CN108484490B - Fluorescent probe for detecting multiple metal ions in water and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for detecting various metal ions in water and a preparation method and application thereof. The probe is prepared from symmetric tetramethyl hexa-component cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine. The preparation method comprises the steps of taking the tetramethyl hexahydric cucurbituril, and dissolving the tetramethyl hexahydric cucurbituril in water to obtain a solution A; dissolving trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in water to obtain a solution B; and mixing the solution A and the solution B, and reacting at normal temperature to obtain the probe. The method is mainly used for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water. The probe provided by the invention can be used for detecting various ions of cesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium in water, and has the characteristics of higher sensitivity, lower detection cost, simple sample treatment, convenience in operation, rapidness in determination and real-time detection.
Description
Technical Field
The invention relates to a fluorescent probe for detecting metal ions in water and a preparation method and application thereof, in particular to a fluorescent probe for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water and a preparation method and application thereof.
Background
At present, the detection and analysis of cesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ions in drinking water are mainly performed by adopting absorption/emission spectroscopy, ion spectroscopy, inductively coupled plasma atomic emission spectroscopy, inductively coupled plasma mass spectrometry and the like. These methods have high accuracy and sensitivity, but these detection devices are expensive and require very specialized detection technicians to complete the detection, which is costly.
The fluorescent probe is a novel detection reagent, and is favored by people due to the advantages of higher sensitivity, lower detection cost, simple sample treatment, convenient operation, quick determination and real-time detection. However, at present, few fluorescent probes for detecting metal ions in water are available, and many fluorescent probes are capable of detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ions in water while detecting single metal ions, and are not reported.
Disclosure of Invention
The invention aims to provide a fluorescent probe for detecting various metal ions in water, and a preparation method and application thereof. The probe provided by the invention can be used for detecting various ions of cesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium in water, and has the characteristics of higher sensitivity, lower detection cost, simple sample treatment, convenience in operation, rapidness in determination and real-time detection.
The technical scheme of the invention is as follows: a fluorescent probe for detecting multiple metal ions in water is prepared from symmetric tetramethyl hexa-membered cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine.
The molecular formula of the fluorescent probe for detecting multiple metal ions in water is C40H44N24O12@C16H19N2I。
In the fluorescent probe for detecting various metal ions in water, the molar ratio of the tetramethyl hexa-component cucurbituril to the trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in the probe is 1: 0.5-2.
In the fluorescent probe for detecting various metal ions in water, the molar ratio of the tetramethyl six-membered cucurbituril to the trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in the probe is 1: 1.
A preparation method of the fluorescent probe for detecting multiple metal ions in water comprises the following steps:
1) taking tetramethyl hexa-component cucurbituril, and dissolving the tetramethyl hexa-component cucurbituril in water to obtain a solution A;
2) dissolving trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in water to obtain a solution B;
3) and mixing the solution A and the solution B, and reacting at normal temperature to obtain the probe.
In the above method for preparing a fluorescent probe for detecting multiple metal ions in water, the water added in step 1) and step 2) is secondary water with pH 7.
The application of the fluorescent probe for detecting various metal ions in water is used for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water.
The application of the fluorescent probe for detecting various metal ions in water comprises the following specific steps:
1) taking the probe, and adding water for dilution to obtain a probe standard solution;
2) adding water to be detected into the probe standard solution prepared in the step 1), standing for 10-20min, then performing fluorescence emission spectrometry with a fixed excitation wavelength of 459nm, and drawing a variation curve of the fluorescence intensity at the excited laser wavelength;
3) calculating a fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added into the fluorescent probe solution according to the curve in the step 2), and detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in the water.
In the application of the fluorescent probe for detecting multiple metal ions in water, in the step 1), the concentration of the standard solution of the probe is 2.0 x 10-5mol/L。
In the step 3), when the change of the fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added is more than +/-10%, the fact indicates that the water to be detected contains cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions; and when the change of the fluorescence emission spectrum intensity change value delta F under 582nm before and after the water to be detected is added is less than +/-10%, indicating that the water to be detected does not contain cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions.
The invention has the advantages of
1. The fluorescent probe can simultaneously detect cesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ions in water, can detect the ions as long as the ions contain one or more ions, and has the advantage of wide detection range.
2. According to the invention, a supermolecule complex is formed by utilizing symmetrical tetramethyl hexahydric cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine, when the metal ions are detected, the ions can damage the probe to form a new complex, and the fluorescence of the probe is quenched, so that the cesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ions in water can be simply, quickly and sensitively detected.
3. Compared with the traditional detection method, the detection cost is greatly reduced, the operation is convenient, and the real-time detection can be realized.
Anti-interference experiment
Separately preparing Li containing alkali metal ions+、Na+、K+And Rb+(ii) a Alkaline earth metal Mg2+、Ca2+、Sr2+And Ba2+(ii) a Transition metal Hg2+、Co2+、Ni2+、Cu2+、Cd2+、Pb2+、Zn2+、Al3+、Fe3+、Fe2+、Y2+、Cr3+And Mn2+(ii) a Rare earth metal La3+、Ce3+、Pr3+、Nd3+、Sm3+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Er3+、Tm3+、Yb3+And Lu3+The molar concentration of the above ions in the solution of (1) is 2.0 x 10-1mol/L。
Adding the above solutions into the solution with concentration of 2.0 x 10-5mol/L of a standard solution of the probe according to the invention, then fluorescence excitation is carried out according to the method of the invention and the results are analyzed.
The detection results are shown in FIGS. 2-5, and the experimental results show that in the aqueous solution, the fluorescence probe independently exists, the fluorescence intensity value at the position of the fixed excitation wavelength 459nm, the slit 5nm and the fluorescence emission wavelength 582nm under the voltage of 510v is strong, and Cs is+,Sr2+,Ba2+,Fe3 +,Cr3+,Hg2+,Eu3+,Tm3+,Yb3+No fluorescence spectrum property, adding Cs into probe standard solution+,Sr2+,Ba2+,Fe3+,Cr3 +,Hg2+,Eu3+,Tm3+,Yb3+Then, the fluorescence emission intensity of the solution corresponding to 582nm is obviously reduced, and the rest metals have no obvious change. The experimental result shows that the fluorescent probe in the alkali metal is used for detecting Cs in the alkali metal+Has good selectivity, and the alkaline earth metal is selective to Sr2+,Ba2+Has good selectivity, and can remove Al from transition metal3+With a slight decrease in the amount of fluorescence probe to Hg2+，Fe3 +，Cr3+Has good selectivity. Rare earth metal middle fluorescent probe pair Eu3+，Tm3+，Yb3+Has good selectivity.
Quantitative analysis
The concentration obtained by the invention is 2.0 x 10-5Adding Cs with different volume fractions into a standard solution of a fluorescent probe with mol/L+The detection result is shown in fig. 6, and it can be seen that the Cs in the standard solution added with different volume fractions is+Are different in concentration, and Cs is different in concentration+Can quench the fluorescent probe solution to different degrees, and the Cs+Line of responseThe sex range is (10.0-70.0) × 10-5mol/L, detection limit of 8.24 x 10-7mol/L。
The concentration obtained by the invention is 2.0 x 10-5Adding Sr into the standard solution of the fluorescent probe with different volume fractions2+Or Ba2+The detection results are shown in fig. 7-8, and it can be seen that Sr in the standard solution is added with different volume fractions2+Or Ba2+In different concentrations of Sr2+Or Ba2+Can quench the fluorescent probe solution to different degrees, and Sr2+Or Ba2+The linear range of the response is (10.0-70.0) × 10-5mol/L, detection limit is 8.47 x 10 respectively-7mol/L and 3.38 x 10-7mol/L。
The concentration obtained by the invention is 2.0 x 10-5Adding Hg contained in different volume fractions into mol/L fluorescent probe standard solution2+、Fe3+Or Cr3+The detection results are shown in FIGS. 9-11, and it can be seen that Hg in the standard solution is added in different volume fractions2+、Fe3+Or Cr3+Are different in concentration, and different concentrations of Hg2+、Fe3+Or Cr3+Can quench the fluorescent probe solution to different degrees, and Hg2+、Fe3+Or Cr3+The linear range of the response is (1.0-8.0) × 10-5mol/L, detection limit is 9.18 x 10 respectively-8mol/L、7.35*10-8mol/L and 8.57 x 10-8mol/L。
The concentration obtained by the invention is 2.0 x 10-5Adding Eu contained in different volume fractions into a standard solution of a fluorescent probe in mol/L3+、Tm3+Or Yb3+The detection results are shown in FIGS. 12-14, and it can be seen that Eu in the standard solution after adding different volume fractions3+、Tm3+Or Yb3+Different concentrations of Eu3+、Tm3+Or Yb3+Can quench the fluorescent probe solution to different degrees, and Eu3+、Tm3+Or Yb3+The linear range of the response is (20.0-140.0) × 10-5mol/L, detection limit is 1.05 x 10 respectively-6mol/L、1.35*10-6mol/L and 1.07 x 10-6mol/L。
Drawings
FIG. 1 is a schematic diagram of the structure of a probe according to the present invention;
FIG. 2 is a fluorescence spectrum curve of a probe standard solution when a solution containing alkali metal ions is added;
FIG. 3 is a fluorescence spectrum curve of a probe standard solution when a solution containing alkaline earth metal ions is added;
FIG. 4 is a fluorescence spectrum curve of a probe standard solution when a solution containing transition metal ions is added;
FIG. 5 is a fluorescence spectrum curve of a probe standard solution when a solution containing rare metal ions is added;
FIG. 6 shows the addition of Cs at various concentrations+The fluorescence spectrum curve of the solution of (1);
FIG. 7 shows the addition of Sr at various concentrations2+The fluorescence spectrum curve of the solution of (1);
FIG. 8 shows the addition of Ba in different concentrations2+The fluorescence spectrum curve of the solution of (1);
FIG. 9 shows the addition of Hg at various concentrations2+The fluorescence spectrum curve of the solution of (1);
FIG. 10 shows the addition of Fe at various concentrations3+The fluorescence spectrum curve of the solution of (1);
FIG. 11 shows the addition of Cr in different concentrations3+The fluorescence spectrum curve of the solution of (1);
FIG. 12 shows the addition of Eu in different concentrations3+The fluorescence spectrum curve of the solution of (1);
FIG. 13 shows the addition of different concentrations of a compound containing Tm3+The fluorescence spectrum curve of the solution of (1);
FIG. 14 shows the addition of Yb in various concentrations3+The fluorescence spectrum curve of the solution (2).
Detailed Description
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Examples of the invention
Example 1: a fluorescent probe for detecting multiple metal ions in water is prepared from symmetrical tetramethyl hexa-membered cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in a molar ratio of 1:1, preparing the composition.
The preparation method of the fluorescent probe for detecting various metal ions in water comprises the following steps:
1) taking tetramethyl hexa-component cucurbituril, and adding secondary water with pH of 7 to dissolve the tetramethyl hexa-component cucurbituril to obtain a solution A;
2) dissolving trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in secondary water with pH 7 to obtain solution B;
3) and mixing the solution A and the solution B, and reacting at normal temperature to obtain the probe.
The method for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water by using the fluorescent probe comprises the following steps:
1) diluting the probe with water to obtain the probe with concentration of 2.0 x 10-5A probe standard solution of mol/L;
2) adding water to be detected into the probe standard solution prepared in the step 1), standing for 15min, then performing fluorescence emission spectrometry with a fixed excitation wavelength of 459nm, and drawing a change curve of the fluorescence intensity at the excited laser wavelength;
3) calculating a fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added into the fluorescence probe solution according to the curve of the step 2), and when the change of the fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added is more than +/-10%, indicating that the water to be detected contains cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions; and when the change of the fluorescence emission spectrum intensity change value delta F under 582nm before and after the water to be detected is added is less than +/-10%, indicating that the water to be detected does not contain cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions.
Example 2: a fluorescent probe for detecting multiple metal ions in water is prepared from symmetrical tetramethyl hexa-membered cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in a molar ratio of 1: 0.5.
The preparation method of the fluorescent probe for detecting various metal ions in water comprises the following steps:
1) taking tetramethyl hexa-component cucurbituril, and adding secondary water with pH of 7 to dissolve the tetramethyl hexa-component cucurbituril to obtain a solution A;
2) dissolving trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in secondary water with pH 7 to obtain solution B;
3) and mixing the solution A and the solution B, and reacting at normal temperature to obtain the probe.
The method for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water by using the fluorescent probe comprises the following steps:
1) diluting the probe with water to obtain the probe with concentration of 2.0 x 10-5A probe standard solution of mol/L;
2) adding water to be detected into the probe standard solution prepared in the step 1), standing for 10min, then performing fluorescence emission spectrometry with a fixed excitation wavelength of 459nm, and drawing a change curve of the fluorescence intensity at the excited laser wavelength;
3) calculating a fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added into the fluorescence probe solution according to the curve of the step 2), and when the change of the fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added is more than +/-10%, indicating that the water to be detected contains cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions; and when the change of the fluorescence emission spectrum intensity change value delta F under 582nm before and after the water to be detected is added is less than +/-10%, indicating that the water to be detected does not contain cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions.
Example 3: a fluorescent probe for detecting multiple metal ions in water is prepared from symmetrical tetramethyl hexa-membered cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in a molar ratio of 1: 2, and (3) preparing.
The preparation method of the fluorescent probe for detecting various metal ions in water comprises the following steps:
1) taking tetramethyl hexa-component cucurbituril, and adding secondary water with pH of 7 to dissolve the tetramethyl hexa-component cucurbituril to obtain a solution A;
2) dissolving trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in secondary water with pH 7 to obtain solution B;
3) and mixing the solution A and the solution B, and reacting at normal temperature to obtain the probe.
The method for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water by using the fluorescent probe comprises the following steps:
1) diluting the probe with water to obtain the probe with concentration of 2.0 x 10-5A probe standard solution of mol/L;
2) adding water to be detected into the probe standard solution prepared in the step 1), standing for 20min, then performing fluorescence emission spectrometry with a fixed excitation wavelength of 459nm, and drawing a change curve of the fluorescence intensity at the excited laser wavelength;
3) calculating a fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added into the fluorescence probe solution according to the curve of the step 2), and when the change of the fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added is more than +/-10%, indicating that the water to be detected contains cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions; and when the change of the fluorescence emission spectrum intensity change value delta F under 582nm before and after the water to be detected is added is less than +/-10%, indicating that the water to be detected does not contain cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions.
Claims (7)
1. A fluorescent probe for detecting various metal ions in water is characterized in that: is prepared from symmetric tetramethyl hexa-component cucurbituril and trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine;
the molecular formula of the probe is C40H44N24O12@C16H19N2I；
The mole ratio of the tetramethyl hexa-component cucurbituril to the trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in the probe is 1: 0.5 to 2;
the preparation method of the fluorescent probe for detecting various metal ions in water comprises the following steps:
1) taking tetramethyl hexa-component cucurbituril, and dissolving the tetramethyl hexa-component cucurbituril in water to obtain a solution A;
2) dissolving trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in water to obtain a solution B;
3) and mixing the solution A and the solution B, and reacting at normal temperature to obtain the probe.
2. The fluorescent probe for detecting various metal ions in water according to claim 1, wherein: the mole ratio of the tetramethyl hexa-component cucurbituril to the trans-4-4 (dimethylamino) styryl-1-methylpyridine iodine in the probe is 1: 1.
3. the fluorescent probe for detecting various metal ions in water according to claim 1, wherein: the water added in the step 1) and the step 2) is secondary water with the pH value of 7.
4. Use of a fluorescent probe for detecting multiple metal ions in water according to any one of claims 1 to 3, wherein: is used for detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in water.
5. The application of the fluorescent probe for detecting various metal ions in water as claimed in claim 4, wherein the specific method is as follows:
1) taking the probe, and adding water for dilution to obtain a probe standard solution;
2) adding water to be detected into the probe standard solution prepared in the step 1), standing for 10-20min, then performing fluorescence emission spectrometry with a fixed excitation wavelength of 459nm, and drawing a variation curve of the fluorescence intensity at the excited laser wavelength;
3) calculating a fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added into the fluorescent probe solution according to the curve in the step 2), and detecting cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions in the water.
6. The use of the fluorescent probe for detecting multiple metal ions in water according to claim 5, wherein: in the step 1), the concentration of the probe standard solution is 2.0 x 10-5mol/L。
7. The use of the fluorescent probe for detecting multiple metal ions in water according to claim 5, wherein: in the step 3), when the change of the fluorescence emission spectrum intensity change value delta F corresponding to 582nm before and after the water to be detected is added is more than +/-10%, the fact indicates that the water to be detected contains cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions; and when the change of the fluorescence emission spectrum intensity change value delta F under 582nm before and after the water to be detected is added is less than +/-10%, indicating that the water to be detected does not contain cesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ions.
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| CN113670867B (en) * | 2021-07-16 | 2023-08-01 | 贵州大学 | Supermolecule fluorescent sensing array and method for detecting multiple metal ions in aqueous solution |
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