CN111849473A - Preparation of highly ordered and stable mesoporous/carbon dot fluorescent probe and application of highly ordered and stable mesoporous/carbon dot fluorescent probe in 2,4, 6-trinitrophenol detection - Google Patents
Preparation of highly ordered and stable mesoporous/carbon dot fluorescent probe and application of highly ordered and stable mesoporous/carbon dot fluorescent probe in 2,4, 6-trinitrophenol detection Download PDFInfo
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Abstract
The invention discloses a preparation method based on a mesoporous/carbon dot fluorescent probe and a detection method of 2,4, 6-trinitrophenol, the method is based on the formation of covalent bonds between 3-glycidoxypropyltrimethoxysilane functionalized mesoporous SBA-15 (SBA-15/560) and polyhydroxy Carbon Dots (CDs), a novel composite fluorescent probe is synthesized, the 2,4, 6-trinitrophenol interacts with surface functional groups of carbon quantum dots to cause the change of the fluorescence intensity of the carbon quantum dots, and the change of the fluorescence intensity of a solution is measured by a fluorescence spectrometer, so that the content of the 2,4, 6-trinitrophenol in the solution system can be rapidly detected. The method has the characteristics of high selectivity, high sensitivity, easy separation and low detection limit.
Description
Technical Field
The invention relates to the field of 2,4, 6-trinitrophenol detection, and particularly relates to a preparation method and application of a highly ordered and stable mesoporous/carbon dot fluorescent probe.
Background
2,4, 6-Trinitrophenol (TNP), also known as picric acid, is a nitroaromatic compound with a strong electron-withdrawing group and has strong danger. Although TNP has not been widely appreciated, it is undeniable that TNP has a greater explosive capacity than 2,4, 6-trinitrotoluene (TNT). TNP is widely used in military and many other industries, such as dye, gunpowder, rocket fuel, pharmaceuticals, etc. However, it is extremely easy to permeate into the environment, contaminating the ground water and soil, and gradually becoming an environmental pollutant. If the patient is carelessly inhaled or contacted with the medicine, symptoms such as anemia, abnormal liver function, and damage to respiratory organs can be caused. Therefore, in order to monitor environmental pollution and prevent terrorism threats, it is urgent to design a reliable TNP measurement method with high sensitivity and selectivity.
Various analytical techniques such as raman spectroscopy, electrochemiluminescence, mass spectrometry, electrochemistry, etc. have been used for TNP measurement. Each of these methods has characteristics, but still has some disadvantages. For example, it is not universal, complicated to operate, time and labor consuming, etc. Therefore, it is necessary to develop a simple method for detecting TNP in water.
As a novel 0-dimensional nano material with the diameter of 1-10 nm, the carbon quantum dots are widely applied to the fields of biological imaging, nano medicine, catalysis and the like due to low toxicity, excellent fluorescence performance and good water solubility. In particular as fluorescent probes in analytical chemistry. Mesoporous materials have attracted considerable attention because of their high surface area, highly uniform pore distribution, and ease of modification and functionalization.
On the basis of the above, the synthetic organic-inorganic hybrid optical sensor is researched. Two mesoporous/carbon dot composite fluorescent probes are prepared, and a method with high sensitivity, high selectivity and low cost for detecting 2,4, 6-trinitrophenol is established.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to develop a novel method for detecting 2,4, 6-trinitrophenol, and the method realizes simple, rapid and sensitive determination of the 2,4, 6-trinitrophenol with lower concentration by utilizing the in-situ supported polyhydroxy Carbon Sites (CDs) of the 3-glycidoxypropyltrimethoxysilane functionalized mesoporous SBA-15 (SBA-15/560) and forming covalent bonds with the SBA-15.
In order to realize the aim, the invention is realized by the following technical scheme that the method for preparing the highly ordered and stable mesoporous/carbon dot fluorescent probe and detecting the 2,4, 6-trinitrophenol comprises the following steps:
1) 1.21 g of tris (hydroxymethyl) aminomethane and 2.1 g of citric acid in a 50 ml beaker and then placed in an oven at 175 ℃ for 1 h (reaction 1 h after melting of the solid). Cooling to room temperature to obtain yellow solid, dissolving in sodium hydroxide solution, dialyzing for 48 hr (retaining molecular weight: 500 Da), and freeze drying to obtain CDs.
2) 2 g of P123 were dissolved in 15 g of water and 60 g of 2 mol/L HCl and the reaction solution was stirred at 35 ℃ until the solution was clear. TEOs was added to the solution with vigorous stirring to transfer the reaction to the kettle at 100 deg.C for 24 h, and the reaction was filtered and washed with water to give a white solid. Calcining the mixture for 6 hours in a muffle furnace at the temperature of 600 ℃ to remove the organic template, and obtaining white solid powder SBA-15.
3) 1 g and 2 mL KH-560 are weighed and dispersed in 100 mL of anhydrous toluene for the mesoporous SBA-15 obtained in the step 2), and stirred and refluxed for 6 h at the temperature of 120 ℃. After the reaction was complete, the SBA-15/560 nanoparticles were washed 3 times with ethanol and the washed powder was dried under vacuum at 40 ℃ for 24 h.
4) 0.5 g of SBA-15/560 from step 3) and 5 mg of CDs from step 1) were dispersed in 20 mL of DMF and reacted at 140 ℃ for 1 h. The SCDs were then dried in powder form by washing with Deionized (DI) water, centrifuging, and freeze-drying for 12 h. The resulting powder was light yellow, different from the white color of SBA-15/560. Finally, the complexed probes were dispersed in 10 ml PBS (0.2M pH 7) and stored at 4 ℃.
5) 2.5 mg of the composite probe was added to 10 mL of PBS (0.2M, pH 7.0), respectively, and sonicated for 10 min to ensure uniform dispersion.
6) Weighing a certain amount of reference substance 2,4, 6-trinitrophenol, and preparing the reference substance into a standard solution; adding different amounts of the standard solution into 5), standing for several minutes, and measuring the fluorescence intensity of the standard solution with a fluorescence spectrometer at an excitation wavelength of 350 nm
7) Establishing a standard curve of the concentration of the 2,4, 6-trinitrophenol and the fluorescence intensity of a fluorescence emission spectrum corresponding to the concentration at the emission wavelength of 430 nm;
8) the fluorescence intensity was measured by adding 2,4, 6-trinitrophenol at various concentrations to 5) as described in step 7).
9) Substituting the fluorescence intensity corresponding to the solution to be detected measured in the step 8) into the standard curve established in the step 7), and solving the concentration of the 2,4, 6-trinitrophenol in the solution to be detected.
Through optimizing the experimental scheme, the preferred technical scheme is as follows: the establishment of the relation between the concentration of the 2,4, 6-trinitrophenol and the fluorescence intensity in the step 7) specifically comprises the following steps: and drawing a standard curve by taking the ratio of the fluorescence intensity corresponding to the 2,4, 6-trinitrophenol standard solutions with different concentrations to the fluorescence intensity corresponding to the standard solution with the concentration of 0 as the ordinate and the concentration of the 2,4, 6-trinitrophenol standard solutions with different concentrations as the abscissa.
Through optimizing the experimental scheme, the preferable technical scheme is that the solution to be detected containing 2,4, 6-trinitrophenol is added into the control sample, the fluorescence intensity corresponding to the solution to be detected is measured according to the method, and the fluorescence intensity is substituted into the equation to obtain the corresponding concentration of the 2,4, 6-trinitrophenol in the solution to be detected.
Through optimizing the experimental scheme, the preferable technical scheme is that the method for detecting the 2,4, 6-trinitrophenol based on the mesoporous/carbon dot fluorescent probe is characterized in that the excitation wavelength is 350 nm, and the emission wavelength is 430 nm.
The invention also provides application of the method for detecting hexavalent chromium ions based on the carbon quantum dots prepared by gelatin in determination of the content of 2,4, 6-trinitrophenol in lake water samples
The invention has the beneficial effects that:
1. the invention synthesizes a novel composite fluorescent probe by forming covalent bonds between 3-glycidoxypropyltrimethoxysilane functionalized mesoporous SBA-15 and polyhydroxy carbon points.
2. The composite fluorescent probe prepared by the invention reserves the excellent fluorescence property of the polyhydroxy carbon point and the highly ordered mesoporous structure.
3. The composite fluorescent probe obtained by the invention is used for rapidly and sensitively measuring 2,4, 6-trinitrophenol, and the detection limit is 0.17 mu mol/L.
Drawings
FIG. 1 is a diagram showing a mechanism of synthesis in example 1;
FIG. 2 is a fluorescence microscopy profile of example 1;
FIG. 3 is the example 2 time-responsive detection of 2,4, 6-trinitrophenol on the composite probe;
FIG. 4 shows the selectivity of the composite probe of example 3 for 2,4, 6-trinitrophenol;
FIG. 5 is a graph showing different fluorescence emission curves of the fluorescent response composite probe of example 4 with different concentrations of 2,4, 6-trinitrophenol added;
FIG. 6 is a linear fit curve of the fluorescence relative intensity of the composite probe and 2,4, 6-trinitrophenol in example 4.
Detailed Description
Example 1
1. 1.21 g of tris (hydroxymethyl) aminomethane and 2.1 g of citric acid were weighed into a 50 ml beaker and then placed in an oven at 175 ℃ for 1 h (reaction 1 h after melting of the solid). Cooling to room temperature to obtain yellow solid, dissolving in sodium hydroxide solution, dialyzing for 48 hr (retaining molecular weight: 500 Da), and freeze drying to obtain CDs.
2. 2 g of P123 were dissolved in 15 g of water and 60 g of 2 mol/L HCl and the reaction solution was stirred at 35 ℃ until the solution was clear. TEOs was added to the solution with vigorous stirring to transfer the reaction to the kettle at 100 deg.C for 24 h, and the reaction was filtered and washed with water to give a white solid. Calcining the mixture for 6 hours in a muffle furnace at the temperature of 600 ℃ to remove the organic template, and obtaining white solid powder SBA-15.
3. 1 g and 2 mL KH-560 are weighed and dispersed in 100 mL of anhydrous toluene for the mesoporous SBA-15 obtained in the step 2, and stirred and refluxed for 6 h at the temperature of 120 ℃. After the reaction was complete, the SBA-15/560 nanoparticles were washed 3 times with ethanol and the washed powder was dried under vacuum at 40 ℃ for 24 h.
4. 0.5 g of SBA-15/560 from step 3 and 5 mg of CDs from step 1 were dispersed in 20 mL of DMF and reacted at 140 ℃ for 1 h. The SCDs were then dried in powder form by washing with Deionized (DI) water, centrifuging, and freeze-drying for 12 h. The resulting powder was light yellow, different from the white color of SBA-15/560. Finally, the complexed probes were dispersed in 10 ml PBS (0.2M pH 7) and stored at 4 ℃.
This example was used to synthesize a composite probe and to measure 2,4,6, -trinitrophenol, the principle of which is shown in FIG. 1.
The composite probe obtained in the embodiment has excellent fluorescence property, and under the excitation of three different colors of red, green and blue observed under a fluorescence confocal fluorescence microscope, the composite probe presents the corresponding fluorescence of three different colors of red, green and blue as shown in figure 2.
Example 2
1. 2.5 mg of the composite probe was added to 10 mL of PBS (0.2M, pH 7.0), respectively, and sonicated for 10 min to ensure uniform dispersion.
2. Weighing a certain amount of reference substance 2,4, 6-trinitrophenol, preparing into standard solution, adding 50 μ M of 2,4, 6-trinitrophenol into the dispersion system obtained in the step 1, respectively standing for 2,4,6, 8, 10, 12, 14, 16, 18 and 20 min, and measuring the fluorescence intensity of the system by using a fluorescence spectrometer with the excitation wavelength of 350 nm.
In order to observe the response time of the composite probe to 2,4, 6-trinitrophenol, FIG. 3 shows that the fluorescence intensity of the system rapidly decreases within 2 min and remains unchanged for 20 min.
Case implementation 3
1. 2.5 mg of the composite probe was added to 10 mL of PBS (0.2M, pH 7.0), respectively, and sonicated for 10 min to ensure uniform dispersion.
2. Preparing standard solutions of 2,4, 6-Trichlorophenol (TCP), 2, 6-Dichlorophenol (DCP), p-nitrobenzoic acid (PNB), p-nitrotoluene (PNT) and Nitrobenzene (NB) with the same concentration with ethanol as solvent, adding the standard solutions with the same concentration to each control group, standing for 5 min, and measuring fluorescence intensity with fluorescence spectrometer with excitation wavelength of 350 nm
FIG. 3 is a graph showing the effect of adding different substituted phenols on the fluorescence intensity of the composite probe in this example, and it can be seen from FIG. 4 that 2,4,6, -trinitrophenol has a significant quenching effect on the composite probe, indicating that the composite probe has good selectivity and specificity for 2,4,6, -trinitrophenol.
Case implementation 4
1. 2.5 mg of the composite probe was added to 10 mL of PBS (0.2M, pH 7.0), respectively, and sonicated for 10 min to ensure uniform dispersion.
2. Weighing a certain amount of reference substance 2,4, 6-trinitrophenol, and preparing the reference substance into a standard solution; adding different amounts of the standard solution into each control group, standing for several minutes, and measuring the fluorescence intensity of the control group by using a fluorescence spectrometer with the excitation wavelength of 350 nm;
3. establishing a standard curve of the concentration of the 2,4, 6-trinitrophenol and the fluorescence intensity of a fluorescence emission spectrum corresponding to the concentration at the emission wavelength of 430 nm;
4. the fluorescence intensity was measured by adding different concentrations of 2,4, 6-trinitrophenol to each control group as described in step 2.
And 5, substituting the fluorescence intensity corresponding to the solution to be detected measured in the step 4 into the standard curve established in the step 3, and solving the concentration of the 2,4, 6-trinitrophenol in the solution to be detected.
FIG. 5 is a graph showing the relationship between the fluorescence intensity and the concentration of 2,4,6, -trinitrophenol in the control group, and the linear fitting curve in FIG. 6 shows that the concentration of 2,4,6, -trinitrophenol in the control group is different from that of 2,4,6, -trinitrophenol in the control group, and the relative fluorescence intensity has a good linear relationship.
Claims (3)
1. A highly ordered and stable mesoporous/carbon dot fluorescent probe is characterized by comprising a 3-glycidoxypropyltrimethoxysilane functionalized mesoporous SBA-15 and polyhydroxy carbon dots, wherein the 3-glycidoxypropyltrimethoxysilane functionalized mesoporous SBA-15 is loaded with the polyhydroxy carbon dots in situ and forms covalent bonds with the polyhydroxy carbon dots.
2. A preparation method of a highly ordered and stable mesoporous/carbon dot fluorescent probe is characterized by comprising the following steps:
1) 1.21 g of tris (hydroxymethyl) aminomethane and 2.1 g of citric acid in a 50 mL beaker, which is then placed in an oven at 175 ℃ for 1 h; cooling to room temperature to obtain yellow solid, dissolving in sodium hydroxide solution, dialyzing for 48 hr, and freeze drying to obtain polyhydroxy CDs;
2) 2 g of P123, 15 g of water and 60 g of 2 mol/L HCl are mixed, and the obtained reaction solution is stirred at 35 ℃ until the solution is clear; adding TEOs into the solution under vigorous stirring, transferring the reaction solution into a reaction kettle, and reacting for 24 h at 100 ℃; carrying out suction filtration on the reaction product, and washing with water to obtain a white solid; calcining the mixture in a muffle furnace at the temperature of 600 ℃ for 6 hours to remove the organic template, and obtaining white solid powder SBA-15;
3) weighing 1 g of SBA-15 obtained in the step 2) and 2 mL of KH-560, dispersing in 100 mL of anhydrous toluene, and stirring and refluxing at 120 ℃ for 6 h; after the reaction is finished, washing the obtained SBA-15/560 nano-particles for 3 times by using ethanol, and carrying out vacuum drying on the washed powder for 24 hours at 40 ℃;
4) Dispersing 0.5 g of SBA-15/560 obtained in step 3) and 5 mg of polyhydroxy CDs obtained in step 1) in 20 mL of DMF, and reacting at 140 ℃ for 1 h; then washing with deionized water, centrifuging, and freeze-drying for 12 h to obtain SCDs dry powder; finally, the composite probe was dispersed in 10 mL PBS of 0.2M, pH =7 and stored at 4 ℃.
3. Use of a fluorescent probe according to claim 1 for the detection of 2,4, 6-trinitrophenol, comprising the steps of:
1) adding 2.5 mg of the composite probe into 10 mL of PBS with 0.2M, pH =7.0 respectively, and carrying out ultrasonic treatment for 10 min to ensure that the composite probe is uniformly dispersed;
2) weighing a certain amount of reference substance 2,4, 6-trinitrophenol, and preparing the reference substance into a standard solution; adding different amounts of the standard solution into each control group, standing for several minutes, and measuring the fluorescence intensity of the control group by using a fluorescence spectrometer with the excitation wavelength of 350 nm;
3) establishing a standard curve of the concentration of the 2,4, 6-trinitrophenol and the fluorescence intensity of a fluorescence emission spectrum corresponding to the concentration at the emission wavelength of 430 nm;
4) adding 2,4, 6-trinitrophenol with different concentrations into each control group according to the method of the step 2), and measuring the fluorescence intensity of the control group;
5) substituting the fluorescence intensity corresponding to the solution to be detected measured in the step 4) into the standard curve established in the step 3), and solving the concentration of the 2,4, 6-trinitrophenol in the solution to be detected.
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| CN115433573A (en) * | 2022-09-28 | 2022-12-06 | 山西大学 | Preparation method of oil-soluble carbon dots for detecting doxycycline hydrochloride |
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| CN105017148A (en) * | 2015-06-23 | 2015-11-04 | 陕西师范大学 | Bis(8-hydroxyquinoline)aluminum fluorescent complex and its use in detection of 2,4,6-trinitrophenol |
| CN111285830A (en) * | 2020-02-11 | 2020-06-16 | 安徽理工大学 | Fluorescent probe for rapidly identifying 2,4, 6-trinitrophenol and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017148A (en) * | 2015-06-23 | 2015-11-04 | 陕西师范大学 | Bis(8-hydroxyquinoline)aluminum fluorescent complex and its use in detection of 2,4,6-trinitrophenol |
| CN111285830A (en) * | 2020-02-11 | 2020-06-16 | 安徽理工大学 | Fluorescent probe for rapidly identifying 2,4, 6-trinitrophenol and preparation method thereof |
Non-Patent Citations (1)
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| XUECHUAN WANG ET AL.: "Determination of 2,4,6-trinitrophenol by in-situ assembly of SBA-15 with multi-hydroxyl carbon dots", 《ANALYTICA CHIMICA ACTA》, vol. 1098, 27 November 2019 (2019-11-27), pages 170 - 180, XP085984719, DOI: 10.1016/j.aca.2019.11.061 * |
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| CN115433573A (en) * | 2022-09-28 | 2022-12-06 | 山西大学 | Preparation method of oil-soluble carbon dots for detecting doxycycline hydrochloride |
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