An amide chain-bridged bis-tetraphenylethylene fluorescent probe and its synthesis method and application

Abstract

The invention discloses an amide chain-bridged bis-tetraphenylethylene fluorescent probe and a synthesis method and application thereof, belonging to the technical field of organic synthesis and analytical chemistry. The fluorescent probe has a structure of an oxalamide-bridged bis-tetraphenylethylene unit and is chemically named 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine, i.e., Bis-TPE. In the invention, 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, 1,2-bis-chloroacetylethylenediamine, and anhydrous potassium carbonate are selected as synthetic raw materials, placed in a dry acetone system for reflux, and after sufficient reaction, the reaction mixture is extracted and distilled under reduced pressure, and the product is separated by silica gel column chromatography, thereby synthesizing the fluorescent probe. The fluorescence intensity of the fluorescent probe of the invention is 1000 nm in Hg 2+ The quenching is obvious in the presence of , and the presence of other ions has little interference with the detection results. The rapid weakening of the fluorescence intensity of the fluorescent probe can be used to detect Hg in the solution. 2+ Highly efficient and selective detection.

Description

Technical Field

[0001] The invention belongs to the technical field of organic synthesis and analytical chemistry, and particularly relates to an amide chain-bridged bis-tetraphenylethylene fluorescent probe and a synthesis method and application thereof. Background Art

[0002] Fluorescent probes are widely favored due to their high selectivity, good sensitivity, simple operation, and real-time analysis. However, many conventional fluorescent materials can emit light well in solution, but once they aggregate or become solid, the fluorescence disappears, which hinders the application of fluorescent materials.

[0003] In recent years, tetraphenylethylene and its derivatives have been increasingly studied due to their excellent photophysical properties, including aggregation-induced emission (AIE), large Stokes shift, excellent photostability, and low toxicity. As an important class of aggregation-induced emission (AIE) active compounds, tetraphenylethylene and its derivatives possess a twisted propeller-like structure. Their luminescence is weak in dilute solutions, but they exhibit strong luminescence efficiency in concentrated solutions or in aggregated states. This phenomenon is known as "aggregation-induced emission."

[0004] Fluorescent probes based on aggregation-induced emission (AIE) not only inherit the advantages of traditional organic molecular fluorescent probes, but also overcome their greatest disadvantage (aggregation-induced quenching, ACQ), providing good fluorescence even at high concentrations or when aggregated. Due to this characteristic, the synthesis and performance of tetraphenylethylene and its derivatives have been widely reported. These derivatives can recognize various ions and organic small molecules, such as plasma molecules, based on the characteristics of their functional groups. The fluorescence before and after recognition changes significantly, making them highly effective organic fluorescent probes for the identification and detection of various ions and organic molecules in aqueous solutions.

[0005] Mercury is a typical silvery-white liquid heavy metal ion. As a highly toxic heavy metal widely present in various environmental media, it poses a significant threat to the environment and organisms. Even at low concentrations, it is highly toxic to human health and can cause permanent damage to the nervous system. Elemental mercury continuously releases volatile mercury vapor at room temperature. Once it enters the human body through various pathways, such as the respiratory tract, skin, or digestive tract, it can cause severe damage to the central nervous system, leading to a range of adverse reactions such as vomiting, diarrhea, respiratory failure, and even death.

[0006] Due to its persistence, mobility, and high bioaccumulation, mercury is one of the most toxic and polluting heavy metals in the natural environment. Therefore, accurate and effective determination of mercury ion levels in environmental and biological samples is crucial for biological science, environmental protection, and medicine. To date, methods for mercury ion detection primarily include atomic absorption emission spectrometry (AAS / AES), electrochemical methods, and inductively coupled plasma mass spectrometry (ICP-MS). These methods offer advantages such as high sensitivity and selectivity, but their slow detection speed, expensive instrumentation, and complex operation limit their application in mercury ion localization. Fluorescent probes, as an emerging detection method, offer advantages such as simplicity, low cost, high specificity and sensitivity, fast response, and real-time visual monitoring of analytes. The development of a highly selective, simple, rapid, and sensitive mercury ion-specific fluorescent probe, which can quickly and easily detect low-concentration mercury ions, holds broad application prospects.

[0007] The invention patent with publication number CN113666896A provides a multifunctional fluorescent probe of α-naphtholphthalein derivatives and its preparation method and application. The fluorescent probe can identify and detect Hg in a mixed solution of dimethyl sulfoxide and water using fluorescence spectrum and / or ultraviolet-visible absorption spectrum. 2+ and Al 3+ However, the volume ratio of dimethyl sulfoxide and water needs to be strictly controlled to be 9:1 to 1:9 during identification. If the test is outside the parameter range, the probe will not be able to detect Hg. 2+ and Al 3+ There is no obvious detection and identification effect; the invention patent with publication number CN113045538A discloses a salicylaldehyde thioacetal fluorescent probe and its preparation method and application. This fluorescent probe uses a boron dipyrrole fluoride fluorescent dye (BODIPY) unit as an energy donor and a rhodamine unit as an energy acceptor. The divalent mercury ion promotes the "on-off" of the spiroamide ring to achieve fluorescence energy resonance transfer between BODIPY and rhodamine units, resulting in fluorescence red shift, which can be used to detect Hg2+ as a fluorescent ratio probe. However, the synthesis and design of ratio probes are usually relatively complex, and multiple factors such as the selection of fluorescent dyes, the connection method of the probes, and the interaction between the probes and the target molecules need to be considered, which will increase the cost of synthesis and the complexity of the experiment. Summary of the Invention

[0008] In order to solve the problems existing in the prior art, the present invention aims to provide an amide chain bridged bis-tetraphenylethylene fluorescent probe and its synthesis method and application, wherein the fluorescence intensity is 2+The quenching is obvious in the presence of , and the presence of other ions has little interference with the detection results of this fluorescent probe. By utilizing the rapid weakening of the fluorescence intensity of the fluorescent probe, the detection of Hg in the solution can be achieved. 2+ Highly efficient and selective detection.

[0009] The technical solutions of the present invention are as follows:

[0010] One of the purposes of the present invention is to provide an amide chain-bridged bis-tetraphenylethylene fluorescent probe, which has a structure of oxalylene units bridged by bis-tetraphenylethylene, labeled as Bis-TPE, and has the following chemical structure:

[0011] The molecular formula is C 106 H 144 N2O8.

[0012] Furthermore, the infrared spectrum of the fluorescent probe is characterized as follows: (KBr), v / cm -1 :3424(NH),1671(C=O));

[0013] H NMR characterization is as follows: (400 MHz, CDCl3), δ ppm: 7.02-7.11 (m, 24H, ArH and NH), 6.58-6.68 (m, 12H, ArH), 4.40 (s, 4H, OCH2CO), 3.86 (t, J = 8.0H, 8H, OCH2), 3.51 (bs, 4H, NCH2), 1.72 (m, 8H, CH2), 1.41 (bs, 8H, CH2), 1.26 (bs, 64H, CH2), 0.88 (t, J = 8.0 Hz, 12H, CH3);

[0014] The NMR characterization is as follows: (100 MHz, CDCl3), δ, ppm: 169.26, 157.63, 155.25, 144.35, 140.00, 138.37, 138.07, 136.20, 132.79, 131.36, 129.19, 127.69, 126.05, 113.85, 113.59, 67.83, 67.06, 53.82, 39.22, 31.74, 29.61, 29.47, 26.11, 22.70, 14.14;

[0015] High-resolution mass spectrometry (m / s): calculated value C 106 H 144 N2O8: 1573.092, measured value is 1573.092[M] + .

[0016] A second object of the present invention is to provide a method for preparing an amide chain-bridged bis-tetraphenylethylene fluorescent probe, comprising the following steps:

[0017] (1) Under nitrogen protection, 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, anhydrous potassium carbonate, potassium iodide, and 1,2-dichloroacetylethylenediamine were added to a reaction vessel, and the mixture was refluxed in dry acetone. The reaction was monitored by thin layer chromatography.

[0018] (2) After the starting material disappears, HCl solution is added dropwise to the reaction mixture, and the mixture is stirred thoroughly. The mixture is then extracted with chloroform to separate the organic phase. Most of the solvent is evaporated under reduced pressure, and the residue is separated by silica gel column chromatography to obtain the compound 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine, which is an amide chain-bridged bis-tetraphenylethylene fluorescent probe.

[0019] Furthermore, the synthesis methods of 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine, 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene and 1,2-bis-chloroacetylethylenediamine were referred to published literature (Zhang, X.; Jiang S.; Lin G.; Guo, H.; Yang, F. Novel fluorescent columnar liquid crystal based on tetraphenylethylene-rufigallol-tetraphenylethylene triads, Journal of Molecular Structure, 2022, 1252, 132210).

[0020] Furthermore, in the step (1), the molar ratio of 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, anhydrous potassium carbonate, potassium iodide and 1,2-di-chloroacetylethylenediamine is 1:1-5:1-5:1.5-2.5.

[0021] Furthermore, the reflux time in step (1) is 12 to 48 hours.

[0022] Furthermore, the concentration of the HCl solution in step (2) is 0.8-1.2M.

[0023] Furthermore, in the silica gel column chromatography separation in step (2), the eluent is a mixed solution of dichloromethane and n-hexane.

[0024] Furthermore, the volume ratio of dichloromethane to n-hexane in the mixed solution is 1:3.

[0025] The third object of the present invention is to provide an application of an amide chain bridged bis-tetraphenylethylene fluorescent probe, wherein a tetrahydrofuran-water mixed solution containing an amide chain bridged bis-tetraphenylethylene fluorescent probe is added to a sample solution to be tested, and the fluorescence intensity is changed with Hg 2+ The concentration of Hg in the sample solution can be determined by comparing the standard working curve with the concentration change. 2+ Rapid and efficient detection of content.

[0026] Furthermore, the fluorescent probe of the present invention was prepared into a tetrahydrofuran-water solution of a certain concentration, and HgCl2 was prepared at a concentration gradient of 0, 0.1, 0.2, 0.4, 0.5, 0.6, 0.8, 1.0, 1.2, 1.4, 1.5, 1.6, 1.8, 2, and 4 times the concentration of the fluorescent probe. 2+ series of solutions, the fluorescent probes are respectively 2+ The solutions were mixed, and then the fluorescence intensity of the mixed solution was measured. The fluorescence intensity was used as the vertical axis, and Hg 2+ The fluorescence intensity with Hg concentration as the horizontal axis changes with 2+ Standard working curve of concentration gradient change.

[0027] Furthermore, the fluorescent probe is mixed with the Hg 2+ The solution was mixed and the fluorescence intensity value after mixing was measured. The obtained fluorescence intensity value was compared with the Hg 2+ Compare with the standard working curve of concentration gradient change and read the Hg content in the test solution from the curve. 2+ content.

[0028] Furthermore, the volume ratio of tetrahydrofuran to water in the mixed solution is 5:95.

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

[0030] 1. The present invention has established an amide chain bridged bis-tetraphenylethylene fluorescent probe with an oxalylene-bridged bis-tetraphenylethylene unit structure, which is an ideal rapid and sensitive detection of Hg 2+ When this fluorescent probe is placed in a tetrahydrofuran-water mixed solution, it emits strong blue-green fluorescence at 480nm, which is nearly 40 times stronger than the fluorescence intensity in pure tetrahydrofuran solution. 2+ The fluorescent probe Bis-TPE can detect Hg 2+ The rapid response and formation of a 1:1 complex caused a significant quenching of the fluorescence of the fluorescent probe Bis-TPE, thereby achieving the detection of Hg 2+ Selective and sensitive detection.

[0031] 2. The fluorescent probe Bis-TPE disclosed in the present invention has strong anti-interference ability and can detect Hg with high selectivity. 2 + In the tests of various ions, the fluorescent probe Bis-TPE was only sensitive to Hg 2+ The response is fast and the fluorescence is significantly quenched. Other ions present in the sample have little effect on its fluorescence intensity. It is suitable for Hg in various biological samples and environmental water samples. 2+ It is a sensitive detection method suitable for a wide pH range, and the detection method is simple and quick. The detection instrument is common and easy to buy, and the test results are accurate and sensitive.

[0032] 3. Compared with existing fluorescent probe technologies, the synthesis method of the fluorescent probe Bis-TPE in the present invention is simple, green and energy-saving. It can be generated by mixing at room temperature and normal pressure. It has the characteristics of a wide source of raw materials and simple operation steps. It does not require high-energy excitation, does not damage biological samples, is environmentally friendly, and can be widely used in life sciences, environmental sciences and other fields. It is one of the important development directions in the field of mercury ion detection research.

[0033] Reference numerals

[0034] Figure 1 This is a process flow chart of the preparation method of the fluorescent probe Bis-TPE of the present invention;

[0035] Figure 2 This is the infrared spectrum of the fluorescent probe Bis-TPE of the present invention;

[0036] Figure 3 is the hydrogen nuclear magnetic resonance spectrum of the fluorescent probe Bis-TPE of the present invention;

[0037] Figure 4 This is the carbon NMR spectrum of the fluorescent probe Bis-TPE of the present invention;

[0038] Figure 5 is the mass spectrum of the fluorescent probe Bis-TPE of the present invention;

[0039] Figure 6 1×10 -5 mol / L tetrahydrofuran-water mixed solution containing the fluorescent probe Bis-TPE of the present invention and 1×10 -5 mol / L fluorescence emission spectrum of each ion, the order of each ion is 1 = blank, 2 = Li + ,3=Na + ,4=K + ,5=Cs + ,6=Mg 2+ ,7=Ca 2+ ,8=Ba2+ ,9=Al 3+ ,10=Cr 3+ ,11=Hg 2+ ,12=Fe 3+ ,13=Ni 2+ ,14=Cu 2+ ,15=Zn 2+ ,16=Ag + ,17=Cd 2+ ,18=Mn 2+ ,19=Co 2+ ,20=Pb 2+ ,21=NH4 + ,22=Cl - ,23=NO3 - ,24=HPO4 2- ,25=H2PO4 - ,26=PO4 3- ;

[0040] Figure 7 1×10 -5 mol / L tetrahydrofuran-water mixed solution containing the fluorescent probe Bis-TPE of the present invention and different concentrations of Hg 2+ Fluorescence spectrum of

[0041] Figure 8 1×10 -5 mol / L tetrahydrofuran-water mixed solution containing the fluorescent probe Bis-TPE of the present invention and different concentrations of Hg 2+ Fluorescence intensity change diagram, including Hg 2+ Standard working curve of solution concentration gradient change and fluorescence intensity change;

[0042] Figure 9 A tetrahydrofuran-water mixed solution containing the fluorescent probe Bis-TPE of the present invention and other ions (or containing Hg 2+ The comparison chart of the ratio of the fluorescence intensity of the reaction with other ions) and the fluorescence intensity of the mixed solution itself. The other ions are in the order of 1 = blank, 2 = Li + ,3=Na + ,4=K + ,5=Cs + ,6=Mg 2+ ,7=Ca 2+ ,8=Ba 2+ ,9=Al 3+ ,10=Cr 3+ ,11=Fe 3+ ,12=Ni 2+ ,13=Cu 2+,14=Zn 2+ ,15=Ag + ,16=Cd 2+ ,17=Mn 2+ ,18=Co 2+ ,19=Pb 2+ ,20=NH4 + ,21=Cl - ,22=NO3 - ,23=HPO4 2- ,24=H2PO4 - ,25=PO4 3- . DETAILED DESCRIPTION

[0043] The present invention will be further described below in conjunction with the accompanying drawings and preferred embodiments. The given embodiments are only for illustrating the present invention, rather than for limiting the scope of the present invention.

[0044] Unless otherwise specified, the materials and reagents used in the following examples can be obtained from commercial sources.

[0045] The quantitative tests in the following examples were repeated three times, and the results were averaged.

[0046] The experimental methods in the following examples are conventional methods unless otherwise specified.

[0047] Example 1

[0048] This embodiment provides an amide chain-bridged bis-tetraphenylethylene fluorescent probe, the synthesis method of which includes the following steps:

[0049] (1) Under nitrogen protection, 1.0 mmol of 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, 1.0 mmol of anhydrous potassium carbonate, 1.0 mmol of potassium iodide, and 1.5 mmol of 1,2-dichloroacetylethylenediamine were added to a 250 mL three-necked flask and refluxed at 60°C for 48 h in dry acetone. The reaction was monitored by thin layer chromatography.

[0050] (2) After the starting material disappears, 30 mL of 1 M HCl solution is added dropwise to the reaction mixture, which is stirred thoroughly. The mixture is then extracted with 30 mL of chloroform, and the organic phase is separated. Most of the solvent is evaporated under reduced pressure, and the residue is subjected to silica gel column chromatography to separate the product, wherein the eluent is a mixed solution of dichloromethane and n-hexane in a volume ratio of 1:3. Finally, the compound 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine is obtained, which is an amide chain-bridged bis-tetraphenylethylene fluorescent probe, with a yield of 61%.

[0051] Example 2

[0052] This embodiment provides a method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe, comprising the following steps:

[0053] (1) Under nitrogen protection, 2.0 mmol of 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, 4.0 mmol of anhydrous potassium carbonate, 4.0 mmol of potassium iodide, and 4.0 mmol of 1,2-dichloroacetylethylenediamine were added to a 250 mL three-necked flask and refluxed at 60°C for 24 h in dry acetone. The reaction was monitored by thin layer chromatography.

[0054] (2) After the starting material disappears, 60 mL of 1.2 M HCl solution is added dropwise to the reaction mixture, and the mixture is stirred thoroughly. The mixture is then extracted with 50 mL of chloroform, and the organic phase is separated. Most of the solvent is evaporated under reduced pressure, and the residue is subjected to silica gel column chromatography to separate the product, wherein the eluent is a mixed solution of dichloromethane and n-hexane in a volume ratio of 1:3. Finally, the compound 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine is obtained, i.e., an amide chain-bridged bis-tetraphenylethylene fluorescent probe, with a yield of 86%.

[0055] Example 3

[0056] This embodiment provides an application of an amide chain-bridged bis-tetraphenylethylene fluorescent probe, comprising the following steps:

[0057] (1) Under nitrogen protection, 1.0 mmol of 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, 5.0 mmol of anhydrous potassium carbonate, 5.0 mmol of potassium iodide, and 2.5 mmol of 1,2-dichloroacetylethylenediamine were added to a 250 mL three-necked flask. The mixture was refluxed at 60°C for 12 h in dry acetone. The reaction was monitored by thin layer chromatography.

[0058] (2) After the starting material disappears, 35 mL of 0.8 M HCl solution is added dropwise to the reaction mixture, and the mixture is stirred thoroughly. The mixture is then extracted with 35 mL of chloroform, and the organic phase is separated. Most of the solvent is evaporated under reduced pressure, and the residue is subjected to silica gel column chromatography to separate the product, wherein the eluent is a mixed solution of dichloromethane and n-hexane in a volume ratio of 1:3. Finally, the compound 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine is obtained, i.e., an amide chain-bridged bis-tetraphenylethylene fluorescent probe, with a yield of 77%.

[0059] (3) A tetrahydrofuran-water mixed solution containing the above-mentioned amide chain-bridged tetraphenylethylene fluorescent probe was prepared, wherein the volume ratio of tetrahydrofuran to water was 5:95, and Hg concentrations were prepared in a gradient manner according to the concentrations of the fluorescent probe at 0, 0.1, 0.2, 0.4, 0.5, 0.6, 0.8, 1.0, 1.2, 1.4, 1.5, 1.6, 1.8, 2, and 4 times the concentration of the fluorescent probe. 2+ series of solutions, the mixed solutions were mixed with Hg 2+ Mix the series of solutions, measure the fluorescence intensity after mixing, and establish the vertical axis as fluorescence intensity, Hg 2+ The standard working curve with concentration as the horizontal axis is as follows: Figure 8 As shown;

[0060] (4) A tetrahydrofuran-water mixed solution containing an amide chain-bridged bis-tetraphenylethylene fluorescent probe was mixed with the Hg 2+ The solution is mixed, and the measured fluorescence intensity value is compared with the standard working curve in step (3), and the Hg to be measured is read from the curve. 2+ Hg in solution 2+ content.

[0061] like Figure 6 As shown in the figure, when different ion tests were performed, the tetrahydrofuran-water mixed solution containing the amide chain bridged bis-tetraphenylethylene fluorescent probe of the present invention was only sensitive to Hg 2+ The rapid response and significant fluorescence quenching indicate that this fluorescent probe is sensitive to Hg 2+ It has good selective detection ability.

[0062] exist Figure 7 Among them, as Hg 2+ After the concentration continues to increase, the fluorescence intensity of the tetrahydrofuran-water mixed solution containing the amide chain bridged bis-tetraphenylethylene fluorescent probe of the present invention shows an obvious downward trend. Therefore, it can be inferred that the fluorescence intensity of the fluorescent probe mixed solution is related to Hg 2+ There is a good linear relationship between the concentrations of Hg 2+ Related quantitative analysis activities.

[0063] Figure 9 I is 1×10 -5 mol / L tetrahydrofuran-water mixed solution containing the amide chain bridged bis-tetraphenylethylene fluorescent probe of the present invention and 1×10 -5 mol / L of other ions (or other ions + Hg 2+ ) The fluorescence intensity of the reaction, I o 1×10 - 5 mol / L mixed solution. Figure 9It can be seen that after adding other ions, the fluorescence ratio of the fluorescent probe is close to 1, indicating that other ions have little effect on the fluorescence of the fluorescent probe. 2+ Afterwards, the fluorescence of the fluorescent probe weakened, indicating that other ions reacted with the fluorescent probe Hg 2+ The sensitive detection interference has little effect.

[0064] The above descriptions are merely embodiments of the present invention and are not intended to limit the patent scope of the present invention. Any equivalent structure or equivalent process transformation made using the contents of the present invention specification, or directly or indirectly applied in other related technical fields, are also included in the patent protection scope of the present invention.

Claims

1. An amide chain-bridged bis-tetraphenylethylene fluorescent probe, characterized in that: The fluorescent probe has a structure of oxalylene units bridged by bis-tetraphenylethylene, labeled as Bis-TPE, and its chemical structure is as follows: The molecular formula is C 106 H 144 N2O8.

2. A method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe as claimed in claim 1, characterized in that: The following steps are involved: (1) Under nitrogen protection, 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, anhydrous potassium carbonate, potassium iodide, and 1,2-dichloroacetylethylenediamine were added to a reaction vessel, and the mixture was refluxed in dry acetone. The reaction was monitored by thin layer chromatography; (2) After the starting material disappears, HCl solution is added dropwise to the reaction mixture, and the mixture is stirred thoroughly. The mixture is then extracted with chloroform to separate the organic phase. Most of the solvent is evaporated under reduced pressure, and the residue is separated by silica gel column chromatography to obtain the compound 1,2-bis(2-(4-(1-phenyl-2,2-di-dodecylphenyl)vinyl)phenoxyacetyl)ethylenediamine, which is an amide chain-bridged bis-tetraphenylethylene fluorescent probe.

3. The method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe according to claim 2, wherein: In the step (1), the molar ratio of 1,1-di-p-dodecyloxyphenyl-2-phenyl-2-p-hydroxyphenylethylene, anhydrous potassium carbonate, potassium iodide and 1,2-di-chloroacetylethylenediamine is 1:1-5:1-5:1.5-2.

5.

4. The method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe according to claim 2, wherein: The reflux time in step (1) is 12 to 48 hours.

5. The method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe according to claim 2, wherein: The concentration of the HCl solution in step (2) is 0.8-1.2M.

6. The method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe according to claim 2, wherein: In the silica gel column chromatography separation in step (2), the eluent is a mixed solution of dichloromethane and n-hexane.

7. The method for synthesizing an amide chain-bridged bis-tetraphenylethylene fluorescent probe according to claim 6, wherein: The volume ratio of dichloromethane to n-hexane in the mixed solution is 1:

3.

8. An amide chain-bridged bis-tetraphenylethylene fluorescent probe as claimed in claim 1 for detecting metal ions Hg 2+ The application is characterized in that The application is non-disease diagnosis application. The fluorescent probe can react with Hg in a tetrahydrofuran-water mixed solution. 2+ The formation of a 1:1 complex quenches the fluorescence of the compound Bis-TPE, thereby achieving the 2+ Selective sensitive detection; the volume ratio of tetrahydrofuran to water in the mixed solution is 5:95.

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