Platinum complex fluorescent probe and application thereof in hypochlorite detection and trivalent metal ion detection

By developing a fluorescent probe of platinum complex, the probe can undergo fluorescence changes in the presence of hypochlorite and trivalent metal ions respectively, solving the problem of lack of compounds in the prior art that simultaneously detect hypochlorite and trivalent metal ions, and achieving high selectivity and sensitive detection effects.

CN120040515AActive Publication Date: 2025-05-27INST OF BIOLOGICAL & MEDICAL ENG GUANGDONG ACAD OF SCI
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Patent Information

Application Number
CN202510193776.8
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-02-21
Publication Date
2025-05-27
Estimated Expiration
2045-02-21

AI Technical Summary

Technical Problem

There is a lack of compounds that can simultaneously and efficiently detect hypochlorite in cells and trivalent metal ions in the environment.

Method used

A fluorescent probe of platinum complex was developed. By changing the structure and ultraviolet absorption characteristics of the platinum complex, it can undergo fluorescence changes in the presence of hypochlorite and trivalent metal ions respectively, thereby achieving detection.

Benefits of technology

High selectivity and sensitive detection of hypochlorite and trivalent metal ions are achieved, filling the gap in the prior art, and the reaction conditions of the preparation method of the probe are mild.

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Abstract

The invention relates to a platinum complex fluorescent probe and application thereof in hypochlorite detection and trivalent metal ion detection, and the structural formula of the platinum complex fluorescent probe is as shown in # imgabs0. The platinum complex fluorescent probe disclosed by the invention has good selectivity and high sensitivity on hypochlorite and trivalent metal ions; the blank that compounds capable of detecting hypochlorite and trivalent metal ions are not found in the prior art is filled up; meanwhile, the preparation method of the platinum complex fluorescent probe is mild in reaction condition.
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Description

Technical Field

[0001] The present application relates to the technical field of fluorescent probes, and specifically relates to a platinum complex fluorescent probe and its applications in the detection of hypochlorite and trivalent metal ions. Background Art

[0002] Intracellular active components / signal molecules are a hot field in life science research. For example, reactive oxygen species (ROS) refer to all highly reactive oxygen-containing free radicals, peroxides, and singlet oxygen species derived from oxygen molecule metabolites. It includes superoxide radical (O 2 – ), hydrogen peroxide (H 2 O 2 ), singlet oxygen ( 1 O 2 ), hydroxyl radical (·OH), hypochlorous acid (HClO), and hypochlorite (ClO – ), etc. Among them, hypochlorite is a relatively common reactive oxygen species, mainly produced by white blood cells in the human immune system, such as neutrophils, for phagocytosis and killing of pathogenic bacteria, and abnormal hypochlorite levels are closely related to damage, aging, inflammation, and cancer, etc. On the other hand, the rapid development and expansion of modern industry have led to a large amount of trivalent metal ions such as Fe 3+ , Al 3+ , Gr 3+ and Ce 3+ entering the environment. Once absorbed by the human body through the food chain, it will cause non-negligible health problems. For example, excessive Fe 3+ may accumulate in organs such as the liver and heart, leading to liver cell damage, liver fibrosis, cirrhosis, and myocardial cell necrosis, increasing the risk of heart attack. Al 3+ poisoning can not only cause indigestion, anemia, osteomalacia, osteoporosis, and cognitive dysfunction, but also may lead to Alzheimer's disease and chronic renal failure. Excessive Cr 3+ intake will cause serious harm to the skin and respiratory system, such as skin erythema, edema, ulcers, and nasal mucosa swelling, cough, headache, etc. Long-term exposure to Ce 3+ may also cause damage to nerve cells, resulting in symptoms such as memory loss, insomnia, and dreaminess. In severe cases, it may even lead to nervous system dysfunction, while damaging the kidneys and liver, resulting in lung inflammation, pulmonary fibrosis, etc. Therefore, it is of great significance to efficiently detect hypochlorite in cells and trivalent metal ions in the environment.

[0003] Most of the currently reported methods for detecting hypochlorite and trivalent metal ions utilize small molecule fluorescent probes, which have advantages such as high efficiency, low cost, and convenience in use. However, in biological systems, organic fluorescent probes also face problems such as obvious background interference, insufficient stability, and low accuracy. Based on transition metal complex probes, due to the spin-orbit coupling effect caused by the heavy atom effect, the quantum efficiency is higher. Especially Ru(II)-, Os(II)-, Re(I)-, Ir(III)-, Cu(I)-, Pt(II)-, and Au(I)-complexes with d 6 -, d 8 -, and d 10 electron configurations not only have the ability to detect in real time, at trace and even ultra-trace levels, no weaker than fluorescent probes, but also have advantages such as high stability, high luminescence efficiency, long luminescence lifetime, large Stokes shift, and easy adjustment of excitation and emission spectra, showing great development prospects in the fields of biosensing and cell imaging. The results of literature retrieval show that currently, fluorescent probes mainly focus on Ru(II) or Ir(III) complexes, while there are relatively few studies on platinum complex fluorescent probes, which are still in the initial stage. There has not been a paper published on the research of platinum complex molecular probes for simultaneous detection of hypochlorite and trivalent metals.

[0004] In summary, no compound that can detect both hypochlorite and trivalent metal ions has been found in the prior art. Summary of the Invention

[0005] To solve the problems existing in the above prior art, the purpose of this application is to provide a platinum complex fluorescent probe and its application in the detection of hypochlorite and trivalent metal ions, so as to fill the gap that no compound that can detect both hypochlorite and trivalent metal ions has been found in the prior art.

[0006] A platinum complex fluorescent probe described in this application has the following structural formula:

[0007]

[0008] R is one or more of H, -CH 3 , -C 2 H 5 , -C(CH 3 ) 3 , -OH, and -CHO.

[0009] Preferably, the R is C(CH 3 ) 3 .

[0010] This application also provides a preparation method of the above platinum complex fluorescent probe, including the following steps:

[0011] Step 1. Take Dissolve it in anhydrous THF and cool to 0 - 5 °C. Dropwise add phenyl lithium solution under an inert atmosphere; the molar ratio of to phenyl lithium is 1:1 - 1.5; after dropping the phenyl lithium solution, raise the temperature to room temperature and stir for 5 h - 24 h to obtain Solution A; add saturated ammonium chloride solution to Solution A, collect the organic phase, add manganese dioxide to the organic phase, stir for 16 h to obtain Solution B; filter the Solution B and remove the solvent in the filtered solution, subject the solution after removing the solvent to column chromatography to obtain Compound a, and the structural formula of Compound a is shown as follows:

[0012]

[0013] Step 2. Dissolve Compound a and K 2 PtCl 4 in a CH 3 CN / H 2 O mixed solution according to a molar ratio of 1:1 - 1.5 to obtain Solution C, and the concentration of Solution C is 0.1 mmol / mL; in the CH 3 CN / H 2 O mixed solution, the volume ratio of CH 3 CN to H 2 O is 1:1 - 2; reflux for 14 h - 36 h under an inert atmosphere to obtain Solution D, remove CH 3 CN from Solution D and filter, collect the solid, and perform column chromatography to obtain Compound b, and the structural formula of Compound b is shown as follows:

[0014]

[0015] Step 3. Dissolve 4-ethynylbenzaldehyde and 2-aminoanthracene in anhydrous DMF according to a molar ratio of 1:1 - 1.2 to obtain Solution E, and the concentration of Solution E is 1 mmol / mL. Add activated 4A molecular sieve, react at 100 - 140 °C under an inert atmosphere for 4 h - 16 h, cool to room temperature after reacting for 4 h - 16 h to obtain Solution F, add methanol to Solution F, filter, collect the solid, and wash the solid with methanol to obtain Compound c, and the structural formula of Compound c is shown as follows:

[0016]

[0017] Step 4: Dissolve the compound b and the compound c in DCM according to a molar ratio of 1:1 to 1.2 to obtain a G solution with a concentration of adding CuI and TEA; the molar ratio of the compound b to the CuI is 1:0.1 to 0.5; the molar ratio of the compound b to the TEA is 1:60 to 100, and react for 15 h to 24 h under conditions of light avoidance, inert atmosphere and room temperature to obtain an H solution; remove the solvent from the H solution and perform column chromatography to obtain the platinum complex fluorescent probe.

[0018] Preferably, in the step 1, the has a molar ratio of 1:1.1 to the phenyllithium, the solvent of the phenyllithium solution is diethyl ether, the concentration of the phenyllithium solution is 1 mol / L, and after dropping the phenyllithium solution, the temperature is raised to room temperature and stirred for 6 h.

[0019] Preferably, in the step 2, the compound a and K 2 PtCl 4 has a molar ratio of 1:1; the volume of the CH 3 CN / H 2 O mixed solution is such that the volume ratio of CH 3 CN to H 2 O is 1:1.

[0020] Preferably, in the step 3, the molar ratio of the 4-ethynylbenzaldehyde to the 2-aminoanthracene is 1:1; react for 5 h under an inert atmosphere at 100 °C.

[0021] Preferably, in the step 4, the molar ratio of the compound b to the compound c is 1:1; the molar ratio of the compound b to the CuI is 1:0.1; the molar ratio of the compound b to the TEA is 1:60; react for 16 h under conditions of light avoidance, inert atmosphere and room temperature.

[0022] Preferably, the inert atmosphere is nitrogen.

[0023] The present application also provides an application of the platinum complex fluorescent probe as described above or the platinum complex fluorescent probe prepared by the preparation method as described above, applying the platinum complex fluorescent probe to detect hypochlorite in living cells.

[0024] The present application also provides an application of the platinum complex fluorescent probe as described above or the platinum complex fluorescent probe prepared by the preparation method as described above, applying the platinum complex fluorescent probe to detect Fe 3+ , Al 3+ , Gr 3+ and Ce 3+ in the environment.

[0025] A platinum complex fluorescent probe described in this application and its applications in hypochlorite detection and trivalent metal ion detection have the following advantages:

[0026] Since the platinum complex fluorescent probe described in the present invention is yellow fluorescent itself, after adding hypochlorite, due to the strong oxidation of hypochlorous acid, the four-coordinate platinum is oxidized to six-coordinate platinum, resulting in a change in the structure of the platinum complex fluorescent probe and a change in the ultraviolet absorption, causing the yellow fluorescence to disappear; while after adding trivalent metal ions Fe 3+ , Al 3 +, Gr 3+ and Ce 3+ , due to the cleavage of the imine group in the probe molecule by the trivalent metal ions, anthracene that emits green fluorescence is generated, resulting in a change in the ultraviolet absorption and causing the yellow fluorescence to turn into green fluorescence; therefore, the platinum complex fluorescent probe described in this application can detect both hypochlorite and trivalent metal ions. It has good selectivity and high sensitivity for hypochlorite and trivalent metal ions, filling the gap in the prior art that there is no compound that can detect both hypochlorite and trivalent metal ions; at the same time, the preparation method of this platinum complex fluorescent probe has mild reaction conditions. Description of the Drawings

[0027] Figure 1 is the ultraviolet absorption spectrum of the platinum complex fluorescent probe in Experimental Example 1 of the present invention after adding different equivalents of hypochlorite;

[0028] Figure 2 is the ultraviolet absorption spectrum of the platinum complex fluorescent probe in Experimental Example 2 of the present invention before and after adding Fe 3+ , Al 3+ , Gr 3+ and Ce 3+ ;

[0029] Figure 3 is the ion competition experimental data graph of the platinum complex fluorescent probe for various reactive oxygen species in Experimental Example 3 of the present invention;

[0030] Figure 4 is the anion and metal cation competition experimental data graph of the platinum complex fluorescent probe in Experimental Example 4 of the present invention;

[0031] Figure 5 is the picture of the platinum complex fluorescent probe for testing trivalent metal ions in Experimental Example 5 of the present invention;

[0032] Figure 6 is the cell imaging graph of the platinum complex fluorescent probe for detecting hypochlorite in cells in Experimental Example 6 of the present invention. Detailed Embodiments

[0033] The present invention will be further described below in conjunction with specific embodiments.

[0034] The raw materials involved in this application can be referred to Table 1.

[0035] Table 1

[0036]

[0037]

[0038] The instruments involved in this application can be referred to Table 2.

[0039] Table 2

[0040]

[0041] In this application, the description of "room temperature" refers to a temperature range of 20 - 25 °C; for the operation of "column chromatography", silica gel with a mesh size of 200 - 300 is used as the packing material for the chromatography column.

[0042] Example 1

[0043] The preparation method of the platinum complex fluorescent probe in this example is as follows:

[0044] (1) Dissolve 2.68 g (10 mmol, 1.0 eq) in 50 mL of anhydrous THF (tetrahydrofuran) and cool to 0 - 5 °C. Slowly add 11 mL of phenyl lithium solution (1 M / ether, 11 mmol, 1.1 eq) dropwise under nitrogen protection, then raise the temperature to room temperature and stir the reaction for 6 h to obtain Solution A. Add saturated ammonium chloride solution to Solution A to quench the excess phenyl lithium, collect the organic phase, add manganese dioxide to the organic phase and stir for 16 h to obtain Solution B; filter Solution B and remove the solvent from the filtered solution. Subject the solution after removing the solvent to column chromatography to obtain Compound a. Compound a is a white solid, and the mass of the obtained Compound a is 2.86 g, with a yield of 83%; the structural formula of Compound a is shown as follows:

[0045]

[0046] (2) Dissolve 344.5 mg (1.0 mmol, 1.0 eq) of Compound a and 415.1 mg (1.0 mmol, 1.0 eq) of K 2 PtCl 4 in a mixed solution of CH 3 CN / H 2 O (20 mL, volume ratio 1:1) to obtain Solution C. Under nitrogen protection, reflux Solution C for 16 h. After the reaction is completed, obtain Solution D and remove CH 3Filtered by CN, the solid was collected and subjected to column chromatography to obtain Compound b. Compound b is a yellow solid. The mass of the obtained Compound b is 447 mg, and the yield is 78%. The structural formula of Compound b is as follows:

[0047]

[0048] (3) Dissolve 130.2 mg of 4-ethynylbenzaldehyde (1.0 mmol, 1.0 eq) and 193.3 mg of 2-aminoanthracene (1.0 mmol, 1.0 eq) in 2 mL of anhydrous DMF (N,N-dimethylformamide), add a few activated 4A molecular sieves, and react at 100 °C for 5 h under nitrogen protection. Then cool to room temperature, add methanol to precipitate a solid, filter, and wash with methanol to obtain 278 mg of a brown-yellow solid, which is Compound c, with a yield of 91%. The structural formula of Compound c is as follows:

[0049]

[0050] (4) Dissolve 57.4 mg (0.1 mmol, 1.0 eq) of Compound b and 30.5 mg (0.1 mmol, 1.0 eq) of Compound c in 10 mL of DCM, add 1.9 mg (0.01 mmol, 0.1 eq) of CuI and 607 mg (6 mmol, 60 eq) of TEA, react at room temperature for 16 h under nitrogen protection in the dark. After the reaction, remove the solvent, and perform column chromatography to obtain 67 mg of a yellow solid, which is the platinum complex fluorescent probe, with a yield of 79%. The structural formula of the platinum complex fluorescent probe is as follows:

[0051]

[0052] Experimental Example 1 UV absorption spectrum test of the response of the platinum complex fluorescent probe to hypochlorous acid

[0053] Using the platinum complex fluorescent probe prepared in Example 1, the test concentration of the platinum complex fluorescent probe is 50 μM, and the test solvent is a mixed solution of THF / PB = 1 / 1. As Figure 1 shown, as the concentration of hypochlorite increases, the absorption peak of the platinum complex fluorescent probe at 209 nm increases significantly, the absorption in the range of 200 - 250 nm enhances, and the absorption in the range of 280 - 500 nm decreases. This is because the strong oxidation of hypochlorous acid oxidizes the four-coordinate platinum to six-coordinate platinum, resulting in a change in the structure of the platinum complex fluorescent probe and a change in the UV absorption situation.

[0054] Experimental Example 2 Based on the platinum complex fluorescent probe for Fe 3+ , Al 3+ , Gr 3+ and Ce3+ Response ultraviolet absorption spectrum test

[0055] Using the platinum complex fluorescent probe prepared in Example 1, the test concentration of the platinum complex fluorescent probe is 20 μM, and the test solvent is a mixed solution of THF / H 2 O = 1 / 1, Figure 2 is the ultraviolet absorption of the platinum complex fluorescent probe before and after adding 40 μM of Fe 3+ , Al 3+ , Gr 3+ and Ce 3+ . As Figure 2 shown, after adding trivalent metal ions to the probe solution, the ultraviolet absorption is significantly enhanced. This is because the trivalent metal ions cause the imine group in the probe molecule to break, generating anthracene that emits green fluorescence, resulting in a change in the ultraviolet absorption.

[0056] Experimental Example 3 Competition experiment of platinum complex fluorescent probe for various reactive oxygen ions

[0057] Using the platinum complex fluorescent probe prepared in Example 1, the concentration of the platinum complex fluorescent probe is 20 μM, the test solvent is a THF / PB = 1 / 1 mixed solution, and the analytes are H 2 O 2 , ·OH, ClO - , 1 O 2 , ·OtBu, TBHP. The fluorescence intensity of the platinum complex fluorescent probe for the analytes is measured at 560 nm. The test results are as Figure 3 shown, Figure 3 The results show that hypochlorite causes a change in the structure of the platinum complex fluorescent probe, and thus the fluorescence intensity decreases, while the absorbance intensity of other reactive oxygen species remains near 1750 a.u. after adding the platinum complex fluorescent probe. That is, except for hypochlorite, other reactive oxygen species cannot cause obvious fluorescence changes in the platinum complex probe, proving that the platinum complex probe has high selectivity for hypochlorite.

[0058] Experimental Example 4 Competition experiment of platinum complex fluorescent probe for anions and metal cations

[0059] Using the platinum complex fluorescent probe prepared in Example 1, Figure 4 in which the origin 0 is the platinum complex fluorescent probe without adding any ions, and the analytes 1 - 24 are Na + , 2 is K + , 3 is Mg 2+ , 4 is Cu 2+ , 5 is Cr 3+ , 6 is Ce 3+ , 7 is Fe3+ 8 is Al 3+ 9 is Zn 2+ 10 is Ni 2+ 11 is Mn 2+ 12 is Ca 2+ 13 is CH 3 COO - 14 is NO 3 - 15 is NO 2- 16 is Cl - 17 is Br - 18 is HCO 3 - 19 is CO 3 2- 20 is SiO 3 2- 21 is SO 4 2- 22 is SO 3 2- 23 is PO 4 3- 24 is HPO 4 2- The concentration of the platinum complex probe is 50 μM, and the test solvent is a mixed solution of THF / H 2 O = 1 / 1. The concentration of the added ions is 100 μM. The results are as Figure 4 shown. Except for trivalent metal ions, other ions do not cause obvious fluorescence changes in the fluorescent probe, proving that the platinum complex probe has high selectivity for trivalent metal ions.

[0060] Experimental Example 5 Identification Performance Experiment of Platinum Complex Fluorescent Probe for Ions

[0061] Using the platinum complex fluorescent probe prepared in Example 1, the luminescence of the platinum complex probe was tested under the irradiation of a 365 nm ultraviolet lamp after adding various ions. Specifically, the solution to be tested was placed in a cuvette, and the platinum complex fluorescent probe was added. The color change of the solution in the cuvette was observed under the irradiation of a 365 nm ultraviolet lamp. The analytes 1 - 24 are Na + 2 is K + 3 is Mg 2+ 4 is Cu 2+ 5 is Cr 3+ 6 is Ce 3+ 7 is Fe 3+ 8 is Al 3+ 9 is Zn 2+ 10 is Ni 2+ 11 is Mn 2+ 12 is Ca 2+, 13 is CH 3 COO - , 14 is NO 3 - , 15 is NO 2- , 16 is Cl - , 17 is Br - , 18 is HCO 3 - , 19 is CO 3 2- , 20 is SiO 3 2- , 21 is SO 4 2- , 22 is SO 3 2- , 23 is PO 4 3- , 24 is HPO 4 2- , the concentration of the platinum complex probe is 50 μM, and the test solvent is a mixed solution of THF / H 2 O = 1 / 1, and the concentration of the added ions is 100 μM. As Figure 5 shown, after the probe is added with Al 3+ , Cr 3+ , Fe 3+ and Ce 3+ , under the irradiation of a 365 nm ultraviolet lamp, the test system changes from yellow fluorescence to yellow-green fluorescence, while there is no obvious change when other ions are added, indicating that the platinum complex fluorescence probe described in this application has a certain "naked eye" recognition effect on Al 3+ , Cr 3+ , Fe 3+ and Ce 3+ .

[0062] Experimental Example 6 Experiment on Detection of Hypochlorite in Cells by Platinum Complex Fluorescence Probe

[0063] Using the platinum complex fluorescence probe prepared in Example 1, the application of the platinum complex probe in cell imaging was investigated by a laser confocal microscope. After Hela cells were resuscitated, 1×10 5 Hela cells were inoculated into a confocal culture dish and cultured in an incubator at 37 °C for 24 h. After changing the medium, 20 μM of the fluorescent probe was added and incubated for 24 h. The medium was removed and the cells were washed 3 times with PBS. Then, 50 μM of hypochlorite (not added in the control group) was added and incubated for 2 h. The cells were washed 3 times with PBS, and the cell imaging was observed and photographed with a confocal microscope. Figure 6 is the cell imaging result of the platinum complex probe, confirming that the probe can effectively enter the cells and detect hypochlorite in the cells.

[0064] In the description of the present application, it should be understood that the orientation or positional relationship indicated by orientation words such as "front, rear, upper, lower, left, right", "lateral, vertical, horizontal" and "top, bottom", etc. is usually based on the orientation or positional relationship shown in the drawings. It is only for the convenience of describing the present application and simplifying the description. Without contrary description, these orientation words do not indicate and imply that the device or element referred to must have a specific orientation or be constructed and operated in a specific orientation. Therefore, it should not be construed as a limitation on the protection scope of the present application.

[0065] For those skilled in the art, according to the technical solutions and concepts described above, various corresponding changes and deformations can be made, and all these changes and deformations should fall within the protection scope of the claims of the present application.

Claims

1. A platinum complex fluorescent probe, characterized in that: The structural formula of the platinum complex fluorescent probe is as follows: R is one or more of H, -CH3, -C2H5, -C(CH3)3, -OH and -CHO.

2. The platinum complex fluorescent probe according to claim 1, characterized in that: The R is C(CH3)3.

3. A method for preparing a platinum complex fluorescent probe as claimed in claim 1 or 2, characterized in that: The following steps are involved: Step 1: Take Dissolve in anhydrous THF and cool to 0-5°C, and add phenyllithium solution dropwise under an inert atmosphere; The molar ratio of the phenyl lithium is 1:1 to 1.5; after adding the phenyl lithium solution dropwise, the temperature is raised to 20 to 25°C and stirred for 5 to 24 hours to obtain a solution A; a saturated ammonium chloride solution is added to the solution A, the organic phase is collected, manganese dioxide is added to the organic phase, and stirred for 16 hours to obtain a solution B; The B solution is filtered and the solvent in the filtered solution is removed, and the solution after the solvent is removed is subjected to column chromatography to obtain compound a, and the structural formula of compound a is as follows: Step 2, dissolving the compound a and K2PtCl4 in a CH3CN / H2O mixed solution at a molar ratio of 1:1 to 1.5 to obtain a C solution, wherein the concentration of the C solution is 0.1 mmol / mL; in the CH3CN / H2O mixed solution, the volume ratio of CH3CN to H2O is 1:1 to 2; reflux under an inert atmosphere for 14h to 36h to obtain a D solution, remove the CH3CN in the D solution and filter, collect the solid, and perform column chromatography to obtain a compound b, wherein the structural formula of the compound b is as follows: Step 3, 4-ethynylbenzaldehyde and 2-aminoanthracene are dissolved in anhydrous DMF at a molar ratio of 1:1 to 1.2 to obtain solution E, wherein the concentration of solution E is 1 mmol / mL, activated 4A molecular sieves are added, and the mixture is reacted for 4 h to 16 h at 100 to 140 ° C in an inert atmosphere, and then cooled to room temperature after reacting for 4 h to 16 h to obtain solution F, methanol is added to the solution F, filtered, the solid is collected, and the solid is washed with methanol to obtain compound c, wherein the structural formula of compound c is as follows: Step 4, dissolving the compound b and the compound c in DCM at a molar ratio of 1:1 to 1.2 to obtain a G solution, wherein the concentration of the G solution is as follows: adding CuI and TEA; the molar ratio of the compound b and the CuI is 1:0.1 to 0.5; the molar ratio of the compound b and the TEA is 1:60 to 100, reacting for 15h to 24h under light-proof, inert atmosphere and room temperature conditions to obtain a H solution; removing the solvent from the H solution and performing column chromatography to obtain the platinum complex fluorescent probe.

4. The preparation method according to claim 3, characterized in that: In the step 1, the The molar ratio of the phenyllithium to the phenyllithium is 1:1.1, the solvent of the phenyllithium solution is ether, the concentration of the phenyllithium solution is 1 mol / L, after the phenyllithium solution is added dropwise, the temperature is raised to room temperature and stirred for 6 hours.

5. The preparation method according to claim 3, characterized in that: In the step 2, the molar ratio of the compound a to K2PtCl4 is 1:1; the volume of the CH3CN / H2O mixed solution is medium, and the volume ratio of CH3CN to H2O is 1:

1.

6. The preparation method according to claim 3, characterized in that: In the step 3, the molar ratio of the 4-ethynylbenzaldehyde to the 2-aminoanthracene is 1:1; the reaction is carried out in an inert atmosphere at 100° C. for 5 hours.

7. The preparation method according to claim 3, characterized in that: In the step 4, the molar ratio of the compound b to the compound c is 1:1; the molar ratio of the compound b to the CuI is 1:0.1; the molar ratio of the compound b to the TEA is 1:60; and the reaction is carried out for 16 hours in a light-proof, inert atmosphere and at room temperature.

8. The preparation method according to claim 3, characterized in that: The inert atmosphere is nitrogen.

9. Use of the platinum complex fluorescent probe according to any one of claims 1 to 2 or the platinum complex fluorescent probe prepared by the preparation method according to any one of claims 3 to 8, characterized in that: The platinum complex fluorescent probe is applied to detecting hypochlorite in living cells.

10. Use of the platinum complex fluorescent probe according to any one of claims 1 to 2 or the platinum complex fluorescent probe prepared by the preparation method according to any one of claims 3 to 8, characterized in that: The platinum complex fluorescent probe is used to detect Fe in the environment 3+ , Al 3+ , Gr 3+ and Ce 3+ .

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