Preparation and application of a 7-dehydrocholesterol-perylene diimide derivative and its fluorescent film

Abstract

The present invention discloses a kind of 7-dehydrocholesterol-perylene diimide derivative and its preparation and application of fluorescent film, and utilizes the advantages such as the rigid structure and multiple chiral centers of 7-dehydrocholesterol to connect the conjugated fluorescent molecule with high fluorescence quantum yield, perylene anhydride, through a connecting arm. The synthesized fluorescent compound is used as a sensing element to prepare a fluorescent film, which can be used to detect a variety of banned drugs such as methamphetamines, and is applied to the field of banned drug detection. The present invention is simple to operate, and the reaction conditions are mild. The prepared fluorescent sensor film has high fluorescence quantum yield, good stability, low detection limit, long service life, and high detection sensitivity. It can be applied in sensors for detecting a variety of banned drugs such as methamphetamines. This type of fluorescent sensor film is installed in a portable fluorescence detector for supporting use to achieve rapid detection of banned drugs and improve the detection efficiency of banned drugs.

Description

Technical Field

[0001] The present invention relates to a fluorescent compound and the preparation and application of a fluorescent film thereof, and in particular to a 7-dehydrocholesterol-ruthenium diimide derivative and the preparation and application of a fluorescent film thereof. Background Art

[0002] Detection instruments based on fluorescence sensing technology are highly favored for their high sensitivity, fast response speed, strong portability, and simple operation. They are particularly suitable for trace detection of banned drugs. However, there are currently few fluorescent sensing materials with excellent properties for methamphetamine-type banned drugs, which is far from meeting social needs. Summary of the Invention

[0003] Purpose of the invention: The present invention aims to overcome the shortcomings of the prior art and provide a method for preparing a 7-dehydrocholesterol-rudder diimide derivative and its fluorescent sensing film with simple operation, mild reaction conditions, excellent sensing performance and high sensitivity, so as to realize the rapid and sensitive detection of vapors of methylphenethylamine-type banned drugs.

[0004] Technical solution: The 7-dehydrocholesterol-rudder diimide derivative of the present invention has a structural formula as shown in formula (I):

[0005]

[0006] Wherein m=7-12; n=2-5; R is 7-dehydrocholesterol.

[0007] The 7-dehydrocholesterol-rudder diimide derivative, wherein m=11; n=2; and R is 7-dehydrocholesterol.

[0008] The preparation method of the 7-dehydrocholesterol-rudder imide derivative comprises the following steps:

[0009] (1) Under nitrogen protection, 7-dehydrocholesterol is dissolved in anhydrous tetrahydrofuran, and then anhydrous sodium carbonate is added and stirred. After ice bath, triphosgene is added dropwise to the anhydrous tetrahydrofuran solution. After the addition is complete, the mixture is stirred in an ice bath for 1-3 hours, and then stirred at room temperature for 10-15 hours. After the reaction is completed, the reactant is diluted with hexane and filtered, and the filtrate is concentrated under reduced pressure. The crude product is separated by pure petroleum ether column chromatography to prepare a transparent oily compound 1, i.e., 7-dehydrocholesterol chloroformate.

[0010] (2) Under nitrogen protection, the alkyl alcohol amine was first dissolved in chloroform and stirred at room temperature. Then, 7-dehydrocholesterol chloroformate in chloroform was slowly added dropwise in an ice bath. After the addition was completed, the mixture was stirred and reacted at room temperature for 10-15 hours. After the reaction was completed, the mixture was washed with dilute hydrochloric acid solution and water, and the organic phase was separated and washed with petroleum ether. The mixture was filtered and dried to obtain a white solid compound 2.

[0011] (3) Under nitrogen protection, 3,4,9,10-tetracarboxylic dianhydride and aminoalkanoic acid were added to N-methylpyrrolidone and refluxed at 100-120°C for 8-12 hours. After the reaction was completed, the mixture was cooled to room temperature and poured into a sodium hydroxide solution. After stirring for 0.2-1.0 hour, the mixture was filtered and the residue was washed with acetic acid. The mixture was filtered and the residue was washed with acetic acid solution to prepare a dark red solid compound 3.

[0012] (4) Under nitrogen protection, compound 3 was dissolved in thionyl chloride and refluxed at 80-120°C for 3-8 hours. After the reaction was completed, the remaining thionyl chloride was removed by rotary evaporation. The crude product was vacuum dried at 40-80°C to obtain a black-red solid compound 4.

[0013] (5) Under nitrogen protection, compound 4 and compound 2 were dissolved in dichloromethane, and anhydrous potassium carbonate was added, and the mixture was refluxed at 45-65°C for 10-15 hours. After the reaction was completed, the mixture was filtered, and the obtained solid was separated by column chromatography using an eluent to obtain the target compound as a red solid.

[0014] In the preparation method of the 7-dehydrocholesterol-ruthenium imide derivative, the eluent is a mixed solvent of dichloromethane and acetone.

[0015] The preparation method of the fluorescent film containing the 7-dehydrocholesterol-ruthenium diimide derivative comprises the following steps:

[0016] (1) The 7-dehydrocholesterol-ruthenium diimide derivative was dissolved in tetrahydrofuran, and then ethyl acetate was added to prepare a 0.3-0.7 mM target solution.

[0017] (2) Preheat the glass tube in a 40-60°C oven, inject the target solution into the glass tube, and naturally evaporate the solvent in a 40-60°C oven for 30-60 minutes to obtain a glass tube coated with a fluorescent film, which is then stored away from light.

[0018] In the preparation method, the glass tube is an organic transparent glass tube, which is ultrasonically washed with pure water and ethanol for 0.5-1.5 hours respectively before use, and dried at 50-70°C for 4-8 hours before use.

[0019] The fluorescent film is prepared by the preparation method.

[0020] The application of the fluorescent film in the preparation of fluorescence sensing.

[0021] The fluorescent film is used in the detection of banned drugs.

[0022] In the application, the banned drug is a methamphetamine banned drug.

[0023] Furthermore, the technical solution adopted to solve the above technical problem consists of the following steps:

[0024] 1) Preparation of Compound 1

[0025] Under nitrogen, 7-dehydrocholesterol was dissolved in anhydrous tetrahydrofuran, followed by the addition of anhydrous sodium carbonate and stirring. The mixture was cooled to 0°C, and a solution of triphosgene in anhydrous tetrahydrofuran was added dropwise. After the addition was complete, the mixture was stirred at 0°C for 2 hours and then at room temperature for 12 hours. After the reaction was complete, the reaction solution was diluted with hexane and filtered. The filtrate was then concentrated under reduced pressure, and the crude product was separated by column chromatography using pure petroleum ether to obtain Compound 1, 7-dehydrocholesterol chloroformate, as a transparent oil.

[0026] 2) Preparation of Compound 2

[0027] Under nitrogen protection, the alkanolamine was first dissolved in chloroform and stirred at room temperature. Then, a chloroformate solution of 7-dehydrocholesterol chloroformate was slowly added dropwise at 0°C. After the addition was complete, the mixture was stirred and reacted at room temperature for 12 hours. After the reaction was completed, the mixture was washed three times with dilute hydrochloric acid solution and three times with pure water. The organic phase was separated, washed with petroleum ether, and filtered to dryness to obtain compound 2 as a white solid.

[0028] 3) Preparation of Compound 3

[0029] Under nitrogen, 3,4,9,10-tetracarboxylic dianhydride and aminoalkanoic acid were suspended in N-methylpyrrolidone and refluxed at 110°C for 8-12 hours. After the reaction was complete, the mixture was cooled to room temperature and poured into a dilute sodium hydroxide solution. After stirring for 0.5 hours, the mixture was filtered with suction. The residue was washed with acetic acid for 0.5 hours, filtered with suction, and the residue was washed three times with acetic acid to obtain a dark red solid, Compound 3.

[0030] 4) Preparation of Compound 4

[0031] Under nitrogen protection, compound 3 was dissolved in thionyl chloride and refluxed at 100°C for 5 hours. After the reaction was completed, the remaining dimethyl sulfoxide was removed by rotary evaporation. The crude product was vacuum dried at 60°C for 2 hours to obtain a black-red solid compound 4.

[0032] 5) Preparation of target compound

[0033] Under nitrogen protection, compound 4 and compound 2 were dissolved in dichloromethane, and anhydrous potassium carbonate was added. The mixture was refluxed at 55°C for 12 hours. After the reaction was completed, the mixture was filtered through diatomaceous earth, the filtrate was passed through a column, and the crude product was separated by column chromatography using dichloromethane / acetone (20:1) to obtain the target compound as a red solid.

[0034] The present invention also reports a method for preparing a fluorescent film responsive to banned drugs using the fluorescent compound, comprising the following steps:

[0035] 1) The prepared target compound solid was dissolved in tetrahydrofuran, and ethyl acetate was added at a volume ratio of 1 / 5 to prepare a 0.5 mM target solution.

[0036] 2) Preheat the glass tube in a 45°C oven, inject 15 μL of the solution into the glass tube, and naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a glass tube coated with a fluorescent film, which is then stored in the dark.

[0037] The glass tube is an organic transparent glass tube with a length of 20 mm, an outer diameter of 5 mm, and an inner diameter of 1 mm. Before use, the glass tube is ultrasonically washed with pure water and ethanol for one hour each, and dried at 60° C. for 5 hours before use.

[0038] Beneficial effects: Compared with the prior art, the present invention has the following technical advantages: (1) The present invention discloses a fluorescent compound with good sensing function for methamphetamine-type banned drugs. The compound consists of two unit parts, 7-dehydrocholesterol and ruthenium anhydride. The rigid structure and multiple chiral centers of 7-dehydrocholesterol are used to connect the ruthenium anhydride conjugated fluorescent molecules with high fluorescence quantum yield through a connecting arm, and the compound is made into a fluorescent film and applied in the field of banned drug detection. The fluorescent film obtained has high fluorescence quantum yield, low detection limit, excellent stability and number of reuses. The obtained fluorescent film device is then used in conjunction with a customized portable fluorescence detector to achieve rapid detection of banned drugs, improve the detection efficiency of banned drugs, and provide technical support for drug enforcement and investigation work. (2) The present invention also discloses a preparation method for preparing a fluorescent compound with response function to methamphetamine-type banned drugs. The method has low raw material price, mild reaction conditions, simple operation steps, good compound stability, and is suitable for batch reaction and large-scale synthesis. (3) The present invention also discloses a method for preparing a fluorescent film using the above-mentioned fluorescent compound, which is to attach a 7-dehydrocholesterol-rudder diimide derivative to the inner layer of a glass tube to obtain a fluorescent sensor component that can quickly respond to methamphetamine-type banned drugs, thereby realizing rapid and sensitive detection of methamphetamine-type banned drug vapors. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1This is the ultraviolet fluorescence spectrum of the 7-dehydrocholesterol-rudder diimide solution prepared by the present invention;

[0040] Figure 2 This is the excitation-emission spectrum of the 7-dehydrocholesterol-rudder diimide solution prepared in the present invention;

[0041] Figure 3 The fluorescence change curve of the 7-dehydrocholesterol-rudder diimide fluorescent sensing film prepared by the present invention under the conditions of methamphetamine-type banned drugs, water, methanol vapor and blank control;

[0042] Figure 4 This is the fluorescence change curve of the 7-dehydrocholesterol-ruthenium diimide fluorescent sensing film prepared by the present invention in the presence of various banned drugs. DETAILED DESCRIPTION

[0043] The present invention is described in detail below by way of examples, but this does not constitute any limitation to the present invention. The specific synthesis steps of the fluorescent compound responsive to methamphetamine-type illicit drugs of the present invention are as follows:

[0044] 1) Preparation of Compound 1

[0045] Under nitrogen, 7-dehydrocholesterol was dissolved in anhydrous tetrahydrofuran, followed by the addition of anhydrous sodium carbonate and stirring. The mixture was cooled to 0°C, and a solution of triphosgene in anhydrous tetrahydrofuran was added dropwise. After the addition was complete, the mixture was stirred at 0°C for 2 hours and then at room temperature for 12 hours. After the reaction was complete, the reaction solution was diluted with hexane and filtered. The filtrate was then concentrated under reduced pressure, and the crude product was separated by column chromatography using pure petroleum ether to obtain Compound 1, 7-dehydrocholesterol chloroformate, as a transparent oil.

[0046] 2) Preparation of Compound 2

[0047] Under nitrogen protection, the alkanolamine was first dissolved in chloroform and stirred at room temperature. Then, a chloroformate solution of 7-dehydrocholesterol chloroformate was slowly added dropwise at 0°C. After the addition was complete, the mixture was stirred and reacted at room temperature for 12 hours. After the reaction was completed, the mixture was washed three times with dilute hydrochloric acid solution and three times with pure water. The organic phase was separated, washed with petroleum ether, and filtered to dryness to obtain compound 2 as a white solid.

[0048] 3) Preparation of Compound 3

[0049] Under nitrogen, 3,4,9,10-tetracarboxylic dianhydride and aminoalkanoic acid were suspended in N-methylpyrrolidone and refluxed at 110°C for 8-12 hours. After the reaction was complete, the mixture was cooled to room temperature and poured into a dilute sodium hydroxide solution. After stirring for 0.5 hours, the mixture was filtered with suction. The residue was washed with acetic acid for 0.5 hours, filtered with suction, and the residue was washed three times with acetic acid to obtain a dark red solid, Compound 3.

[0050] 4) Preparation of Compound 4

[0051] Under nitrogen protection, compound 3 was dissolved in thionyl chloride and refluxed at 100°C for 5 hours. After the reaction was completed, the remaining dimethyl sulfoxide was removed by rotary evaporation. The crude product was vacuum dried at 60°C for 2 hours to obtain a black-red solid compound 4.

[0052] 5) Preparation of target compound

[0053] Under nitrogen protection, compound 4 and compound 2 were dissolved in dichloromethane, and anhydrous potassium carbonate was added. The mixture was refluxed at 55°C for 12 hours. After the reaction was completed, the mixture was filtered through diatomaceous earth, the filtrate was passed through a column, and the crude product was separated by column chromatography using dichloromethane / acetone (20:1) to obtain the target compound as a red solid.

[0054] The present invention also reports a method for preparing a fluorescent film responsive to banned drugs using the fluorescent compound, comprising the following steps:

[0055] 1) The prepared target compound solid was dissolved in tetrahydrofuran, and ethyl acetate was added at a volume ratio of 1 / 5 to prepare a 0.5 mM target solution.

[0056] 2) Preheat the glass tube in a 45°C oven, inject 15 μL of the solution into the glass tube, and naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a glass tube coated with a fluorescent film, which is then stored in the dark.

[0057] The glass tube is an organic transparent glass tube with a length of 20 mm, an outer diameter of 5 mm, and an inner diameter of 1 mm. Before use, the glass tube is ultrasonically washed with pure water and ethanol for one hour each, and dried at 60° C. for 5 hours before use.

[0058] Example 1

[0059]

[0060] 1) Under nitrogen, 1 g of 7-dehydrocholesterol was dissolved in 15 mL of anhydrous tetrahydrofuran. 1.32 g of anhydrous sodium carbonate was added, and the mixture was cooled to 0°C. 1.48 g of triphosgene was dissolved in 2 mL of anhydrous tetrahydrofuran and slowly added dropwise in an ice bath. After the addition was complete, the mixture was allowed to react in an ice bath for two hours, and then stirred at room temperature for 12 hours. After the reaction, the reaction mixture was diluted with hexane and filtered. The filtrate was concentrated under reduced pressure, and the crude product was separated by column chromatography using pure petroleum ether to obtain 0.76 g of a transparent oily compound, 7-dehydrocholesterol chloroformate. ESI-MS (m / z): 451.33 [M+H] + The molar ratio of 7-dehydrocholesterol, triphosgene and anhydrous sodium carbonate is 1:2:4.8.

[0061]

[0062] 2) Under nitrogen, 0.14 g of ethanolamine was dissolved in 10 mL of chloroform and stirred at room temperature until the solution became homogeneous and transparent. 0.76 g of 7-dehydrocholesterol chloroformate was then dissolved in 10 mL of chloroform and slowly added dropwise to the reaction flask in an ice bath. After the addition was complete, the mixture was stirred and reacted at room temperature for 12 hours. After the reaction, the mixture was washed three times with dilute hydrochloric acid and three times with pure water. The organic phase was separated, dried, and washed with petroleum ether to obtain 0.33 g of 7-dehydrocholesterol ethanolamine as a white solid. ESI-MS (m / z): 476.41 [M+H] + The molar ratio of 7-dehydrocholesterol chloroformate and ethanolamine is 1:1.1, and the value of n is 2.

[0063]

[0064] 3) Under nitrogen, 0.8 g of 3,4,9,10-tetracarboxylic dianhydride and 1.7 g of 12-aminododecanoic acid were added to 15 mL of N-methylpyrrolidone, stirred at room temperature until the solution was homogeneous, and then refluxed at 110°C for 12 hours. After the reaction, the mixture was cooled to room temperature and poured into 20 mL of 0.5 mol / L sodium hydroxide solution. After stirring for 0.5 hour, the mixture was filtered with suction. The residue was washed with acetic acid for 0.5 hour, filtered with suction, and then washed twice with acetic acid and filtered with suction to obtain 1.6 g of a dark red solid compound, 1,2-diimide-dodecanoic acid. 1 H NMR (300 MHz, Chloroform-d+CF3COOH) δ 8.77 (d, J = 8.0 Hz, 4H), 8.71 (d, J = 8.2 Hz, 4H), 4.27 (t, J = 7.8 Hz, 4H), 2.48 (t, J = 7.5 Hz, 4H), 1.75 (dt, J = 27.6, 7.4 Hz, 8H), 1.50-1.27 (m, 28H). wherein m is 11.

[0065]

[0066] 4) Under nitrogen, 0.8 g of rutile diimide-dodecanoic acid was added to 15 mL of thionyl chloride. The mixture was refluxed at 100°C for 5 hours. After the reaction was complete, the thionyl chloride was removed by rotary evaporation and dried under vacuum at 60°C for 2 hours to obtain 0.72 g of rutile diimide-dodecanoic acid chloride, which was used directly in the next reaction without purification. The molar ratio of rutile diimide-dodecanoic acid to thionyl chloride was 1:3, and the value of m was 11.

[0067]

[0068] 5) Under nitrogen, 0.63 g of imide-dodecyl chloride and 0.33 g of 7-dehydrocholesterol ethanolamine were dissolved in dichloromethane and stirred to make the suspension uniform. Anhydrous potassium carbonate was added and the mixture was refluxed at 55°C for 12 hours. After the reaction was completed, the solvent was removed by filtration. The resulting solid was separated by column chromatography using dichloromethane:acetone = 20:1 as the eluent to obtain 0.13 g of a red solid compound, which was the target product. The molar ratio of imide-dodecyl chloride and 7-dehydrocholesterol ethanolamine was 1:2, m was 11, and n was 2. 1H NMR (300 MHz, Chloroform-d) δ 8.66 (d, J = 7.9 Hz, 4H), 8.58 (d, J = 8.2 Hz, 4H), 5.65 (s, 4H), 4.58 (d, J = 11.1 Hz, 2H), 4.15 (dd, J = 16.6, 6.5 Hz, 8H), 3.43 (d, J = 5.9 Hz, 4H), 2.31 (t, J = 7.6 Hz, 4H), 2.01-0.99 (m, 86H), 0.89-0.82 (m, 18H), 0.70 (d, J = 49.0 Hz, 12H). MALDI-TOF MS: 1702.18[M+H] + .

[0069] 6) Dissolve 2.5 mg of the target compound in 2.94 mL of tetrahydrofuran, then add 0.58 mL of ethyl acetate and shake thoroughly. Preheat the glass tube in a 45°C oven. Inject 15 μL of the solution into the tube. Naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a fluorescent film-coated glass tube. Store in the dark to obtain a fluorescent film responsive to methamphetamine-type illicit drugs.

[0070] See also Figure 1 , is the ultraviolet fluorescence spectrum of the fluorescent compound prepared in this example. It can be seen from the figure that the maximum absorption wavelength is 489nm in the chloroform solution state.

[0071] See also Figure 2 , which is the excitation-emission spectrum of the fluorescent compound and film prepared in this example, wherein Ex(a) and Em(a) are the excitation and emission spectra of the fluorescent compound in chloroform, respectively. It can be seen from the figure that its maximum excitation wavelength is 482nm and the emission wavelength is 539nm.

[0072] See also Figure 3Fluorescence curves of the 7-dehydrocholesterol-rudder diimide fluorescent sensor film prepared for this embodiment under methamphetamine-type illegal drugs, water, methanol vapor and blank control. As can be seen from the figure, the film has a high sensitivity to the detection of trace methamphetamine (ice).

[0073] See also Figure 4 The fluorescence curves of the 7-dehydrocholesterol-rudder diimide fluorescent sensor film prepared in this embodiment in the presence of various banned drugs are shown. As can be seen from the figure, the film has the best specific response to methamphetamine.

[0074] Example 2

[0075] 1) Under nitrogen, dissolve 3g of 7-dehydrocholesterol in 25mL of anhydrous tetrahydrofuran. Add 3.92g of anhydrous sodium carbonate, cool to 0°C, and slowly add 3.43g of triphosgene in 6mL of anhydrous tetrahydrofuran dropwise in an ice bath. After complete addition, allow to react in an ice bath for two hours, then stir at room temperature for 12 hours. After completion of the reaction, dilute the reaction with hexane and filter. The filtrate is concentrated under reduced pressure, and the crude product is separated by column chromatography using pure petroleum ether to yield 2.23g of a transparent oily compound, 7-dehydrocholesterol chloroformate. The molar ratio of 7-dehydrocholesterol, triphosgene, and anhydrous sodium carbonate is 1:2:4.8.

[0076]

[0077] 2) Under nitrogen protection, 0.29g of alkyl alcohol amine was dissolved in 10mL of chloroform and stirred at room temperature until the solution was homogeneous and transparent. Then, 2.23g of 7-dehydrocholesterol chloroformate was dissolved in 10mL of chloroform and slowly added dropwise to the reaction flask under an ice bath. After the addition was complete, stirring and reacting were continued at room temperature for 12 hours. After the reaction was completed, the mixture was washed three times with dilute hydrochloric acid solution and three times with pure water. The organic phase was separated, dried, and washed with petroleum ether to obtain 1.70g of 7-dehydrocholesterol propanolamine as a white solid. The molar ratio of 7-dehydrocholesterol chloroformate to propanolamine was 1:1.1, and n was 3.

[0078]

[0079] 3) Under nitrogen, 0.8 g of 3,4,9,10-tridecanoic dianhydride and 1.7 g of aminoalkanoic acid were added to 15 mL of N-methylpyrrolidone, stirred at room temperature until the solution was homogeneous, and then refluxed at 110°C for 12 hours. After the reaction, the mixture was cooled to room temperature and poured into 20 mL of 0.5 mol / L sodium hydroxide solution. After stirring for 0.5 hour, the mixture was filtered with suction. The residue was washed with acetic acid for 0.5 hour, filtered with suction, and then washed twice with acetic acid and filtered with suction to obtain 1.6 g of a dark red solid compound, tridecanoic acid, wherein m is 12.

[0080]

[0081] 4) Under nitrogen, 1.6 g of rutile imide-tridecanoic acid was added to 15 mL of thionyl chloride. The mixture was refluxed at 100°C for 5 hours. After the reaction was complete, the thionyl chloride was removed by rotary evaporation and dried under vacuum at 60°C for 2 hours to obtain 1.4 g of rutile imide-tridecanoic acid chloride, which was used directly in the next reaction without purification. The molar ratio of rutile imide-tridecanoic acid to thionyl chloride was 1:3, and the value of m was 12.

[0082]

[0083] 5) Under nitrogen, 1.21 g of rutile diimide-tridecyl chloride and 1.70 g of 7-dehydrocholesterol propanolamine were dissolved in dichloromethane. After stirring to homogenize the suspension, anhydrous potassium carbonate was added and the mixture was refluxed at 55°C for 12 hours. After completion of the reaction, the reaction was filtered and the solvent removed. The resulting solid was separated by column chromatography using dichloromethane:acetone = 15:1 as the eluent to obtain 0.71 g of a red solid compound, the target product. The molar ratio of rutile diimide-tridecyl chloride to 7-dehydrocholesterol propanolamine was 1:2, m was 12, n was 3, and R was 7-dehydrocholesterol. 1H NMR (300MHz, Chloroform-d) δ8.63 (d, J=8.1Hz, 4H), 8.50 (d, J=8.2Hz, 4H), 4.90 (s, 2H), 4.78 (d, J=11.1Hz, 2H), 4.35 (dd, J=15.6, 6.6Hz, 8H), 3.55 (d, J=5.9Hz, 4H), 2.29 (t, J=7.5Hz, 4H), 2.12-0.80 (m, 120H), 0.65 (d, J=49.0Hz, 12H).

[0084] 6) Dissolve 2.5 mg of the target compound in 2.94 mL of tetrahydrofuran, then add 0.58 mL of ethyl acetate and shake thoroughly. Preheat the glass tube in a 45°C oven. Inject 15 μL of the solution into the tube. Naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a fluorescent film-coated glass tube. Store in the dark to obtain a fluorescent film responsive to methamphetamine-type illicit drugs.

[0085] Example 3

[0086] 1) Under nitrogen, dissolve 1 g of 7-dehydrocholesterol in 15 mL of anhydrous tetrahydrofuran. Add 1.31 g of anhydrous sodium carbonate and cool to 0°C. Then, dissolve 1.37 g of triphosgene in 2 mL of anhydrous tetrahydrofuran and slowly add dropwise in an ice bath. After complete addition, allow to react in an ice bath for two hours, then stir at room temperature for 12 hours. After completion of the reaction, dilute the reaction with hexane and filter. The filtrate is concentrated under reduced pressure, and the crude product is separated by column chromatography using pure petroleum ether to yield 0.64 g of a transparent oily compound, 7-dehydrocholesterol chloroformate. The molar ratio of 7-dehydrocholesterol, triphosgene, and anhydrous sodium carbonate is 1:2:4.8.

[0087]

[0088] 2) Under nitrogen protection, 0.10g of alkyl alcohol amine was dissolved in 10mL of chloroform and stirred at room temperature until the solution was homogeneous and transparent. Then, 0.64g of 7-dehydrocholesterol chloroformate was dissolved in 10mL of chloroform and slowly added dropwise to the reaction flask under an ice bath. After the addition was complete, stirring and reacting were continued at room temperature for 12 hours. After the reaction was completed, the mixture was washed three times with dilute hydrochloric acid solution and three times with pure water. The organic phase was separated, dried, and washed with petroleum ether to obtain 0.26g of 7-dehydrocholesterol butanolamine as a white solid. The molar ratio of 7-dehydrocholesterol chloroformate to butanolamine was 1:1.1, and n was 4.

[0089]

[0090] 3) Under nitrogen, 0.8 g of 3,4,9,10-hexadecanoic dianhydride and 1.7 g of aminoalkanoic acid were added to 15 mL of N-methylpyrrolidone, stirred at room temperature until the solution was homogeneous, and then refluxed at 110°C for 12 hours. After the reaction, the mixture was cooled to room temperature and poured into 20 mL of 0.5 mol / L sodium hydroxide solution. After stirring for 0.5 hour, the mixture was filtered. The residue was washed with acetic acid for 0.5 hour, filtered, and then washed twice with acetic acid. 1.6 g of a dark red solid compound, hexadecanoic acid, was obtained, with m being 10.

[0091]

[0092] 4) Under nitrogen, 0.8 g of rutile diimide-undecanoic acid was added to 15 mL of thionyl chloride and refluxed at 100°C for 5 hours. After the reaction was complete, the thionyl chloride was removed by rotary evaporation and dried under vacuum at 60°C for 2 hours to obtain 0.72 g of rutile diimide-undecanoyl chloride, which was used directly in the next reaction without purification. The molar ratio of rutile diimide-undecanoic acid to thionyl chloride was 1:3, and m was 10.

[0093]

[0094] 5) Under nitrogen, 0.22 g of dapoxetine-undecyl chloride and 0.26 g of 7-dehydrocholesterol butanolamine were dissolved in dichloromethane. After stirring to homogenize the suspension, anhydrous potassium carbonate was added and the mixture was refluxed at 55°C for 12 hours. After completion of the reaction, the reaction was filtered and the solvent removed. The resulting solid was separated by column chromatography using dichloromethane:acetone = 15:1 as the eluent to obtain 0.21 g of a red solid compound, the target product. The molar ratio of dapoxetine-undecyl chloride to 7-dehydrocholesterol butanolamine was 1:2, m was 10, n was 4, and R was 7-dehydrocholesterol. 1H NMR (300MHz, Chloroform-d) δ8.62 (d, J=8.0Hz, 4H), 8.55 (d, J=8.4Hz, 4H), 4.88 (s, 2H), 4.63 (d, J=10.8Hz, 2H), 4.10 (dd, J=16 .5, 5.5Hz, 8H), 3.44 (d, J=6.1Hz, 4H), 2.30 (t, J=7.6Hz, 4H), 2.03-0.99 (m, 98H), 0.84-0.79 (m, 20H), 0.72 (d, J=49.0Hz, 12H).

[0095] 6) Dissolve 2.5 mg of the target compound in 2.94 mL of tetrahydrofuran, then add 0.58 mL of ethyl acetate and shake thoroughly. Preheat the glass tube in a 45°C oven. Inject 15 μL of the solution into the tube. Naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a fluorescent film-coated glass tube. Store in the dark to obtain a fluorescent film responsive to methamphetamine-type illicit drugs.

[0096] Example 4

[0097] 1) Under nitrogen, dissolve 2g of 7-dehydrocholesterol in 20mL of anhydrous tetrahydrofuran. Add 2.62g of anhydrous sodium carbonate, cool to 0°C, and slowly add 3.36g of triphosgene in 6mL of anhydrous tetrahydrofuran dropwise in an ice bath. After complete addition, allow to react in an ice bath for two hours, then stir at room temperature for 12 hours. After completion of the reaction, dilute the reaction with hexane and filter. The filtrate is concentrated under reduced pressure, and the crude product is separated by column chromatography using pure petroleum ether to yield 1.27g of a transparent oily compound, 7-dehydrocholesterol chloroformate. The molar ratio of 7-dehydrocholesterol, triphosgene, and anhydrous sodium carbonate is 1:2:4.8.

[0098]

[0099] 2) Under nitrogen protection, 0.26g of alkyl alcoholamine was dissolved in 10mL of chloroform and stirred at room temperature until the solution was homogeneous and transparent. Then, 1.27g of 7-dehydrocholesterol chloroformate was dissolved in 10mL of chloroform and slowly added dropwise to the reaction flask under an ice bath. After the addition was complete, stirring and reacting were continued at room temperature for 12 hours. After the reaction was completed, the mixture was washed three times with dilute hydrochloric acid solution and three times with pure water. The organic phase was separated, dried, and washed with petroleum ether to obtain 0.82g of 7-dehydrocholesterol pentanolamine as a white solid. The molar ratio of 7-dehydrocholesterol chloroformate to pentanolamine was 1:1.1, and n was 5.

[0100]

[0101] 3) Under nitrogen, 0.8 g of 3,4,9,10-ruthenium tetracarboxylic dianhydride and 1.7 g of aminoalkanoic acid were added to 15 mL of N-methylpyrrolidone, stirred at room temperature until the solution was homogeneous, and then refluxed at 110°C for 12 hours. After the reaction, the mixture was cooled to room temperature and poured into 20 mL of 0.5 mol / L sodium hydroxide solution. After stirring for 0.5 hour, the mixture was filtered. The residue was washed with acetic acid for 0.5 hour, filtered, and then washed twice with acetic acid. 1.6 g of a dark red solid compound, ruthenium diimide-octadecanoic acid, was obtained, with an m value of 7.

[0102]

[0103] 4) Under nitrogen, 0.8 g of rutile imide-octadecanoic acid was added to 15 mL of thionyl chloride. The mixture was refluxed at 100°C for 5 hours. After the reaction was complete, the thionyl chloride was removed by rotary evaporation and dried under vacuum at 60°C for 2 hours to obtain 0.72 g of a dark red solid, rutile imide-octadecanoic acid chloride, which was used directly in the next reaction without purification. The molar ratio of rutile imide-octadecanoic acid to thionyl chloride was 1:3, and the value of m was 7.

[0104]

[0105] 5) Under nitrogen, 0.87 g of oxadiimide-octadecyl chloride and 0.82 g of 7-dehydrocholesterol pentanolamine were dissolved in dichloromethane. After stirring to homogenize the suspension, anhydrous potassium carbonate was added and the mixture was refluxed at 55°C for 12 hours. After completion of the reaction, the reaction was filtered and the solvent removed. The resulting solid was separated by column chromatography using dichloromethane:acetone = 15:1 as the eluent to obtain 0.34 g of a red solid compound, the target product. The molar ratio of oxadiimide-octadecyl chloride to 7-dehydrocholesterol pentanolamine was 1:2, m was 7, n was 5, and R was 7-dehydrocholesterol. 1H NMR (300MHz, Chloroform-d) δ8.76 (d, J=7.9Hz, 4H), 8.60 (d, J=8.1Hz, 4H), 4.88 (s, 2H), 4.59 (d, J=11.1Hz, 2H), 4.24 (dd, J=16.5, 6.5Hz, 8H), 3.40 (d, J=6.0Hz, 4H), 2.23 (t, J=8.6Hz, 4H), 2.15-0.89 (m, 114H), 0.68 (d, J=48.0Hz, 12H).

[0106] 6) Dissolve 2.5 mg of the target compound in 2.94 mL of tetrahydrofuran, then add 0.58 mL of ethyl acetate and shake thoroughly. Preheat the glass tube in a 45°C oven. Inject 15 μL of the solution into the tube. Naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a fluorescent film-coated glass tube. Store in the dark to obtain a fluorescent film responsive to methamphetamine-type illicit drugs.

[0107] Example 5

[0108] 1) Under nitrogen, dissolve 1.5 g of 7-dehydrocholesterol in 15 mL of anhydrous tetrahydrofuran. Add 1.96 g of anhydrous sodium carbonate and cool to 0°C. Then, dissolve 2.86 g of triphosgene in 4 mL of anhydrous tetrahydrofuran and slowly add dropwise in an ice bath. After complete addition, allow to react in an ice bath for two hours, then stir at room temperature for 12 hours. After completion of the reaction, dilute the reaction with hexane and filter. The filtrate is concentrated under reduced pressure, and the crude product is separated by column chromatography using pure petroleum ether to yield 0.97 g of a transparent oily compound, 7-dehydrocholesterol chloroformate. The molar ratio of 7-dehydrocholesterol, triphosgene, and anhydrous sodium carbonate is 1:2:4.8.

[0109]

[0110] 2) Under nitrogen, 0.24 g of ethanolamine was dissolved in 10 mL of chloroform and stirred at room temperature until the solution became homogeneous and transparent. Then, 0.97 g of 7-dehydrocholesterol chloroformate was dissolved in 10 mL of chloroform and slowly added dropwise to the reaction flask under an ice bath. After complete addition, stirring was continued at room temperature for 12 hours. After the reaction, the mixture was washed three times with dilute hydrochloric acid and three times with purified water. The organic phase was separated, dried, and washed with petroleum ether to obtain 0.61 g of 7-dehydrocholesterol ethanolamine as a white solid. The molar ratio of 7-dehydrocholesterol chloroformate to ethanolamine was 1:1.1, and n was 2.

[0111]

[0112] 3) Under nitrogen, 0.8 g of 3,4,9,10-hexadecanoic dianhydride and 1.7 g of aminoalkanoic acid were added to 15 ml of N-methylpyrrolidone, stirred at room temperature until the solution was homogeneous, and then refluxed at 110°C for 12 hours. After the reaction, the mixture was cooled to room temperature and poured into 20 mL of 0.5 mol / L sodium hydroxide solution. After stirring for 0.5 hour, the mixture was filtered with suction. The residue was washed with acetic acid for 0.5 hour, filtered with suction, and then washed twice with acetic acid. 1.6 g of a dark red solid compound, hexadecanoic acid, was obtained, with an m value of 8.

[0113]

[0114] 4) Under nitrogen, 0.8 g of rutile imide-nonadecanoic acid was added to 15 mL of thionyl chloride and refluxed at 100°C for 5 hours. After the reaction was complete, the thionyl chloride was removed by rotary evaporation and dried under vacuum at 60°C for 2 hours to obtain 0.72 g of a dark red solid, rutile imide-nonadecanoic acid chloride, which was used directly in the next reaction without purification. The molar ratio of rutile imide-nonadecanoic acid to thionyl chloride was 1:3, and m was 8.

[0115]

[0116] 5) Under nitrogen, 0.71 g of ruthenium diimide-nonadecyl chloride and 0.61 g of 7-dehydrocholesterol ethanolamine were dissolved in dichloromethane. After stirring to homogenize the suspension, anhydrous potassium carbonate was added and the mixture was refluxed at 55°C for 12 hours. After completion of the reaction, the reaction was filtered and the solvent removed. The resulting solid was separated by column chromatography using dichloromethane:acetone = 15:1 as the eluent to obtain 0.13 g of a red solid compound, the target product. The molar ratio of ruthenium diimide-nonadecyl chloride to 7-dehydrocholesterol ethanolamine was 1:2, m was 8, n was 2, and R was 7-dehydrocholesterol. 1H NMR (300MHz, Chloroform-d) δ8.76 (d, J=7.9Hz, 4H), 8.59 (d, J=8.5Hz, 4H), 4.88 (s, 2H), 4.68 (d, J=11.5Hz, 2H), 4.35 (dd, J=16.6, 6.5Hz, 8H), 3.43 (d, J=5.8Hz, 4H), 2.30 (t, J=7.6Hz, 4H), 2.11-0.81 (m, 110H), 0.69 (d, J=50.0Hz, 12H).

[0117] 6) Dissolve 2.5 mg of the target compound in 2.94 mL of tetrahydrofuran, then add 0.58 mL of ethyl acetate and shake thoroughly. Preheat the glass tube in a 45°C oven. Inject 15 μL of the solution into the tube. Naturally evaporate the solvent in a 45°C oven for 40 minutes to obtain a fluorescent film-coated glass tube. Store in the dark to obtain a fluorescent film responsive to methamphetamine-type illicit drugs.

[0118] Example 6

[0119] The preparation method of a fluorescent sensor film having a sensing function for methamphetamine-type illicit drugs in this embodiment comprises the following steps:

[0120] In step 6 of Example 1, the prepared target compound solid was dissolved in tetrahydrofuran, and ethyl acetate was added at a volume ratio of one-fifth to prepare a 0.75 mM target solution. 1.4 mg of the above target compound was dissolved in 1.092 mL of tetrahydrofuran, and 0.218 mL of ethyl acetate was added and shaken evenly. The glass tube was preheated in a 45 ° C oven, 15 μL of the solution was injected into the glass tube, and the solvent was naturally evaporated in a 45 ° C oven for 40 minutes to obtain a glass tube coated with a fluorescent film. The glass tube was then stored in the dark to obtain a fluorescent film that responds to methamphetamine-type illicit drugs.

[0121] The other steps are similar to those in Example 1 to prepare a fluorescent sensing film.

[0122] Example 7

[0123] The preparation method of a fluorescent sensor film having a sensing function for methamphetamine-type illicit drugs in this embodiment comprises the following steps:

[0124] In step 6 of Example 1, the prepared target compound solid was dissolved in tetrahydrofuran, and ethyl acetate was added at a volume ratio of one-fifth to prepare a 1.0 mM target solution. 1.0 mg of the above target compound was dissolved in 0.588 mL of tetrahydrofuran, and 0.118 mL of ethyl acetate was added and shaken evenly. The glass tube was preheated in a 45 ° C oven, 15 μL of the solution was injected into the glass tube, and the solvent was naturally evaporated in a 45 ° C oven for 40 minutes to obtain a glass tube coated with a fluorescent film. The glass tube was then stored in the dark to obtain a fluorescent film that responds to methamphetamine-type illicit drugs.

[0125] The other steps are similar to those in Example 1 to prepare a fluorescent sensing film.

[0126] The inventors conducted a large number of exploratory experiments using the 7-dehydrocholesterol-rudder diimide derivative synthesized in Example 1 and found that the film prepared therefrom can achieve rapid and sensitive detection of methamphetamine.

[0127] Example 8

[0128] Sensitivity testing

[0129] Fluorescent films of different materials were prepared according to the steps of Example 1 (the rest of the steps were the same, except that 7-dehydrocholesterol was replaced in step 1), wherein m was 11, n was 2, and R was selected from 7-dehydrocholesterol, cholesterol, β-sitosterol, stigmasterol, ergosterol, and dihydrocholesterol.

[0130] Where R is cholesterol: 1 H NMR (300 MHz, Chloroform-d) δ 8.65 (d, J = 8.2 Hz, 4H), 8.43 (d, J = 8.1 Hz, 4H), 5.31 (d, J = 5.0 Hz, 2H), 5.10 (s, 2H), 4.54 (dt, J = 11.8, 6.2 Hz, 2H), 4.28 (td, J = 11.1, 10.0, 6.5 Hz, 8H), 3.69-3.31 (m, 4H), 2.37 (dt, J = 11.5, 8.5 Hz, 8H), 2.15-0.88 (m, 110H), 0.73 (d, J = 49.0 Hz, 12H). R is β-sitosterol: 1H NMR (300 MHz, Chloroform-d) δ 8.61 (dd, J = 7.9, 1.5 Hz, 4H), 8.33 (dd, J = 8.1, 2.3 Hz, 4H), 5.29 (d, J = 5.0 Hz, 2H), 4.94 (s, 2H), 4.51 (dt, J = 11.8, 6.2 Hz, 2H), 4.19 (td, J = 11.0, 10.0, 6.6 Hz, 8H), 3.59-3.35 (m, 4H), 2.35 (dt, J = 10.5, 7.5 Hz, 8H), 2.16-0.73 (m, 124H), 0.63 (s, 6H). R is stigmasterol: 1 H NMR (300MHz, Chloroform-d) δ8.69 (dd, J=7.9, 1.5Hz, 4H), 8.42 (dd, J=8.1, 2.3Hz, 4H), 5.48 (dd, J=10.5, 6.2Hz, 4H), 5.31 (d, J=5.0Hz, 2H), 5.01 (s, 2H ), 4.55 (dt, J=11.8, 6.2Hz, 2H), 4.22 (td, J=11.0, 10.0, 6.6Hz, 8H), 3.60-3 .33(m, 4H), 2.25(dt, J=10.5, 7.5Hz, 8H), 2.10-0.83(m, 110H), 0.66(s, 6H). R is ergosterol: 1H NMR (300 MHz, Chloroform-d) δ 8.65 (d, J = 7.9 Hz, 4H), 8.49 (d, J = 8.2 Hz, 4H), 5.65 (s, 4H), 5.48 (dd, J = 10.5, 6.5 Hz, 4H), 4.48 (d, J = 11.1 Hz, 2H), 4.25 (dd, J = 16.6, 6.5 Hz, 8H), 3.44 (d, J = 5.9 Hz, 4H), 2.30 (t, J = 7.6 Hz, 4H), 2.20-0.80 (m, 98H), 0.65 (d, J = 49.0 Hz, 12H). R is dihydrocholesterol: 1H NMR (300 MHz, Chloroform-d) δ 8.70 (d, J = 7.9 Hz, 4H), 8.44 (d, J = 8.2 Hz, 4H), 4.88 (s, 2H), 4.55 (d, J = 11.1 Hz, 2H), 4.18 (dd, J = 16.6, 6.5 Hz, 8H), 3.53 (d, J = 5.9 Hz, 4H), 2.34 (t, J = 7.6 Hz, 4H), 2.13-0.83 (m, 116H), 0.71 (d, J = 49.0 Hz, 12H).

[0131] The fluorescent sensor film of each of the above materials is used in conjunction with a portable illicit drug detector, and each group of blank controls and 400ng of methamphetamine are parallel tested 5 times, and initial voltage compensation value, the instrument response value of blank group, and the instrument response value of sample addition group are recorded. Referring to Table 1, R obtained for the present embodiment is the response value of the fluorescent sensor film of different materials in a portable illicit drug detector to methamphetamine. As can be seen from the table, the film of R being 7-dehydrocholesterol not only has the lowest initial voltage compensation value compared, i.e., the reuse rate is high, and the sensitivity to methamphetamine is higher simultaneously.

[0132] Table 1

[0133]

[0134]

[0135] Example 9

[0136] The 7-dehydrocholesterol-ruthenium diimide fluorescent film glass tube prepared by the present invention was used in conjunction with a portable illegal drug detector to detect the response of the glass tube to various illegal drugs (such as heroin, morphine, ketamine, methcathinone, and phenacetin). Each group of parallel experiments was repeated 5 times, with 200 ng of sample loaded each time, and the instrument alarm value was recorded. Figure 4 The fluorescence curves of the 7-dehydrocholesterol-rudder diimide fluorescent sensor film prepared in this embodiment in the presence of various banned drugs are shown. As can be seen from the figure, the film has the best specific response to methamphetamine.

[0137] In summary, the fluorescent compound responsive to methamphetamines is readily available and inexpensive, capable of mass production under mild reaction conditions. The resulting fluorescent sensor film exhibits advantages such as simple film-forming conditions, low production costs, stable film-forming properties, high luminous efficiency, and a sensitive response to methamphetamines. This invention has significant implications for areas such as drug prevention and control.

Claims

1. A 7-dehydrocholesterol-rudder diimide derivative, characterized in that: The structural formula is shown in formula (I): Wherein m=11; n=2; R is 7-dehydrocholesterol.

2. A method for preparing the 7-dehydrocholesterol-cholesterol imide derivative according to claim 1, characterized in that: The following steps are involved: (1) Under nitrogen protection, 7-dehydrocholesterol is dissolved in anhydrous tetrahydrofuran, and then anhydrous sodium carbonate is added and stirred. The mixture is placed in an ice bath, and triphosgene is added dropwise to the anhydrous tetrahydrofuran solution. After the addition is complete, the mixture is stirred in an ice bath for 1-3 hours, and then stirred at room temperature for 10-15 hours. After the reaction is completed, the reactant is diluted with hexane and filtered, and the filtrate is concentrated under reduced pressure. The crude product is separated by column chromatography using pure petroleum ether to obtain a transparent oily compound 1, i.e., 7-dehydrocholesterol chloroformate. (2) Under nitrogen protection, ethanolamine was first dissolved in chloroform and stirred at room temperature. Then, 7-dehydrocholesterol chloroformate in chloroformate solution was slowly added dropwise in an ice bath. After the addition was completed, the mixture was stirred and reacted at room temperature for 10-15 hours. After the reaction was completed, the mixture was washed with dilute hydrochloric acid solution, washed with water, and the organic phase was separated and washed with petroleum ether. The organic phase was filtered and dried to obtain a white solid compound 2, i.e., 7-dehydrocholesterol ethanolamine. (3) Under nitrogen protection, 3,4,9,10-tetracarboxylic dianhydride and 12-aminododecanoic acid were added to N-methylpyrrolidone and refluxed at 100-120°C for 8-12 hours; after the reaction was completed, the mixture was cooled to room temperature and poured into a sodium hydroxide solution, stirred for 0.2-1.0 hours, and filtered. The filter residue was washed with acetic acid, filtered, and the filter residue was washed with acetic acid solution to prepare a dark red solid compound 3, i.e., imide-dodecanoic acid; (4) Under nitrogen protection, compound 3 was dissolved in thionyl chloride and refluxed at 80-120°C for 3-8 hours. After the reaction was completed, the remaining thionyl chloride was removed by rotary evaporation. The crude product was vacuum dried at 40-80°C to obtain a black-red solid compound 4, i.e., imide-dodecyl chloride; (5) Under nitrogen protection, compound 4 and compound 2 were dissolved in dichloromethane, and anhydrous potassium carbonate was added, and the mixture was refluxed at 45-65°C for 10-15 hours. After the reaction was completed, the mixture was filtered, and the obtained solid was separated by column chromatography using an eluent to obtain the target compound as a red solid.

3. The method for preparing 7-dehydrocholesterol-cholesterol imide derivative according to claim 2, characterized in that: The eluent is a mixed solvent of dichloromethane and acetone.

4. A method for preparing a fluorescent film containing the 7-dehydrocholesterol-ruthenium diimide derivative according to claim 1, characterized in that: The following steps are involved: (1) dissolving the 7-dehydrocholesterol-ruthenium diimide derivative according to claim 1 in tetrahydrofuran, and then adding ethyl acetate to prepare a 0.3-0.7 mM target solution; (2) Preheat the glass tube in a 40-60°C oven, inject the target solution into the glass tube, and naturally evaporate the solvent in a 40-60°C oven for 30-60 minutes to obtain a glass tube coated with a fluorescent film, which is then stored away from light.

5. The preparation method according to claim 4, characterized in that The glass tube is an organic transparent glass tube. Before use, the glass tube is ultrasonically washed with pure water and ethanol for 0.5-1.5 hours respectively, and dried at 50-70° C. for 4-8 hours before use.

6. A fluorescent film, characterized in that: It is prepared by the preparation method according to claim 4 or 5.

7. Use of the fluorescent film according to claim 6 in the preparation of fluorescent sensor components.

8. Use of the fluorescent film according to claim 6 in the detection of banned drugs.

9. The use according to claim 8, characterized in that The banned drugs are methamphetamine-type banned drugs.

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