A-D-A' type dual-channel fluorescent material, its preparation method and application

Abstract

The present invention provides an A-D-A'-type dual-channel fluorescent material, a preparation method thereof, and an application thereof. The A-D-A'-type dual-channel fluorescent material is {4-[3,6-di-tert-butyl-1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazol-9-yl]phenyl}(phenyl)methanone. In the present invention, 3,6-di-tert-butylcarbazole is selected as the electron-donating unit (D), and benzophenone (A) and triphenyltriazine (A') are respectively introduced at the N atom or the 1-position of carbazole as the electron-withdrawing units, so as to design and obtain an A-D-A'-type organic molecule. The A-D-A'-type dual-channel fluorescent material has two inconsistent CT properties, thereby realizing CT-state luminescence with different properties, and finally obtaining dual-peak fluorescence emission when excited by light. In addition, the solution of the fluorescent material can recognize and respond to triethylamine, so it can be used as the recognition and response of triethylamine in the detection of triethylamine.

Description

Technical Field

[0001] The present invention relates to the technical field of luminescent materials, and particularly to an A-D-A' type dual-channel fluorescent material, a preparation method thereof, and an application thereof. Background Art

[0002] Organic luminescent materials have wide applications in fields such as detection and display. When excited by light, a compound absorbs energy and transitions from the ground state to the excited state, and then relaxes to the first excited state through internal conversion (ISC), and finally releases energy and returns to the ground state in the form of fluorescence radiation from the first excited state. Limited by Kasha's rule, the emission spectrum (emission peak) of organic fluorescent materials is mainly determined by the energy level difference between the first excited state (S1) and the ground state (S0), and usually exhibits the luminescence property of single-peak emission. It is challenging to achieve single-molecule dual luminescence (double-peak emission).

[0003] Currently, the following main methods are used to construct single-molecule dual-luminescence materials: (1) Designing luminescent materials with properties such as TICT can obtain dual luminescence of the LE and CT states; (2) Obtaining planar compounds with strong Π-Π interactions, which generate an additional luminescence channel through intermolecular interactions in the aggregated state to form exciplexes or excimers, thereby obtaining simultaneous luminescence of single molecules and the aggregated state; (3) Single-molecule substances achieve dual emission of fluorescence and phosphorescence through the heavy-atom effect or crystallization-induced room-temperature phosphorescence.

[0004] However, the above molecular design strategies all have inconsistent disadvantages: (1) TICT compounds usually use aniline and its derivatives as electron-donating units, and the acceptor unit is connected to the benzene ring, with certain limitations in molecular design, and the quantum yield of the obtained compounds is usually not high. (2) Exciplexes / excimers need to interact in the aggregated state, and it is difficult to achieve dual-emission properties in the solution state. (3) Room-temperature phosphorescence needs to be achieved by introducing heavy atoms or constructing a rigid crystalline environment, with harsh conditions, and the position of the obtained phosphorescence emission peak is accidental. It is difficult to speculate the possible position of its triplet phosphorescence emission through existing fluorescent groups, and the triplet luminescence is also affected by factors such as temperature and oxygen and quenched. Summary of the Invention

[0005] The purpose of the present invention is to provide an A-D-A' type dual-channel fluorescent material, which can obtain dual-peak fluorescence emission when excited by light.

[0006] Another purpose of the present invention is to provide a preparation method of an A-D-A' type dual-channel fluorescent material, which has simple operation and controllable parameters and is suitable for large-scale industrial production.

[0007] The third object of the present invention is to provide the application of A-D-A'-type dual-channel fluorescent material as the recognition response of triethylamine in the detection of triethylamine.

[0008] The present invention solves its technical problems by adopting the following technical solutions.

[0009] The present invention provides an A-D-A'-type dual-channel fluorescent material, and the A-D-A'-type dual-channel fluorescent material is {4-[3,6-di-tert-butyl-1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazol-9-yl]phenyl}(phenyl)methanone, and its structural formula is:

[0010]

[0011] The present invention provides a preparation method of an A-D-A'-type dual-channel fluorescent material, comprising the following steps:

[0012] S1. Preparation of 1-bromo-3,6-di-tert-butyl-9H-carbazole: Mix 3,6-di-tert-butylcarbazole, silica gel powder and dichloromethane and stir vigorously, then dropwise add N-bromosuccinimide / dichloromethane mixed solution and react in the dark for 3.5 - 4.5 h, filter and extract and wash with ethyl acetate to obtain a first organic layer, and the first organic layer is dried, rotary evaporated, concentrated and separated to obtain the 1-bromo-3,6-di-tert-butyl-9H-carbazole;

[0013] S2. Preparation of {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone: After reacting the 1-bromo-3,6-di-tert-butyl-9H-carbazole, sodium hydride and N-methylformamide for 0.8 - 1.2 h, add 4-fluorobenzophenone / dimethylformamide mixed solution to react, cool to room temperature and add water to terminate the reaction, then extract and wash with ethyl acetate to obtain a second organic layer, and the second organic layer is dried, concentrated and separated to obtain the {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone;

[0014] S3. Add 2,4-diphenyl-6-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine B, Pd2(dba)3, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tetrabutylammonium iodide, toluene and K2CO3 to the {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone in sequence, react in a nitrogen atmosphere, cool and extract and wash with ethyl acetate to obtain a third organic layer, and the third organic layer is dried, rotary evaporated and separated to obtain the A-D-A'-type dual-channel fluorescent material.

[0015] The present invention provides the application of the above A-D-A'-type dual-channel fluorescent material in the detection of triethylamine as an identification response to triethylamine.

[0016] The beneficial effects of the A-D-A'-type dual-channel fluorescent material, its preparation method, and application in the embodiments of the present invention are as follows:

[0017] The present invention selects 3,6-ditert-butylcarbazole as the electron-donating unit (D), and introduces benzophenone (A) and triphenyltriazine (A') as electron-withdrawing units at the N atom or the 1-position of carbazole respectively, thereby designing an A-D-A'-type organic molecule. Limited by steric hindrance, there will be a large torsional angle between benzophenone and triphenyltriazine and the carbazole unit, and there will be charge transfer channels between carbazole and benzophenone and triphenyltriazine units in the molecule at the same time. Since benzophenone and triphenyltriazine have different electron-withdrawing abilities, the properties of the intramolecular charge transfer of these two are different. Therefore, this compound will obtain two inconsistent CT properties, thus realizing CT-state luminescence with different properties, and finally obtaining dual-peak fluorescence emission when excited by light. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the following will briefly introduce the drawings required to be used in the embodiments. It should be understood that the following drawings only show some embodiments of the present invention, and therefore should not be regarded as limiting the scope. For those of ordinary skill in the art, other related drawings can be obtained based on these drawings without creative efforts.

[0019] Figure 1 It is the preparation flow chart of the A-D-A'-type dual-channel fluorescent material of the present invention;

[0020] Figure 2 It is the ultraviolet-visible absorption spectrum of the A-D-A'-type dual-channel fluorescent material of Example 1 of the present invention in different solutions;

[0021] Figure 3 It is the fluorescence emission spectrum of the A-D-A'-type dual-channel fluorescent material of Example 1 of the present invention in different solvents;

[0022] Figure 4 It is the fluorescence emission spectrum of the solid of the A-D-A'-type dual-channel fluorescent material of Example 1 of the present invention;

[0023] Figure 5 It is the fluorescence emission spectrum of the A-D-A'-type dual-channel fluorescent material of Example 1 of the present invention at different excitation wavelengths;

[0024] Figure 6Fluorescence emission spectra of THF solutions of A-D-A'-type dual-channel fluorescent materials with different triethylamine contents. Detailed implementation manners

[0025] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. For those not specified in the embodiments, the conventional conditions or the conditions recommended by the manufacturer are followed. The reagents or instruments not specified by the manufacturer can all be obtained as conventional products through commercial purchase.

[0026] The A-D-A'-type dual-channel fluorescent materials of the embodiments of the present invention, their preparation methods, and applications will be specifically described below.

[0027] An A-D-A'-type dual-channel fluorescent material provided by an embodiment of the present invention, the A-D-A'-type dual-channel fluorescent material is {4-[3,6-di-tert-butyl-1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazol-9-yl]phenyl}(phenyl)methanone, and its structural formula is:

[0028]

[0029] The present invention selects 3,6-di-tert-butylcarbazole as the electron-donating unit (D), and introduces benzophenone (A) and triphenyltriazine (A') as the electron-withdrawing units at the N atom or the 1st position of carbazole respectively, so as to obtain an A-D-A'-type organic molecule. Limited by the steric hindrance effect, there will be a large torsional angle between benzophenone and triphenyltriazine and the carbazole unit, and there will be charge transfer channels between carbazole and benzophenone and triphenyltriazine units in the molecule at the same time. Since benzophenone and triphenyltriazine have different electron-withdrawing abilities, the properties of these two intramolecular charge transfers are different. Therefore, this compound will obtain two inconsistent CT properties, so as to realize CT-state luminescence with different properties, and finally double-peak fluorescence emission can be obtained when excited by light.

[0030] Refer to Figure 1 As shown, the present invention also provides a preparation method of an A-D-A'-type dual-channel fluorescent material, including the following steps:

[0031] S1. Preparation of 1-bromo-3,6-di-tert-butyl-9H-carbazole (Compound B): Mix 3,6-di-tert-butylcarbazole, silica gel powder and dichloromethane (DCM), and stir vigorously. Then, dropwise add a mixed solution of N-bromosuccinimide / dichloromethane (NBS / DCM) and react in the dark for 3.5 - 4.5 h. After filtering off the silica gel powder, extract with ethyl acetate (EA) and wash with saturated brine. Repeat the separation three times to obtain the first organic layer. The first organic layer is dried over anhydrous magnesium sulfate, rotary evaporated, concentrated, and then separated by silica gel column chromatography to obtain 1-bromo-3,6-di-tert-butyl-9H-carbazole.

[0032] Further, in a preferred embodiment of the present invention, the mass-volume ratio of 3,6-di-tert-butylcarbazole, the silica gel powder and the dichloromethane is 1:1 - 1.5:122 - 128 (g / mL).

[0033] Further, in a preferred embodiment of the present invention, in the N-bromosuccinimide / dichloromethane mixed solution, the mass-volume ratio of N-bromosuccinimide and dichloromethane is 1:183 - 185 (g / mL), and the mass ratio of N-bromosuccinimide and 3,6-di-tert-butylcarbazole is 1:1.45 - 1.49.

[0034] S2. Preparation of {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone (Compound C): React 1-bromo-3,6-di-tert-butyl-9H-carbazole, NaH, and N,N-dimethylformamide (DMF) for 0.8 - 1.2 h, then add a mixed solution of 4-fluorobenzophenone / dimethylformamide and react. After cooling to room temperature and adding water to terminate the reaction, the product is extracted with ethyl acetate and washed with saturated brine. Repeat the separation three times to obtain the second organic layer. The second organic layer is dried over anhydrous magnesium sulfate, concentrated and separated, and then separated by silica gel column chromatography to obtain {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone.

[0035] Further, in a preferred embodiment of the present invention, the mass-volume ratio of 1-bromo-3,6-di-tert-butyl-9H-carbazole, the NaH and the N,N-dimethylformamide is 59 - 61:26 - 28:1 (mg / mL).

[0036] Further, in a preferred embodiment of the present invention, in the 4-fluorobenzophenone / dimethylformamide mixed solution, the mass-volume ratio of 4-fluorobenzophenone and dimethylformamide is 36 - 38:1 (mg / mL), and the mass ratio of 4-fluorobenzophenone and 1-bromo-3,6-di-tert-butyl-9H-carbazole is 1:1.62 - 1.64.

[0037] Further, in a preferred embodiment of the present invention, the temperature of the reaction is 95-105 °C, and the reaction time is 1.8-2.2 h. Preferably, the reaction temperature is 100 °C, and the reaction time is 2 h.

[0038] S3. 2,4-Diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine B, Pd2(dba)3, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tetrabutylammonium iodide (TBAI), toluene (TOL), and K2CO3 were successively added to {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone. After purging with nitrogen to remove oxygen, the reaction was carried out under a nitrogen atmosphere. After the product was cooled, it was extracted with ethyl acetate, washed with saturated brine, and separated to obtain a third organic layer. The third organic layer was dried over anhydrous magnesium sulfate, rotary evaporated, and then separated by silica gel column chromatography to obtain the A-D-A'-type dual-channel fluorescent material (Compound D), namely {4-[3,6-di-tert-butyl-1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazol-9-yl]phenyl}(phenyl)methanone.

[0039] Further, in a preferred embodiment of the present invention, the mass-to-volume ratios of {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone, 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine B, Pd2(dba)3, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tetrabutylammonium iodide, and toluene are 15-17:4-5:1.2-1.5:1.7-2:4.8-5.2:1 (mg / mL).

[0040] Further, in a preferred embodiment of the present invention, the temperature of the reaction is 95-105 °C, and the reaction time is 22-26 h. Preferably, the reaction temperature is 100 °C, and the reaction time is 24 h.

[0041] The present invention also provides the application of the A-D-A'-type dual-channel fluorescent material in the detection of triethylamine as an identification response to triethylamine.

[0042] The features and properties of the present invention will be further described in detail below in conjunction with examples.

[0043] Example 1

[0044] This example provides an A-D-A'-type dual-channel fluorescent material, which is prepared according to the following steps:

[0045] (1) Preparation of 1-bromo-3,6-di-tert-butyl-9H-carbazole: Add 3,6-di-tert-butylcarbazole (3.00 g, 10.8 mmol), silica gel powder (4.00 g), and 375 mL of DCM into a single-neck flask. Stir vigorously. Prepare a solution by dissolving NBS (2.03 g, 11.4 mmol) in 375 mL of DCM and slowly add it dropwise to the single-neck flask. React at room temperature in the dark for 4 hours, and then filter to remove the silica gel powder. Extract the product with EA, wash it with saturated brine, repeat three times, separate the organic layer, dry it over anhydrous magnesium sulfate, rotary evaporate to collect the organic layer, and after concentration, separate it by silica gel column chromatography to obtain 3.20 g of a pale yellow viscous oil, namely 1-bromo-3,6-di-tert-butyl-9H-carbazole, with a yield of 82.40%.

[0046] (2) Preparation of {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone: Add compound B (181 mg, 0.51 mmol), NaH (81 mg, 3.4 mol), and 3 mL of DMF into a two-neck flask. React at room temperature for 1 hour, and then add 4-fluorobenzophenone (111 mg, 0.56 mol) dissolved in 3 mL of DMF. Heat to 100 °C and react in a nitrogen atmosphere for 2 hours. Cool to room temperature, add water to terminate the reaction, extract the product with EA, wash it with saturated brine, repeat three times, dry the organic layer over anhydrous magnesium sulfate, and after concentration and separation, separate it by silica gel column chromatography to obtain 95 mg of a yellow solid product, namely {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone, with a yield of 31.7%.

[0047] (3) Preparation of {4-[3,6-Di-tert-butyl-1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazol-9-yl]phenyl}(phenyl)methanone: In a two-necked flask, compound C (95.5 mg, 0.17 mmol), 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine B (26.5 mg, 0.1787 mmol), Pd2(dba)3 (8.2 mg, 0.0085 mmol), 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl (11.2 mg, 0.027 mmol), TBAI (30 mg), TOL (6 mL), and K2CO3 (2 mol / ml) were added successively. After purging with nitrogen to remove oxygen, the reaction was carried out in a nitrogen atmosphere at 100 °C for 24 hours. After cooling, the product was extracted with EA and washed with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated by rotary evaporation. The organic layer was collected and separated by silica gel column chromatography to obtain 25.20 mg of a yellow solid product, which is an A-D-A’ type dual-channel fluorescent material with a yield of 19%. δH (400 MHz, Chloroform-d) 7.84–7.68 (12H, m), 7.57–7.37 (10H, m), 6.73–6.60 (6H, m), 3.07 (18H, d, J 1.9). δC (101 MHz, Chloroform-d) 195.61, 153.74, 139.75, 133.18, 132.86, 131.56, 130.30, 129.88, 128.79, 128.45, 125.18, 125.12, 110.98, 40.47, 30.14.

[0048] Test Example 1

[0049] This test example studied the effects of different solvents (TOL, DCM, THF, EA, AC, DMF) on the ultraviolet-visible absorption spectra of the A-D-A’ type dual-channel fluorescent material in Example 1.

[0050] As Figure 2 shown are the ultraviolet-visible absorption spectra of the A-D-A’ type dual-channel fluorescent material in Example 1 in different solvents. As Figure 2 can be seen, the A-D-A’ type dual-channel fluorescent material shows similar absorption behavior, with an obvious absorption peak near 340 nm, corresponding to the charge transfer from the electron donor unit to the electron acceptor unit in the compound. From toluene to DMF, as the polarity of the solvent increases, the absorption peak shifts from 340 nm to 349 nm.

[0051] Test Example 2

[0052] In this test example, the fluorescence emission spectra of the A-D-A'-type dual-channel fluorescent material of Example 1 were studied with an excitation wavelength of 300 nm in different solvents.

[0053] As Figure 3 shown are the fluorescence emission spectra of the A-D-A'-type dual-channel fluorescent material of Example 1 in different solvents. From Figure 3 it can be seen that the A-D-A'-type dual-channel fluorescent material shows two types of single emission and dual emission in different solvents. In dichloromethane and acetone solutions, only single-peak emissions were observed, and the corresponding emission peak positions were 386 nm and 400 nm, respectively. While in toluene, ethyl acetate, tetrahydrofuran, and N,N-dimethylformamide, there are dual emission peaks, where the short-wave emission peak is in the short-wave range of 350 - 450 nm, and the long-wave emission peak is in the range of 450 - 600 nm. In the short-wave and long-wave regions, the emission peaks of the compound gradually redshift with the increase of solvent polarity, showing a typical charge transfer effect (CT). Combining with the structure of the compound, it should be respectively due to the charge transfer from the carbazole unit in the compound to the benzophenone and triphenyltriazine units. Since benzophenone and triphenyltriazine have relatively large unit volumes, when they are respectively connected to the N atom and the 1st position of the carbazole unit, due to the volume effect, they will respectively form a relatively large twisted structure with the carbazole unit.

[0054] Test Example 3

[0055] This test example studied the fluorescence emission spectrum of the solid of the A-D-A'-type dual-channel fluorescent material of Example 1.

[0056] As Figure 4 shown is the fluorescence emission spectrum of the solid of the A-D-A'-type dual-channel fluorescent material of Example 1. From Figure 4 it can be seen that the A-D-A'-type dual-channel fluorescent material shows sky-blue fluorescence single-peak emission when in solid state, and its emission peak is at 456 nm.

[0057] Test Example 4

[0058] This test example studied the influence of different excitation wavelengths on the fluorescence emission spectra of the A-D-A'-type dual-channel fluorescent material of Example 1 in THF solution.

[0059] As Figure 5 shown are the fluorescence emission spectra of the A-D-A'-type dual-channel fluorescent material of Example 1 at different excitation wavelengths. From Figure 5It can be seen that the emission spectra of the A-D-A'-type dual-channel fluorescent materials exhibit excitation spectrum dependence. In the test range of 250 nm to 360 nm, the compounds all show dual-emission behavior in THF solution. However, as the excitation wavelength increases, the relative intensity of the emission peak near 380 nm gradually decreases, while the relative emission peak intensity near 500 nm gradually increases. Different from traditional organic fluorescent materials whose emission peaks are not affected by the excitation wavelength, this compound exhibits specific excitation spectrum dependence behavior. This is mainly because the dual-emission peaks of the compound in THF solution originate from different CT effects, and each peak corresponds to a different optimal excitation wavelength. The optimal excitation wavelength corresponding to the short-wave emission is mainly concentrated below 300 nm, while the optimal excitation wavelength corresponding to the long-wave emission exceeds 300 nm. Therefore, as the excitation wavelength redshifts, the corresponding emission peaks of the compound in THF solution generally show a trend of decreasing short-wave and increasing long-wave.

[0060] Experimental Example 5

[0061] This experimental example studies the influence of different triethylamine contents on the fluorescence emission spectra of the THF solution (10 -5 mol / L) of the A-D-A'-type dual-channel fluorescent material in Example 1.

[0062] As Figure 6 shown is the fluorescence emission spectrum diagram of the THF solution of the A-D-A'-type dual-channel fluorescent material under different triethylamine contents. As Figure 6 can be seen, the solution of the A-D-A'-type dual-channel fluorescent material can recognize and respond to triethylamine. When 10 eq of triethylamine is added to its solution, its fluorescence emission intensity rapidly decreases by nearly 30%, showing an obvious change. Therefore, this compound can be applied as a recognition response for triethylamine.

[0063] The embodiments described above are some, but not all, of the embodiments of the present invention. The detailed description of the embodiments of the present invention is not intended to limit the scope of the claimed invention, but merely represents selected embodiments of the present invention. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts fall within the scope of protection of the present invention.

Claims

1. A dual-channel fluorescent material of the A-D-A' type, characterized in that, The A-D-A'-type dual-channel fluorescent material is {4-[3,6-di-tert-butyl-1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazol-9-yl]phenyl}(phenyl)methanone, and its structural formula is: 。 2. A method for preparing the A-D-A'-type dual-channel fluorescent material according to claim 1, characterized in that, It includes the following steps: S1. Preparation of 1-bromo-3,6-di-tert-butyl-9H-carbazole: Mix 3,6-di-tert-butylcarbazole, silica gel powder and dichloromethane and stir vigorously, then dropwise add a mixed solution of N-bromosuccinimide / dichloromethane and react in the dark for 3.5 - 4.5 h. After filtration, extract and wash with ethyl acetate to obtain a first organic layer. The first organic layer is dried, rotary evaporated, concentrated and separated to obtain the 1-bromo-3,6-di-tert-butyl-9H-carbazole; S2. Preparation of {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone: After reacting the 1-bromo-3,6-di-tert-butyl-9H-carbazole, sodium hydride and N-methylformamide for 0.8 - 1.2 h, add a mixed solution of 4-fluorobenzophenone / N,N-dimethylformamide and react. After cooling to room temperature and adding water to terminate the reaction, extract and wash with ethyl acetate to obtain a second organic layer. The second organic layer is dried, concentrated and separated to obtain the {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone; S3. Add 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine B, Pd2(dba)3, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tetrabutylammonium iodide, toluene and K2CO3 to the {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone in sequence, react in a nitrogen atmosphere, and after cooling, extract and wash with ethyl acetate to obtain a third organic layer. The third organic layer is dried, rotary evaporated and separated to obtain the A-D-A'-type dual-channel fluorescent material.

3. The preparation method according to claim 2, wherein In step S1, the mass-volume ratio of the 3,6-di-tert-butylcarbazole, the silica gel powder and the dichloromethane is 1:1 - 1.5:122 - 128 (g / mL).

4. The preparation method according to claim 2, wherein In step S1, in the mixed solution of N-bromosuccinimide / dichloromethane, the mass-volume ratio of N-bromosuccinimide and dichloromethane is 1:183 - 185 (g / mL), and the mass ratio of N-bromosuccinimide and the 3,6-di-tert-butylcarbazole is 1:1.45 - 1.

49.

5. The preparation method according to claim 2, characterized in that, In step S2, the mass-volume ratio of the 1-bromo-3,6-di-tert-butyl-9H-carbazole, the sodium hydride and the N-methylformamide is 59 - 61:26 - 28:1 (mg / mL).

6. The preparation method according to claim 2, wherein In step S2, in the mixed solution of 4-fluorobenzophenone / N,N-dimethylformamide, the mass-volume ratio of 4-fluorobenzophenone and N,N-dimethylformamide is 36 - 38:1 (mg / mL), and the mass ratio of 4-fluorobenzophenone and the 1-bromo-3,6-di-tert-butyl-9H-carbazole is 1:1.62 - 1.

64.

7. The preparation method according to claim 2, characterized in that, In step S2, the temperature of the reaction is 95 to 105 °C, and the reaction time is 1.8 to 2.2 h.

8. The preparation method according to claim 2, characterized in that, In step S3, the mass-to-volume ratio of {4-[1-bromo-3,6-di-tert-butylcarbazol-9-yl]phenyl}phenylmethanone, 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine B, Pd2(dba)3, 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl, tetrabutylammonium iodide, and toluene is 15 to 17:4 to 5:1.2 to 1.5:1.7 to 2:4.8 to 5.2:1 (mg / mL).

9. The preparation method according to claim 2, characterized in that, In step S3, the temperature of the reaction is 95 to 105 °C, and the reaction time is 22 to 26 h.

10. Use of the A-D-A'-type dual-channel fluorescent material according to claim 1 in the preparation of a reagent for detecting triethylamine.

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