Preparation method of probe capable of detecting PPi and PFOS, probe and application

Abstract

The invention relates to the technical field of preparation of fluorescent materials, in particular to a preparation method of a probe capable of detecting PPi and PFOS, the probe and application. The preparation method comprises the following steps: a parent preparation step: carrying out Suzuki coupling reaction on a tetraphenyl ethylene derivative and pyridine boronic acid to generate a parent unit; and a salt forming step: adopting the parent unit and the connection reactive group unit to generate a target probe capable of detecting PPi and PFOS through a salt forming reaction. The preparation method disclosed by the invention is simple, environment-friendly and good in operability; the probe shows nM-level sensitivity in PFOS (perfluorooctane sulfonate) detection, shows obvious'open 'type fluorescence response in pyrophosphoric acid detection, and has the detection limit as low as nM level.

Description

Technical Field

[0001] The present application relates to the technical field of fluorescent material preparation, and specifically to a preparation method, probe and application of a probe capable of detecting PPi and PFOS. Background Art

[0002] In the field of environmental pollutant monitoring and biomolecular analysis, the development of efficient and multifunctional sensing technology is one of the core challenges of current research. PPi (inorganic pyrophosphate) is a key molecule in energy metabolism (such as ATP hydrolysis, bone mineralization) and disease regulation in the body. Dynamic detection is of great significance for the study of pathological mechanisms; and PFOS (perfluorooctane sulfonic acid) is a widely existing persistent organic pollutant. Due to its high toxicity, bioaccumulation and environmental persistence, it has been included in the control list of the Stockholm Convention.

[0003] Existing detection technologies are mostly limited to the analysis of a single target, and face problems such as insufficient sensitivity, complex operation or weak resistance to matrix interference, making it difficult to meet the urgent needs of simultaneous detection of multiple components in complex systems. In recent years, aggregation-induced emission (AIE) materials have advantages in the field of chemical sensing due to their unique "aggregation state fluorescence enhancement" properties. Unlike traditional fluorescent probes, AIE molecules have weak fluorescence in a dispersed state, but enhance luminescence when aggregated or bound to specific targets. This property not only effectively overcomes the aggregation-induced quenching effect, but also greatly improves the stability of detection in complex environments. Among them, tetraphenylethylene, as a classic AIE skeleton, has become an ideal skeleton for constructing multifunctional probes due to its strong modifiability and excellent photophysical properties.

[0004] However, how to achieve specific differentiation response of probes to different targets through molecular design is still a technical bottleneck that needs to be broken through in this field. Summary of the invention

[0005] To solve the above problems, the embodiments of the present application provide a method for preparing a probe that can detect PPi and PFOS, a probe and an application thereof. The probe is a bifunctional AIE probe based on a tetraphenylethylene skeleton. By introducing specific recognition groups and signal transduction modules, high-selectivity and high-sensitivity dual detection of PPi and PFOS is successfully achieved, thereby overcoming or at least partially overcoming the shortcomings of the prior art.

[0006] In a first aspect, the present application provides a method for preparing a probe capable of detecting PPi and PFOS, the method comprising:

[0007] Preparing the parent unit: using a tetraphenylethylene derivative and pyridine boronic acid to generate a parent unit through a Suzuki coupling reaction; and

[0008] Salt formation step: The target probe for detecting PPi and PFOS is generated by a salt formation reaction using the parent unit and the linking reactive group unit.

[0009] Optionally, in the above method, after the salt formation step, the method further includes:

[0010] Purification step: The product of the salt formation step is subjected to suction filtration, and the filter cake is stirred and washed in a purification solvent for 1 to 4 hours and then repeatedly suction filtered. The obtained filter cake is vacuum dried at 60 to 120 °C for 1 to 3 days to obtain the purified target probe.

[0011] Optionally, in the above method, the parent preparation step specifically includes:

[0012] Disperse the tetraphenylethylene derivative and the pyridine boronic acid powder in the first mixed solvent, stir until completely dissolved, add the coupling catalyst, and react for the first specified duration under a nitrogen atmosphere and at the first specified temperature.

[0013] Optionally, in the above method, the coupling catalyst includes a palladium catalyst, a phase transfer catalyst, and a base;

[0014] The base is cesium carbonate;

[0015] The palladium catalyst is one or more of bis(tri-tert-butylphosphine)palladium, tetrakis(triphenylphosphine)palladium, palladium trifluoroacetate, or palladium chloride, preferably tetrakis(triphenylphosphine)palladium;

[0016] The phase transfer catalyst is tetrabutylammonium iodide.

[0017] Optionally, in the above method, the tetraphenylethylene derivative is 1-(4-bromophenyl)-1,2,2-triphenylethylene;

[0018] The first mixed solvent is a mixed solution composed of at least two of toluene, ethanol, and water;

[0019] The first specified temperature is 80 to 85 °C, preferably 85 °C;

[0020] The first specified duration is 3 to 6 days, preferably 3 days.

[0021] Optionally, in the above method, the salt formation step specifically includes:

[0022] Dissolve the parent unit and the linking reactive group unit in the second mixed solvent, and stir and react for the second specified duration under a nitrogen atmosphere and at the second specified temperature;

[0023] The molar ratio of the tetraphenylethylene derivative to the linking reactive group unit is 1:0.1 to 1.5, preferably 1:0.5.

[0024] Optionally, in the above method, the second mixed solvent is one or more of acetonitrile, toluene, dichloromethane, N,N-dimethylformamide, tetrahydrofuran, 1,2-dichloroethane, 1,4-dioxane, chloroform or dimethyl sulfoxide, preferably a mixed solution of dichloromethane and acetonitrile.

[0025] Optionally, in the above method, the linking reaction group unit is selected from one or more of benzyl bromide, 1,4-bis(bromomethyl)benzene and o-dichlorobenzene, preferably 1,4-bis(bromomethyl)benzene;

[0026] The second specified temperature is 100°C - 120°C, preferably 110°C;

[0027] The second specified duration is 3 - 6 d, preferably 3 d.

[0028] In a second aspect, the present application also provides a probe capable of detecting PPi and PFOS, and the probe capable of detecting PPi and PFOS is prepared by using the preparation method of any one of the above-mentioned probes capable of detecting PPi and PFOS.

[0029] In a third aspect, the present application also provides an application of a probe capable of detecting PPi and PFOS. The probe capable of detecting PPi and PFOS is used to detect pyrophosphate ions and potassium perfluorooctanesulfonate, the concentration of the pyrophosphate ions is at least 48 nmol / L at the lowest, and the concentration of the potassium perfluorooctanesulfonate is at least 51 nmol / L at the lowest.

[0030] The above at least one technical solution adopted in the embodiments of the present application can achieve the following beneficial effects:

[0031] The present application provides a dual-functional AIE probe based on a tetraphenylethylene skeleton. By introducing a specific recognition group and a signal transduction module, the high-selectivity and high-sensitivity dual detection of pyrophosphate (PPi) and potassium perfluorooctanesulfonate (PFOS) is successfully realized. The probe of the present application not only realizes dual-channel analysis through fluorescence "turn-on" and ratio-type signal changes, but also has advantages such as a low detection limit, providing a new theoretical reference for the multi-target sensing design of AIE materials. Moreover, the preparation method of the present application is simple, environmentally friendly, and has good operability; it shows nM-level sensitivity in PFOS detection, and in pyrophosphate detection, the probe exhibits a significant "turn-on" fluorescence response with a detection limit as low as the nM level. Description of the Drawings

[0032] The drawings described herein are used to provide a further understanding of the present application, and constitute a part of the present application. The schematic embodiments of the present application and their descriptions are used to explain the present application and do not constitute an improper limitation to the present application. In the drawings:

[0033] Figure 1 Shows a schematic flow chart of a method for preparing a probe capable of detecting PPi and PFOS according to an embodiment of the present application;

[0034] Figure 2 Shows a schematic diagram of the results of nuclear magnetic measurement of the probe prepared according to Example 1 of the present application;

[0035] Figure 3 Shows a schematic diagram of the results of ultraviolet absorption spectrum measurement of the probe prepared according to Example 1 of the present application under solvents with different concentrations;

[0036] Figure 4 Shows a schematic diagram of the results of fluorescence spectrum measurement of the probe prepared according to Example 1 of the present application under solvents with different concentrations;

[0037] Figure 5 Shows a schematic diagram of the results of fluorescence spectrum measurement of the probe prepared according to Example 1 of the present application for PPi with different concentrations;

[0038] Figure 6 Shows a schematic diagram of the results of fluorescence spectrum measurement of the probe prepared according to Example 1 of the present application for PFOS with different concentrations. Detailed implementation manners

[0039] To make the objectives, technical solutions and advantages of the present application clearer, the technical solutions of the present application will be clearly and completely described below in conjunction with specific embodiments of the present application and the corresponding drawings. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those of ordinary skill in the art without making creative efforts shall fall within the protection scope of the present application.

[0040] The concept of the present application lies in: aiming at the specific differential response of the probe to different target substances, a cationic probe (denoted as T2N) is provided, and its fluorescence response behaviors to PFOS and PPi are systematically explored. It shows sensitivity at the nM level in PFOS detection, attributed to the synergistic regulation of fluorescence enhancement by the anionic properties of PFOS and the electrostatic and hydrophobic interactions between the probe. In PPi detection, the molecule T2N with a high content of tetraphenylethylene TPE exhibits a significant "turn-on" fluorescence response, and its detection limit is as low as 48 nM.

[0041] The following examples elaborate in detail the synthesis route from raw materials to the final samples, including the specific reactant ratios, optimization of reaction conditions, and characterization analysis of the products, such as ultraviolet-visible absorption spectra, fluorescence emission spectra, etc., to verify the excellent performance of the prepared AIE materials. The experimental results show that the obtained materials have fluorescence responses to PPi and PFOS, providing a solid foundation for subsequent optical applications.

[0042] For details, please refer to Figure 1 , Figure 1 FIG. shows a schematic flow chart of a method for preparing a probe capable of detecting PPi and PFOS according to an embodiment of the present application. From Figure 1 it can be seen that this embodiment includes:

[0043] Matrix preparation step S110: A matrix unit is generated by subjecting a tetraphenylethylene derivative and pyridine boronic acid to a Suzuki coupling reaction.

[0044] The tetraphenylethylene derivative and pyridine boronic acid are subjected to a Suzuki coupling reaction, and the resulting reactant is denoted as matrix unit TPE-1N. Matrix unit TPE-1N is shown as follows:

[0045]

[0046] In some embodiments, specifically, the tetraphenylethylene derivative and pyridine boronic acid powder are dispersed in a first mixed solvent, stirred until completely dissolved, and then a coupling catalyst is added, and the reaction is carried out for a first specified duration under a nitrogen atmosphere and at a first specified temperature.

[0047] The tetraphenylethylene derivative mainly refers to tetraphenylethylene with substituents, such as halogenated tetraphenylethylene. In some embodiments of the present application, the tetraphenylethylene derivative is preferably 1-(4-bromophenyl)-1,2,2-triphenylethylene.

[0048] In some embodiments, the coupling catalyst mainly includes a palladium catalyst, a phase transfer catalyst, and a base; among them, the base is preferably cesium carbonate; the palladium catalyst is one or more of bis(tri-tert-butylphosphine)palladium, tetrakis(triphenylphosphine)palladium, palladium trifluoroacetate, or palladium chloride, preferably tetrakis(triphenylphosphine)palladium; the phase transfer catalyst is tetrabutylammonium iodide.

[0049] In some embodiments, the first mixed solvent is a mixed solution composed of at least two of dichloromethane, toluene, ethanol, and water.

[0050] In some embodiments, the first specified temperature is 80-85°C, preferably 85°C; that is, after adding the coupling catalyst, the temperature is controlled to be 80-85°C, and the preferred temperature is 85°C.

[0051] In some embodiments, the first specified duration is 3 - 6 days, preferably 3 days, that is, the Suzuki coupling is a heating reaction, and its time control is: 3 - 6 days, preferably 3 days. And the Suzuki coupling reaction is preferably carried out under a nitrogen atmosphere throughout the process.

[0052] Formula 1 shows the reaction expression of the Suzuki coupling reaction in one embodiment:

[0053]

[0054] And the salt - forming step S120: Using the parent unit and the linking reaction group unit to generate a target probe capable of detecting PPi and PFOS through a salt - forming reaction.

[0055] Through the salt - forming reaction, reacting the parent unit TPE - 1N with the linking reaction group unit can obtain the target probe capable of detecting PPi and PFOS. Specifically, dissolve the parent unit and the linking reaction group unit in a second mixed solvent, and stir - react for a second specified duration under a nitrogen atmosphere and at a second specified temperature.

[0056] The function of the linking reaction group unit is to incorporate one or more parent units into a molecule, increasing the content of tetraphenylethylene (TPE) in the molecule. In some embodiments, the linking reaction group unit is selected from one or more of benzyl bromide, 1,4 - bis(bromomethyl)benzene, and o - dichlorobenzene, preferably 1,4 - bis(bromomethyl)benzene.

[0057] In some embodiments, the molar ratio of the tetraphenylethylene derivative to the linking reaction group unit is 1:0.1 - 1.5, preferably 1:0.5.

[0058] In some embodiments, the second mixed solvent is one or more of acetonitrile, toluene, dichloromethane, N,N - dimethylformamide, tetrahydrofuran, 1,2 - dichloroethane, 1,4 - dioxane, chloroform, or dimethyl sulfoxide, preferably a mixed solution of dichloromethane and acetonitrile.

[0059] In some embodiments, the second specified temperature is 100°C - 120°C, preferably 110°C; the second specified duration is 3 - 6 days, preferably 3 days.

[0060] Formula 2 shows the reaction expression of the salt - forming reaction in one embodiment:

[0061]

[0062] As can be seen from the product of Formula 2, the probe prepared in this application exhibits nM-level sensitivity in PFOS detection, which is attributed to the synergistic regulation of fluorescence enhancement by the anion characteristics of PFOS and the electrostatic and hydrophobic interactions between the probe. In the detection of PPi, the probe molecule T2N with a high content of TPE exhibits a significant "turn-on" fluorescence response, and its detection concentration can be as low as 48 nM through experiments.

[0063] In order to further purify the product, in some embodiments of this application, after the salting step, the method further includes: a purification step: subjecting the product of the salting step to suction filtration, and stirring and washing the filter cake in a purification solvent for 1 to 4 hours and performing suction filtration repeatedly, and drying the obtained filter cake in a vacuum at 60 to 120 °C for 1 to 3 days, preferably 1 day, to obtain the purified target probe.

[0064] For example, immediately after the salting reaction S120 ends, suction filtration is performed, the filter cake is stirred and washed in acetonitrile for 1 to 4 hours and then suction filtered, and after repeated washing and suction filtration, the filter cake is dried in a vacuum to obtain the purified target probe.

[0065] It should be noted that in steps S110 and S120, steps such as purification can be added according to the common technical knowledge in the art, such as purifying the product through a rotary evaporator and chromatographic separation technology, etc. This application does not make any limitations in this regard.

[0066] The probe prepared in this application has dual functions and can efficiently detect pyrophosphate ions and potassium perfluorooctanesulfonate. In some embodiments, the pyrophosphate ions can come from but are not limited to sodium pyrophosphate or disodium pyrophosphate.

[0067] During detection, the detection agent is added to a solvent containing pyrophosphate ions and potassium perfluorooctanesulfonate salt, and the probe is detected under a mixed condition of stirring, ultrasonic or shaking. Through detection, it is found that the lowest detection concentration of the probe in this application for pyrophosphate ions is 48 nmol / L, and the lowest detection concentration for potassium perfluorooctanesulfonate is 51 nmol / L.

[0068] Example 1

[0069] Step 1: Dissolve 1-(4-bromophenyl)-1,2,2-triphenylethylene (2 g, 4.8 mmol), pyridine-4-boronic acid (0.89 g, 7.3 mmol), and tetrabutylammonium iodide (0.85 g, 2.4 mmol) in toluene (40 mL) and ethanol (10 mL), and place them in a 250 mL Schlenk tube. Subsequently, add 10 mL of 2 M cesium carbonate solution and Pd(PPh3)4 (277 mg, 0.24 mmol) to the reaction system, and continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully replaced. The reaction mixture is heated and stirred at 85 °C for 3 days, and the reaction progress is monitored regularly by TLC during this period to ensure that the reaction proceeds completely.

[0070] After the reaction is completed, the solvent is rotary evaporated and purified by column chromatography, with dichloromethane and methanol (volume ratio 20:1) as the eluent. After separation and purification, 1.3 g of yellow solid product TPE-1N is finally obtained, with a yield of 67%.

[0071] Step 2: Dissolve TPE-1N (40 mg, 0.09 mmol) and 1,4-bis(bromomethyl)benzene (12.8 mg, 0.05 mmol) in 25 mL of dichloromethane and 25 mL of acetonitrile, and continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully replaced. The reaction mixture is heated and stirred at 110 °C for 3 days. After the reaction is completed, the reaction solution is concentrated by a rotary evaporator to remove the solvent to obtain a crude product. Subsequently, it is washed and filtered with dichloromethane. After separation and purification, 28 mg of yellow solid product is finally obtained, with a yield of 64%.

[0072] Example 2

[0073] Step 1: Dissolve 1-(4-bromophenyl)-1,2,2-triphenylethylene (2 g, 4.8 mmol), pyridine-4-boronic acid (0.89 g, 7.3 mmol), and tetrabutylammonium iodide (0.85 g, 2.4 mmol) in toluene (40 mL) and ethanol (10 mL), and place them in a 250 mL Schlenk tube. Subsequently, add 10 mL of 2 M cesium carbonate solution and Pd(PPh3)4 (277 mg, 0.24 mmol) to the reaction system, and continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully replaced. The reaction mixture is heated and stirred at 85 °C for 3 days, and the reaction progress is monitored regularly by TLC during this period to ensure that the reaction proceeds completely. After the reaction is completed, the solvent is rotary evaporated and purified by column chromatography, with dichloromethane and methanol (volume ratio 20:1) as the eluent. After separation and purification, 1.3 g of yellow solid product is finally obtained, with a yield of 67%.

[0074] Step 2: Dissolve TPE-1N (40 mg, 0.09 mmol) and benzyl bromide (16.6 mg, 0.009 mmol) in 25 mL of dichloromethane and 25 mL of acetonitrile. Continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully displaced. The reaction mixture is heated and stirred at 110 °C for 3 days. After the reaction is completed, the solvent of the reaction solution is removed by a rotary evaporator to obtain a crude product. Subsequently, it is washed and filtered with dichloromethane, and after separation and purification, 28.4 mg of a yellow solid product is finally obtained, with a yield of 56%.

[0075] Example 3

[0076] Step 1: Dissolve 1-(4-bromophenyl)-1,2,2-triphenylethylene (2 g, 4.8 mmol), pyridine-4-boronic acid (0.89 g, 7.3 mmol), and tetrabutylammonium iodide (0.85 g, 2.4 mmol) in dichloromethane (40 mL) and ethanol (10 mL), and place them in a 250 mL Schlenk tube. Subsequently, add 10 mL of 2 M cesium carbonate solution and Pd(PPh3)4 (277 mg, 0.24 mmol) to the reaction system, and continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully displaced. The reaction mixture is heated and stirred at 85 °C for 3 days, and the reaction progress is regularly monitored by TLC during this period to ensure that the reaction proceeds completely. After the reaction is completed, the solvent is rotary evaporated and purified by column chromatography, with dichloromethane and methanol (volume ratio 20:1) as the eluent. After separation and purification, 1.11 g of a yellow solid product is finally obtained, with a yield of 56%.

[0077] Step 2: Dissolve TPE-1N (40 mg, 0.09 mmol) and 1,4-bis(bromomethyl)benzene (12.8 mg, 0.05 mmol) in 25 mL of dichloromethane and 25 mL of acetonitrile. Continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully displaced. The reaction mixture is heated and stirred at 110 °C for 3 days. After the reaction is completed, the solvent of the reaction solution is removed by a rotary evaporator to obtain a crude product. Subsequently, it is washed and filtered with dichloromethane, and after separation and purification, 286 mg of a yellow solid product is finally obtained, with a yield of 64%.

[0078] Example 4

[0079] Step 1: Dissolve 1-(4-bromophenyl)-1,2,2-triphenylethylene (2 g, 4.8 mmol), pyridine-4-boronic acid (0.89 g, 7.3 mmol), and tetrabutylammonium iodide (0.85 g, 2.4 mmol) in dichloromethane (40 mL) and ethanol (10 mL), and place them in a 250 mL Schlenk tube. Subsequently, add 10 mL of 2 M cesium carbonate solution and Pd(PPh3)4 (277 mg, 0.24 mmol) to the reaction system, and continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully replaced. The reaction mixture is heated and stirred at 85 °C for 3 days, and the reaction progress is regularly monitored by TLC during this period to ensure that the reaction proceeds completely. After the reaction is completed, the solvent is rotary evaporated and purified by column chromatography, using dichloromethane and methanol (volume ratio 20:1) as the eluent. After separation and purification, 1.11 g of yellow solid product is finally obtained, with a yield of 56%.

[0080] Step 2: Dissolve TPE-1N (40 mg, 0.09 mmol) and 1,4-bis(bromomethyl)benzene (12.8 mg, 0.05 mmol) in 25 mL of N,N-dimethylformamide, and continuously introduce nitrogen for 20 min to ensure that the oxygen in the reaction system is fully replaced. The reaction mixture is heated and stirred at 110 °C for 3 days. After the reaction is completed, the solvent is removed from the reaction solution by a rotary evaporator to obtain a crude product. Subsequently, it is washed and filtered with dichloromethane, and after separation and purification, 150 mg of yellow solid product is finally obtained, with a yield of 33%.

[0081] Test Example 1: NMR determination

[0082] The target product T2N obtained in Example 1 was subjected to NMR determination, and the Figure 2 results shown were obtained. It can be seen from Figure 2 that the target product T2N was successfully prepared.

[0083] Test Example 2: UV absorption spectrum determination

[0084] The UV absorption spectrum of the target product T2N obtained in Example 1 in aqueous solutions of different concentrations was determined.

[0085] Specifically, aqueous solutions of different concentrations of T2N (4 mL, 1×10 -5 mol / L) were prepared in 5 mL sample tubes. The methanol stock solution of T2N was diluted to aqueous solutions containing 10% - 90%. 4 mL of the T2N molecules to be measured were pipetted and transferred to a 5 mL cuvette. The preset UV absorption wavelength range was determined to be between 200 nm and 800 nm. First, a blank test was performed to deduct the blank interference of the solvent used, and finally, the UV absorption spectrum of the test solution was determined. The Figure 3 .

[0086] Test Example 3: Probe Response Fluorescence Spectrometry

[0087] Fluorescence Spectrometry of the Target Product T2N in Example 1 in Aqueous Solutions of Different Concentrations

[0088] Prepare aqueous solutions of different concentrations of T2N (4 mL, 1×10 -5 mol / L) in a 5 mL sample tube. Dilute the methanol stock solution of T2N to an aqueous solution containing 10%-90%. Pipette 4 mL of the test solution of T2N molecules and transfer it to a 5 mL cuvette. After the fluorescence spectrometer scans in reverse, the maximum excitation wavelength is determined to be 395 nm, and the fluorescence spectra of the samples with different concentrations of solvents added are measured. Obtain Figure 4 .

[0089] Test Example 4: Probe Response Fluorescence Spectrometry

[0090] Fluorescence Emission Spectrometry of the Target Product T2N in Example 1 with Different Concentrations of PPi Added

[0091] Add T2N solution (4 mL, 1.1×10 -5 mol / L) and different concentrations of PPi solution to a 5 mL sample tube. Pipette 4 mL of the test solution of T2N molecules and transfer it to a 5 mL cuvette. After the fluorescence spectrometer scans in reverse, the maximum excitation wavelength is determined to be 395 nm. Measure the fluorescence emission spectra with different concentrations of PPi added. Obtain Figure 5 .

[0092] Test Example 5: Probe Response Fluorescence Spectrometry

[0093] Fluorescence Emission Spectrometry of the Target Product T2N in Example 1 with Different Concentrations of PFOS Added

[0094] Add T2N solution (4 mL, 1.1×10 -5 mol / L) and different concentrations of PFOS solution to a 5 mL sample tube. Pipette 4 mL of the test solution of T2N molecules and transfer it to a 5 mL cuvette. After the fluorescence spectrometer scans in reverse, the maximum excitation wavelength is determined to be 395 nm. Measure the fluorescence emission spectra with different concentrations of PFOS added. Obtain Figure 6 .

[0095] The above-described embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that: they can still modify the technical solutions recorded in the foregoing embodiments, or perform equivalent replacements on some of the technical features; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the various embodiments of the present invention, and should all be included within the protection scope of the present invention.

Claims

1. A preparation method of a probe for detecting PPi and PFOS, characterized in that, The method includes: The step of preparing the parent body: generating a parent unit by the Suzuki coupling reaction of a tetraphenylethylene derivative and pyridine boronic acid; and The step of salt formation: generating a target probe capable of detecting PPi and PFOS by the salt formation reaction of the parent unit and a linking reaction group unit.

2. The preparation method according to claim 1, wherein After the step of salt formation, the method further includes: The purification step: subjecting the product of the salt formation step to suction filtration, stirring and washing the filter cake in a purification solvent for 1 to 4 hours and performing suction filtration repeatedly, and drying the obtained filter cake in vacuo at 60 to 120 °C for 1 to 3 days to obtain the purified target probe.

3. The preparation method according to claim 1, characterized in that, The step of preparing the parent body specifically includes: Dispersing the tetraphenylethylene derivative and pyridine boronic acid powder in a first mixed solvent, stirring until completely dissolved, adding a coupling catalyst, and reacting for a first specified duration under a nitrogen atmosphere and at a first specified temperature.

4. The preparation method according to claim 3, wherein The coupling catalyst includes a palladium catalyst, a phase transfer catalyst, and a base; The base is cesium carbonate; The palladium catalyst is one or more of bis(tri-tert-butylphosphine)palladium, tetrakis(triphenylphosphine)palladium, palladium trifluoroacetate, or palladium chloride, preferably tetrakis(triphenylphosphine)palladium; The phase transfer catalyst is tetrabutylammonium iodide.

5. The preparation method according to claim 3, characterized in that, The tetraphenylethylene derivative is 1-(4-bromophenyl)-1,2,2-triphenylethylene; The first mixed solvent is a mixed solution composed of at least two of toluene, ethanol, and water; The first specified temperature is 80 to 85 °C, preferably 85 °C; The first specified duration is 3 to 6 days, preferably 3 days.

6. The preparation method according to claim 1, wherein, The step of salt formation specifically includes: Dissolving the parent unit and the linking reaction group unit in a second mixed solvent, and stirring and reacting for a second specified duration under a nitrogen atmosphere and at a second specified temperature; The molar ratio of the tetraphenylethylene derivative to the linking reaction group unit is 1:0.1 to 1.5, preferably 1:0.

5.

7. The preparation method according to claim 6, characterized in that, The second mixed solvent is one or more of acetonitrile, toluene, dichloromethane, N,N-dimethylformamide, tetrahydrofuran, 1,2-dichloroethane, 1,4-dioxane, chloroform, or dimethyl sulfoxide, preferably a mixed solution of dichloromethane and acetonitrile; 8. The preparation method according to claim 6, characterized in that, The linking reaction group unit is selected from one or more of benzyl bromide, 1,4-bis(bromomethyl)benzene, and o-dichlorobenzene, preferably 1,4-bis(bromomethyl)benzene; The second specified temperature is 100 °C - 120 °C, preferably 110 °C; The second specified duration is 3 - 6 days, preferably 3 days.

9. A probe capable of detecting PPi and PFOS, characterized in that, The probe capable of detecting PPi and PFOS is prepared by the preparation method of the probe capable of detecting PPi and PFOS according to any one of claims 1 to 9.

10. Use of the probe capable of detecting PPi and PFOS according to claim 9, characterized in that, The probe capable of detecting PPi and PFOS is used for detecting pyrophosphate ions and potassium perfluorooctanesulfonate, the concentration of the pyrophosphate ions is at least 48 nmol / L, and the concentration of the potassium perfluorooctanesulfonate is at least 51 nmol / L.

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