Use according to claim 7, wherein the fluorescent probe has an excitation wavelength of 680nm and an emission wavelength of 735 nm.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113149931A (en) * | 2021-03-18 | 2021-07-23 | 赣南医学院 | Sulfur negative ion fluorescent probe material and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102115610A (en) * | 2010-01-05 | 2011-07-06 | 大连理工大学 | Fluorescent dye, preparation method and application thereof |
| CN104946240A (en) * | 2015-05-28 | 2015-09-30 | 中国科学院海洋研究所 | Sulfide fluorescent probe and preparation method thereof |
| CN108329302A (en) * | 2018-03-22 | 2018-07-27 | 中国药科大学 | A kind of half flower cyanines class near infrared fluorescent probe compound of sulfide specificly-response and its preparation method and application |
| CN110128418A (en) * | 2019-06-27 | 2019-08-16 | 许昌学院 | A kind of near infrared fluorescent probe and its preparation method and application based on half flower cyanines structural derivative |
| CN110724114A (en) * | 2018-07-16 | 2020-01-24 | 北京工商大学 | Fluorescent probe for detecting bisulfite and hydrogen sulfide |
-
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102115610A (en) * | 2010-01-05 | 2011-07-06 | 大连理工大学 | Fluorescent dye, preparation method and application thereof |
| CN104946240A (en) * | 2015-05-28 | 2015-09-30 | 中国科学院海洋研究所 | Sulfide fluorescent probe and preparation method thereof |
| CN108329302A (en) * | 2018-03-22 | 2018-07-27 | 中国药科大学 | A kind of half flower cyanines class near infrared fluorescent probe compound of sulfide specificly-response and its preparation method and application |
| CN110724114A (en) * | 2018-07-16 | 2020-01-24 | 北京工商大学 | Fluorescent probe for detecting bisulfite and hydrogen sulfide |
| CN110128418A (en) * | 2019-06-27 | 2019-08-16 | 许昌学院 | A kind of near infrared fluorescent probe and its preparation method and application based on half flower cyanines structural derivative |
Non-Patent Citations (1)
| Title |
|---|
| LONGBIN XU等: "A novel near-infrared fluorescent probe for detecting intracellular alkaline phosphatase and imaging of living cells", 《J. MATER. CHEM. B》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113149931A (en) * | 2021-03-18 | 2021-07-23 | 赣南医学院 | Sulfur negative ion fluorescent probe material and preparation method and application thereof |
| CN113149931B (en) * | 2021-03-18 | 2023-04-28 | 赣南医学院 | Sulfur anion fluorescent probe material and preparation method and application thereof |
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