CN111704724B - Preparation method of luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity and product - Google Patents
Preparation method of luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity and product Download PDFInfo
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Abstract
The invention discloses a method for preparing a luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity and a product thereof, cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-di (4-pyridine) ethylene-fluorene are added into a mixed solution of water and N, N-dimethylacetamide, and are stirred to prepare a stable suspension; placing the prepared suspension in a closed reaction kettle for heating reaction, then slowly cooling to room temperature, filtering, washing and drying the product to obtain the luminescent crystal material [ Cd2(L)(BPEA)(H2O)]n. The invention has the advantage of obtaining the luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]n。
Description
Technical Field
The invention belongs to the technical field of luminescent crystal materials, and particularly relates to a preparation method and a product of a luminescent crystal material capable of detecting picric acid in an aqueous solution with high sensitivity.
Background
As the use of explosive materials in industrial fields has become increasingly widespread, the risks to the environment, human health and homeland security have received much attention, and how to detect these explosives efficiently and reliably has become a hot spot of recent research.
As a main explosive, picric acid is widely applied to industries such as fireworks, dyes, leather and the like, not only causes pollution to soil and water systems, but also influences human health and causes symptoms such as vomiting, nervous system injury and the like. Therefore, the real-time monitoring of picric acid is of great significance to protect the environment and human health. Luminescent crystalline materials have been used to detect picric acid due to their high sensitivity and selectivity in detection applications.
Water stability is a key attribute of the material in practical application, however, most of the luminescent crystal materials reported earlier are sensitive to water, and the practical application of the luminescent crystal materials is limited by the instability of water, so that the preparation of the water-stable luminescent crystal materials for detecting picric acid is more practical.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made keeping in mind the above and/or other problems occurring in the prior art.
Therefore, the present invention aims at overcoming the shortcomings of the prior art and providing a method for preparing a luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity.
In order to solve the technical problems, the invention provides the following technical scheme: a method for preparing luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity comprises adding cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene into mixed solution of water and N, N-dimethylacetamide, and stirring to obtain stable suspension; placing the prepared suspension in a closed reaction kettle for heating reaction, then slowly cooling to room temperature, filtering, washing and drying the product to obtain the luminescent crystal material [ Cd2(L)(BPEA)(H2O)]n(ii) a Wherein the molar ratio of the reaction starting materials of cadmium nitrate, 4, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene is 1: 0.5-2.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the method comprises the step of adding cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene into a mixed solution of water and N, N-dimethylacetamide, wherein the volume range of the mixed solvent of water and N, N-dimethylacetamide for adding 0.1mmol of cadmium nitrate is 5-10 mL.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the volume ratio of the solvent water to the N, N-dimethylacetamide is 1: 0.5-2.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the volume ratio of the solvent water to the N, N-dimethylacetamide is 1: 1.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the temperature of the heating reaction is 140-180 ℃.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the heating reaction time is 68-82 h.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the reaction cooling rate is 2-7 ℃/h.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: and stirring to prepare a stable suspension, wherein the stirring speed is 500-800 r/min, and the stirring time is 30-60 min.
As a preferred embodiment of the method for preparing the luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity, the invention is characterized in that: the molar ratio of the reaction starting materials of cadmium nitrate, 4, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene is 0.1: 0.1: 0.05.
it is a further object of the present invention to overcome the deficiencies of the prior art by providing a product made by the method of making a luminescent crystalline material that is capable of detecting picric acid in an aqueous solution with high sensitivity.
The invention has the beneficial effects that:
(1) the invention provides a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method adopts a hydrothermal synthesis method, has simple synthesis route, easy control, simple preparation of synthesis raw materials, high crystal purity and high yield; prepared [ Cd ]2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability, and can detect picric acid in water by high-sensitivity fluorescence.
(2) [ Cd ] prepared by the invention2(L)(BPEA)(H2O)]nThe material has good propertiesThe stability of the compound is high, and simultaneously, the picric acid can be detected by luminescence quenching in aqueous solution.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without inventive exercise. Wherein:
FIG. 1 shows a crystalline material [ Cd ] obtained in example 1 of the present invention2(L)(BPEA)(H2O)]nA three-dimensional structure diagram (some atoms are omitted).
FIG. 2 shows a crystalline material [ Cd ] obtained in example 1 of the present invention2(L)(BPEA)(H2O)]nPowder X-ray diffraction pattern of (1).
FIG. 3 shows a crystalline material [ Cd ] obtained in example 1 of the present invention2(L)(BPEA)(H2O)]nTo which aqueous suspensions of picric acid (1 mmole per liter) were added in different volumes.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, specific embodiments thereof are described in detail below with reference to examples of the specification.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
The raw materials in the invention are as follows: 9-bis (4-pyridine) etheno-fluorene, which is patented (application No. 2019109808914), and is published by: zhang J F, Ren S M, Xia H C, Jia W, Zhang C, AIE-ligand-based luminescence Cd (II) -organic frame work as the first "turn-on" Fe3+ sensor in aqueous medium [ J ]. Journal of Materials Chemistry C.2020,8: 1427-.
Example 1
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.1mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 6mL of water and N, N-dimethylacetamide (V: V ═ 1:1) and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 160 ℃, reacting for 72 hours, slowly cooling to room temperature at the rate of 5 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Detecting the detection performance of picric acid: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively.
FIG. 1 shows the crystalline material [ Cd ] obtained in this example2(L)(BPEA)(H2O)]nA three-dimensional structure diagram (some atoms are omitted). FIG. 2 shows the crystalline material [ Cd ] obtained in this example2(L)(BPEA)(H2O)]nPowder X-ray diffraction pattern of (1). As can be seen, the crystalline material [ Cd ] prepared2(L)(BPEA)(H2O)]nThe powder X-ray diffraction pattern is basically consistent with the X-ray diffraction pattern calculated by theory, which shows that the crystal material prepared by the invention has high purity. At the same time, the prepared crystalThe X-ray diffraction pattern of the bulk material after being soaked in water for one week is basically consistent with the X-ray diffraction pattern calculated theoretically, which shows that the prepared crystal has good stability in water.
FIG. 3 shows the crystalline material [ Cd ] obtained in this example2(L)(BPEA)(H2O)]nTo which aqueous suspensions of picric acid (1 mmole per liter) were added in different volumes. It can be seen that the fluorescence intensity of the aqueous suspension of the material was measured under excitation at a wavelength of 319nm, and then 1 mmol/l of an aqueous solution of picric acid was gradually added dropwise to the aqueous suspension of the material, and the luminescence intensity of the aqueous suspension of the material was remarkably decreased as the amount of picric acid was increased, whereby it can be seen that the material can detect picric acid in a highly sensitive aqueous phase.
Example 2
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.1mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 6mL of water and N, N-dimethylacetamide (V: V ═ 1:1) and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 150 ℃, reacting for 72 hours, slowly cooling to room temperature at the rate of 5 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Detecting the detection performance of picric acid: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively. With the increase of the amount of picric acid, the luminous intensity of the material water suspension is obviously reduced, picric acid can be detected by high-sensitivity fluorescence in water, and simultaneously, the prepared [ Cd2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability.
Example 3
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.1mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 6mL of water and N, N-dimethylacetamide (V: V ═ 1:1) and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 160 ℃, reacting for 70 hours, slowly cooling to room temperature at the rate of 5 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Detecting the detection performance of picric acid: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively. With the increase of the amount of picric acid, the luminous intensity of the material water suspension is obviously reduced, picric acid can be detected by high-sensitivity fluorescence in water, and simultaneously, the prepared [ Cd2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability.
Example 4
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.1mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 8mL of water and N, N-dimethylacetamide (V: V ═ 1:1) and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 160 ℃, reacting for 72 hours, slowly cooling to room temperature at the rate of 5 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Picric acid detection performance detection: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively. With the increase of the amount of picric acid, the luminous intensity of the material water suspension is obviously reduced, picric acid can be detected by high-sensitivity fluorescence in water, and simultaneously, the prepared [ Cd2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability.
Example 5
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.1mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 6mL of water and N, N-dimethylacetamide (V: V ═ 1:1) and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 160 ℃, reacting for 72 hours, slowly cooling to room temperature at the rate of 2 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Detecting the detection performance of picric acid: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively. With the increase of the amount of picric acid, the luminous intensity of the material water suspension is obviously reduced, picric acid can be detected by high-sensitivity fluorescence in water, and simultaneously, the prepared [ Cd2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability.
Example 6
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.2mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 6mL of water and N, N-dimethylacetamide (V: V ═ 1:1) and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 160 ℃, reacting for 72 hours, slowly cooling to room temperature at the rate of 2 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Detecting the detection performance of picric acid: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively. With the increase of the amount of picric acid, the luminous intensity of the material water suspension is obviously reduced, picric acid can be detected by high-sensitivity fluorescence in water, and simultaneously, the prepared [ Cd2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability.
Example 7
The invention relates to a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method comprises the following steps:
firstly, adding 0.1mmol of cadmium nitrate, 0.1mmol of 4, 4-diphenylethylene dicarboxylic acid and 0.05mmol of 9-bis (4-pyridine) ethylene-fluorene into 6mL of water and N, N-dimethylacetamide (V: V ═ 1:2), and stirring to prepare a stable suspension, wherein the stirring speed is 800r/min, and the stirring time is 30 min;
and step two, placing the suspension prepared in the step one in a closed reaction kettle, heating to 160 ℃, reacting for 72 hours, slowly cooling to room temperature at the rate of 2 ℃ per hour, filtering, washing and drying to obtain the crystal material.
Detecting the detection performance of picric acid: the prepared crystalline material (1 mg) was dispersed in 3 ml of water, to which different volumes of aqueous solutions (1 mmol per liter) containing picric acid were added, and the fluorescence intensities thereof were measured under excitation light of 319nm, respectively. With the increase of the amount of picric acid, the luminous intensity of the material aqueous suspension is remarkably reduced, and the material aqueous suspension can be subjected to high-sensitivity fluorescence detection in waterPicric acid, and simultaneously, the prepared [ Cd ]2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability.
The yield of the product of the invention is calculated based on the amount of added cadmium ions, and the results of the determination of examples 1-7 are shown in Table 1.
TABLE 1
As can be seen from Table 1, the molar ratio of the reaction starting materials cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene had a large influence on the yield, and when the ratio of the reactants added exceeded the optimum ratio, the yield was not good. Meanwhile, the volume ratio of the solvent water to the N, N-dimethylacetamide is larger than the volume ratio of the solvent water to the N, N-dimethylacetamide, so that the yield is greatly influenced, and the optimal ratio is 1: when the addition volume is larger than the optimum ratio, less crystal is precipitated and the yield is lowered.
The invention provides a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nPreparation method of (1), crystalline material [ Cd ] prepared by the method2(L)(BPEA)(H2O)]nThe powder X-ray diffraction pattern is basically consistent with the X-ray diffraction pattern calculated by theory, which shows that the crystal material prepared by the invention has high purity. Meanwhile, the X-ray diffraction pattern of the prepared crystal material after being soaked in water for one week is basically consistent with the X-ray diffraction pattern calculated by theory, which shows that the prepared crystal has good stability in water.
Crystalline material [ Cd ] prepared in the invention2(L)(BPEA)(H2O)]nThe change in fluorescence of the aqueous suspension of the material upon addition of different volumes of aqueous solution of picric acid (1 mmol per liter) was observed, as the fluorescence intensity of the aqueous suspension of the material was measured under excitation at a wavelength of 319nm, and then 1mmol per liter of aqueous solution of picric acid was gradually added dropwise to the aqueous suspension of the material, the luminescence intensity of which decreased significantly as the amount of picric acid increasedTherefore, the material can detect picric acid in a high-sensitive water phase.
The invention provides a luminescent crystal material [ Cd ] capable of detecting picric acid in aqueous solution with high sensitivity2(L)(BPEA)(H2O)]nThe preparation method adopts a hydrothermal synthesis method, has simple synthesis route, easy control, simple preparation of synthesis raw materials, high crystal purity and high yield; prepared [ Cd ]2(L)(BPEA)(H2O)]nThe material has good chemical and optical stability, and can detect picric acid in water by high-sensitivity fluorescence. [ Cd ] prepared by the invention2(L)(BPEA)(H2O)]nThe material has good water stability, and can be used for detecting picric acid by luminescence quenching in an aqueous solution.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.
Claims (6)
1. A method for preparing a luminescent crystal material capable of detecting picric acid in aqueous solution with high sensitivity is characterized in that: comprises the steps of (a) preparing a mixture of a plurality of raw materials,
adding cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene into a mixed solution of water and N, N-dimethylacetamide, and stirring to obtain a stable suspension;
placing the prepared suspension in a closed reaction kettle for heating reaction, then slowly cooling to room temperature, filtering, washing and drying the product to obtain the luminescent crystal material [ Cd2(L)(BPEA)(H2O)]nL is 9-di (4-pyridine) ethylene-fluorene, BPEA is 4, 4-diphenylethylene dicarboxylic acid; wherein the content of the first and second substances,
the molar ratio of the reaction starting materials of cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene is 1: 0.5-2;
the volume range of water and the N, N-dimethylacetamide mixed solvent required by adding 0.1mmol of cadmium nitrate is 5-10 mL;
the volume ratio of the solvent water to the N, N-dimethylacetamide is 1: 1.
2. The method for preparing a luminescent crystalline material for highly sensitive detection of picric acid in an aqueous solution according to claim 1, wherein: the temperature of the heating reaction is 140-180 ℃.
3. The method for preparing a luminescent crystalline material for highly sensitive detection of picric acid in an aqueous solution according to claim 1, wherein: the heating reaction time is 68-82 h.
4. The method for preparing a luminescent crystalline material for highly sensitive detection of picric acid in an aqueous solution according to claim 1, wherein: the reaction cooling rate is 2-7 ℃/h.
5. The method for preparing a luminescent crystalline material for highly sensitive detection of picric acid in an aqueous solution according to claim 1, wherein: and stirring to prepare a stable suspension, wherein the stirring speed is 500-800 r/min, and the stirring time is 30-60 min.
6. The method for preparing a luminescent crystalline material for highly sensitive detection of picric acid in an aqueous solution according to claim 1, wherein: the molar ratio of the reaction starting materials of cadmium nitrate, 4-diphenylethylene dicarboxylic acid and 9-bis (4-pyridine) ethylene-fluorene is 0.1: 0.1: 0.05.
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