A fluorescence probe for detecting hypochlorite based on ESIPT and AIE synergistic effect of benzothiazole structure and preparation method and application thereof

Abstract

This invention discloses a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE in a benzothiazole structure, its preparation method, and its application, belonging to the field of fluorescent probe technology. The invention uses 2-aminobenzylthiophenol and 2-hydroxy-5-methoxybenzaldehyde as starting materials, condensing them to form a benzothiazole derivative as the fluorescent core. A diaminomaleitrile recognition group is introduced through an aldehyde-amine condensation reaction to synthesize the fluorescent probe. After the probe undergoes a specific oxidation reaction with hypochlorite, the C=N double bond breaks, and the ESIPT and AIE effects are synergistically activated, resulting in a significant enhancement of fluorescence. This probe exhibits a fast response, a linear range of 0-200 μM, a detection limit of 29.1 nM, excellent selectivity and anti-interference properties, and stability under pH 6-10 conditions, making it suitable for highly sensitive detection of hypochlorite in aqueous solutions and complex systems.

Description

Technical Field

[0001] This invention belongs to the field of fluorescent probe technology, specifically relating to a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with benzothiazole structure, its preparation method, and its application. Background Technology

[0002] Hypochlorite (ClO) - As one of the key reactive oxygen species (ROS) in organisms, ClO plays a central role in innate immune defense, clearing pathogens and maintaining homeostasis by mediating inflammatory responses. However, ClO... - Its strong oxidizing properties make it prone to oxidative stress damage when its content is imbalanced. Excessive accumulation can lead to cell membrane lipid peroxidation, DNA breakage, and protein denaturation, which are closely related to various pathological processes such as rheumatoid arthritis, cardiovascular disease, neurodegenerative diseases, and even cancer. Therefore, it is necessary to establish a highly sensitive and selective ClO₂ solution. - The detection method has important physiological and pathological significance and practical application value.

[0003] Fluorescent probes have become one of the mainstream technologies for detecting reactive oxygen species due to their rapid response, non-invasiveness, visualization, and excellent biocompatibility. Benzothiazole derivatives are a classic framework for constructing excited-state intramolecular proton transfer (ESIPT) luminescent systems. Their phenolic hydroxyl groups and the nitrogen atoms of the thiazole ring can form stable intramolecular hydrogen bonds, achieving rapid proton transfer in the excited state and producing characteristic fluorescence with a large Stokes shift, effectively avoiding interference from background fluorescence in biological samples. Simultaneously, aggregation-induced emission (AIE) overcomes the bottleneck of traditional fluorescent molecule aggregation quenching, maintaining high-efficiency luminescence in aqueous solutions and complex biological environments.

[0004] Single luminescence mechanisms often struggle to balance high signal-to-noise ratio and environmental adaptability, while the synergistic effect of ESIPT and AIE can achieve complementary enhancement of fluorescence performance: ESIPT imparts characteristic emission and a large Stokes shift to the probe, while AIE improves its luminescence efficiency and stability in the aggregated state. Currently, for ClO... - Benzothiazolium probes still suffer from insufficient selectivity and high detection limits. Therefore, ClO2, which combines the characteristics of ESIPT and AIE, was designed and developed. - Specific probes have become a research hotspot in this field. Summary of the Invention

[0005] The first technical problem solved by this invention is to provide a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE in a benzothiazole structure. This probe has a novel structure, high specificity, low detection limit, and rapid response, enabling highly sensitive and selective on / off fluorescent detection of hypochlorite in aqueous solutions and complex systems. The second technical problem solved by this invention is to provide a method for preparing the fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE in a benzothiazole structure. This method has a simple synthetic route, mild reaction conditions, readily available raw materials, low cost, simple purification, and stable yield. It can be efficiently prepared through only three conventional organic reactions, making it suitable for large-scale production. The third technical problem solved by this invention is to provide the application of this fluorescent probe in the detection of hypochlorite ions.

[0006] To solve the above-mentioned technical problems, the technical solution adopted by the present invention is as follows:

[0007] A fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE in the benzothiazole structure, wherein the structural formula of the fluorescent probe is as follows:

[0008] .

[0009] Furthermore, the preparation method of the fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with benzothiazole structure includes the following steps:

[0010] (1) Mix 2-aminothiophenol, 2-hydroxy-5-methoxybenzaldehyde and sodium metabisulfite, then add DMF for reflux reaction, cool and pour into ice water to precipitate, filter, dry and recrystallize from ethanol to obtain intermediate T1.

[0011] (2) Mix the intermediate T1 obtained in step (1) with hexamethylenetetramine, add trifluoroacetic acid to dissolve, reflux reaction, cool and add water to continue reflux, cool and pour into ice water to precipitate, filter, wash with water until neutral, dry and recrystallize with ethanol to obtain intermediate T2.

[0012] (3) The intermediate T2 obtained in step (2) was mixed with diaminomaleitrile, ethanol was added, glacial acetic acid was added dropwise, the reaction was refluxed under nitrogen protection, cooled and filtered, washed, and the crude product was purified by silica gel column chromatography to obtain the fluorescent probe.

[0013] Furthermore, in step (1), the molar ratio of 2-aminothiophenol, 2-hydroxy-5-methoxybenzaldehyde and sodium metabisulfite is 1:1:1.

[0014] Furthermore, in step (1), the reflux reaction temperature is 120℃ and the reaction time is 6h.

[0015] Furthermore, in step (2), the molar ratio of intermediate T1 to hexamethylenetetramine is 1:2, and the amount of trifluoroacetic acid used is 30 mL.

[0016] Furthermore, in step (2), the reaction temperature is 72°C, the reflux time is 10h, and then water is added to continue reflux for 0.5h.

[0017] Furthermore, in step (3), the molar ratio of intermediate T2 to diaminomaleitrile is 1:1.5, and the amount of ethanol used is 25 mL.

[0018] Furthermore, in step (3), the reflux reaction temperature is 80°C and the time is 12h.

[0019] Furthermore, in step (3), the eluent purified by silica gel column chromatography is petroleum ether / ethyl acetate at a volume ratio of 5:1.

[0020] Furthermore, the application of the synergistic effect of ESIPT and AIE based on the benzothiazole structure for detecting hypochlorite ions in hypochlorite ion detection.

[0021] Compared with the prior art, the present invention has the following advantages:

[0022] (1) The present invention is simple to synthesize and low in cost: Compared with the probes in the prior art that require multiple synthesis and complex purification processes, the probes of the present invention can be prepared with only basic reactions and mild reaction conditions, which greatly reduces the synthesis cost and time cost and is suitable for batch preparation.

[0023] (2) The present invention is environmentally friendly and has no secondary pollution: the probe itself and the reaction products are low-toxicity organic compounds, which can be directly used for the detection of actual samples such as environmental water samples and tap water. No special post-processing steps are required, and it will not cause secondary pollution to the environment.

[0024] (3) This invention has high specificity recognition capability and can effectively eliminate false positive interference: the imine bond (C=N) in the probe molecule can be converted by hypochlorite (ClO) - It exhibits specific oxidative cleavage, while common reactive oxygen species, reactive nitrogen species, metal cations, and inorganic anions in the system cannot trigger this specific reaction, significantly improving the accuracy and reliability of the detection results. Attached Figure Description

[0025] Figure 1 This is a synthetic route diagram of the probe molecule in this application;

[0026] Figure 2 The above is the 1H NMR spectrum of the probe molecule in this application;

[0027] Figure 3 The carbon NMR spectrum of the probe molecule in this application;

[0028] Figure 4 This is the mass spectrum of the probe molecule in this application;

[0029] Figure 5 The probe molecule of this application is in ClO - UV absorption spectra in the presence of (0, 100, 160 μM);

[0030] Figure 6 The probe molecules (20 μM) and different concentrations of ClO in this application - Fluorescence spectra of the reaction (0-200 μM);

[0031] Figure 7 The fluorescence intensity of the probe molecule and ClO in this application - Linear fitting curves for concentrations (0-200 μM);

[0032] Figure 8 This is a graph showing the tolerance of the probe molecule (20 μM) of this application at different pH levels;

[0033] Figure 9 The probe molecule (20 μM) of this application is for ClO - The response time curve;

[0034] Figure 10 The probe molecule (20 μM) of this application is effective against different substances (100 μM: K). + Na + Ca 2+ Al 3+ Zn 2+ Mg 2+ Pb 2 + SO4 2+ NO2 - NO3 - CO3 2- HCO3 - CH3COO - H2PO4 - HPO4 2- PO4 3- H2O2, O2 - ·, S2O3 2- Fluorescence response diagrams of H2S, GSH, Cys, and Hcy;

[0035] Figure 11 The probe molecule of this application was modified by adding different interfering substances (100 μM: K) + Na + Ca 2+ Al 3+ Zn2+ Mg 2+ Pb 2+ SO4 2+ NO2 - NO3 - CO3 2- HCO3 - CH3COO - H2PO4 - HPO4 2- PO4 3- H2O2, O2 - ·, S2O3 2- H2S, GSH, Cys, Hcy) followed by ClO - (100μM) Anti-interference diagram;

[0036] Figure 12 This is a comparison diagram of the orbital energy levels of HOMO and LUMO before and after the reaction of the probe molecule in this application. Detailed Implementation

[0037] The present invention will be further illustrated below with reference to specific embodiments. These embodiments are implemented based on the technical solutions of the present invention, and it should be understood that these embodiments are only used to illustrate the present invention and are not intended to limit the scope of the present invention.

[0038] The 2-aminobenzylthiophenol and 2-hydroxy-5-methoxybenzaldehyde used in the following examples were purchased from Shanghai Titan Technology Co., Ltd., sodium metabisulfite from Shanghai Lingfeng Chemical Reagent Co., Ltd., N,N-dimethylformamide, glacial acetic acid, and dimethyl sulfoxide from Tianjin Jingxi Chemical Pesticide Manufacturing Co., Ltd., ethanol, petroleum ether, and ethyl acetate from Wuxi Yasheng Chemical Co., Ltd., hexamethylenetetramine and sodium hypochlorite solution from Saen Chemical Technology (Shanghai) Co., Ltd., purified water from Hangzhou Wahaha Group Co., Ltd., trifluoroacetic acid from Shanghai Aladdin Biochemical Technology Co., Ltd., and diaminomaleonitrile from Shanghai Dipo Chemical Technology Co., Ltd.

[0039] The probe design principle prepared in the following examples is as follows:

[0040] The probe uses benzothiazole-phenol as its core fluorescent backbone. The phenolic hydroxyl group and the nitrogen atom of the benzothiazole ring can form stable intramolecular hydrogen bonds, possessing the potential for excited-state intramolecular proton transfer (ESIPT) luminescence. (The text abruptly ends here, likely due to an incomplete sentence or missing information.) - During the reaction, the Schiff base (-CH=N-) structure formed by the condensation of the ortho-aldehyde group of the phenolic hydroxyl group and diaminomaleonitrile acts as a strong electron-withdrawing unit. Through photoinduced electron transfer (PET) or intramolecular charge transfer (ICT) effects, it effectively quenches the fluorescence of benzothiazole-phenol, resulting in a weakly fluorescent probe. ClO -As a highly reactive oxygen species, it can specifically oxidize and cleave the C=N double bond of Schiff bases. After the C=N double bond is cleaved, the PET / ICT fluorescence quenching pathway is completely released, and the phenolic hydroxyl group and benzothiazole ring undergo rapid proton transfer in the excited state, activating the ESIPT effect and producing the characteristic orange fluorescence with a large Stokes shift. Simultaneously, the reaction products readily aggregate in solution, restricting intramolecular rotation and vibration through the AIE effect, reducing non-radiative energy dissipation, and further amplifying the fluorescence signal, thus achieving the effect of oxidizing ClO₂. - The "weak fluorescence → strong fluorescence" switching response.

[0041] Example 1

[0042] like Figure 1 As shown, this embodiment provides a method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure, including the following steps:

[0043] (1) Weigh 1.72 g of 2-aminothiophenol, 2.28 g of 2-hydroxy-5-methoxybenzaldehyde and 2.85 g of sodium metabisulfite into a 100 mL round-bottom flask, add 25.0 mL of DMF and heat to 120 °C and reflux for 6 h. After cooling to room temperature, pour into 200 mL of ice water, a large amount of white precipitate is produced. After filtration and drying, recrystallize with ethanol to obtain 3.05 g of intermediate T1, with a mass yield of 79.12%.

[0044] (2) Weigh 2.06 g of intermediate T1 and 2.24 g of hexamethylenetetramine into a 100 mL round-bottom flask, add 30 mL of trifluoroacetic acid to dissolve all the solids, heat to 72 °C and reflux for 10 h, cool to room temperature and pour in 40 mL of H2O and continue reflux for 0.5 h. After cooling to room temperature again, pour in 300 mL of ice water, a large amount of yellow precipitate is produced, stir and filter, wash continuously with H2O until the waste liquid is neutral, dry and recrystallize with ethanol to obtain 1.75 g of pure intermediate T2, with a mass yield of 76.67%.

[0045] (3) Weigh 1.14 g of T2 intermediate and 0.65 g of diaminomaleonitrile into a 100 mL round-bottom flask, add 25 mL of ethanol and then add 2-3 drops of glacial acetic acid. Heat to 80 °C under N2 protection and reflux for 12 h. After cooling to room temperature, filter and collect the filter cake. Wash the filter cake several times with water and ethanol (v:v = 1:1). Separate the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (5:1 / v:v) as the eluent. The final probe is 0.98 g, with a mass yield of 65.33%. The 1H NMR spectrum of the probe molecule is shown below. Figure 2 As shown, the carbon NMR spectrum is as follows: Figure 3 As shown, the mass spectrum is as follows Figure 4 As shown. 1H NMR (500 MHz, DMSO-d6) δ12.34 (s,1H), 8.70 (s, 1H), 8.21 (d, J = 8.0 Hz, 1H), 8.16-8.11 (m, 3H), 7.92 (d, J =3.1 Hz, 1H),7.69 (d, J = 3.1 Hz, 1H), 7.64-7.57 (m, 1H), 7.56-7.49 (m, 1H), 3.89 (s, 3H) ppm. 13 C NMR (126 MHz, DMSO-d6) δ166.32, 152.81, 151.78, 151.53,133.99, 129.20, 127.44, 126.33, 124.34, 122.76, 119.69, 117.50, 117.04,114.91, 114.33, 110.59, 104.60, 103.37, 56.51 ppm. HRMS(ESI-): [C 19 H 13 N5O2S] - =374.41, found: 374.07.

[0046] Example 2

[0047] Probe stock solution: Weigh 37.54 mg of probe using a balance and dissolve it in 1 mL of DMSO. Dilute with deionized water to prepare a stock solution with a concentration of 20 μM.

[0048] Sodium hypochlorite solution: Take 9.45 μL of 7.5% sodium hypochlorite solution, add deionized water to 10 mL to obtain a 1000 μM / L stock solution, and then add different multiples of deionized water to dilute to obtain the solution of the required concentration. Store the prepared solution in the dark at low temperature.

[0049] Superoxide anion stock solution: The desired solution is obtained by dissolving an appropriate amount of potassium dioxide in DMSO. Other stock solutions are prepared directly from the corresponding solid or salt using deionized water to obtain the required concentration.

[0050] Example 3

[0051] UV-Vis absorption spectroscopy test:

[0052] Take 2.0 mL of ClO at different concentrations -Solutions (0 μM, 100 μM, 160 μM) were thoroughly mixed with 2.0 mL of probe stock solution, and after standing in the dark for 10 min, the UV absorption curves of each mixed solution were measured using a UV spectrophotometer. The changes in the curves were used to determine the relative activity of the probe and ClO₂. - Specific reaction details. For example... Figure 5 As shown, the probe's absorption peak is at 476 nm, and with ClO - As the concentration increases, the absorption peak at 476 nm gradually becomes larger, indicating that the probe and ClO... - A reaction occurred. Furthermore, the probe solution appears pale orange-yellow under natural light, with ClO... - The orange color gradually deepens with the addition of [a substance], which indicates that the probe reacts with ClO [a substance]. - A reaction occurred.

[0053] Example 4

[0054] Fluorescence emission spectroscopy test:

[0055] Take 2.0 mL of ClO at different concentrations - The solutions (0-200 μM) were thoroughly mixed with 2.0 mL of probe stock solution, and after standing in the dark for 10 min, the concentrations of ClO were recorded using a fluorescence spectrophotometer. - The fluorescence emission spectrum after the reaction of the solution and the probe was used to identify ClO. - The relationship between concentration and probe fluorescence intensity. (λex = 476 nm; λem = 500-80 nm; slit: 10 nm / 10 nm). For example... Figure 6 As shown, without the addition of ClO - At that time, the probe exhibited relatively weak fluorescence at 578 nm. With ClO - As the concentration gradually increased, the fluorescence of the probe at 578 nm gradually increased, from the initial 414.8 au to 2098.6 au. Figure 7 As shown, when ClO - When the concentration is between 0 μM and 200 μM, the fluorescence intensity and ClO - The concentrations exhibit an ideal linear relationship, and the fitted linear equation is y = 8.41025x + 464.20003, with a correlation coefficient R0. 2 = 0.99005. (LOD=3 using the formula) / K (where LOD is the minimum detection limit; : Standard deviation of multiple tests on blank samples; K: Slope of the linear fitting equation) The detection limit of the probe is calculated, and finally the probe can detect ClO - The lowest concentration was 29.1 nM.

[0056] Example 5

[0057] pH stability test of the probe:

[0058] Take 2.0 mL of ClO at different pH values - The 100 μM solution was thoroughly mixed with 2.0 mL of probe stock solution, and after standing in the dark for 10 min, the ClO₂ content at each pH was recorded using a fluorescence spectrophotometer. - Fluorescence curves after the reaction of the solution and probe were used to compare the fluorescence intensity and stability of the probe at different pH values ​​(λex = 476 nm; λem = 500-800 nm; slit: 10 nm / 10 nm). Figure 8 As shown, without the addition of ClO - At this pH range, the fluorescence intensity of the free probe changes negligibly within the pH range of 4-10, indicating that the probe can exist relatively stably within this range. When ClO is added... - Subsequently, the fluorescence intensity showed an increasing trend within the pH range of 2-5, stabilized at around pH 6, and began to decrease above pH 10. Therefore, it can be concluded that the probe can exhibit a relatively stable and good fluorescence signal within the pH range of 6-10 before and after the response. Thus, it can be concluded that the probe can actively achieve fluorescence response to ClO under weakly acidic, neutral, and alkaline conditions. - It responds to ensure that its own fluorescence signal is not drastically affected.

[0059] Example 6

[0060] probe for ClO - Response time test:

[0061] Take 12 portions of 2.0 mL ClO - The 100 μM solution was thoroughly mixed with 2.0 mL of probe stock solution, and then immediately placed in a fluorescence spectrophotometer to measure the fluorescence emission intensity. Measurements for each mixed solution were taken 5 seconds apart. After all measurements were completed, a line graph of time versus fluorescence intensity was plotted to illustrate the probe's response time (λex = 476 nm; λem = 496-800 nm; slit size: 10 nm / 10 nm). Figure 9 As shown, when ClO is added - At 10 seconds, the fluorescence intensity of the probe reached its peak, indicating that the probe had reacted with ClO. - Complete reaction.

[0062] Example 7

[0063] Selectivity testing of probes:

[0064] Take 2.0 mL of other common non-ClO - Solution of the substance (100 μM: K) + Na+ Ca 2+ Al 3+ Zn 2+ Mg 2+ Pb 2+ SO4 2+ NO2 - NO3 - CO3 2- HCO3 - CH3COO - H2PO4 - HPO4 2- PO4 3- H2O2, O2 - ·, S2O3 2- H₂S, GSH, Cys, and Hcy were each mixed thoroughly with 2.0 mL of probe stock solution. After standing in the dark for 10 min, the fluorescence curves of each solution and probe were recorded using a fluorescence spectrophotometer to confirm the selectivity of the probe (λex = 476 nm; λem = 500-800 nm; slit width: 10 nm / 10 nm). Figure 10 As shown, only when with ClO - The fluorescence intensity was significantly enhanced after the solutions were mixed, while other ion solutions caused almost no change in fluorescence intensity. Therefore, it can be concluded that the probe is effective against ClO₂. - It offers good selectivity.

[0065] Example 8

[0066] Probe anti-interference test:

[0067] Take 2.0 mL of other non-ClO - Solution of the substance (100 μM: K) + Na + Ca 2+ Al 3+ Zn 2+ Mg 2+ Pb 2+ SO4 2+ NO2 - NO3 - CO3 2- HCO3 - CH3COO - H2PO4 - HPO4 2- PO4 3- H2O2, O2 - ·, S2O3 2-H2S, GSH, Cys, and Hcy were each mixed thoroughly with 2.0 mL of probe stock solution, allowed to stand in the dark for 10 min, and then an equal volume of ClO was added. - After mixing the solutions thoroughly, allow them to stand in the dark for 10 minutes. Record the fluorescence curves of each solution and probe reaction using a fluorescence spectrophotometer to confirm the probe's anti-interference ability (λex = 476 nm; λem = 500-800 nm; slit width: 10 nm / 10 nm). Figure 11 As shown, the fluorescence intensity did not change significantly after the addition of interfering ions, especially when phosphate ions were present as interference. This indicates that the probe can target ClO₂. - It can provide excellent response while also performing accurate detection in complex physiological environments.

[0068] Example 9

[0069] Gaussian quantization calculation:

[0070] Using Gaussian software, the probe and probe-ClO were calculated at the #B3LYP / 6 -311G level based on density functional theory (DFT). - The HOMO and LUMO of the products after the reaction. Figure 12 It can be seen that the HOMO electron cloud density of the probe is mainly concentrated on the recognition groups diaminomaleitrile and the phenol backbone. The electron cloud in the LUMO orbital shifts towards the benzothiazole fluorescent group, at which point the energy level difference is 3.05965 eV. (The last sentence appears to be incomplete and possibly refers to a different probe.) - After the reaction, the PET / ICT was interrupted, and the energy level difference after the reaction was 3.6885 eV, which is greater than the energy level difference when the probe is present alone. This is similar to the effect of adding ClO to the probe. - This is consistent with the subsequent phenomenon of increased fluorescence.

[0071] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE using a benzothiazole structure, characterized in that, The structural formula of the fluorescent probe is: 。 2. The method for preparing the ESIPT and AIE synergistic effect based on the benzothiazole structure for detecting hypochlorite as described in claim 1, characterized in that: Includes the following steps: (1) Mix 2-aminothiophenol, 2-hydroxy-5-methoxybenzaldehyde and sodium metabisulfite, then add DMF for reflux reaction, cool and pour into ice water to precipitate, filter, dry and recrystallize from ethanol to obtain intermediate T1. (2) Mix the intermediate T1 obtained in step (1) with hexamethylenetetramine, add trifluoroacetic acid to dissolve, reflux reaction, cool and add water to continue reflux, cool and pour into ice water to precipitate, filter, wash with water until neutral, dry and recrystallize with ethanol to obtain intermediate T2. (3) The intermediate T2 obtained in step (2) was mixed with diaminomaleitrile, ethanol was added, glacial acetic acid was added dropwise, the reaction was refluxed under nitrogen protection, cooled and filtered, washed, and the crude product was purified by silica gel column chromatography to obtain the fluorescent probe.

3. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (1), the molar ratio of 2-aminothiophenol, 2-hydroxy-5-methoxybenzaldehyde and sodium metabisulfite is 1:1:

1.

4. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (1), the reflux reaction temperature is 120℃ and the reaction time is 6h.

5. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (2), the molar ratio of intermediate T1 to hexamethylenetetramine is 1:2, and the amount of trifluoroacetic acid used is 30 mL.

6. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (2), the reaction temperature is 72℃, the reflux time is 10h, and then water is added to continue reflux for 0.5h.

7. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (3), the molar ratio of intermediate T2 to diaminomaleitrile is 1:1.5, and the amount of ethanol used is 25 mL.

8. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (3), the reflux reaction temperature is 80℃ and the time is 12h.

9. The method for preparing a fluorescent probe for detecting hypochlorite based on the synergistic effect of ESIPT and AIE with a benzothiazole structure according to claim 2, characterized in that: In step (3), the eluent purified by silica gel column chromatography is petroleum ether / ethyl acetate in a volume ratio of 5:

1.

10. The application of the ESIPT and AIE synergistic effect based on the benzothiazole structure of claim 1 for detecting hypochlorite ions.

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