Organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoate as well as preparation method and application of organic fluorescent probe Tri-ATPM

Abstract

The invention discloses an organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoate as well as a preparation method and application of the organic fluorescent probe Tri-ATPM, and belongs to the technical field of organic synthesis and analytical chemistry. The organic fluorescent probe Tri-ATPM is a compound of a crown ether bridged tetraphenylimidazole derivative, and the chemical name of the organic fluorescent probe Tri-ATPM is 1, 2-(pyridine-4-(1, 4, 5-triphenyl-1H-imidazolyl-2-yl)) acetyl triethylene glycol ester; the preparation method comprises the following steps: uniformly mixing 4-(1, 4, 5-triphenyl-1H-imidazolyl-2-yl) pyridine and triethylene glycol dichloro acetate in dry acetonitrile by taking KI as a catalyst in a nitrogen atmosphere, stirring, refluxing and reacting, filtering reactants, decompressing and concentrating to obtain a crude product, washing with ethanol, performing secondary decompressing and concentrating, washing and concentrating with a mixture of methylbenzene and dichloromethane, and drying to obtain the 4-(1, 4, 5-triphenyl-1H-imidazolyl-2-yl) pyridine. The dried yellow green solid is collected, and the yellow green solid is the organic fluorescent probe Tri-ATPM. The organic fluorescent probe Tri-ATPM can be used as an ideal fluorescent probe for rapidly detecting bromoxynil octanoate.

Description

Technical Field

[0001] The invention belongs to the technical field of organic synthesis and analytical chemistry, and specifically relates to an organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoyl and a preparation method and application thereof. Background Art

[0002] Bromoxynil octanoate has a molecular formula of C 15 H 17 Br2NO2, molecular weight is 403.11, chemical name is 3,5-dibromo-4-octanoyloxybenzonitrile. Octanoyl bromoxynil belongs to the benzonitrile contact herbicide, which achieves the purpose of killing weeds by inhibiting various processes of photosynthesis, especially the Hill reaction of photosynthesis, causing rapid necrosis of plant tissues. It accelerates leaf death when the temperature is high. Octanoyl bromoxynil can control annual or perennial broadleaf weeds, and at the same time has high selectivity for gramineous crops, and can be safely used in all growth stages of crops. Due to its significant herbicidal performance, octanoyl bromoxynil is widely used in wheat fields, corn, sorghum, sugarcane, flax, onion and other crop fields to control a variety of broadleaf weeds such as Polygonum, Chenopodium, Amaranth, Oleraceum, Solanum nigrum, Xanthium sibiricum, and Bindweed.

[0003] However, when bromoxynil is used as a pesticide, it has high water solubility and volatility. Based on these characteristics, it is easy to cause loss, thus reducing the effect of weed control; at the same time, bromoxynil is more likely to enter the water body and evaporate into the air, causing environmental pollution and threatening human health. Studies have shown that bromoxynil exhibits high biological toxicity. If humans accidentally inhale or ingest it, it will cause problems such as high body temperature, reproductive organ damage, and even death. Therefore, it is necessary to develop an effective detection method to reduce the negative impact of bromoxynil on the environment and humans.

[0004] At present, the detection methods of bromoxynil include gas chromatography / liquid chromatography (GC / LC), gas chromatography tandem mass spectrometry (GC-MS), enzyme-linked immunosorbent assay (ELISA), etc. For example, a Chinese patent with publication number CN112014482A and application date of May 29, 2019 discloses a method for detecting herbicide residues in grains and their products, comprising the steps of mixing a grain and oil matrix, water and formic acid acetonitrile and performing a first extraction to obtain a first extract; mixing the first extract with anhydrous magnesium sulfate and sodium chloride and performing a second extraction to obtain a second extract; centrifuging the second extract to obtain a supernatant as a matrix extract, mixing the matrix extract with a purifier and purifying the matrix extract, and then centrifuging the purified material to obtain a supernatant as a test solution; using ultra-high performance liquid chromatography-tandem mass spectrometry to measure the test solution, the method can achieve simultaneous detection of 62 herbicides including bromoxynil; Sun Jiong, Sun Shanzhi, Wang Ting, etc. published "High Performance Liquid Chromatography for Detection of Bromoxynil Residues in Wheat Flour" in Liaoning Chemical Industry in November 2018, aiming to establish a high performance liquid chromatography method for analyzing the residues of bromoxynil in wheat flour. The method of ultrasonic extraction with 0.5% acid acetonitrile solution, purification with distilled water, anhydrous sodium sulfate and diatomaceous earth, detection by HPLC 1260 and quantification by external standard method is simple in pretreatment and highly accurate, which meets the technical requirements of pesticide residue analysis. However, the above detection methods all have the disadvantages of complex instrument use, high detection cost and long time consumption, which limits the wide application of these detection methods in many daily scenarios.

[0005] Organic fluorescent probes use fluorescent substances as indicators and produce fluorescence under the excitation of light of a certain wavelength, and detect the generated fluorescence to achieve qualitative or quantitative analysis of the substance being detected. As an excellent fluorescent sensor, organic fluorescent probes have excellent biosensitivity, high sensitivity, rapid response, and strong anti-interference ability in cells. They have been successfully used in the detection of various molecules and ions, and play an important role in biological detection, medical diagnosis, environmental monitoring, and materials science. With the continuous advancement of science and technology, the performance research of organic fluorescent probes has continued to mature, and its application fields have become more extensive, but organic fluorescent probes for identifying bromoxynil are rare.

[0006] As an important active ingredient of pesticides, bromoxynil has been widely used in the fields of crop pest control, weeding and sterilization. In order to ensure food security and improve the quality of agricultural products, it is urgent to design an organic fluorescent probe with high sensitivity, high selectivity, high stability and biocompatibility that can be easily used in various detection scenarios of bromoxynil. Summary of the invention

[0007] In order to solve the problems existing in the prior art, the present invention provides an organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoyl and a preparation method and application thereof. The organic fluorescent probe Tri-ATPM can form a complex with bromoxynil octanoyl in a dimethyl sulfoxide-water mixed solution to enhance the fluorescence intensity, and can be used as an ideal fluorescent probe for rapid detection of bromoxynil octanoyl.

[0008] The technical solution of the present invention is as follows:

[0009] One of the purposes of the present invention is to provide a preparation method of an organic fluorescent probe Tri-ATPM. In a nitrogen atmosphere, KI is used as a catalyst, 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine and triethylene glycol dichloroacetate are uniformly mixed, stirred and refluxed in dry acetonitrile for reaction, after the reaction is completed, the reactant is filtered and the filtrate is concentrated under reduced pressure to obtain a crude product, the crude product is washed with ethanol, the washing liquid is collected for secondary reduced pressure concentration, and the concentrated product is washed with a mixture of toluene and dichloromethane, and the dried yellow-green solid is collected to obtain the organic fluorescent probe Tri-ATPM.

[0010] Further, the synthetic route is as follows:

[0011]

[0012] Furthermore, the molar ratio of 4-(1,4,5-triphenyl-1H-imidazol-2-yl)pyridine, triethylene glycol dichloroacetate and KI is 6-2:1:6-16.

[0013] Furthermore, the 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine was prepared according to the method of the public document "Analytical Chemistry, 2017, 89(18):10085-10093".

[0014] Furthermore, the triethylene glycol dichloroacetate is prepared according to the method of the public document "New Journal of Chemistry, 2020, 44(27): 11746-11751".

[0015] Furthermore, the stirring and reflux conditions are stirring and reflux in 20-40 mL of dry acetonitrile for 6-24 h.

[0016] Furthermore, the reduced pressure concentration is performed by reducing the pressure with a water pump to evaporate the filtrate to a substantially solvent-free state.

[0017] Furthermore, the secondary vacuum concentration is performed by reducing the pressure with a water pump to evaporate the washing liquid to a substantially solvent-free state.

[0018] Furthermore, the molar ratio of toluene and dichloromethane in the mixture is 1:1.

[0019] The second object of the present invention is to provide an organic fluorescent probe Tri-ATPM, wherein the organic fluorescent probe Tri-ATPM is a compound of a tetraphenylimidazole derivative bridged by a crown ether, and its molecular formula is C 62 H 54 I2N6O6, chemical name is 1,2-(pyridine-4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)) acetyl triglycol ester.

[0020] Furthermore, the specific structure of the organic fluorescent probe Tri-ATPM is:

[0021]

[0022] Furthermore, the organic fluorescent probe Tri-ATPM H NMR spectrum (400 MHz, DMSO-d6) ppm: 8.90 (d, J = 8.0 Hz, 4H, ArH), 7.87 (d, J = 8.0 Hz, 4H, ArH), 7.27-7.55 (m, 30H, ArH), 5.65 (d, J = 16.0 Hz, 4H, CH2N + ),4.29(m,4H,OCOCH2),3.66(m,4H,OCH2),3.55(m,4H,OCH2).

[0023] Carbon NMR (100 MHz, DMSO-d6) ppm: 166.65, 146.03, 144.58, 140.12, 136.39, 135.45, 133.03, 130.92, 130.23, 130.00, 129.34, 128.73, 128.51, 127.63, 126.59, 123.31, 69.76, 67.96, 65.58, 64.89, 59.50, 41.16. MALDI-TOF-MS (C 62 H 54 I2N6O6)Calcd.For m / z(-2I - )=979.149,found:979.041.Anal.Calcd.for C 62 H 54 I2N6O6: C 60.40; H 4.41; N6.82. Found: C 60.44; H 4.37; N 6.78.

[0024] The third object of the present invention is to provide an organic fluorescent probe Tri-ATPM for use in a rapid and sensitive detection environment for bromoxynil octanoate.

[0025] Furthermore, in a dimethyl sulfoxide-water mixed solution, the organic fluorescent probe Tri-ATPM emits a weak green fluorescence at 505 nm and can form a 1:1 complex with bromoxynil, thereby significantly enhancing its fluorescence intensity. In a certain range, the degree of fluorescence enhancement is proportional to the concentration of bromoxynil, and the content of bromoxynil in the solution can be obtained by comparing the fluorescence intensity value with the standard curve of the gradient change of bromoxynil concentration.

[0026] Furthermore, the volume ratio of the two in the dimethyl sulfoxide-water mixed solution is 5:95.

[0027] Furthermore, the organic fluorescent probe Tri-ATPM was prepared into a solution of a certain concentration, and a series of bromoxynil solutions with gradient concentrations were prepared at molar multiples of 0, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.4, 0.6, 0.8, 1.0, 2.0, 3.0, 4.0, and 5.0. The organic fluorescent probe Tri-ATPM solution was fully shaken and mixed with the series of bromoxynil solutions of different concentrations one by one, and the fluorescence intensity of the mixed solution was measured to establish a standard curve of the gradient change of bromoxynil concentration with the bromoxynil concentration as the horizontal axis and the fluorescence intensity of the mixed solution as the vertical axis.

[0028] Furthermore, the organic fluorescent probe Tri-ATPM is mixed with a solution containing bromoxynil pesticide of unknown concentration, the fluorescence intensity value of the mixed solution is measured and compared with the standard curve of bromoxynil concentration gradient change, and the bromoxynil content in the bromoxynil solution of unknown concentration can be read from the curve.

[0029] Compared with the prior art, the present invention has the following beneficial effects:

[0030] 1. The present invention discloses for the first time a compound of 1,2-(pyridine-4-(1,4,5-triphenyl-1H-imidazol-2-yl))acetyl triglycol ester, which is a tetraphenyl imidazole derivative bridged by a crown ether, as an organic fluorescent probe Tri-ATPM. The organic fluorescent probe Tri-ATPM appears green in a dimethyl sulfoxide solution and emits green fluorescence at 501 nm. In a dimethyl sulfoxide-water (V / V, 5:95) mixed solution, it emits weak green fluorescence at 505 nm. However, when bromoxynil is present in the solution environment, the organic fluorescent probe Tri-ATPM can form a 1:1 complex with bromoxynil, significantly enhancing the fluorescence intensity. In a certain range, the degree of fluorescence enhancement is proportional to the concentration of bromoxynil. The organic fluorescent probe Tri-ATPM can be applied to the sensitive detection of bromoxynil in various sample environments and is an ideal fluorescent probe for rapid detection of bromoxynil.

[0031] 2. The organic fluorescent probe Tri-ATPM designed by the present invention has the advantages of high sensitivity, high selectivity and high stability, and the fluorescence changes significantly in the presence of bromoxynil. It can not only detect low concentrations of the target molecule bromoxynil, with a detection limit of 5.7 μM, but also maintain good sensitivity and stability when other pesticides or ions are present, and basically does not interfere with the detection of bromoxynil, ensuring the accuracy of detecting bromoxynil pesticides in complex environments and real samples. In addition, the organic fluorescent probe Tri-ATPM can also realize real-time online detection and visual detection, which is suitable for various bromoxynil detection scenarios that require rapid response, and intuitively displays the detection results through the visualization of fluorescent signals.

[0032] 3. The present invention provides a simple and easy-to-operate preparation method for the organic fluorescent probe Tri-ATPM, and can simultaneously ensure high yield and purity of the probe molecule. Compared with other types of probes, the preparation method of the present invention does not require complicated pretreatment or special reaction equipment, and has a relatively low synthesis cost, is suitable for large-scale production, and is conducive to reducing application costs, and can meet the large demand for detecting bromoxynil in practical applications. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 This is an infrared spectrum of the functional group structure of the organic fluorescent probe Tri-ATPM described in Example 1 of the present invention;

[0034] Figure 2 This is a hydrogen nuclear magnetic resonance spectrum of the organic fluorescent probe Tri-ATPM structure described in Example 1 of the present invention;

[0035] Figure 3 This is the carbon nuclear magnetic resonance spectrum of the organic fluorescent probe Tri-ATPM structure described in Example 1 of the present invention;

[0036] Figure 4 This is the mass spectrum of the organic fluorescent probe Tri-ATPM structure described in Example 1 of the present invention;

[0037] Figure 5 1.0×10 -5 mol / L of the organic fluorescent probe Tri-ATPM was mixed with 5.0×10 -5 mol / L fluorescence emission spectra of various common pesticide molecules or ions mixed;

[0038] Figure 6 1.0×10 -5mol / L of the organic fluorescent probe Tri-ATPM after mixing with different concentrations of bromoxynil octanoate in dimethyl sulfoxide-water solution (V / V, 5:95), wherein 1=Tri-ATPM, 2=1+bromoxynil octanoate, 3=1+pymetrozine, 4=1+imidacloprid, 5=1+glufosinate, 6=1+glyphosate isopropylamine salt, 7=1+mancozeb, 8=1+carbendazim, 9=1+paclobutrazol, 10=1+hypromexyl, 11=1+clopyralid, 12=1+thiophanate-methyl, 13=1+sulfuron-methyl, 14=1+thiamethoxam, 15=1+metoclopramide, 16=1+metoclopramide, 17=1+spirulinamidol ethanolamine salt, 18=1+metaaldehyde, 19=1+tricyclazole, 20=1+Na + , 21=1+K + , 22=1+Al 3+ , 23=1+Ba 2+ , 24=1+Ca 2+ , 25 = 1 + Mg 2+ , 26=1+Cu 2+ , 27=1+Zn 2+ , 28=1+NH4 + , 29=1+SO4 2- , 30=1+Cl - , The illustration is the fluorescence comparison before and after recognition of bromoxynil octanoyl;

[0039] Figure 7 The present invention is based on performance testing Figure 6 The standard curve of bromoxynil concentration gradient change and fluorescence intensity change established by fluorescence emission spectrum;

[0040] Figure 8 The graph of the change in fluorescence intensity of the organic fluorescent probe Tri-ATPM described in the performance test of the present invention before and after adding other guests to a mixed solution of bromoxynil in dimethyl sulfoxide-water solution (V / V, 5:95), wherein 1=Tri-ATPM+bromoxynil, 2=1+pymetrozine, 3=1+imidacloprid, 4=1+phosphinothricin, 5=1+glyphosate isopropylamine salt, 6=1+mancozeb, 7=1+carbendazim, 8=1+paclobutrazol, 9=1+hypromexyl, 10=1+clopyralid, 11=1+thiophanate-methyl, 12=1+sulfuron-methyl, 13=1+thiamethoxam, 14=1+metoclopramide, 15=1+metosulfuron, 16=1+spirulinamidol ethanolamine salt, 17=1+metaformaldehyde, 18=1+tricyclazole, 19=1+Na + , 20=1+K + , 21=1+Al 3+ , 22=1+Ba 2+ , 23=1+Ca 2+ , 24 = 1 + Mg2+ , 25=1+Cu 2+ , 26=1+Zn 2+ , 27=1+NH4 + , 28=1+SO4 2- , 29=1+Cl - . DETAILED DESCRIPTION

[0041] The present invention is further described below in conjunction with preferred embodiments. The endpoints of the ranges disclosed in the present invention and any values ​​are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be deemed to be specifically disclosed herein.

[0042] The experimental methods in the following examples, unless otherwise specified, are conventional methods and are performed according to the techniques or conditions described in the literature in the art or according to the product instructions.

[0043] Unless otherwise specified, the materials and reagents used in the following examples can be obtained from commercial sources.

[0044] The 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine described in the following examples was prepared according to the method of the public document "Analytical Chemistry, 2017, 89(18):10085-10093".

[0045] The triethylene glycol dichloroacetate described in the following examples was prepared according to the method of the public document "New Journal of Chemistry, 2020, 44(27): 11746-11751".

[0046] Example 1

[0047] This embodiment provides a method for preparing an organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoyl, which specifically comprises the following steps:

[0048] S1. Under nitrogen atmosphere, 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine (2 mmol), triethylene glycol dichloroacetate (1 mmol) and KI (6 mmol) were stirred and refluxed in 40 mL of dry acetonitrile for 24 hours;

[0049] S2, TLC monitoring the reaction progress, after the reaction is completed, the solution is filtered, the filtrate is evaporated to a substantially solvent-free state by a water pump under reduced pressure to obtain a crude product, the crude product is washed with ethanol and the washing liquid is collected for secondary reduced pressure concentration, and the washing liquid is evaporated to a substantially solvent-free state by a water pump under reduced pressure to obtain a concentrated product;

[0050] S3. Wash the concentrated product three times with a mixture of toluene and dichloromethane in a molar ratio of 1:1, collect the dried yellow-green solid, which is the organic fluorescent probe Tri-ATPM, with a yield of 54%.

[0051] The infrared spectra of the functional group structures of the organic fluorescent probe Tri-ATPM prepared in this example are shown in Figure 2. Figure 1 As shown; the nuclear magnetic resonance hydrogen spectrum is shown Figure 2 As shown; the carbon NMR spectrum is as shown Figure 3 As shown; the mass spectrum is as Figure 4 shown.

[0052] Example 2

[0053] This embodiment provides a method for preparing an organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoyl, which specifically comprises the following steps:

[0054] S1. Under nitrogen atmosphere, 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine (6 mmol), triethylene glycol dichloroacetate (1 mmol) and KI (12 mmol) were stirred and refluxed in 30 mL of dry acetonitrile for 6 hours;

[0055] S2, TLC monitoring the reaction progress, after the reaction is completed, the solution is filtered, the filtrate is evaporated to a substantially solvent-free state by a water pump under reduced pressure to obtain a crude product, the crude product is washed with ethanol and the washing liquid is collected for secondary reduced pressure concentration, and the washing liquid is evaporated to a substantially solvent-free state by a water pump under reduced pressure to obtain a concentrated product;

[0056] S3. Wash the concentrated product three times with a mixture of toluene and dichloromethane in a molar ratio of 1:1, collect the dried yellow-green solid, which is the organic fluorescent probe Tri-ATPM, with a yield of 49%.

[0057] Example 3

[0058] This embodiment provides a method for preparing an organic fluorescent probe Tri-ATPM for detecting bromoxynil octanoyl, which specifically comprises the following steps:

[0059] S1. Under nitrogen atmosphere, 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine (4 mmol), triethylene glycol dichloroacetate (1 mmol) and KI (16 mmol) were stirred and refluxed in 20 mL of dry acetonitrile for 12 hours;

[0060] S2, TLC monitoring the reaction progress, after the reaction is completed, the solution is filtered, the filtrate is evaporated to a substantially solvent-free state by a water pump under reduced pressure to obtain a crude product, the crude product is washed with ethanol and the washing liquid is collected for secondary reduced pressure concentration, and the washing liquid is evaporated to a substantially solvent-free state by a water pump under reduced pressure to obtain a concentrated product;

[0061] S3. Wash the concentrated product three times with a mixture of toluene and dichloromethane in a molar ratio of 1:1, collect the dried yellow-green solid, which is the organic fluorescent probe Tri-ATPM, with a yield of 58%.

[0062] Performance Testing

[0063] 1. Selective testing

[0064] In a dimethyl sulfoxide-water solution (V / V, 5:95), 1.0×10 -5 mol / L organic fluorescent probe Tri-ATPM and 5.0×10 -5 mol / L of various common pesticide molecules or ions were mixed, and the fluorescence intensity was measured respectively. The fluorescence emission spectrum was constructed with the wavelength as the horizontal axis and the fluorescence intensity as the vertical axis.

[0065] Fluorescence emission spectra such as Figure 5 As shown, in the tests of various pesticide molecules or ions, the organic fluorescent probe Tri-ATPM only responds significantly to bromoxynil and the fluorescence is significantly enhanced, indicating that the organic fluorescent probe Tri-ATPM can perform good selective recognition on bromoxynil.

[0066] 2. Correlation test

[0067] In a dimethyl sulfoxide-water solution (V / V, 5:95), 1.0×10 -5 mol / L organic fluorescent probe Tri-ATPM was mixed with bromoxynil solutions of different concentrations. The concentrations of bromoxynil were 0, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.4, 0.6, 0.8, 1.0, 2.0, 3.0, 4.0 and 5.0 molar multiples of the concentration of the organic fluorescent probe Tri-ATPM, respectively. The fluorescence emission spectrum was constructed with the wavelength as the abscissa and the fluorescence intensity as the ordinate, and a standard curve of bromoxynil concentration gradient change and fluorescence intensity change was established based on this.

[0068] Fluorescence emission spectra such as Figure 6 As shown in the figure, the fluorescence intensity of the organic fluorescent probe Tri-ATPM showed a significant upward trend with the increase of the concentration of bromoxynil. Figure 7 As shown, when the concentration of bromoxynil is 0~1×10 -6 In the mol / L range, the enhancement of the fluorescence intensity of the mixed system of organic fluorescent probe Tri-ATPM and bromoxynil is linearly related to the concentration of bromoxynil, and has a good correlation, which can be used as a standard working curve for the control detection of bromoxynil concentration.

[0069] 3. Sensitivity test

[0070] In a dimethyl sulfoxide-water solution (V / V, 5:95), 1.0×10 -5 mol / L organic fluorescent probe Tri-ATPM and bromoxynil octanoyl as well as the fluorescence intensity of the mixed system before and after adding other interfering objects. The concentration of the mixed system after adding other interfering objects is 2.0×10 -5 mol / L.

[0071] like Figure 8 As shown in the fluorescence intensity change graph, the detection of bromoxynil by the organic fluorescent probe Tri-ATPM of the present invention is not disturbed after adding other objects, indicating that the detection of bromoxynil by the organic fluorescent probe Tri-ATPM has the characteristic of high sensitivity.

[0072] It should be noted that, in this article, relational terms such as "first" and "second" are only used to distinguish one entity or operation from another entity or operation, and do not necessarily require or imply any such actual relationship or order between these entities or operations. The terms "include", "comprises" or any other variants thereof are intended to cover non-exclusive inclusion, so that a process, method, article or device including a series of elements includes not only those elements, but also other elements not explicitly listed, or also includes elements inherent to such process, method, article or device. In the absence of further restrictions, the elements defined by the sentence "comprises a ..." do not exclude the presence of other identical elements in the process, method, article or device including the elements.

[0073] The above are only preferred embodiments of the present application and do not constitute any form of limitation to the present application. Any technician familiar with the profession can make some changes or modify the technical contents disclosed above into equivalent embodiments with equivalent changes without departing from the scope of the technical solution of the present application. However, any simple modification, equivalent change and modification made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application still fall within the scope of the technical solution of the present application.

Claims

1. A method for preparing an organic fluorescent probe Tri-ATPM, characterized in that: In a nitrogen atmosphere, KI is used as a catalyst, 4-(1,4,5-triphenyl-1H-imidazol-2-yl)pyridine and triethylene glycol dichloroacetate are mixed evenly, stirred and refluxed in dry acetonitrile for reaction, and after the reaction is completed, the reactant is filtered and the filtrate is concentrated under reduced pressure to obtain a crude product, the crude product is washed with ethanol, the washing liquid is collected and concentrated under reduced pressure for a second time, and the concentrated product is washed with a mixture of toluene and dichloromethane, and the dried yellow-green solid is collected to obtain the organic fluorescent probe Tri-ATPM.

2. The method for preparing an organic fluorescent probe Tri-ATPM according to claim 1, characterized in that: The molar ratio of the 4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)pyridine, triethylene glycol dichloroacetate and KI is 6-2:1:6-16.

3. The method for preparing an organic fluorescent probe Tri-ATPM according to claim 1, characterized in that: The stirring and reflux conditions are stirring and reflux in 20-40 mL of dry acetonitrile for 6-24 hours.

4. The method for preparing an organic fluorescent probe Tri-ATPM according to claim 1, characterized in that: The reduced pressure concentration is carried out by reducing the pressure with a water pump to evaporate the filtrate to a substantially solvent-free state.

5. The method for preparing an organic fluorescent probe Tri-ATPM according to claim 1, characterized in that: The secondary vacuum concentration is carried out by reducing the pressure with a water pump to evaporate the washing liquid to a substantially solvent-free state.

6. The method for preparing an organic fluorescent probe Tri-ATPM according to claim 1, characterized in that: The molar ratio of toluene and dichloromethane in the mixture is 1:

1.

7. An organic fluorescent probe Tri-ATPM prepared according to any one of claims 1 to 6, characterized in that: The organic fluorescent probe Tri-ATPM is a compound composed of a crown ether-bridged tetraphenylimidazole derivative, and its molecular formula is C 62 H 54 I2N6O6, chemical name is 1,2-(pyridine-4-(1,4,5-triphenyl-1H-imidazolyl-2-yl)) acetyl triglycol ester.

8. The organic fluorescent probe Tri-ATPM according to claim 7, characterized in that: The specific structure of the organic fluorescent probe Tri-ATPM is:

9. Use of the organic fluorescent probe Tri-ATPM according to any one of claims 7-8 in a rapid and sensitive detection environment of bromoxynil octanoate.

10. The use of an organic fluorescent probe Tri-ATPM in a rapid and sensitive detection environment of bromoxynil octanoyl according to claim 9, characterized in that: In a dimethyl sulfoxide-water mixed solution, the organic fluorescent probe Tri-ATPM emits weak green fluorescence at 505 nm and can form a 1:1 complex with bromoxynil, significantly enhancing its fluorescence intensity. In a certain range, the degree of fluorescence enhancement is proportional to the concentration of bromoxynil. The content of bromoxynil in the solution can be obtained by comparing the fluorescence intensity value with the standard curve of the gradient change of bromoxynil concentration.

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