Cyanostilbene derivative, preparation method thereof and application of cyanostilbene derivative in zinc ion recognition

Abstract

The invention relates to the field of organic light-emitting materials and ion recognition, and particularly provides a cyano stilbene derivative, a preparation method thereof and application of the cyano stilbene derivative in zinc ion recognition and recovery rate detection. Firstly, a tris (2-aminoethyl) amine tripod bridged cyano-stilbene derivative TCS is designed and synthesized, cyano-stilbene groups on three sides of the tris (2-aminoethyl) amine tripod bridged cyano-stilbene derivative TCS provide fluorophores for the molecule, and the tris (2-aminoethyl) amine tripod provides a flexible framework bridged with the cyano-stilbene groups. Under the driving of supramolecular self-assembly, the single-component TCS can perform fluorescence colorimetric detection on zinc ions in a THF / H2O system under the condition that the detection limit is as low as 41nM, the fluorescence color is changed from yellow green to cyan, and the single-component TCS has an efficient single recognition characteristic; by means of the characteristic, the TCS can be widely applied to drinking water quality monitoring and industrial wastewater discharge detection, and the water quality safety guarantee level is remarkably improved.

Description

Technical Field

[0001] The present application belongs to the technical field of organic luminescent materials and ion recognition, and specifically relates to a cyanophenylethylene derivative and a preparation method thereof and an application thereof in zinc ion recognition. Background Art

[0002] In modern analytical chemistry and environmental monitoring, the efficient identification and detection of zinc ions has become increasingly important, especially because of the key role of zinc in biological systems and its potential harm to environmental pollution. Supramolecular fluorescent materials use the unique advantages of supramolecular chemistry to construct precise fluorescent sensing systems through non-covalent interactions (such as hydrogen bonds, π-π stacking, electrostatic interactions, metal coordination, etc.). Due to their excellent optical properties, molecular recognition capabilities and high design flexibility, they have become a core area of ​​functional material research in recent years. Especially in the recognition of zinc ions, supramolecular fluorescent materials can efficiently recognize and respond to the presence of zinc ions through precise coordination, which makes them have great application potential in complex environments and biological systems.

[0003] Supramolecular fluorescent sensors for zinc ions can achieve sensitive detection of zinc ions through changes in fluorescence intensity, color changes or quenching phenomena. As environmental pollution problems become increasingly severe, 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 can not only provide high sensitivity and low detection limit for quantitative analysis of zinc ions in complex matrices, but also show strong anti-interference and rapid response capabilities, providing practical solutions for environmental protection and life and health. With the deepening of the understanding of the importance of zinc ions, the development and application of such sensors will play an increasingly critical role in pollution monitoring, human trace element balance regulation and industrial wastewater treatment. Summary of the invention

[0004] In order to solve the above technical problems, the present application provides a cyanostilbene derivative (hereinafter referred to as compound TCS) and its preparation method and application in zinc ion recognition.

[0005] To achieve the above object, the scheme of the present invention is as follows:

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

[0007]

[0008] In a second aspect, the present invention provides a method for preparing a cyanophenylvinylbenzene derivative, the method comprising: adding compound a, compound b and EtOH to a reaction container under a N2 atmosphere, and stirring the reaction at room temperature for 12 hours; 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 cyanophenylvinylbenzene derivative;

[0009] The compound a is The compound b is

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

[0011] Furthermore, in the preparation method, the dosage of each component is according to the following ratio: compound a is 0.50 g, 2.0 mmol; compound b is 0.10 g, 0.67 mmol; EtOH is 50 mL.

[0012] Furthermore, the preparation method also includes preparing compound a, specifically including the following steps: reacting p-hydroxyphenylacetonitrile and benzaldehyde at room temperature under alkaline conditions of NaOH / EtOH to obtain an intermediate product 2-(4-hydroxyphenyl)-3-phenylacrylonitrile; adding hexamethylenetetramine to the 2-(4-hydroxyphenyl)-3-phenylacrylonitrile, using TFA / AcOH as a solvent, heating under reflux under nitrogen protection to react, and obtaining the 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 and hexamethylenetetramine is 1:1.2-1.7.

[0014] In a third aspect, the present invention provides the use of the above-mentioned cyanostilbene derivatives in the field of zinc ion recognition and recovery rate detection. Because the cyanostilbene derivatives provided in the present application have a Schiff base structure and have a strong coordination effect, they can be used as metal ion recognition reagents.

[0015] Furthermore, a method for applying the cyanophenylvinylbenzene derivative to zinc ion recognition comprises the following steps: preparing the cyanophenylvinylbenzene derivative and THF / H2O into a mixed solution with a concentration of 20 μM, and obtaining self-assembled nanoparticles after ultrasonic treatment for 5 minutes; wherein the volume ratio of THF to H2O in THF / H2O is 4:6; adding different samples to the nanoparticles, and obtaining recognition results after ultrasonic treatment for 3 minutes; 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 blue-shifts from the original 533nm emission to 491nm 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 applying the cyanostilbene derivative to ion recovery rate detection in real water samples comprises the following steps: preparing the cyanostilbene derivative with a real water sample into a TCS solution with a water content of 60% and a concentration of 20 μM; 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 minutes to obtain test solutions with different concentrations of zinc ions added; using a fluorescence spectrophotometer to test the change in fluorescence intensity of the test solutions with different concentrations of zinc ions added, drawing a regression curve with the obtained fluorescence intensity and calculating the recovery rate of zinc ions.

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

[0019] 1. The cyanophenylethylene derivatives provided in the present application have a simple synthesis method, cheap and readily available raw materials, and low preparation cost;

[0020] 2. The cyanostilbene derivative provided in the present 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 enhanced to twice the original, and the detection limit is only 41nM, which is better than many existing zinc ion recognition probes. In addition, its ion recognition has efficient and unique recognition when adding other metal cations and non-metal anions, without interference. This property 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 is still highly efficient and unique in real water samples. By utilizing this characteristic, the identification of zinc ions in real water samples can be achieved, thereby improving the level of water quality safety assurance;

[0022] 4. The cyanophenylvinylbenzene derivatives provided in this application can be used as a single high-efficiency supramolecular fluorescent probe material for zinc ion recognition, which is of great significance for the future development of multi-channel applications of single-component organic light-emitting recognition materials. BRIEF DESCRIPTION OF THE DRAWINGS

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

[0024] Figure 2 is the hydrogen nuclear magnetic resonance spectrum of the compound TCS provided in the present application;

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

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

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

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

[0029] Figure 7 It is the linear fitting of the titration spectrum and fluorescence intensity change of the compound TCS provided in the present application as zinc ions are gradually added;

[0030] Figure 8 The present application provides the anti-interference application of the compound TCS in ion recognition;

[0031] Fig. 9 This is the application of the recovery rate of the compound TCS in real water samples provided by this application. DETAILED DESCRIPTION

[0032] The present application is further described in detail below in conjunction with the examples. It is particularly noted that if no specific conditions are specified in the following examples, the experiments are carried out according to conventional conditions or the conditions recommended by the manufacturer. Unless otherwise specified, the raw materials used in the following examples can be obtained from common commercial sources.

[0033] The present application provides a cyanostilbene derivative, a preparation method thereof, and an application in zinc ion identification. The synthesized target compound TCS has excellent selectivity and sensitivity to zinc ions in a mixed solution of THF / H2O=4 / 6 (v / v). After adding zinc ions, the fluorescence of the compound TCS significantly blue-shifts from the yellow-green color of 533nm to the cyan color of 491nm, and the fluorescence intensity is enhanced to twice the original. 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.

[0034] First, the present application provides a cyanophenylvinylbenzene derivative that can be synthesized by a three-step reaction. The TCS synthesis is a three-step synthesis, specifically, the synthesis of compound a requires two steps, plus the last step of compound a and compound b condensation, a total of three steps. In its structure, the three-sided cyanophenylvinylbenzene groups provide a fluorophore for the molecule, and the middle tris(2-aminoethyl)amine triangle serves as a flexible skeleton bridging the cyanophenylvinylbenzene. The structure of the compound TCS is shown in formula (I):

[0035]

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

[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, dissolved in EtOH (50 mL), and stirred for reaction at room temperature for 12 h; after the reaction is complete, the filter cake is filtered off, a small amount of DCM is used to dissolve the filter cake, a large amount of EtOH is added to reduce its solubility, recrystallization is precipitated, filtering, and vacuum drying 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, and a dry molecular sieve is placed in the water separator 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 comprises the following two steps: (1) reacting p-hydroxyphenylacetonitrile and benzaldehyde under alkaline conditions of NaOH / EtOH at room temperature to obtain an intermediate product 2-(4-hydroxyphenyl)-3-phenylacrylonitrile; (2) adding hexamethylenetetramine, using TFA / AcOH as solvent, and heating under reflux under nitrogen protection to prepare compound a.

[0043] In the preparation process 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 be further reacted with hexamethylenetetramine is 1:1.5.

[0044] Furthermore, the present application provides an application of a cyanostilbene derivative, specifically, applying the cyanostilbene derivative in the field of zinc ion recognition, and the application method comprises 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 were obtained with a concentration of 20 μM;

[0046] S12. Add different samples (samples include metal cations and non-metal anions) to the nanoparticles, sonicate for 3 minutes with slight shaking, 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 added concentration of the metal cation and the non-metal anion is 20 μM.

[0049] The compound TCS was treated with ultrasound for 5 minutes in a THF / H2O=4 / 6 mixed system to obtain self-assembled nanoparticles. The yellow-green fluorescent nanoparticles have efficient zinc ion recognition. After adding 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] Among all the samples, only when zinc ions were added did the fluorescence change from the original yellow-green to cyan. Measured using a fluorescence spectrophotometer, the fluorescence emission blue-shifted from the original 533nm emission to 491nm emission, and the fluorescence intensity was significantly enhanced to twice the original level, indicating that the probe has a single and efficient recognition ability for zinc ions.

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

[0052] The present invention provides the ion recognition characteristics of compound TCS. A compound TCS mixed solution with a water content of 60% is prepared. After zinc ions are added, the fluorescence of the solution undergoes a significant blue shift compared with the initial solution, the color changes from yellow-green to cyan, and the fluorescence intensity is enhanced to twice the original. The amount of blue shift and the intensity enhancement of the fluorescence are positively correlated with the concentration of the added zinc ions, that is, as zinc ions are gradually added, the fluorescence gradually blue shifts and enhances until it stops changing after reaching the optimal binding ratio. The ion recognition is as follows: Figure 1 shown.

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

[0054] Using the compound TCS's high efficiency recognition performance for zinc ions, it is used as a probe to determine the recovery rate of zinc ions in real water samples, specifically including the following steps:

[0055] S21. Compound TCS was prepared into a solution 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, adding 0 μM, 4 μM, 6 μM, 8 μM, and 10 μM zinc ions to the newly prepared TCS solution, respectively, and ultrasonically treating for 3 min, and testing the change of fluorescence intensity by fluorescence spectrophotometer;

[0057] S23. Draw a regression curve of the fluorescence intensity of the test with different concentrations of zinc ions added, and calculate the recovery rate of zinc ions.

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

[0059] Example

[0060] Example 1

[0061] Preparation of compound TCS:

[0062] Under N2 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, dissolved in EtOH (50 mL), and stirred at room temperature for 12 h. After the reaction was complete, the filter cake was filtered off and dissolved with a small amount of DCM. A large amount of EtOH was added to reduce the solubility, and recrystallization was precipitated. The mixture was filtered and vacuum dried to obtain orange solid TCS (0.42 g, 75%).

[0063] The H 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 NMR spectrum of compound TCS is shown in Figure 2 It can be seen that the position and number of hydrogen on the compound TCS correspond one to one with the H NMR spectrum, and the H NMR spectrum proves that the structure of the 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 NMR carbon spectrum of compound TCS is shown in Figure 3 It can be seen that the number of carbon atoms at different positions on the compound TCS corresponds one to one with the carbon NMR spectrum, and the carbon NMR spectrum proves that the structure of the compound TCS is correct.

[0065] High-resolution mass spectrometry of compound TCS Figure 4 Shown: HRMS (ESI) m / z:calcd for C 54 H 45 N7O3.[M+H] + =840.3657,found=840.3655. Figure 4 The high-resolution mass spectrum of compound TCS is shown in Figure 4 It can be seen that the molecular structure of compound TCS when hydrogen is added can be matched from the high-resolution mass spectrum, and the high-resolution mass spectrum further proves the structure of compound TCS.

[0066] According to the above experimental characterization, the structure of compound TCS is determined as follows:

[0067]

[0068] Example 2

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

[0070] The aqueous solution of compound TCS was prepared at a test concentration of 20 μM, with tetrahydrofuran as a good solvent and water as a poor solvent. In the figure, the fluorescence intensity first increases and then decreases as the water content increases, as shown in Figure 5 shown. Figure 5 This is a test of the AIE behavior of compound TCS. (a) is the fluorescence spectrum of compound TCS as the water content increases, and (b) is a line graph of the fluorescence intensity at 533 nm. Figure 5 It can be seen that when the water content is 60%, the fluorescence intensity of the mixed solvent is the strongest, which is more obvious before and after the recognition of zinc ions, and can be used for single and efficient recognition of zinc ions.

[0071] Example 3

[0072] Zinc ion recognition properties of compound TCS:

[0073] A compound TCS mixed solution with a water content of 60% was prepared. After adding zinc ions, the fluorescence of the solution was significantly blue-shifted compared with the initial solution, and the color changed from yellow-green to cyan, and the fluorescence intensity increased to twice the original. The amount of blue-shift and intensity enhancement of fluorescence 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 enhanced until it reached the optimal binding ratio and stopped changing, such as Figure 6 and Figure 7 shown. Figure 7 (a) is the fluorescence spectrum of zinc ion titration, and (b) is the linear fitting of the fluorescence intensity change with the addition of zinc ions. Figure 7 It can be seen that in the fluorescence titration test, with the continuous addition of zinc ions, the fluorescence intensity at 491nm continues to increase, and reaches a maximum value when it reaches one equivalent. Then a linear curve is fitted, and according to the detection limit formula, it can be calculated that the detection limit of zinc ion recognition is 41nM.

[0074] Example 4

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

[0076] Step 1, weigh 16.8 mg of compound TCS into a 5 mL volumetric flask, add tetrahydrofuran to make up to 5 mL, and prepare a 4 mM mother solution;

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

[0078] Step 3, use a pipette to transfer 20 μL of the mother solution of compound TCS to a 5 mL centrifuge tube, add 1580 μL of acetonitrile, 2400 μL of water and 20 μL of other metal cations in sequence, and configure the concentration of TCS to 20 μM. After ultrasonication for 3 minutes, water-dispersed nanoparticles are formed, and the water content is 60%;

[0079] Step 4: Among all samples, only when zinc ions were added did the fluorescence change from the original yellow-green to cyan. Using a fluorescence spectrophotometer to measure, the fluorescence emission blue-shifted from the original 533nm emission to 491nm emission, and the fluorescence intensity was significantly enhanced to twice the original. This shows 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 that there was no significant change in fluorescence color and emission intensity, indicating that the probe has excellent anti-interference ability. Figure 8 In this embodiment, the ultrasonic instrument used is an ultrasonic cleaning machine commonly used in laboratories, and the frequency is 40kHz.

[0081] Example 5

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

[0083] Step 1: The compound TCS is prepared into a solution 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);

[0084] Step 2: Add 0 μM, 4 μM, 6 μM, 8 μM, and 10 μM zinc ions to the TCS solution prepared just now, respectively, perform ultrasonic treatment for 3 minutes, and use a fluorescence spectrophotometer to test the change in fluorescence intensity;

[0085] Step 3: Draw a regression curve for the fluorescence intensity of the test with different concentrations of zinc ions added, and calculate the recovery rate of zinc ions; Fig. 9 shown. Fig. 9 The figure shows the recovery test of compound TCS for zinc ion recognition in different real water samples. Fig. 9 It can be seen that there is almost no effect on the compound detection of zinc ions in different real water samples, indicating that the compound TCS for the identification of zinc ions can be applied to a variety of real water samples, and the detection is single, efficient and practical.

[0086] The above is only an exemplary embodiment of the present application, but the protection scope of the present application is not limited thereto. Any changes or substitutions that can be easily thought of by a person skilled in the art within the technical scope disclosed in the present application should be included in the protection scope of the present application. Therefore, the protection scope of the present application should be based on the protection scope of the claims.

Claims

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

2. A method for preparing a cyanostilbene derivative, characterized in that: The preparation method comprises: Under a N2 atmosphere, compound a, compound b and EtOH were added to a reaction container, and the mixture was stirred at room temperature for 12 h. The obtained product was filtered to obtain a filter cake. After the filter cake was dissolved with DCM, EtOH was added to precipitate crystals, and the mixture was filtered and vacuum dried to obtain the cyanophenylvinylbenzene derivative. The compound a is The compound b is 3. The method for preparing a cyanostilbene derivative according to claim 2, characterized in that: In the preparation method, the molar ratio of the compound a to the compound b is 3:0.9-1.

1.

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

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

6. The method for preparing a 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 and hexamethylenetetramine is 1:1.2-1.

7.

7. Use of the cyanostilbene derivative as claimed in claim 1 in the field of zinc ion recognition and recovery rate detection.

8. The use according to claim 7, characterized in that: The method for applying the cyanostilbene derivative in zinc ion recognition comprises the following steps: The cyanostilbene derivative and THF / H2O are prepared into a mixed solution with a concentration of 20 μM; wherein the volume ratio of THF to H2O in THF / H2O is 4:6, and self-assembled nanoparticles are obtained after ultrasonic treatment for 5 minutes; Different samples were added to the nanoparticles and ultrasonically treated for 3 min to obtain 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 original yellow-green to cyan, and the fluorescence emission blue-shifts from original 533nm emission to 491nm emission.

9. The use according to claim 8, characterized in that: The cyanostilbene derivative was used as a zinc ion probe with a detection limit of 41 nM.

10. The use according to claim 7, characterized in that: The method for applying the cyanostilbene derivative to ion recovery detection in a real water sample comprises the following steps: The cyanostilbene derivative is prepared into a TCS solution with a water content of 60% and a concentration of 20 μM using a real water sample; wherein the real water sample includes tap water, lake water, ditch water or green tea water; 0 μM, 4 μM, 6 μM, 8 μM, and 10 μM zinc ions were added to the TCS solution respectively, and ultrasonic treatment was performed for 10 minutes to obtain test solutions with different concentrations of zinc ions added; The fluorescence intensity change of the test solution to which zinc ions of different concentrations were added was tested by a fluorescence spectrophotometer, and a regression curve was drawn based on the obtained fluorescence intensity to calculate the recovery rate of zinc ions.

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