2-aroyl-1, 5-diaryl-1, 5-pentanedione derivative as well as synthesis method and application thereof

Abstract

The invention relates to a 2-aroyl-1, 5-diaryl-1, 5-pentanedione derivative and a synthesis method and application thereof.The synthesis method comprises the steps that 3-aryl propargyl alcohol and 1, 3-diaryl-1, 3-propanedione are subjected to a series Meyer-Schuster rearrangement / nucleophilic addition reaction in the presence of a first catalyst and a first organic solvent, and the 2-aroyl-1, 5-diaryl-1, 5-pentanedione derivative is obtained; the invention discloses a 1, 5-pentanedione derivative. Compared with the prior art, the 2-aroyl-1, 5-diaryl-1, 5-pentanedione derivative prepared by the preparation method disclosed by the invention has no substituent group at the position 3, has good fluorescence emission performance and metal ion recognition performance, can be used as an organic small molecule fluorescent material molecule, and is applied to the fields of metal ion detection, fluorescent probes and the like.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic synthesis, and in particular to a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative and a synthesis method and application thereof. BACKGROUND

[0002] With the continuous innovation and breakthrough of technology, materials with fluorescence emission performance play an important role in the field of heavy metal ion detection, and provide solid technical support for environmental protection, biomedical research and food safety guarantee.

[0003] 1,5-diketone compounds are a class of organic molecules with a double carbonyl structure, and their core properties are derived from their unique molecular configuration and electronic effect. The 1,5-bicarbonyl spacing of such compounds endows them with conformational flexibility, and the strong electron-withdrawing property of the carbonyl oxygen atom causes the adjacent carbon atom to exhibit electron-deficient characteristics, making them prone to condensation, cyclization and nucleophilic addition reactions. For example, the twisted conformation of the pentane-1,5-dione unit can be stabilized by intramolecular C-H···O hydrogen bonding, while the aromatic ring-substituted derivatives form a rigid planar structure due to the conjugation effect, which significantly affects their fluorescence properties.

[0004] There are many types of aromatic ring-substituted 1,5-diketone compounds, such as naphthalene ring substitution, benzene ring substitution, thiophene ring substitution, furan substitution, and pyridine substitution. The main method for synthesizing 1,5-diketone compounds is the Michael addition reaction of nucleophilic reagents with chalcone derivatives. However, due to the substitution at position 1 of the chalcone derivative, the synthesized 1,5-diketone compounds have a substitution at position 3. SUMMARY

[0005] The present application aims to overcome the shortcomings of the prior art and provides a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative and a synthesis method and application thereof. The prepared 2-aroyl-1,5-diaryl-1,5-pentanedione derivative has no substitution at position 3, has good fluorescence emission performance and metal ion recognition performance, and can be used as an organic small molecule fluorescent material molecule for metal ion detection and fluorescence probe fields.

[0006] The object of the present application can be achieved by the following technical solutions:

[0007] One of the technical solutions of the present application is to provide a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative, characterized in that its structural formula is as shown in formula (1):

[0008]

[0009] wherein Ar1, Ar2 and Ar3 are aromatic substituents.

[0010] Further, Ar1 is selected from any one of benzene, 4-methylthio, 4-methylbenzene, 4-methoxybenzene, 4-chlorobenzene, 4-fluorobenzene, 4-bromobenzene, 3-chlorobenzene, 3-fluorobenzene, 3-bromobenzene, p-biphenyl, naphthalene, 2-chlorobenzene, 2-fluorobenzene, 2-bromobenzene, 2-methylbenzene, 2-methoxybenzene, 3-thiophene, 2-fluorene, 2-isopropylbenzene, 4-(1,2,2-triphenylvinyl)benzene;

[0011] Ar2 is selected from any one of benzene, 4-methylbenzene, 3-methylbenzene, 2-methylbenzene, 4-chlorobenzene, 4-cyanobenzene.

[0012] The second technical scheme of the present application provides a synthesis method of 2-aroyl-1,5-diaryl-1,5-pentanedione derivative, characterized in that 3-aryl propargyl alcohol reacts with 1,3-diaryl-1,3-propanedione to obtain the 2-aroyl-1,5-diaryl-1,5-pentanedione derivative, wherein the structural formula of 3-aryl propargyl alcohol is shown as formula (2), and the structural formula of 1,3-diaryl-1,3-propanedione is shown as formula (3),

[0013]

[0014] Further, the 3-aryl propargyl alcohol and the 1,3-diaryl-1,3-propanedione undergo a Meyer-Schuster rearrangement / nucleophilic addition reaction in series in the presence of a first catalyst and a first organic solvent to obtain the 2-aroyl-1,5-diaryl-1,5-pentanedione derivative.

[0015] Further, the first catalyst includes scandium triflate (Sc(OTf)3), copper difluoromethanesulfonate (Cu(OTf)2), silver fluoromethanesulfonate (AgOTf), iron triflate Fe(OTf)3, zinc difluoromethanesulfonate (Zn(OTf)2), and iron chloride (FeCl3).

[0016] The first organic solvent includes 1,4-dioxane, tetrahydrofuran, dichloromethane, dichloroethane, acetonitrile, and nitromethane.

[0017] The amount ratio of the 3-aryl propargyl alcohol, the 1,3-diaryl-1,3-propanedione, the first catalyst, and the first organic solvent is 1 mmol:1-1.5 mmol:0.1-0.3 mmol:0.2-2 mL.

[0018] Further, the 3-arylpropargyl alcohol, the catalyst, the 1,3-diaryl-1,3-propanedione and the organic solvent are mixed, and the mixture is refluxed at 80-120°C, and the reaction is monitored by TLC until the 3-arylpropargyl alcohol disappears completely, and the reaction is completed to obtain the 2-aroyl-1,5-diaryl-1,5-pentanedione derivative.

[0019] Further, the 3-arylpropargyl alcohol is synthesized by a Sonogashira coupling reaction of a halogenated hydrocarbon and a propargyl alcohol in the presence of a second catalyst, a co-catalyst and a basic solvent, the propargyl alcohol has a structural formula as shown in formula (4), and the aryl halogenated hydrocarbon has a structural formula as shown in formula (5),

[0020]

[0021] Further, the second catalyst is Pd(PPh3)2Cl2, the co-catalyst is Cul, and the basic solvent is triethylamine.

[0022] The halogenated hydrocarbon, the propargyl alcohol, the second catalyst, the co-catalyst and the basic solvent are used in a ratio of 1 mmol: 1-1.5 mmol: 0.05-0.15 mmol: 0.02-0.08 mmol: 1-5 mL.

[0023] Further, the halogenated hydrocarbon, the second catalyst and the co-catalyst are mixed, and then vacuumized and filled with nitrogen for protection, the basic solvent is added, the temperature is lowered to 0-5°C, the propargyl alcohol is slowly added dropwise under the condition that the temperature is maintained at 0-5°C, and then the temperature is raised to 50-60°C for reaction, and the reaction process is monitored by TLC until the aryl halogenated hydrocarbon is completely reacted, and then the reaction is stopped to obtain the 3-arylpropargyl alcohol.

[0024] Further, the 1,3-diaryl-1,3-propanedione is synthesized by a Claisen condensation reaction of an aryl ethanone and an aryl ethyl formate in the presence of a strong base and a second organic solvent, the aryl ethanone has a structural formula as shown in formula (6), and the aryl ethyl formate has a structural formula as shown in formula (7),

[0025]

[0026] Further, the strong base is NaH, and the second organic solvent is THF.

[0027] The aryl ethanone, the aryl ethyl formate, the strong base and the second organic solvent are used in a ratio of 1 mmol: 1-1.5 mmol: 2-3 mmol: 0.5-5 mL.

[0028] Further, the strong base is flushed with nitrogen, cooled to 0-5 DEG C, a second organic solvent, aryl ethanone, aryl ethyl formate are added, aryl ethyl formate is continuously added, and the reaction is carried out at 50-70 DEG C for 10-30 hours, and then cooled to room temperature, and the aryl ethanone is detected by TLC to be completely reacted, and 1,3-diaromatic-1,3-propanedione is obtained.

[0029] The third technical scheme of the present application provides an application of the 2-aroyl-1,5-diaromatic-1,5-pentanedione derivative in the field of metal ion detection and fluorescent probe.

[0030] Compared with the prior art, the present application has the following advantages:

[0031] (1) The 2-aroyl-1,5-diaromatic-1,5-pentanedione derivative prepared by the present application has no substituent at the 3 position.

[0032] (2) The present application uses the Meyer-Schuster rearrangement reaction as the core, and combines the affinity addition reaction (Michael addition reaction) to realize the one-pot sequential synthesis, and the synthesis operation is simple, the intermediate separation and purification steps are reduced, the atomic economy is improved, the reaction feasibility is high, and the production can be scaled up.

[0033] (3) The first catalyst of the present application uses fluoromethanesulfonate, and the molar mass is 10% to 30% of the 3-aryl propargyl alcohol, the amount is low, and no noble metal catalyst is needed, so the cost is low and the pollution is small. Compared with the traditional strong base or transition metal catalyst, the catalytic efficiency and substrate compatibility are higher.

[0034] (4) The present application is compatible with the primary and secondary alcohols (partially applicable) of aryl propargyl alcohol and the 1,3-diketone containing various substituents (such as methyl, methoxy, halogen, cyano, etc.).

[0035] (5) The 2-aroyl-1,5-diaromatic-1,5-pentanedione derivative prepared by the present application has less side reactions, good regioselectivity, and high activity of electron-withdrawing substrates.

[0036] (6) The 2-aroyl-1,5-diaromatic-1,5-pentanedione derivative of the present application exhibits fluorescence emission performance, especially 2-benzoyl-1-phenyl-5-(4-(1,2,2-triphenylvinyl) phenyl) pentane-1,5-dione has good fluorescence emission performance, and can specifically identify Cd 2+ ion in water. BRIEF DESCRIPTION OF DRAWINGS

[0037] Figure 1 The synthesis route of the 3-aryl propargyl alcohol shown in the present application is as follows:

[0038] Figure 2A synthetic route map of 1,3-diaryl-1,3-propanedione shown in the present application;

[0039] Figure 3 A synthetic route map of 2-aroyl-1,5-diaryl-1,5-pentanedione derivative shown in the present application;

[0040] Figure 4 A UV absorption spectrum of compound 1a, 1g, 1i, 1j in the present application;

[0041] Figure 5 A nuclear magnetic hydrogen spectrum of compound 1a in the present application;

[0042] Figure 6 A UV absorption spectrum (a) and fluorescence emission spectrum (b) of compound 1a in the present application;

[0043] Figure 7 A UV absorption spectrum (a) and fluorescence emission spectrum (b) of compound 1a in the present application and metal ions such as Cd, Pd and Cu. DETAILED DESCRIPTION

[0044] The present application will be described in detail below with reference to the accompanying drawings and specific examples. The present embodiment is implemented on the premise of the technical solution of the present application, and detailed implementation and specific operation process are given, but the protection scope of the present application is not limited to the following examples. Based on the given examples, all other examples obtained by those skilled in the art without making creative efforts are within the scope of the present application.

[0045] Unless otherwise specified, the reagents, methods, instruments and equipment used in the present application are conventional reagents, methods, instruments and equipment in the art. In the following examples, the drugs and reagents such as 1,4-dioxane, Pd(PPh3)2Cl2 and Sc(OTf)3 are purchased from Shanghai Titan Technology Co., Ltd.

[0046] The equipment and manufacturer information used in the following examples are as follows:

[0047] The stirrer is Shanghai Meiyinpu MYPII-2 constant temperature magnetic stirrer;

[0048] The circulating water pump is Shanghai Yukang circulating multi-purpose vacuum pump SHB-IIIA;

[0049] The rotary evaporator is Shanghai Yukang rotary evaporator W.S206B;

[0050] The oil pump is Shanghai Yukang 2XZ-2 rotary vane vacuum pump;

[0051] The UV detector is Shanghai Phoenix Ke Instrument UV1900;

[0052] Fluorescence detector: Hitachi F-4600.

[0053] A method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative, comprising the steps of:

[0054] (1) Synthesis of 3-arylpropargyl alcohol: Sonogashira coupling reaction Figure 1 ).

[0055] A magnetic stirrer was selected and placed in a 50 mL round-bottom flask, halogenated hydrocarbon (10.0 mmol), Pd(PPh3)2Cl2(1 mmol), CuI (0.5 mmol) were added to the flask, the bottle mouth was capped with a rubber plug, sealed with a film, and connected to a vacuum oil pump to perform vacuumization and nitrogen protection (continuous charging and discharging three times) in the round-bottom flask. 15 mL of triethylamine was added to the flask. The reaction device was fixed on the magnetic stirrer and placed in an ice water bath for cooling. After cooling for 15 minutes, the temperature was lowered to 0°C, and propargyl alcohol (11.0 mmol) was added dropwise with a syringe under stirring. After adding propargyl alcohol, the system was cooled to 0°C, and the reaction device was moved into a constant temperature oil bath to gradually heat to 55°C for reaction. The reaction progress was monitored by TLC, and the heating was stopped after the halogenated hydrocarbon was completely reacted. The device was naturally cooled to room temperature, the rubber plug was opened, 20 mL of saturated ammonium chloride solution was added to the reaction system to quench the reaction, and 50 mL of ethyl acetate was extracted three times. The obtained organic phase was combined and dried with anhydrous sodium sulfate. The obtained organic phase was transferred to a clean flask, most of the solvent was removed by rotary evaporation under reduced pressure, and then column chromatography was used for separation and purification (silica gel 300 mesh; a mixture of petroleum ether and ethyl acetate (petroleum ether / ethyl acetate 15 / 1 to 8 / 1, which can be adjusted according to actual conditions) as eluent). The reaction yield was 75%-98%.

[0056] (2) Synthesis of 1,3-diaryl-1,3-propanedione: Claisen condensation reaction Figure 2 ).

[0057] Sodium hydride (60% in mineral oil, 1.0 g, 25 mmol) was added to a 100 mL three-necked round bottom flask. The solution was flushed with nitrogen. The reaction mixture was cooled to 0 °C and a mixture of an aryl ethanone (10 mmol, 1.340 g) and aryl ethyl formate (1.0 mmol, 0.150 g) was added. After stirring for 20 min, another portion of the aryl ester (10 mmol, 1.500 g) was added to the reaction mixture. The mixture was refluxed for 16 h. The reaction mixture was cooled to room temperature. 200 mL of ethyl acetate and 50 mL of 10% dilute HCI were added to dissolve the various solids. The organic phase was separated and washed with brine (50 mL) three times. The organic phase was dried over anhydrous magnesium sulfate. The organic solvent was concentrated and the residue was purified by column chromatography eluting with petroleum ether / ethyl acetate (v / v = 80 / 1) to give the product. The reaction yield was 40-90%.

[0058] (3) Synthesis of 2-arylformyl-1,5-diaryl-1,5-pentanedione derivatives: Meyer-Schuster rearrangement / nucleophilic addition reaction in a cascade fashion. Figure 3

[0059] A magnetic stir bar was placed in a 15 mL thick-walled pressure tube. A 3-arylpropargyl alcohol (1.0 mmol), Sc(OTf)3(0.1 mmol) and 1,3-diarylpropanedione (1.0 mmol) were added to the thick-walled pressure tube in this order. 0.5 mL of 1,4-dioxane was added as solvent. The thick-walled pressure tube was placed in an oil bath at 100 °C and refluxed. The reaction was monitored by TLC until the complete disappearance of the propargyl alcohol. Then, the reaction was quenched by the addition of a saturated sodium chloride solution and the aqueous phase was extracted three times with 5 mL of ethyl acetate. The organic phases were combined, dried over anhydrous Na2S04and concentrated under reduced pressure on a rotary evaporator to give a concentrated solution. Finally, the concentrated solution was purified by column chromatography (silica gel 200-300 mesh; a mixture of petroleum ether and ethyl acetate (petroleum ether / ethyl acetate 15 / 1 to 8 / 1) as eluent) to give the 2-arylformyl-1,5-diaryl-1,5-pentanedione derivative. The reaction yield was 72-83%.

[0060] ​In a 15 mL thick-walled pressure tube, a magnetic stirrer bar of appropriate size was placed, and 3-arylpropargyl alcohol (1.0 mmol), Sc(OTf)3(0.3 mmol) and 1,3- diarylphenyl-1,3-propanedione (1.2 mmol) were sequentially added into the thick-walled pressure tube, and 2 mL of 1,4-dioxane was added as solvent. The thick-walled pressure tube was placed in an oil bath at 100°C for reflux, and the reaction was detected by TLC until the complete disappearance of propargyl alcohol. Then, saturated sodium chloride solution was added to quench the reaction, and the aqueous phase was extracted with 5 mL of ethyl acetate three times. The organic phase was combined, dried with an appropriate amount of anhydrous Na2SO4, and concentrated under reduced pressure on a rotary evaporator to obtain a concentrated solution. Finally, the concentrated solution was separated and purified by column chromatography (silica gel 200-300 mesh; a mixture of petroleum ether and ethyl acetate (petroleum ether / ethyl acetate 15 / 1 to 8 / 1) as eluent), to obtain a 2-arylformyl-1,5-diaryl-1,5-pentanedione derivative. The reaction yield was 68%-85%.

[0061] In a 15 mL thick-walled pressure tube, a magnetic stirrer bar of appropriate size was placed, and 3-arylpropargyl alcohol (1.0 mmol), Sc(OTf)3(0.2 mmol) and 1,3- diarylphenyl-1,3-propanedione (1.5 mmol) were sequentially added into the thick-walled pressure tube, and 0.5 mL of 1,4-dioxane was added as solvent. The thick-walled pressure tube was placed in an oil bath at 100°C for reflux, and the reaction was detected by TLC until the complete disappearance of propargyl alcohol. Then, saturated sodium chloride solution was added to quench the reaction, and the aqueous phase was extracted with 5 mL of ethyl acetate three times. The organic phase was combined, dried with an appropriate amount of anhydrous Na2SO4, and concentrated under reduced pressure on a rotary evaporator to obtain a concentrated solution. Finally, the concentrated solution was separated and purified by column chromatography (silica gel 300 mesh; a mixture of petroleum ether and ethyl acetate (petroleum ether / ethyl acetate 15 / 1 to 8 / 1, which can be adjusted according to actual conditions) as eluent), to obtain a 2-arylformyl-1,5-diaryl-1,5-pentanedione derivative. The reaction yield was 80%-92%.

[0062] The structure of the 2-arylacyl-1,5-diaryl-1,5-pentanedione derivative is shown in formula (1):

[0063]

[0064] wherein Ar1 is selected from any one of benzene, 4-methylbenzene, 4-methoxybenzene, 4-chlorobenzene, 4-fluorobenzene, 4-bromobenzene, p-biphenyl, naphthalene, 3-thiophene, and 4-(1,2,2-triphenylvinyl)phenyl;

[0065] Ar2 is selected from any one of benzene, 4-methylbenzene, 3-methylbenzene, 2-methylbenzene, 4-chlorobenzene, 4-cyanobenzene Ar3 is selected from any one of benzene, 4-methylbenzene, 3-methylbenzene, 2-methylbenzene, 4-chlorobenzene, 4-cyanobenzene.

[0066] The present application obtains a series of compounds of formula (1) by the above reaction, the structural formula and the nuclear magnetic hydrogen spectrum data are listed in Table 1, Examples 1-16.

[0067] The specific operation of UV-vis of the examples is as follows: the compound to be detected is prepared into a solution with a concentration of 10 -5 M PBS (phosphate buffer) dilute solution. Two quartz cuvettes with a volume of 3 mL and an inner diameter width of 1 cm are selected. Not more than 2 / 3 of the solution is loaded into the above-mentioned two quartz cuvettes, one of which is loaded with PBS blank control sample, and the other is loaded with the sample to be detected. During the loading process, bubbles should be avoided. If bubbles occur, the outer wall of the cuvette should be gently tapped to make it discharge. The cuvette containing the sample is placed into the ultraviolet detector which has completed the baseline calibration. On the operation interface of the ultraviolet detector, the spectral scanning range is set to 250-800 nm, and the scanning step is 1 nm. After the setting is completed, the "start" button is selected to start the scanning program. During the scanning process, the instrument will automatically collect data according to the set parameters. Then select start, save the corresponding spectrum after the scanning is completed and make a good record.

[0068] The specific operation of the fluorescence detector is as follows: the instrument is preheated and the light source is turned on: turn on the power switch of the fluorescence detector, and let the instrument preheat for 15 min to ensure that all parts of the instrument reach a stable working state. After preheating, turn on the deuterium lamp to provide a suitable light source for subsequent detection. According to the spectrum information obtained by UV-vis test, the characteristic absorption peak position of the compound to be detected is determined, and the corresponding excitation wavelength of the fluorescence detector is set based on this. The selection of excitation wavelength is crucial to the accuracy and sensitivity of the fluorescence detection result, and it needs to ensure that it can effectively excite the compound to produce fluorescence. Each compound is accurately prepared into a solution with a concentration of 10 -5 M PBS dilute solution, the method is the same as the sample preparation step in the UV-vis test. Use one quartz cuvette with a volume of 3 mL and an inner diameter width of 1 cm, and load 2 / 3 of the volume of the sample to be detected. Similarly, bubbles should be avoided during the loading process, and the cuvette should be clean and free of impurities. The cuvette containing the sample is placed into the fluorescence detector, the "scan emission spectrum" function is selected on the operation interface, and the corresponding excitation wavelength is set. After the setting is completed, the scanning program is started, and the instrument will record the fluorescence intensity of the compound at different emission wavelengths to generate an emission spectrum.

[0069] Structural formula of a series of 2-aroyl-1,5-diaryl-1,5-pentanedione derivatives obtained in Table 1 Examples 1-16

[0070]

[0071]

[0072]

[0073] Table 2: Yields of each step and NMR data of a series of 2-aroyl-1,5-diaryl-1,5- pentanedione derivatives obtained in Examples 1-16

[0074]

[0075]

[0076]

[0077] Note: 1,3-diaryl-1,3-propanedione in Examples 1-10 is 1,3-diphenyl-1,3- propanedione, which is a commercial reagent purchased from Shanghai Titan Technology Co., Ltd., so there is no yield data for Step (2) in Examples 1-10, and the remaining steps are self-made.

[0078] Since the selected compounds 1a, 1g, 1i, and 1j have a larger conjugated range in structure, screening is performed in these four compounds for subsequent testing. Figure 4 is the UV absorption spectrum of compound 1a, 1g, 1i, and 1j. As can be seen from the figure, compound 1a exhibits a relatively significant UV absorption characteristic. Therefore, compound 1a is selected for subsequent testing. The NMR hydrogen spectrum of compound 1a prepared in Example 1 is shown in Figure 5 , which is used to confirm the structure of compound 1a.

[0079] Figure 6 is the UV absorption spectrum and fluorescence emission spectrum of compound 1a. Figure 7 is the UV absorption spectrum and fluorescence emission spectrum of compound 1a with metal ions such as Cd, Pd, and Cu. As can be seen from the figure, Figure 6 and 7 It can be found that compound 1a has a significant response signal to Cd 2+ . This may be due to the coordination of cation Cd 2+ with the carbonyl group in compound 1a. The coordination may make the molecule form a more rigid planar structure, and the rigid planar structure of the molecule enhances the delocalization of electrons, reduces the energy of the excited state of the molecule, and makes the fluorescence emission wavelength move to the long wave direction, that is, red shift. The compound 1a of the present application in a PBS solution containing metal ions has a significant response signal to Cd 2+There is an obvious response signal. Therefore, the compound can be used as an organic small molecule fluorescent material, and applied to the fields of metal ion detection and fluorescent probe.

[0080] Although the present application has been described in detail with general description, specific embodiments and experiments, some modifications or improvements can be made on the basis of the present application, which is obvious to those skilled in the art. Therefore, these modifications or improvements made on the basis of not deviating from the spirit of the present application, all belong to the scope of the present application claimed.

Claims

1. A 2-aroyl-1,5-diaryl-1,5-pentanedione derivative, characterized in that: Its structural formula is shown in formula (1): Among them, Ar1, Ar2, and Ar3 are aromatic substituents.

2. A 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 1, characterized in that: The Ar1 is selected from any one of benzene, 4-methylthio, 4-methylbenzene, 4-methoxybenzene, 4-chlorobenzene, 4-fluorobenzene, 4-bromobenzene, 3-chlorobenzene, 3-fluorobenzene, 3-bromobenzene, biphenyl, naphthalene, 2-chlorobenzene, 2-fluorobenzene, 2-bromobenzene, 2-methylbenzene, 2-methoxybenzene, 3-thiophene, 2-fluorene, 2-isopropylphenyl, and 4-(1,2,2-triphenylvinyl)phenyl; Ar2 is selected from any one of benzene, 4-methylbenzene, 3-methylbenzene, 2-methylbenzene, 4-chlorobenzene, and 4-cyanobenzene; Ar3 is selected from any one of benzene, 4-methylbenzene, 3-methylbenzene, 2-methylbenzene, 4-chlorobenzene, and 4-cyanobenzene.

3. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 1 or 2, characterized in that: 3-aryl propargyl alcohol reacts with 1,3-diaryl-1,3-propanedione to obtain the 2-aroyl-1,5-diaryl-1,5-pentanedione derivative, wherein the structural formula of 3-aryl propargyl alcohol is shown in formula (2), and the structural formula of 1,3-diaryl-1,3-propanedione is shown in formula (3).

4. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 3, characterized in that: The 3-aryl propargyl alcohol and 1,3-diaryl-1,3-propanedione undergo a tandem Meyer-Schuster rearrangement / nucleophilic addition reaction in the presence of a first catalyst and a first organic solvent to obtain the 2-aroyl-1,5-diaryl-1,5-pentanedione derivative.

5. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 4, characterized in that: The first catalyst includes Sc(OTf)3, Cu(OTf)2, AgOTf, Fe(OTf)3, Zn(OTf)2, and FeCl3; The first organic solvent includes 1,4-dioxane, tetrahydrofuran, dichloromethane, dichloroethane, acetonitrile, and nitromethane; The usage ratio of the 3-aryl propargyl alcohol, 1,3-diaryl-1,3-propanedione, the first catalyst, and the first organic solvent is 1 mmol: 1-1.5 mmol: 0.1-0.3 mmol: 0.2-2 mL.

6. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 3, characterized in that: The synthesis process of the 3-aryl propargyl alcohol is as follows: a halogenated hydrocarbon and propargyl alcohol undergo a Sonogashira coupling reaction in the presence of a second catalyst, a co-catalyst, and an alkaline solvent to obtain 3-aryl propargyl alcohol, wherein the structural formula of the propargyl alcohol is as shown in formula (4), and the structural formula of the aryl halogenated hydrocarbon is as shown in formula (5).

7. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 6, characterized in that: The second catalyst is Pd(PPh3)2Cl2, the co-catalyst is CuI, and the alkaline solvent is triethylamine; The ratio of the amount of halogenated hydrocarbon, propargyl alcohol, the second catalyst, the co-catalyst and the alkaline solvent is 1 mmol: 1-1.5 mmol: 0.05-0.15 mmol: 0.02-0.08 mmol: 1-5 mL.

8. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 3, characterized in that: The synthesis process of the 1,3-diaryl-1,3-propanedione is as follows: aryl ethyl ketone and aryl ethyl formate undergo Claisen condensation reaction in the presence of a strong base and a second organic solvent to obtain the 1,3-diaryl-1,3-propanedione, wherein the structural formula of the aryl ethyl ketone is as shown in Formula (6), and the structural formula of the aryl ethyl formate is as shown in Formula (7).

9. The method for synthesizing a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 8, characterized in that: The strong base is NaH, and the second organic solvent is THF; The ratio of the amount of the aryl ethyl ketone, the aryl ethyl formate, the strong base and the second organic solvent is 1 mmol: 1-1.5 mmol: 2-3 mmol: 0.5-5 mL.

10. Use of a 2-aroyl-1,5-diaryl-1,5-pentanedione derivative according to claim 1 or 2 in the fields of metal ion detection and fluorescent probe.

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