Preparation method and application of a fluorescent probe for methamphetamine based on light-driven aggregate transformation

Abstract

The application relates to a preparation method and application of a methylphenylamine fluorescent probe based on light-driven aggregate transformation, and belongs to the field of fluorescent probe materials. The prepared probe is a Tz-3PD compound, has a triazine-phenanthridine D-A structure, and can spontaneously form a ground-state pre-association aggregate in a solution; the probe emits monomer fluorescence (400 nm) under 365 nm excitation, and emits excimer fluorescence (500 nm) under 400 nm excitation; the addition of a methylphenylamine analogue (MPEA) induces the aggregation of the probe molecules to form large-particle-size aggregates, the deconstruction-reconstruction transformation of the aggregates is driven by light, 450 nm and 575 nm characteristic double-emission peaks are generated, and particle size reduction and fluorescence lifetime change are accompanied. The application realizes the high-selectivity identification of MPEA through the orthogonal response of a 365 nm excitation kinetic quenching mode and a 400 nm excitation chroma double-emission mode.

Description

Technical Field

[0001] This invention belongs to the field of fluorescent probe materials. Background Technology

[0002] Methamphetamine (MA, commonly known as "ice") and its analogues are among the most widely abused synthetic drugs, possessing extremely high addictiveness and social harm. N-methylphenethylamine (MPEA), as a structural analogue and synthetic precursor of MA, is frequently used in simulation studies and illicit production, making it a key target for source control. Existing detection technologies, including chromatography-mass spectrometry, electrochemical methods, surface-enhanced Raman scattering, and immunoassay, while sensitive and accurate, rely on large equipment, resulting in time-consuming and costly methods. Furthermore, existing portable methods, while simple to operate, lack selectivity. Therefore, developing convenient and accurate detection methods is an urgent practical need.

[0003] Fluorescent sensors have been widely used in recent years due to their non-invasiveness and ease of operation. However, they still face the following challenges: MPEA possesses structural characteristics of both aliphatic and aromatic amines, but lacks the high nucleophilicity of aliphatic amines or the high energy levels of aromatic amines. Existing probes struggle to effectively distinguish structurally similar interfering amines; most probes rely on energy level matching to prepare photoinduced electron transfer fluorescent probes, exhibiting a single enhancement-quenching effect, and the single signal is highly sensitive to photobleaching and environmental fluctuations, limiting their accuracy. This invention aims to provide a fluorescent probe system based on light-driven aggregated state structural transformation, allowing light to act as a structural modulation mechanism, generating characteristic dual-emission signals, and enabling the probe to spontaneously form ground-state pre-associative aggregates without requiring high concentration conditions. Summary of the Invention

[0004] The purpose of this invention is to solve the problem of insufficient selectivity of existing fluorescent probes for methamphetamine, which leads to poor detection accuracy, and to provide a method for preparing and applying a methamphetamine fluorescent probe based on photo-driven aggregation state transformation.

[0005] A method for preparing a methamphetamine fluorescent probe based on light-driven aggregation state transformation is specifically carried out according to the following steps:

[0006] 1. Add 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and 2-aminophenylboronic acid pinacol ester to a two-necked flask, then add tetrahydrofuran to dissolve them, then add a saturated potassium carbonate aqueous solution, add a catalyst in a liquid nitrogen environment, purge and release nitrogen several times, thaw under a nitrogen atmosphere, and then reflux the reaction under a nitrogen atmosphere and at 80°C. After the reaction is completed, perform post-treatment to obtain a white solid, which is intermediate 1.

[0007] 2. Place intermediate 1 in a round-bottom flask, add dichloromethane to dissolve it, stir under 0°C ice-water bath conditions, add triethylamine, continue stirring under ice-water bath conditions, then add hexanoyl chloride dichloromethane solution dropwise, stir the reaction at room temperature, after the reaction is complete, concentrate the solution, add n-hexane, filter, and obtain a white solid, which is intermediate 2.

[0008] 3. Add intermediate 2 and phosphorus pentoxide to a two-necked flask, then add phosphorus oxychloride to dissolve it completely. After purging and releasing nitrogen several times, reflux the reaction under nitrogen atmosphere and at 110°C. After the reaction is complete, perform post-processing to obtain a light yellow solid Tz-3PD, which is a methamphetamine fluorescent probe based on photo-driven aggregation state transformation.

[0009] The principle of this invention:

[0010] The probe prepared in this invention is a Tz-3PD compound with a triazine-phenanthridine DA structure, which can spontaneously form ground-state pre-associated aggregates in solution. This probe emits monomeric localized excited-state fluorescence (400 nm) under 365 nm excitation and excimer fluorescence (500 nm) under 400 nm excitation. The addition of a methamphetamine analogue (MPEA) induces the aggregation of probe molecules to form large-particle aggregates. Irradiation drives the deconstruction-reconstruction transformation of these aggregates, producing characteristic dual emission peaks at 450 nm and 575 nm, accompanied by a decrease in particle size and a change in fluorescence lifetime. This invention achieves high-selectivity recognition of MPEA through the orthogonal response of the 365 nm kinetic quenching mode and the 400 nm chromatic dual emission mode. The probe prepared in this invention is suitable for drug screening, food safety, and environmental monitoring.

[0011] The beneficial effects of this invention are:

[0012] I. Compared with traditional fluorescent probes, this invention is based on a photo-driven aggregation state conversion reaction;

[0013] II. This invention is a multifunctional fluorescent probe that can simultaneously detect primary amines, secondary amines, and tertiary amines, exhibiting high selectivity;

[0014] Third, this invention solves the interference problem in MPEA detection, and can achieve a clear difference in fluorescence color;

[0015] IV. The fluorescent probe in this invention can achieve photo-driven structural conversion of primary amines, secondary amines, and tertiary amines for dual-mode fluorescence detection.

[0016] V. The detection limit of MPEA in this invention is 10 μM. Attached Figure Description

[0017] Figure 1The 1H NMR spectrum of the Tz-3PD prepared in step two of Example 1;

[0018] Figure 2 The liquid chromatography-mass spectrum of Tz-3PD prepared in step two of Example 1;

[0019] Figure 3 In the figure, a represents the change in particle size after the addition of MPEA; b represents the change in lifetime after the addition of MPEA.

[0020] Figure 4 The results were obtained using a Shimadzu RF-6000 fluorescence spectrometer, including 10 at 365 nm excitation. -4 The fluorescence spectra of M Tz-3PD solution with 10 μM MPEA, TEA (triethylamine), DEA (diethylamine), and Cad (cadherinine) were obtained, as well as the fluorescence spectra of the solution after 30 s to 90 s under 365 nm UV light irradiation.

[0021] Figure 5 The results were obtained using a Shimadzu RF-6000 fluorescence spectrometer, including 10 at 365 nm excitation. -4 Fluorescence spectra of M Tz-3PD solution with 10 μM MPEA, TEA (triethylamine), DEA (diethylamine), and Cad (cadherinine) were obtained, along with fluorescence spectra after 30 to 90 s of 365 nm UV irradiation and fluorescence fingerprinting at 0–120 s. Detailed Implementation

[0022] Specific Implementation Method 1: This implementation method is a method for preparing a methamphetamine fluorescent probe based on light-driven aggregation state transformation, specifically completed according to the following steps:

[0023] 1. Add 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and 2-aminophenylboronic acid pinacol ester to a two-necked flask, then add tetrahydrofuran to dissolve them, then add a saturated potassium carbonate aqueous solution, add a catalyst in a liquid nitrogen environment, purge and release nitrogen several times, thaw under a nitrogen atmosphere, and then reflux the reaction under a nitrogen atmosphere and at 80°C. After the reaction is completed, perform post-treatment to obtain a white solid, which is intermediate 1.

[0024] 2. Place intermediate 1 in a round-bottom flask, add dichloromethane to dissolve it, stir under 0°C ice-water bath conditions, add triethylamine, continue stirring under ice-water bath conditions, then add hexanoyl chloride dichloromethane solution dropwise, stir the reaction at room temperature, after the reaction is complete, concentrate the solution, add n-hexane, filter, and obtain a white solid, which is intermediate 2.

[0025] 3. Add intermediate 2 and phosphorus pentoxide to a two-necked flask, then add phosphorus oxychloride to dissolve it completely. After purging and releasing nitrogen several times, reflux the reaction under nitrogen atmosphere and at 110°C. After the reaction is complete, perform post-processing to obtain a light yellow solid Tz-3PD, which is a methamphetamine fluorescent probe based on photo-driven aggregation state transformation.

[0026] Specific Implementation Method Two: This implementation method differs from Specific Implementation Method One in that the molar ratio of 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and 2-aminophenylboronic acid pinacol ester in step one is 1:3.2; the mass-to-volume ratio of 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine, tetrahydrofuran, and saturated potassium carbonate aqueous solution in step one is 1g:(20 mL~24 mL):(5 mL~6 mL). Other steps are the same as in Specific Implementation Method One.

[0027] Specific Implementation Method 3: This implementation method differs from Specific Implementation Method 1 or 2 in that: the reflux reaction time at 80°C in step 1 is 30-40 hours; the catalyst mentioned in step 1 is tetrakis(triphenylphosphine)palladium. Other steps are the same as in Specific Implementation Method 1 or 2.

[0028] Specific Implementation Method Four: This implementation method differs from Specific Implementation Methods One to Three in that: in step one, nitrogen gas is released 2-4 times, followed by thawing under a nitrogen atmosphere; the post-processing method after the reaction in step one is as follows: first, extraction is performed using ethyl acetate, the organic phases are combined and washed with water, then the organic layer is dried with anhydrous magnesium sulfate, concentrated, and passed through a column. The eluent for column chromatography is a mixture of ethyl acetate and petroleum ether at a volume ratio of 1:20, yielding a white solid, which is intermediate 1. Other steps are the same as in Specific Implementation Methods One to Three.

[0029] Specific Implementation Method Five: This implementation method differs from Specific Implementation Methods One to Four in that: the molar ratio of intermediate 1, triethylamine, and hexanoyl chloride in step two is 1:2.8:1.26; the mass ratio of intermediate 1 to dichloromethane in step two is 1 g:70 mL; and the concentration of the hexanoyl chloride solution in dichloromethane in step two is 70 mmol / L to 75 mmol / L. The other steps are the same as in Specific Implementation Methods One to Four.

[0030] Specific Implementation Method Six: This implementation method differs from Specific Implementation Methods One to Five in that: the stirring time in step two is 10-20 minutes; the stirring reaction time at room temperature in step two is 4-6 hours. Other steps are the same as in Specific Implementation Methods One to Five.

[0031] Specific Implementation Method Seven: This implementation method differs from Specific Implementation Methods One to Six in that: the molar ratio of intermediate 2 and phosphorus pentoxide in step three is 1:32; the mass ratio of intermediate 2 to phosphorus oxychloride in step three is 1 g:(20 mL~25 mL); after purging and releasing nitrogen 2~4 times in step three, the reaction is refluxed at 110°C under a nitrogen atmosphere for 40 h~50 h. Other steps are the same as in Specific Implementation Methods One to Six.

[0032] Specific Implementation Method Eight: This implementation method differs from Specific Implementation Methods One through Seven in that: after the reaction in Step Three is complete, the post-processing method is as follows: the reaction solution is placed in ice-cold ethyl acetate, and the pH of the system is adjusted to 7 using a 20% sodium hydroxide solution. The combined organic phases are extracted and washed with water. The organic layer is dried with anhydrous magnesium sulfate, concentrated, and then passed through a column chromatography column. The eluent for column chromatography is a mixture of triethylamine, ethyl acetate, and petroleum ether in a volume ratio of 0.2:1:20, yielding a yellow solid, which is Tz-3PD. Other steps are the same as in Specific Implementation Methods One through Seven.

[0033] Specific Implementation Method Nine: This implementation method is based on a photo-driven aggregated state transformation methamphetamine fluorescent probe for the simultaneous and highly selective detection of primary, secondary, and tertiary amines.

[0034] Specific Implementation Method Ten: This implementation method differs from Specific Implementation Methods One to Nine in that: when detecting primary, secondary, and tertiary amines, the fluorescent probe uses photo-driven complex structural conversion for dual-mode fluorescence detection. Other steps are the same as in Specific Implementation Methods One to Nine.

[0035] The beneficial effects of the present invention are verified using the following embodiments:

[0036] Example 1: A method for preparing a methamphetamine fluorescent probe based on light-driven aggregation state transformation, specifically completed according to the following steps:

[0037] I. Preparation of intermediate 1:

[0038] 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and pinacol ester of 2-aminophenylboronic acid were added to a two-necked flask, then tetrahydrofuran was added to dissolve them, followed by a saturated aqueous solution of potassium carbonate. The catalyst tetra(triphenylphosphine)palladium was added in a liquid nitrogen environment. After purging and releasing nitrogen three times, the mixture was thawed under a nitrogen atmosphere and then refluxed at 80°C for 36 h under a nitrogen atmosphere. After the reaction was completed, the mixture was extracted with ethyl acetate, the organic phases were combined and washed with water, and the organic layer was dried with anhydrous magnesium sulfate and concentrated and passed through a column. The eluent for column chromatography was a mixture of ethyl acetate and petroleum ether at a volume ratio of 1:20, yielding a white solid, which is intermediate 1.

[0039] The molar ratio of 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and 2-aminophenylboronic acid pinacol ester in step one is 1:3.2;

[0040] The mass-to-volume ratio of 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine, tetrahydrofuran, and saturated potassium carbonate aqueous solution in step one is 1 g: 20 mL: 5 mL.

[0041] The reaction equation for step one is as follows:

[0042] ;

[0043] II. Preparation of intermediate 2:

[0044] Intermediate 1 was placed in a round-bottom flask, dissolved in dichloromethane, and stirred for 15 min in an ice-water bath at 0°C. Triethylamine was added, and stirring was continued for another 15 min in an ice-water bath. Then, a dichloromethane solution of hexanoyl chloride was slowly added dropwise using a constant-pressure funnel. The reaction was stirred at 25°C for 5 h. After the reaction was completed, the solution was concentrated by rotary evaporation under reduced pressure. Hexane was added, and the mixture was filtered to obtain a white solid, which was Intermediate 2.

[0045] The molar ratio of intermediate 1, triethylamine, and hexanoyl chloride mentioned in step two is 1:2.8:1.26;

[0046] The mass ratio of intermediate 1 to dichloromethane in step two is 1 g: 70 mL;

[0047] The concentration of the hexanoyl chloride solution in dichloromethane mentioned in step two is 73 mmol / L;

[0048] The reaction equation for step two is as follows:

[0049] ;

[0050] III. Preparation of Tz-3PD:

[0051] Intermediate 2 and phosphorus pentoxide were added to a two-necked flask, followed by the addition of phosphorus oxychloride until completely dissolved. After purging and releasing nitrogen three times, the mixture was refluxed at 110°C under a nitrogen atmosphere for 48 h. After the reaction was complete, the reaction solution was placed in ice-cold ethyl acetate. The pH of the system was adjusted to 7 using a 20% sodium hydroxide solution. The organic phases were extracted and combined, and washed with water. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and passed through a column chromatography column. The eluent for column chromatography was a mixture of triethylamine, ethyl acetate, and petroleum ether in a volume ratio of 0.2:1:20, yielding a yellow solid, which was Tz-3PD.

[0052] The molar ratio of intermediate 2 and phosphorus pentoxide mentioned in step 3 is 1:32;

[0053] The mass ratio of intermediate 2 to phosphorus oxychloride in step 3 is 1 g: 23 mL;

[0054] The reaction equation for step three is as follows:

[0055] .

[0056] Compound structure confirmation:

[0057] The 1H NMR spectrum of the Tz-3PD molecule prepared in Example 1 is shown below. Figure 1 As shown, the 1H NMR spectrum, using deuterated chloroform as the deuteration reagent, revealed the following after integration: doublets at 9.55 ppm, multiplets at 8.97 ppm, 8.53 ppm, 8.34 ppm, and 8.01 ppm; multiplets at 7.67-7.60 ppm; and multiplets at 7.55-7.48 ppm, all attributed to hydrogens from phenanthrene dimethyl ether. The multiplets at 3.54 ppm, 2.1 ppm, 1.67 ppm, and 1.01 ppm were attributed to hydrogens from the alkyl chain. Furthermore, the total number of hydrogens after integration was 54, corresponding to the number of hydrogens in the molecule, indicating successful synthesis of Tz-3PD. The liquid chromatography-mass spectrum of the Tz-3PD molecule is shown below. Figure 2 As shown, from Figure 2 It can be seen that the peak data in the liquid chromatography-mass spectrometry chromatogram are test data, and the molecular weight result is 823.53, which is basically consistent with the actual molecular weight M=823.1, proving that the Tz-3PD product was successfully synthesized.

[0058] Figure 3 The value of 'a' was obtained by measuring the nanoparticle potentiometer using a NANOTRAC WAVE II nanoparticle potentiometer, utilizing 10 -3 M and 10 -5 M Tz-3PD tetrahydrofuran solution, 10 -3 A Tz-3PD tetrahydrofuran solution was mixed with 10 μM MPEA and irradiated in situ at 365 nm for 20 s and 40 s. This confirms that the particle size of the Tz-3PD tetrahydrofuran solution changed after the addition of MPEA; Figure b shows the results obtained using an FLS1000 steady-state and transient fluorescence spectrometer, using 10 μM MPEA. -4 The lifetime of the Tz-3PD tetrahydrofuran solution was tested by adding 10 μM MPEA to the Tz-3PD tetrahydrofuran solution and then irradiating it in situ at 365 nm for 60 s. This test confirmed that the solution changed before and after the test.

[0059] The Tz-3PD probe interacted with different types of amine compounds; the probe exhibited differentiated photochromic changes in response to different amines, indicating its ability to recognize the structure of amines. The mechanism was studied using N-methylphenethylamine (MPEA) as an example: Tz-3PD was reacted with a tetrahydrofuran solution (10... -4 Adding 10 μM MPEA to the solution (M) resulted in an increase in particle size using dynamic light scattering (DLS) analysis; after illumination, the particle size distribution broadened. Simultaneously, the fluorescence lifetime decreased from 4.14 ns to 1.44 ns, before recovering to 1.78 ns after illumination. These results indicate that illumination drives internal structural rearrangement in the aggregates, transforming them from a loose network state to a compact, ordered state.

[0060] Figure 4 The results were obtained using a Shimadzu RF-6000 fluorescence spectrometer, including 10 at 365 nm excitation. -4 Fluorescence spectra of M Tz-3PD solution with 10 μM MPEA, TEA (triethylamine), DEA (diethylamine), and Cad (cadherinine), as well as fluorescence spectra of the solution after 30 s to 90 s under 365 nm UV light irradiation.

[0061] For the fluorescence spectrum changes of Tz-3PD in the presence of different analytes, please refer to [reference needed]. Figure 4 Under 365 nm excitation conditions, the original Tz-3PD tetrahydrofuran solution exhibited an emission peak at 400 nm. Different amines showed differentiated responses upon addition: MPEA quenched fluorescence; DEA enhanced fluorescence; TEA quenched fluorescence; and Cad showed no significant change. After illumination, all systems exhibited varying degrees of fluorescence quenching; the triethylamine system showed strong quenching in the initial stage of illumination, followed by fluorescence enhancement with prolonged illumination.

[0062] Figure 5 The results were obtained using a Shimadzu RF-6000 fluorescence spectrometer, including 10 at 365 nm excitation. -4 The fluorescence spectra of M Tz-3PD solution with 10 μM MPEA, TEA, DEA, and Cad were obtained, and the fluorescence spectra were obtained after 30 s to 90 s under 365 nm UV lamp irradiation, as well as the fluorescence fingerprint spectrum from 0 to 120 s.

[0063] Under 400 nm excitation conditions, the original Tz-3PD tetrahydrofuran solution exhibited an emission peak at 500 nm. After adding different types of amines, most systems showed no significant response. With prolonged illumination, all solutions exhibited bimodal emission (450 nm and 575 nm). These two emission peaks at 450 nm and 575 nm originated from different excited-state relaxation pathways of the same complex, and the intensity ratio of the bimodal peaks differed for different amines. This difference reflects the combined effect of the amine's electron-donating ability and steric hindrance, thus forming a unique spectral fingerprint for each amine. Furthermore, the emission spectra of different amine systems exhibited unique evolution patterns with illumination time. Based on the excitation wavelength dependence, a time-dependent dimension was introduced, enabling different amines to form unique spectral fingerprints. (See [link to relevant documentation]). Figure 5 .

Claims

1. A method for preparing a methamphetamine fluorescent probe based on photo-driven aggregated state transformation, characterized in that... The preparation method is specifically carried out according to the following steps:

1. Add 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and 2-aminophenylboronic acid pinacol ester to a two-necked flask, then add tetrahydrofuran to dissolve them, then add a saturated potassium carbonate aqueous solution, add a catalyst in a liquid nitrogen environment, purge and release nitrogen several times, thaw under a nitrogen atmosphere, and then reflux the reaction under a nitrogen atmosphere and at 80°C. After the reaction is completed, perform post-treatment to obtain a white solid, which is intermediate 1.

2. Place intermediate 1 in a round-bottom flask, add dichloromethane to dissolve it, stir under 0°C ice-water bath conditions, add triethylamine, continue stirring under ice-water bath conditions, then add hexanoyl chloride dichloromethane solution dropwise, stir the reaction at room temperature, after the reaction is complete, concentrate the solution, add n-hexane, filter, and obtain a white solid, which is intermediate 2.

3. Add intermediate 2 and phosphorus pentoxide to a two-necked flask, then add phosphorus oxychloride to dissolve it completely. After purging and releasing nitrogen several times, reflux the reaction under nitrogen atmosphere and at 110°C. After the reaction is complete, perform post-processing to obtain a light yellow solid Tz-3PD, which is a methamphetamine fluorescent probe based on photo-driven aggregation state transformation.

2. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... The molar ratio of 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine and 2-aminophenylboronic acid pinacol ester in step one is 1:3.2; the mass-volume ratio of 2,4,6-tris-(4-bromophenyl)-[1,3,5]triazine, tetrahydrofuran and saturated potassium carbonate aqueous solution in step one is 1 g:(20 mL~24 mL):(5 mL~6 mL).

3. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... The reflux reaction in step one at 80°C lasts for 30-40 hours; the catalyst in step one is tetra(triphenylphosphine)palladium.

4. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... After purging nitrogen 2-4 times in step one, the mixture is thawed under a nitrogen atmosphere. The post-processing method after the reaction in step one is as follows: first, extract with ethyl acetate, combine the organic phases and wash with water, then dry the organic layer with anhydrous magnesium sulfate, concentrate and pass through a column. The eluent for column chromatography is a mixture of ethyl acetate and petroleum ether at a volume ratio of 1:20, to obtain a white solid, which is intermediate 1.

5. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... The molar ratio of intermediate 1, triethylamine and hexanoyl chloride in step two is 1:2.8:1.26; the mass ratio of intermediate 1 to dichloromethane in step two is 1 g:70 mL; the concentration of the dichloromethane solution of hexanoyl chloride in step two is 70 mmol / L~75 mmol / L.

6. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... The stirring time in step two is 10 min to 20 min; the stirring reaction time at room temperature in step two is 4 h to 6 h.

7. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... The molar ratio of intermediate 2 and phosphorus pentoxide in step three is 1:32; the mass ratio of intermediate 2 to phosphorus oxychloride in step three is 1 g:(20 mL~25 mL); after purging and releasing nitrogen gas 2~4 times in step three, the reaction is refluxed at 110℃ under nitrogen atmosphere for 40 h~50 h.

8. The method for preparing a methamphetamine fluorescent probe based on photodriven aggregation state transformation according to claim 1, characterized in that... The post-processing method after the reaction in step three is as follows: the reaction solution is placed in ice-cold ethyl acetate, and the pH value of the system is adjusted to 7 using a 20% sodium hydroxide solution. The organic phases are extracted and combined and washed with water. The organic layer is dried with anhydrous magnesium sulfate and then concentrated and passed through a column. The eluent for column chromatography is a mixture of triethylamine, ethyl acetate and petroleum ether in a volume ratio of 0.2:1:20, which yields a yellow solid, namely Tz-3PD.

9. The application of the methamphetamine fluorescent probe based on photodriven aggregation state transformation prepared by the preparation method according to claim 1, characterized in that... A photo-driven aggregated-state transformation-based fluorescent probe for methamphetamine is used for highly selective detection of primary, secondary, and tertiary amines.

10. The application of the methamphetamine fluorescent probe based on light-driven aggregation state transformation according to claim 9, characterized in that... When detecting primary, secondary, and tertiary amines, fluorescent probes utilize photo-driven complex structural transformation for dual-mode fluorescence detection.

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