Cyanobrythril derivatives, their preparation methods, and their applications in zinc ion recognition

Abstract

This application relates to the fields of organic light-emitting materials and ion recognition, and more specifically, it provides a cyanostilbene derivative, its preparation method, and its application in zinc ion recognition and recovery detection. Firstly, this application designs and synthesizes a tri(2-aminoethyl)amine triangular framework-bridged cyanostilbene derivative TCS. The cyanostilbene groups on its three sides provide the fluorophore, while the tri(2-aminoethyl)amine triangular framework provides the flexible framework bridging the cyanostilbene groups. Driven by supramolecular self-assembly, this single-component TCS can perform fluorescence colorimetric detection of zinc ions in a THF / H2O system with a detection limit as low as 41 nM. The fluorescence color changes from yellow-green to cyan, exhibiting highly efficient single-recognition characteristics. Utilizing this characteristic, TCS can be widely applied to drinking water quality monitoring and industrial wastewater discharge detection, significantly improving water quality safety assurance levels.

Description

Technical Field

[0001] This application belongs to the field of organic light-emitting materials and ion recognition technology, specifically relating to a cyanoblastin derivative, its preparation method, and its application in zinc ion recognition. Background Technology

[0002] In modern analytical chemistry and environmental monitoring, the efficient identification and detection of zinc ions is becoming increasingly important, especially due to zinc's crucial role in biological systems and its potential environmental hazards. Supramolecular fluorescent materials, leveraging the unique advantages of supramolecular chemistry, construct precise fluorescence sensing systems through non-covalent interactions (such as hydrogen bonding, π-π stacking, electrostatic interactions, and metal coordination). Due to their excellent optical properties, molecular recognition capabilities, and high design flexibility, they have become a core area of ​​functional materials research in recent years. Particularly in zinc ion recognition, supramolecular fluorescent materials can efficiently identify and respond to the presence of zinc ions through precise coordination, making them extremely promising for applications in complex environments and biological systems.

[0003] Supramolecular fluorescent sensors for zinc ions can sensitively detect zinc ions through changes in fluorescence intensity, color changes, or quenching phenomena. With increasingly severe environmental pollution, accurate detection of zinc ions has become particularly urgent, especially in environmental monitoring, biomedicine, and industrial production. By introducing functionalized supramolecular fluorescent materials, these sensors not only provide highly sensitive and low-detection-limit quantitative analysis of zinc ions in complex matrices, but also exhibit strong anti-interference capabilities and rapid response, offering practical solutions for environmental protection and life sciences. As our understanding of the importance of zinc ions deepens, the development and application of these sensors will undoubtedly play an increasingly crucial role in pollution monitoring, the regulation of trace element balance in the human body, and industrial wastewater treatment. Summary of the Invention

[0004] To address the aforementioned technical problems, this application provides a cyanostilbene derivative (hereinafter referred to as compound TCS), its preparation method, and its application in zinc ion recognition.

[0005] To achieve the above objectives, the present invention provides the following solution:

[0006] In a first aspect, the present invention provides a cyanostilbene derivative, the structure of which is shown in formula (I):

[0007]

[0008] Secondly, the present invention provides a method for preparing a cyanostilbene derivative, the method comprising: adding compound a, compound b and EtOH to a reaction vessel under a N2 atmosphere, stirring the reaction at room temperature for 12 h; filtering the obtained product to obtain a filter cake; dissolving the filter cake with DCM, adding EtOH to precipitate crystals, and then filtering and vacuum drying to obtain the cyanostilbene derivative;

[0009] The compound a is The compound b is

[0010] Furthermore, in this preparation method, the molar ratio of compound a to compound b is 3:0.9 to 1.1.

[0011] Furthermore, in this preparation method, the amounts of each component are as follows: compound a is 0.50 g and 2.0 mmol; compound b is 0.10 g and 0.67 mmol; and EtOH is 50 mL.

[0012] Furthermore, the preparation method also includes the preparation of compound a, specifically comprising the following steps: reacting p-hydroxyphenylacetonitrile and benzaldehyde at room temperature under NaOH / EtOH alkaline conditions to obtain the intermediate product 2-(4-hydroxyphenyl)-3-phenylacrylonitrile; then adding hexamethylenetetramine to the 2-(4-hydroxyphenyl)-3-phenylacrylonitrile, using TFA / AcOH as solvent, and heating under reflux under nitrogen protection to react, and obtaining compound a after the reaction is completed.

[0013] Furthermore, the molar ratio of p-hydroxyphenylacetonitrile, sodium hydroxide, and benzaldehyde is 1:(2-2.5):(1-1.5); the molar ratio of 2-(4-hydroxyphenyl)-3-phenylacrylonitrile to hexamethylenetetramine is 1:1.2-1.7.

[0014] Thirdly, this invention provides the application of the cyanostilbene derivatives described above in the fields of zinc ion identification and recovery detection. Because the cyanostilbene derivatives provided in this application possess a Schiff base structure and exhibit strong coordination activity, they can be used as metal ion identification reagents.

[0015] Furthermore, the method for applying the cyanostilbene derivative in zinc ion recognition includes the following steps: preparing a 20 μM mixed solution of the cyanostilbene derivative and THF / H2O, and ultrasonically treating it for 5 min to obtain self-assembled nanoparticles; wherein the volume ratio of THF to H2O in THF / H2O is 4:6; adding different samples to the nanoparticles, ultrasonically treating them for 3 min, and obtaining recognition results; the samples include metal cations and non-metal anions; when zinc ions are present in the sample, the fluorescence of the mixed solution changes from the original yellow-green to cyan, and the fluorescence emission shifts from the original 533 nm emission to 491 nm emission.

[0016] Furthermore, the cyanostilbene derivative was used as a zinc ion probe, with a detection limit of 41 nM.

[0017] Furthermore, a method for detecting the ion recovery rate of the cyanostilbene derivative in real water samples includes the following steps: preparing a 20 μM TCS solution with a water content of 60% using the cyanostilbene derivative; wherein the real water sample includes tap water, lake water, ditch water, or green tea water; adding 0 μM, 4 μM, 6 μM, 8 μM, and 10 μM zinc ions to the TCS solution respectively, and ultrasonically treating for 10 min to obtain test solutions with different concentrations of zinc ions; measuring the fluorescence intensity changes of the test solutions with different concentrations of zinc ions using a fluorescence spectrophotometer, plotting regression curves based on the obtained fluorescence intensities, and calculating the zinc ion recovery rate.

[0018] Compared with the prior art, this application has the following beneficial effects:

[0019] 1. The cyanostilbene derivative provided in this application has a simple synthesis method, uses inexpensive and readily available raw materials, and has a low preparation cost;

[0020] 2. The cyanostilbene derivative provided in this application has the characteristic of single and efficient recognition of zinc ions in the THF / H2O system. The fluorescence color changes from the original yellow-green to cyan, and the fluorescence intensity is increased to twice the original value. The detection limit is only 41 nM, which is better than many existing zinc ion recognition probes. In addition, its ion recognition is highly efficient and unique in the addition of other metal cations and non-metal anions without interference. This performance enables it to efficiently detect zinc ions in water and can be widely used in drinking water quality monitoring and industrial wastewater discharge detection, significantly improving the level of water quality safety assurance.

[0021] 3. The zinc ion recognition of the cyanostilbene derivative provided in this application remains highly efficient and unique in real water samples. Utilizing this characteristic, the recognition of zinc ions in real water samples can be achieved, thereby improving the level of water quality safety assurance.

[0022] 4. The cyanostilbene derivative provided in this application can be used as a supramolecular fluorescent probe material for single-component, high-efficiency zinc ion recognition, which is of great significance for the future development of multi-channel applications of single-component organic light-emitting recognition materials. Attached Figure Description

[0023] Figure 1 This is a schematic diagram of the zinc ion recognition process of the compound TCS provided in this application;

[0024] Figure 2 This is the 1H NMR spectrum of the compound TCS provided in this application;

[0025] Figure 3 This is the carbon NMR spectrum of the compound TCS provided in this application;

[0026] Figure 4 This is a high-resolution mass spectrum of the compound TCS provided in this application;

[0027] Figure 5 This is the fluorescence spectrum of the AIE effect of the compound TCS provided in this application;

[0028] Figure 6 This is the fluorescence spectrum of zinc ion recognition of the compound TCS provided in this application;

[0029] Figure 7 The titration spectrum and fluorescence intensity change of the compound TCS provided in this application are linearly fitted to the titration spectrum and fluorescence intensity change of zinc ions as zinc ions are gradually added.

[0030] Figure 8 This application describes the anti-interference application of the compound TCS provided in this application for ion recognition;

[0031] Figure 9 This application demonstrates the recovery rate of the compound TCS provided in this application in real water samples. Detailed Implementation

[0032] The following detailed description of this application is provided in conjunction with the embodiments. It should be noted that: unless otherwise specified, the conditions in the following embodiments are performed under conventional conditions or conditions recommended by the manufacturer. Unless otherwise specified, the raw materials used in the following embodiments are all from commercially available sources.

[0033] This application provides a cyanostilbene derivative, its preparation method, and its application in zinc ion recognition. The synthesized target compound TCS exhibits excellent selectivity and sensitivity for zinc ions in a THF / H₂O mixed solution of 4 / 6 (v / v). Upon addition of zinc ions, the fluorescence of compound TCS significantly shifts from a yellow-green hue at 533 nm to a cyan hue at 491 nm, and the fluorescence intensity doubles. This property enables efficient detection of zinc ions in water, and can be widely applied to drinking water quality monitoring and industrial wastewater discharge detection, significantly improving water quality safety assurance.

[0034] First, this application provides a cyanostilbene derivative that can be synthesized via a three-step reaction. Specifically, the synthesis of compound a requires two steps, plus a final step involving the condensation of compounds a and b, totaling three steps. In its structure, the three cyanostilbene groups on the three sides provide the fluorophore, while the tris(2-aminoethyl)amine triangular framework in the middle serves as a flexible bridging skeleton for the cyanostilbene. The structure of compound TCS is shown in formula (I):

[0035]

[0036] Secondly, this application provides a method for preparing a cyanobystilbene derivative, wherein compound TCS is prepared by dehydration condensation of compound a and compound b, and the reaction equation is as follows:

[0037]

[0038] Compound a is Compound b is

[0039] Specifically, the preparation method of compound TCS includes the following steps: under N2 atmosphere, compound a (0.50 g, 2.0 mmol) and compound b (0.10 g, 0.67 mmol) are added to a 100 mL three-necked flask and dissolved in EtOH (50 mL). The mixture is stirred at room temperature for 12 h. After the reaction is complete, the mixture is filtered and the filter cake is retained. The filter cake is dissolved with a small amount of DCM, and a large amount of EtOH is added to reduce its solubility and recrystallize it. The mixture is filtered and dried under vacuum to obtain orange solid TCS (0.42 g, 75%).

[0040] Preferably, the molar ratio of compound a to compound b is 3:1.

[0041] In the preparation of compound TCS, the reaction vessel needs to be connected to a water separator. The water separator is filled with dry molecular sieves to remove the water generated during the reaction, and finally a yellow solid is obtained, which is compound TCS.

[0042] The preparation method of compound a includes the following two steps: (1) 2-(4-hydroxyphenyl)-3-phenylacrylonitrile is obtained by reacting p-hydroxyphenylacetonitrile and benzaldehyde at room temperature under NaOH / EtOH alkaline conditions; (2) hexamethylenetetramine is added and compound a is prepared by heating under reflux with TFA / AcOH as solvent under nitrogen protection.

[0043] In the preparation of compound a, the molar ratio of p-hydroxyphenylacetonitrile, sodium hydroxide, and benzaldehyde is 1:2:1.2; the molar ratio of the prepared product to hexamethylenetetramine is 1:1.5.

[0044] Furthermore, this application provides an application of a cyanoblastane derivative. Specifically, it describes the application of the cyanoblastane derivative in the field of zinc ion recognition, and the application method includes the following steps:

[0045] S11. Compound TCS was prepared into a mixed solution of THF / H2O = 4 / 6, and after ultrasonic treatment for 5 min, self-assembled nanoparticles with a concentration of 20 μM were obtained.

[0046] S12. Add different samples (including metal cations and non-metal anions) to the nanoparticles, sonicate for 3 minutes and shake gently, and wait for the identification results.

[0047] Preferably, in step S11, the test concentration of the THF / H2O mixed system is 20 μM, and the excitation wavelength of the THF / H2O system is 322 nm.

[0048] More preferably, in step S12, the concentration of both the metal cation and the non-metal anion is 20 μM.

[0049] Compound TCS was subjected to ultrasonic treatment for 5 min in a THF / H2O = 4 / 6 mixture to obtain self-assembled nanoparticles. The yellow-green fluorescent nanoparticles have efficient zinc ion recognition. After the addition of zinc ions, the fluorescence color of the yellow-green fluorescent nanoparticles changed from yellow-green to cyan, and the fluorescence intensity was significantly enhanced to twice the original value.

[0050] Of all the samples, only when the fluorescence of the added zinc ions changed from the original yellow-green to cyan, and when measured with a fluorescence spectrophotometer, the fluorescence emission shifted from the original 533nm emission to 491nm emission, and the fluorescence intensity was significantly enhanced to twice the original, indicating that the probe has a single and efficient recognition ability for zinc ions.

[0051] It can be seen that the compound TCS prepared in this invention has strong fluorescence emission at 533 nm. In a mixed solution of tetrahydrofuran and water, the fluorescence intensity first increases and then decreases with the increase of water content. The emission intensity reaches the highest when the water content is 60%. Water is a poor solvent and tetrahydrofuran is a good solvent.

[0052] This invention provides the ion recognition characteristics of the compound TCS. A mixed solution of TCS with a water content of 60% was prepared. After adding zinc ions, the fluorescence of the solution showed a significant blue shift compared to the initial solution, changing from yellow-green to cyan, and the fluorescence intensity increased to twice its original value. Both the amount of blue shift and the intensity increase were positively correlated with the concentration of added zinc ions; that is, with the gradual addition of zinc ions, the fluorescence gradually blue-shifted and increased until an optimal binding ratio was reached, after which the change ceased. Ion recognition is as follows: Figure 1 As shown.

[0053] The anti-interference test of the compound TCS provided in this application for single zinc ion recognition was also performed. After zinc ion recognition was completed, other metal cations and non-metal anions were added. The results showed that there was no significant change in fluorescence color and emission intensity, indicating that it has excellent anti-interference ability.

[0054] Utilizing the high zinc ion recognition efficiency of compound TCS, it was applied as a probe to determine the zinc ion recovery rate in real water samples, specifically including the following steps:

[0055] S21. Prepare a solution of compound TCS with a water content of 60% and a concentration of 20 μM using real water samples (tap water, lake water, ditch water, green tea water);

[0056] S22. Add 0 μM, 4 μM, 6 μM, 8 μM and 10 μM zinc ions to the freshly prepared TCS solution respectively, sonicate for 3 min, and test the change in fluorescence intensity using a fluorescence spectrophotometer.

[0057] S23. Plot regression curves for the fluorescence intensity of tests with different concentrations of zinc ions, and calculate the recovery rate of zinc ions.

[0058] Preferably, in step S21, the real water samples are all freshly obtained and used after secondary filtration through filter paper and a sample filter. The water content of the freshly prepared TCS solutions for different real water samples is all 60%. In step S22, the recovery rate calculation method for each concentration is to take the average of three sets of data.

[0059] Example

[0060] Example 1

[0061] Preparation of compound TCS:

[0062] Under a nitrogen atmosphere, compound a (0.50 g, 2.0 mmol) and compound b (0.10 g, 0.67 mmol) were added to a 100 mL three-necked flask and dissolved in EtOH (50 mL). The mixture was stirred at room temperature for 12 h. After the reaction was complete, the mixture was filtered, and the filter cake was collected. The filter cake was dissolved with a small amount of DCM, and a large amount of EtOH was added to reduce its solubility, causing recrystallization. The solution was filtered and dried under vacuum to obtain an orange solid TCS (0.42 g, 75%).

[0063] The proton NMR spectrum of compound TCS is as follows: Figure 2 As shown: 1 HNMR (300MHz, CDCl3): δ (ppm) = 14.05 (s, 3H, -OH), 8.26 (s, 3H, N = CH-), 7.77-7.74 (m, 6H, Ar-H), 7.49-7.46 (m, 3H, Ar-H), 7.39-7.37 (m, 9H, Ar -H),7.25(d,J=3.0Hz,3H,Ar-H),7.20(s,3H,=CH-),6.97(d,J=9.0Hz,3H,Ar-H),3.68(t,J=4.5Hz,6H,-CH2-),2.96(t,J=6.0Hz,6H,-CH2-). Figure 2 The middle image shows the 1H NMR spectrum of compound TCS. Figure 2 As can be seen from the data, the positions and numbers of hydrogen atoms on compound TCS correspond one-to-one with those on the 1H NMR spectrum, which proves that the structure of compound TCS is correct.

[0064] The carbon NMR spectrum of compound TCS is as follows: Figure 3 As shown: 13 C NMR (75MHz, CDCl3): δ (ppm) = 165.7, 163.1, 139.7, 133.8, 130.1, 129.4, 129.3, 129.1, 128.9, 124.4, 118.3, 118.0, 110.5, 57.2, 55.6. Figure 3 The middle image shows the carbon NMR spectrum of compound TCS. Figure 3 As can be seen from the data, the number of carbons at different positions on the compound TCS corresponds one-to-one with the carbon NMR spectrum, which proves that the structure of the compound TCS is correct.

[0065] High-resolution mass spectra of compound TCS, such as Figure 4 As shown: HRMS(ESI)m / z:calcd for C 54 H 45 N7O3.[M+H] + =840.3657,found=840.3655. Figure 4 The middle image shows the high-resolution mass spectrum of compound TCS. Figure 4 As can be seen from the high-resolution mass spectrometry, the molecular structure of compound TCS with the addition of hydrogen can be obtained from the high-resolution mass spectrometry, which further confirms the structure of compound TCS.

[0066] Based on the above experimental characterization, the structure of compound TCS was determined to be:

[0067]

[0068] Example 2

[0069] Aggregation-induced emission (AIE) property testing of compound TCS:

[0070] An aqueous solution of compound TCS was prepared at a test concentration of 20 μM, using tetrahydrofuran as a good solvent and water as a poor solvent. The fluorescence intensity in the figure first increases and then decreases with increasing water content, as shown in the figure. Figure 5 As shown. Figure 5 The AIE behavior test of compound TCS is shown in Figure (a), which displays the fluorescence spectrum of compound TCS as the water content increases, and Figure (b) shows the line graph of fluorescence intensity at 533 nm. Figure 5 As can be seen, the fluorescence intensity of the mixed solvent is strongest when the water content is 60%, which is more obvious before and after the identification of zinc ions, and can identify zinc ions efficiently.

[0071] Example 3

[0072] Zinc ion recognition properties of compound TCS:

[0073] A mixed solution of compound TCS with a water content of 60% was prepared. After adding zinc ions, the fluorescence of the solution showed a significant blue shift compared to the initial solution, changing the color from yellow-green to cyan, and the fluorescence intensity increased to twice the original value. Both the amount of blue shift and the increase in intensity were positively correlated with the concentration of added zinc ions; that is, with the gradual addition of zinc ions, the fluorescence gradually blue-shifted and increased until the optimal binding ratio was reached, after which the change ceased. Figure 6 and Figure 7 As shown. Figure 7 In the image, (a) shows the titration fluorescence spectrum of zinc ions, and (b) shows the linear fit of the fluorescence intensity change with the addition of zinc ions. Figure 7 As can be seen from the results, in the fluorescence titration test, the fluorescence intensity at 491 nm continuously increases with the continuous addition of zinc ions, reaching its maximum value when it reaches one equivalent. Subsequently, a linear curve is fitted, and the detection limit for zinc ion recognition can be calculated to be 41 nm according to the formula for the detection limit.

[0074] Example 4

[0075] Compound TCS in ion recognition and anti-interference effects:

[0076] Step 1: Weigh 16.8 mg of compound TCS into a 5 mL volumetric flask, add tetrahydrofuran and dilute to 5 mL to prepare a 4 mM stock solution;

[0077] Step 2: Transfer 20 μL of the mother liquor of compound TCS to a 5 mL centrifuge tube using a pipette, add 1580 μL of tetrahydrofuran and 2400 μL of water in sequence, and sonicate for 3 min to form aqueous phase dispersed nanoparticles with a water content of 60%.

[0078] Step 3: Transfer 20 μL of the mother liquor of compound TCS to a 5 mL centrifuge tube using a pipette, and add 1580 μL of acetonitrile, 2400 μL of water and 20 μL of other metal cations in sequence to prepare a TCS concentration of 20 μM. After sonication for 3 min, nanoparticles with an aqueous phase dispersion and a water content of 60% are formed.

[0079] Step 4: Among all samples, only when the fluorescence of the added zinc ions changed from the original yellow-green to cyan, and the fluorescence emission was measured with a fluorescence spectrophotometer, the fluorescence emission shifted from the original 533nm emission to 491nm emission, and the fluorescence intensity was significantly enhanced to twice the original, indicating that the probe has a single and efficient recognition ability for zinc ions.

[0080] Step 5: After zinc ion recognition, other metal cations and non-metal anions were added. The results showed no significant change in fluorescence color and emission intensity, indicating that the probe has excellent anti-interference capabilities. Figure 8 As shown. In this embodiment, the ultrasonic instrument used is a commonly used laboratory ultrasonic cleaner with a frequency of 40kHz.

[0081] Example 5

[0082] Application of TCS compound recovery rate in real water samples:

[0083] Step 1: Prepare a 60% water content solution (20 μM) of the compound TCS using real water samples (tap water, lake water, ditch water, green tea water);

[0084] Step 2: Add 0 μM, 4 μM, 6 μM, 8 μM and 10 μM zinc ions to the freshly prepared TCS solution respectively, sonicate for 3 min, and test the change in fluorescence intensity using a fluorescence spectrophotometer.

[0085] Step 3: Plot regression curves for the fluorescence intensity of samples tested with different concentrations of zinc ions, and calculate the recovery rate of zinc ions; for example... Figure 9 As shown. Figure 9 The image shows the recovery rate of compound TCS for zinc ion recognition in different real water samples. Figure 9 As can be seen, the compound TCS has almost no effect on the detection of zinc ions in different real water samples, indicating that the identification of zinc ions by the compound TCS can be applied to a variety of real water samples, and the detection is highly efficient and practical.

[0086] The above description is merely an exemplary embodiment of this application, but the scope of protection of this application is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the scope of the technology disclosed in this application should be included within the scope of protection of this application. Therefore, the scope of protection of this application should be determined by the scope of the claims.

Claims

1. A cyanostilbene derivative, characterized in that, The structure of this cyanostilbene derivative is shown in formula (I):

2. A method for preparing a cyanostilbene derivative, characterized in that, The preparation method includes: Under a nitrogen atmosphere, compounds a, b, and EtOH were added to a reaction vessel and stirred at room temperature for 12 hours. The resulting product was filtered to obtain a filter cake. The filter cake was dissolved with DCM, and EtOH was added to precipitate crystals. The product was then filtered and vacuum dried to obtain the cyanostilbene derivative. The compound a is The compound b is 3. The method for preparing the cyanostilbene derivative according to claim 2, characterized in that, In this preparation method, the molar ratio of compound a to compound b is 3:0.9 to 1.

1.

4. The method for preparing the cyanostilbene derivative according to claim 2, characterized in that, In this preparation method, the amounts of each component are used in the following proportions: compound a is 0.50 g and 2.0 mmol; compound b is 0.10 g and 0.67 mmol; and EtOH is 50 mL.

5. The method for preparing the cyanostilbene derivative according to claim 2, characterized in that, The preparation method also includes the preparation of compound a, specifically comprising the following steps: reacting p-hydroxyphenylacetonitrile and benzaldehyde at room temperature under NaOH / EtOH alkaline conditions to obtain the intermediate product 2-(4-hydroxyphenyl)-3-phenylacrylonitrile; then adding hexamethylenetetramine to the 2-(4-hydroxyphenyl)-3-phenylacrylonitrile, using TFA / AcOH as solvent, and heating under reflux under nitrogen protection to react, and obtaining compound a after the reaction is completed.

6. The method for preparing the cyanostilbene derivative according to claim 5, characterized in that, The molar ratio of p-hydroxyphenylacetonitrile, sodium hydroxide, and benzaldehyde is 1:(2-2.5):(1-1.5); the molar ratio of 2-(4-hydroxyphenyl)-3-phenylacrylonitrile to hexamethylenetetramine is 1:1.2-1.

7.

7. The application of the cyanostilbene derivative as described in claim 1 in the field of zinc ion identification and recovery rate detection, in non-disease diagnosis and treatment.

8. The application according to claim 7, characterized in that, The method for applying the cyanostilbene derivative in zinc ion recognition includes the following steps: The cyanostilbene derivative was prepared into a 20 μM mixed solution with THF / H2O; wherein the volume ratio of THF to H2O in THF / H2O was 4:

6. After ultrasonic treatment for 5 min, self-assembled nanoparticles were obtained. Different samples were added to the nanoparticles, and the samples were ultrasonically treated for 3 minutes to obtain the identification results. The sample includes metal cations and non-metal anions; when zinc ions are present in the sample, the fluorescence of the mixed solution changes from yellow-green to cyan, and the fluorescence emission shifts from 533nm to 491nm.

9. The application according to claim 8, characterized in that, The cyanostilbene derivative was used as a zinc ion probe, and the detection limit was 41 nM.

10. The application according to claim 7, characterized in that, A method for detecting ion recovery rate in real water samples using the cyanostilbene derivative includes the following steps: The cyanostilbene derivative was prepared into a TCS solution with a water content of 60% and a concentration of 20 μM using real water samples; wherein, the real water samples included tap water, lake water, ditch water or green tea water; Zinc ions of 0 μM, 4 μM, 6 μM, 8 μM, and 10 μM were added to the TCS solution, and the solution was sonicated for 10 min to obtain test solutions with different concentrations of zinc ions. The fluorescence intensity changes of the test solutions with different concentrations of zinc ions were measured using a fluorescence spectrophotometer. Regression curves were plotted based on the obtained fluorescence intensities, and the recovery rate of zinc ions was calculated.

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