CN111116458A - Fluorescent probe for detecting aluminum ions, and preparation method and application thereof - Google Patents
Fluorescent probe for detecting aluminum ions, and preparation method and application thereof Download PDFInfo
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- CN111116458A CN111116458A CN201911274985.6A CN201911274985A CN111116458A CN 111116458 A CN111116458 A CN 111116458A CN 201911274985 A CN201911274985 A CN 201911274985A CN 111116458 A CN111116458 A CN 111116458A
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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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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- G—PHYSICS
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The invention discloses a fluorescent probe for detecting aluminum ions, and a preparation method and application thereof, and belongs to the technical field of fluorescent probes. The molecular formula of the fluorescent probe for detecting aluminum ions is C78H60Br4N4O4The chemical name is N, N '-tetra (2-oxo-2-phenylethyl) -4,4' -tetra (4-pyridyl) tetraphenylethylenebromonium salt, and the structural formula shown in the formula (I):
the invention also discloses a preparation method and application of the fluorescent probe for detecting aluminum ions. The invention takes the onium salt of pyridine based on tetraphenylethylene as a fluorescent probe, and can realize rapidness, high sensitivity and high sensitivitySelectively detect the aluminum ions in the solution, realize naked eye qualitative detection and fluorescence quantitative detection of the aluminum ions, and have wide application prospects in the fields of biochemistry, analytical chemistry and environmental science.
Description
Technical Field
The invention relates to a fluorescent probe for detecting aluminum ions, a preparation method and application thereof, and belongs to the technical field of fluorescent probes.
Background
Aluminum is not an essential trace element for the human body, and no cases of aluminum are found without any doubt. People take 10mg to 18mg of aluminum from their diets every day, most of which is excreted via the digestive tract with the feces, and a small percentage of which accumulates in the testes, kidneys, spleen, muscles, bones and brain tissue. Although aluminum has been considered to have little influence on human health, the brain content of patients with near-senile dementia or mental disorder is 10-30 times higher than that of normal persons. Further research proves that the food contains excessive aluminum, which can cause early aging of people, and the accumulation of aluminum in the brain can cause the degeneration of cranial nerves, the memory decline, the intelligence and the character can be affected, even the senile dementia is shown. When the accumulation of aluminum in vivo exceeds 5-16 times of normal, it can inhibit the absorption of phosphorus by intestinal tract, and interfere normal metabolism of calcium and phosphorus.
The prior art methods for detecting aluminum ions include atomic spectrometry, ion chromatography, electrochemical analysis, plasma emission spectrometry, mass spectrometry and the like. However, the above detection method has many disadvantages, such as high requirements for instruments, complicated operation process, long detection time, etc.
Compared with the detection method, the fluorescent probe has the following characteristics: 1) the time consumption is short; 2) the sensitivity is high; 3) The selectivity is good; 4) the detection limit is low; 5) is convenient and quick. Aggregation Induced Emission (AIE) is a particular fluorescence emission phenomenon discovered in recent years, which refers to the phenomenon in which dye molecules do not emit fluorescence in dilute solutions, but emit stronger fluorescence in concentrated solutions or aggregates. Tetraphenylethylene is a typical compound with AIE properties. The tetraphenyl ethylene derivative has a large conjugated system in its molecule, shows a plurality of unique photoelectric properties and biological activities, and is widely applied to a plurality of fields, such as biological probes, Metal Organic Frameworks (MOFs), medical imaging and chemical sensors.
However, at present, there are few reports on fluorescent probes for detecting aluminum ions, and therefore, it is necessary to enhance the research and development of aluminum ion fluorescent probes and expand the application range of fluorescent probes.
Disclosure of Invention
One of the purposes of the present invention is to provide a fluorescent probe for detecting aluminum ions. The invention takes the onium salt of pyridine based on tetraphenylethylene as a fluorescent probe, can quickly detect aluminum ions in a solution with high sensitivity and high selectivity, realizes naked eye qualitative detection and fluorescent quantitative detection of the aluminum ions, and has wide application prospect in the fields of biochemistry, analytical chemistry and environmental science.
The technical scheme for solving the problems is as follows: a fluorescent probe for detecting aluminum ions has a molecular formula of C78H60Br4N4O4The chemical name is N, N '-tetra (2-oxo-2-phenylethyl) -4,4' -tetra (4-pyridyl) tetraphenylethylenebromonium salt, and the structural formula shown in the formula (I):
the invention has the beneficial effects that:
the invention takes the onium salt of pyridine based on tetraphenylethylene as a fluorescent probe, can quickly detect aluminum ions in a solution with high sensitivity and high selectivity, realizes naked eye qualitative detection and fluorescent quantitative detection of the aluminum ions, and has wide application prospect in the fields of biochemistry, analytical chemistry and environmental science.
The molecular formula of the fluorescent probe for detecting aluminum ions is C78H60Br4N4O4Nuclear magnetic hydrogenSpectrum:1h NMR (400MHz, DMSO) δ 9.01(d, J ═ 6.3Hz,8H),8.65(d, J ═ 6.4Hz,8H), 8.10(t, J ═ 8.3Hz,16H),7.82(t, J ═ 7.3Hz,4H),7.68(t, J ═ 7.5Hz, 8H),7.46(d, J ═ 8.1Hz,8H),6.49(s, 8H). Nuclear magnetic carbon spectrum:13C NMR(100MHz,DMSO) δ191.6,154.8,146.8,146.7,141.9,135.3,134.2,132.8,129.7,128.9, 124.6,66.1。
on the basis of the technical scheme, the invention can be further improved as follows.
Further, the detection limit of the fluorescent probe for detecting aluminum ions on the aluminum ions is 1 × 10-6mol/L。
The adoption of the further beneficial effects is as follows: the invention can realize the detection limit of the aluminum ions to be 1 multiplied by 10- 6The mol/L can be used for detecting aluminum ions with high selectivity and high sensitivity, has low detection limit and high sensitivity, and has important practical application value for detecting the aluminum ions in the complex environment.
The second object of the present invention is to provide a method for preparing the fluorescent probe for detecting aluminum ions. The fluorescent probe for detecting aluminum ions has the advantages of simple preparation method, high yield of the onium salt for synthesizing the tetraphenylethylene pyridine, easy operation, wide market prospect and suitability for large-scale popularization and application.
The technical scheme for solving the problems is as follows: a preparation method of a fluorescent probe for detecting aluminum ions comprises the following steps:
step 1: taking 0.10g of 2-bromoacetophenone, placing the 2-bromoacetophenone in a three-neck flask, and adding 10mL of solvent for dissolving;
step 2: dissolving 0.14g of tetra (4-pyridine biphenyl) ethylene in 5mL of solvent consistent with the step 1, slowly adding the solution into the three-neck flask obtained in the step 1, and reacting for 1-24h under the reflux condition, wherein the reaction temperature is 80-90 ℃;
and step 3: cooling the reactant to room temperature, filtering, taking precipitate, washing for 3 times by using the solvent consistent with the step 1, drying to obtain the compound shown in the formula (I),
The principle of the invention is as follows:
when the probe molecules are monodisperse in the solution, the luminescence is very weak, and when the system contains aluminum ions, the probe molecules are aggregated due to the complexation between the probe molecules and the metal ions, and the fluorescence of the probe system is obviously enhanced, so that the aim of detecting the aluminum ions is fulfilled.
The chemical reaction formula of the invention is as follows:
on the basis of the technical scheme, the invention can be further improved as follows.
Further, in the step 1, the step 2 and the step 3, the solvent is any one of acetonitrile, chloroform, methanol, ethanol, N-dimethylformamide, tetrahydrofuran, 1, 4-dioxane and cyclohexane.
Further, in the step 3, the drying mode is vacuum drying, the vacuum degree is-0.098 MPa, the temperature is 60 ℃, and the time is 5 hours.
The adoption of the further beneficial effects is as follows: with the above parameters, the drying effect is optimal.
The third purpose of the invention is to provide the application of the fluorescent probe for detecting aluminum ions. The fluorescent probe for detecting aluminum ions or the prepared fluorescent probe for detecting aluminum ions can be used for preparing aluminum ions in a detection solution. The fluorescent probe for detecting aluminum ions described above is preferred for aluminum ions and for other ions (e.g., Mn)2+、Cr3+、Zn2+、Pb2+、Cd2+、Ag+、Co2+、 Mg2+、Na+、Ca2+、Cu2+、Hg+And Fe3+Etc.) response is weak, thereby exhibiting excellent selectivity.
The technical scheme for solving the problems is as follows: the fluorescent probe for detecting aluminum ions or the prepared fluorescent probe for detecting aluminum ions is applied to detecting aluminum ions in a solution.
The fourth objective of the present invention is to provide a method for detecting aluminum ions in a solution. The method for detecting the aluminum ions in the solution is simple, easy to operate and suitable for popularization and application.
The technical scheme for solving the problems is as follows: a method for detecting aluminum ions in a solution comprises the steps of adding an aluminum ion solution with gradient concentration and the fluorescent probe into a mixed solution, wherein the volume ratio of a water-soluble organic solvent to water in the mixed solution is 30:1, measuring corresponding fluorescence intensity, then drawing a graph by taking the concentration of aluminum ions as an abscissa and the fluorescence intensity as an ordinate, establishing a standard line of the gradient change of the concentration of the aluminum ion solution and the change value of the fluorescence intensity of the reaction solution, and reading the concentration of the aluminum ions in the solution to be measured from the graph according to the fluorescence intensity during application.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the water-soluble organic solvent is any one of acetonitrile, chloroform, methanol, ethanol, N-dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, N-dimethylacetamide, 1, 4-dioxane and cyclohexane.
Drawings
FIG. 1 shows nuclear magnetic hydrogen spectrum of the fluorescent probe for detecting aluminum ions according to the present invention.
FIG. 2 is a nuclear magnetic carbon spectrum of the fluorescent probe for detecting aluminum ions of the present invention.
FIG. 3 is a fluorescence emission spectrum of a probe for detecting aluminum ions according to the present invention after adding different metal ions.
FIG. 4 shows Al added3+The fluorescence emission spectrum of the probe for detecting aluminum ions of the invention increases in concentration step by step.
FIG. 5 is a fluorescence emission spectrum of the fluorescent probe for detecting aluminum ions of the present invention in methanol.
FIG. 6 is a fluorescence emission spectrum of the fluorescent probe for detecting aluminum ions of the present invention in ethanol.
FIG. 7 is a fluorescence emission spectrum of the fluorescent probe for detecting aluminum ions of the present invention in N, N-dimethylformamide.
FIG. 8 is a fluorescence emission spectrum of the fluorescent probe for detecting aluminum ions of the present invention in N, N-dimethylacetamide.
FIG. 9 is a fluorescence emission spectrum of the fluorescent probe for detecting aluminum ions of the present invention in dimethyl sulfoxide.
FIG. 10 is a fluorescence emission spectrum of the fluorescent probe for detecting aluminum ions of the present invention in water.
Detailed Description
The principles and features of this invention are described below in conjunction with the following detailed drawings, which are given by way of illustration only and are not intended to limit the scope of the invention.
Example 1: the preparation method of the fluorescent probe for detecting the aluminum ions comprises the following steps:
step 1: taking 0.10g of 2-bromoacetophenone, placing the 2-bromoacetophenone in a three-neck flask, adding 10mL of trichloromethane, and dissolving;
step 2: dissolving 0.14g of tetra (4-pyridine biphenyl) ethylene in 5mL of trichloromethane, slowly adding the solution into the three-neck flask obtained in the step 1, and reacting for 1-24h under the reflux condition, wherein the reaction temperature is 80-90 ℃;
and step 3: cooling the reactant to room temperature, filtering, taking precipitate, washing with chloroform for 3 times, drying to obtain the compound shown in formula (I),
The nuclear magnetic hydrogen spectrum of the fluorescent probe for detecting aluminum ions is shown in fig. 1. Nuclear magnetic hydrogen spectrum:1H NMR(400MHz,DMSO)δ9.01(d,J＝6.3Hz,8H),8.65(d,J＝6.4Hz,8H), 8.10(t,J＝8.3Hz,16H),7.82(t,J＝7.3Hz,4H),7.68(t,J＝7.5Hz, 8H),7.46(d,J＝8.1Hz,8H),6.49(s,8H)。
nuclear magnetism of the above fluorescent probe for detecting aluminum ionCarbon spectrum, as shown in FIG. 2. Nuclear magnetic carbon spectrum:13C NMR(100MHz,DMSO)δ191.6,154.8,146.8,146.7,141.9,135.3,134.2, 132.8,129.7,128.9,124.6,66.1。
the molecular formula of the fluorescent probe for detecting aluminum ions is C78H60Br4N4O4The chemical name is N, N '-tetra (2-oxo-2-phenylethyl) -4,4' -tetra (4-pyridyl) tetraphenylethylene bromonium salt.
Example 2: fluorescent probe selectivity
The fluorescent probe prepared in example 1 was added to the mixed solution, and the concentration of the fluorescent probe prepared in example 1 was 10. mu.M and the concentration of the metal ion to be detected was 20. mu.M. The volume ratio of the water-soluble organic solvent to the water in the mixed solution is 30:1, the water-soluble organic solvent is any one of acetonitrile, trichloromethane, methanol, ethanol, N-dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, N-dimethylacetamide, 1, 4-dioxane and cyclohexane. The excitation wavelength in the spectrometry experiment was set to 380nm, the excitation and emission slit widths were both set to 5nm, and the fluorescence emission intensity from 400nm to 740nm was recorded. Metal ion (Mn)2+、Cr3+、K+、Zn2+、Al3+、Pb2+、Cd2+、 Ag+、Co2+、Mg2+、Na+、Ca2+、Cu2 +、Hg+And Fe3+) Added separately to the probe. The test results are shown in FIG. 3. Adding Al3+Thereafter, the fluorescence intensity of the probe was significantly increased, and the solution visually changed from orange-red to fluorescent yellow (see fig. 4 for test results). After other metal ions are added, the color of the solution is changed into orange, and the change of the fluorescence intensity is relatively insignificant.
Example 3: probe pair Al3+Detection limit test of
With Al3+Titration experiments were carried out on 10. mu.M of the fluorescent probe prepared in example 1 (0.1 eq, 0.2eq, 0.4eq, 0.6eq, 0.8eq, 1.0eq, 2.0eq, 3.0eq, 4.0eq and 5.0eq, respectively). With Al3+The higher the concentrationThe higher the probe, the higher the intensity of maximum fluorescence emission at 595 nm. When Al in solution3+When 4 equivalents are reached, the fluorescence emission intensity is highest and no further change occurs. From this, it can be concluded that the probe is directed to Al3+The saturation detected was 4 equivalents. For Al under the experimental conditions3+Has a lower detection limit of 1x10-6mol/L. The test results are shown in FIG. 5.
Example 4: probe to Al in different solvents3+Sensitivity test of
5 kinds of water-soluble organic solvents (methanol, ethanol, N-dimethylformamide, N-dimethylacetamide, and dimethylsulfoxide) were selected, and the fluorescent probe prepared in example 1 was dissolved therein to obtain a composite solution. In these composite solutions, the concentration of the probe was 10. mu.M, the concentration of the metal ion was 20. mu.M, and the volume ratio of the organic solvent to water was 30: 1. The test results are shown in fig. 6-10. The conclusion is that: the best effect is achieved by using N, N-dimethylformamide as a solvent.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. The fluorescent probe for detecting the aluminum ions is characterized in that the molecular formula of the fluorescent probe for detecting the aluminum ions is C78H60Br4N4O4The chemical name is N, N '-tetra (2-oxo-2-phenylethyl) -4,4' -tetra (4-pyridyl) tetraphenylethylenebromonium salt, and the structural formula shown in the formula (I):
2. the fluorescent probe for detecting aluminum ions according to claim 1, wherein the fluorescent probe for detecting aluminum ions has a detection limit of 1x10 for aluminum ions-6mol/L。
3. A preparation method of a fluorescent probe for detecting aluminum ions is characterized by comprising the following steps:
step 1: taking 0.10g of 2-bromoacetophenone, placing the 2-bromoacetophenone in a three-neck flask, and adding 10mL of solvent for dissolving;
step 2: dissolving 0.14g of tetra (4-pyridine biphenyl) ethylene in 5mL of solvent consistent with the step 1, slowly adding the solution into the three-neck flask obtained in the step 1, and reacting for 1-24h under the reflux condition, wherein the reaction temperature is 80-90 ℃;
and step 3: cooling the reactant to room temperature, filtering, taking precipitate, washing for 3 times by using the solvent consistent with the step 1, drying to obtain the compound shown in the formula (I),
4. The method of claim 3, wherein in the steps 1, 2 and 3, the solvent is any one of acetonitrile, chloroform, methanol, ethanol, N-dimethylformamide, tetrahydrofuran, 1, 4-dioxane and cyclohexane.
5. The method for preparing a fluorescent probe for detecting aluminum ions as claimed in claim 3, wherein in step 3, the drying mode is vacuum drying, the vacuum degree is-0.098 MPa, the temperature is 60 ℃, and the time is 5 h.
6. Use of the fluorescent probe for detecting aluminum ions according to any one of claims 1 to 2 or the fluorescent probe for detecting aluminum ions prepared according to any one of claims 3 to 5 for detecting aluminum ions in a detection solution.
7. A method for detecting aluminum ions in a solution, characterized in that an aluminum ion solution having a gradient concentration and the fluorescent probe according to any one of claims 1 to 2 are added to a mixed solution in which a volume ratio of a water-soluble organic solvent to water is 30:1, measuring corresponding fluorescence intensity, then drawing a graph by taking the concentration of aluminum ions as an abscissa and the fluorescence intensity as an ordinate, establishing a standard line of the gradient change of the concentration of the aluminum ion solution and the change value of the fluorescence intensity of the reaction solution, and reading the concentration of the aluminum ions in the solution to be measured from the graph according to the fluorescence intensity during application.
8. The method for detecting aluminum ions in a solution according to claim 7, wherein the water-soluble organic solvent is any one of acetonitrile, chloroform, methanol, ethanol, N-dimethylformamide, tetrahydrofuran, dimethylsulfoxide, N-dimethylacetamide, 1, 4-dioxane, and cyclohexane.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113666822A (en) * | 2021-08-24 | 2021-11-19 | 桂林医学院 | Small molecule fluorescent probe for aluminum ion detection and cell imaging and application thereof |
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| CN113666822A (en) * | 2021-08-24 | 2021-11-19 | 桂林医学院 | Small molecule fluorescent probe for aluminum ion detection and cell imaging and application thereof |
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Application publication date: 20200508 |