Aggregation-induced emission material and application thereof in light penetrator patch

By developing the aggregation-induced luminescent materials TBPPMF and TBPPM, combined with the light penetrator patch technology, the problem of insufficient visible light penetration in photodynamic therapy is solved, deep photodynamic therapy and antibacterial effects are achieved, and a non-invasive effect is provided. , safe treatment plan.

CN119143784AInactive Publication Date: 2024-12-17THE CHINESE UNIV OF HONG KONG (SHENZHEN)
View PDF 6 Cites 0 Cited by

Patent Information

Application Number
CN202411284998.2
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-09-13
Publication Date
2024-12-17
Estimated Expiration
Not applicable · inactive patent

AI Technical Summary

Technical Problem

The existing photodynamic therapy (PDT) limits the effectiveness of deep tissue treatment due to insufficient visible light penetration and low near-infrared photosensitizer efficiency. The fiber implantation technology has the risk of infection, making it difficult to achieve non-invasive treatment.

Method used

Develop an aggregation-induced luminescent material, including compounds TBPPMF and TBPPM, synthesized by Suzukii coupling reaction, and mixed with hyaluronic acid methacryloyl and photoinitiator, to prepare a photopenetrator patch to enhance the tissue penetration depth of visible light and the efficacy of activated photosensitizers.

Benefits of technology

It improves the tissue penetration depth of visible light and realizes deep photodynamic therapy. The patch form is convenient for wound treatment, has antibacterial activity, and is suitable for wearable treatment equipment.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN119143784A_ABST
    Figure CN119143784A_ABST
Patent Text Reader

Abstract

The invention discloses an aggregation-induced emission material and application thereof in a light penetrator patch, and belongs to the technical field of luminescent materials, and the aggregation-induced emission material comprises TBPPMF and / or TBPPM. The invention further provides an aggregation-induced emission light penetrator patch, the aggregation-induced emission light penetrator patch comprises the aggregation-induced emission material, and a preparation method of the aggregation-induced emission light penetrator patch comprises the following steps: uniformly mixing the aggregation-induced emission material, hyaluronic acid methacryloyl and a photoinitiator, pouring the mixture into a mold for drying, and performing ultraviolet irradiation to obtain the aggregation-induced emission light penetrator patch. And continuously pouring a mixed solution containing hyaluronic acid methacryloyl and a photoinitiator into the mold, drying again, and demolding to obtain the aggregation-induced emission light penetrator patch. The light penetrator patch obtained by the invention has huge potential in photodynamic therapy as an antibacterial medical dressing, and has a remarkable inhibitory activity effect on methicillin-resistant staphylococcus aureus.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] The present invention belongs to the technical field of luminescent materials, and in particular relates to an aggregation-induced luminescent material and an application thereof in a light penetrator patch. Background Art

[0002] Photodynamic therapy (PDT) has attracted widespread attention as an effective treatment modality due to its non-surgical treatment that can selectively eradicate diseased tissue while minimizing damage to normal tissue. However, limited visible light penetration restricts PDT to surface treatments. Although near-infrared (NIR) lasers offer enhanced tissue penetration, synthesis challenges and weak photodynamic efficiency have limited the development of NIR photosensitizers, most of which are mainly used for bioimaging purposes. In addition, fiber optic implantation technology has also been applied in clinical deep PDT. However, this method, which requires minimally invasive surgery, carries the risk of infection and contradicts the non-invasive nature of PDT.

[0003] Therefore, how to improve the penetration depth of visible light and optimize the efficacy of visible light-activated photosensitizers is a technical problem that technicians in this field urgently need to solve. Summary of the invention

[0004] In order to solve the above technical problems, the present invention proposes an aggregation-induced luminescence material and its application in a light penetrator patch.

[0005] To achieve the above object, the present invention provides the following technical solutions:

[0006] An aggregation-induced emission material, comprising the following compounds:

[0007] and / or Wherein, the R1 is selected from One or any of the following;

[0008] The R2 is selected from One or any several of, wherein n=0-20;

[0009] The R3 is selected from and / or R4 is selected from F, Cl, Br, I and One or any of the following;

[0010] The X is selected from one or any combination of Cl, Br, I, PF6, OTf and CF3SO2O.

[0011] Beneficial effects:

[0012] Preferably, the synthetic route of the TBPPMF is as follows:

[0013]

[0014]

[0015] The preparation method comprises the following steps:

[0016] Compound a is reacted with a boronic acid containing an R1 substituent through Suzukii coupling reaction to obtain compound b, and then compound b is reacted with Compound c is obtained through Suzukii coupling reaction, and then compound c is reacted with a halogenated R2 compound in the presence of an ammonium salt through Suzukii coupling reaction to obtain compound TBPPMF.

[0017] More preferably, the method specifically comprises the following steps:

[0018] (1) Compound a, boric acid containing an R1 substituent, potassium carbonate and tetratriphenylphosphine palladium are added to a double-necked round-bottom flask, and distilled toluene and water are added, and then heated to reflux for 6 hours under a nitrogen environment, cooled to room temperature, poured into water, and extracted three times with dichloromethane. The organic phase obtained after extraction is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound b;

[0019] (2) Compound b, tetrakistriphenylphosphine palladium, CuI, EtN3 and Add to a double-necked round-bottom flask, then add THF, then heat under reflux for 6 hours under nitrogen, cool to room temperature, pour into water, and extract three times with dichloromethane. The organic phase obtained after extraction is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound c;

[0020] (3) Compound c was dissolved in acetone, and then the halogenated R2 compound was added, and the mixture was heated under reflux for 48 h under nitrogen. After the reaction was completed, the solvent was removed, and the obtained solid was dispersed in acetonitrile by stirring, and a saturated NH4X solution was added dropwise during the stirring and dispersion. After reflux for 8 h, the precipitate was separated by vacuum filtration, and washed with deionized water at least 3 times, and the precipitate was collected and dried under high vacuum to obtain a reddish brown solid, i.e., the aggregation-induced emission material TBPPMF.

[0021] Preferably, the synthesis route of the TBPPM is as follows:

[0022]

[0023] The preparation method comprises the following steps:

[0024] Compound a is reacted with a boronic acid containing an R1 substituent through Suzukii coupling reaction to obtain compound b, and then compound b is reacted with Compound c is obtained by Suzukii coupling reaction, and then compound c is reacted with a nitrile reagent containing an R3 substituent to obtain compound d, and then compound d is reacted with a halogenated R2 compound in the presence of an ammonium salt by Suzukii coupling reaction to obtain compound TBPPM.

[0025] More preferably, the method specifically comprises the following steps:

[0026] (1) Compound a, boric acid containing an R1 substituent, potassium carbonate and tetratriphenylphosphine palladium (catalyst) are added to a double-necked round-bottom flask, and distilled toluene and water are added, and then heated to reflux for 6 hours under a nitrogen environment, cooled to room temperature, poured into water, and extracted three times with dichloromethane. The organic phase obtained after extraction is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated, and purified by silica gel column chromatography to obtain compound b;

[0027] (2) Compound b, tetrakistriphenylphosphine palladium, CuI, EtN3 and Add to a double-necked round-bottom flask, then add THF, then heat under reflux for 6 hours under nitrogen, cool to room temperature, pour into water, and extract three times with dichloromethane. The organic phase obtained after extraction is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound c;

[0028] (3) Sodium hydride is dissolved in dry N,N-dimethylformamide, and a raw material containing an R3 substituent is added at 0°C to react for 30 minutes, and then carbon disulfide is added to react at room temperature for 2 hours to obtain a mixture. Compound c obtained in step (2) is dissolved in dry N,N-dimethylformamide, added to the mixture, and stirred at 80°C overnight, and then cooled to room temperature and poured into water, extracted three times with dichloromethane, and the organic phase obtained by extraction is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound d;

[0029] (4) Compound d was dissolved in acetone, and then the halogenated R2 compound was added, and the mixture was heated under reflux for 48 h under nitrogen. After the reaction was completed, the solvent was removed, and the obtained solid was dispersed in acetonitrile by stirring, and a saturated NH4X solution was added dropwise during the stirring and dispersion. After refluxing for 8 h, the precipitate was separated by vacuum filtration, and washed with deionized water at least 3 times, and the precipitate was collected and dried under high vacuum to obtain a reddish brown solid, i.e., the aggregation-induced emission material TBPPM.

[0030] Application of an aggregation-induced emission material in a light penetrator patch.

[0031] A aggregation-induced luminescence light penetrator patch comprises the above-mentioned aggregation-induced luminescence material.

[0032] A method for preparing an aggregation-induced emission light penetrator patch comprises the following steps:

[0033] The aggregation-induced luminescence material, hyaluronic acid methacryloyl and photoinitiator are mixed evenly and poured into a mold for drying. After irradiation with ultraviolet light, a mixed solution including hyaluronic acid methacryloyl and photoinitiator is continuously poured into the mold, and the mold is demolded after drying again to obtain the aggregation-induced luminescence light penetrator patch.

[0034] Preferably, the mixed solution also includes the aggregation-induced emission material.

[0035] Preferably, the photoinitiator is phenyl (2,4,6-trimethylbenzoyl) phosphate lithium salt.

[0036] Preferably, the ultraviolet light irradiation is irradiation with ultraviolet light of wavelength 405nm for 5 minutes.

[0037] Application of an aggregation-induced luminescence light penetrator patch in the preparation of medical dressings.

[0038] Compared with the prior art, the present invention has the following advantages and technical effects:

[0039] The light penetrator patch based on aggregation-induced luminescence material provided by the present invention can increase or decrease the tissue penetration depth of visible light, and can realize deep photodynamic therapy by loading aggregation-induced luminescence photosensitizer. Its patch form is easy to use as a medical dressing and is convenient for wound treatment. It is a matrix with great potential for wound dressing development. When it is applied, the mobile mini light source can quickly activate the aggregation-induced luminescence material loaded in the light penetrator and kill methicillin-resistant Staphylococcus aureus, and it has great potential as a wearable therapeutic device. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] The drawings constituting a part of the present application are used to provide a further understanding of the present application. The illustrative embodiments and descriptions of the present application are used to explain the present application and do not constitute an improper limitation on the present application. In the drawings:

[0041] Figure 1 This is the manufacturing process of the aggregation-induced luminescence light penetrator patch in Example 2 of the present invention;

[0042] Figure 2 This is a light transmittance test diagram of the aggregation-induced luminescence light penetrator patch obtained in Example 2 of the present invention;

[0043] Figure 3This is a diagram showing the antibacterial effect of the aggregation-induced luminescence light penetrator patch obtained in Example 2 of the present invention under different conditions;

[0044] Figure 4 The treatment (left) and effect diagram (right) of the aggregation-induced luminescence light penetrator patch obtained in Example 2 of the present invention;

[0045] Among them, I: infection group treated with irradiation of the aggregation-induced luminescence light penetrator patch; II: infection group treated with vancomycin; III: infection group treated with the aggregation-induced luminescence light penetrator patch without irradiation; IV: infection group treated with a blank patch; V: untreated infection group;

[0046] Figure 5 This is the antibacterial activity of the aggregation-induced luminescence light penetrator patch obtained in Example 4. DETAILED DESCRIPTION

[0047] The following will be combined with the drawings in the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0048] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the present invention is further described in detail below with reference to the accompanying drawings and specific embodiments.

[0049] Unless otherwise specified, the raw materials in the examples of the present invention were purchased from commercial sources (Zhengzhou Alpha Company);

[0050] Wherein, the structural formula of compound a is:

[0051] The structural formula of compound b is:

[0052] The structural formula of compound 1 is:

[0053] Compound 2 is CH3I;

[0054] The structural formula of compound 3 is:

[0055] The structural formula of compound 4 is:

[0056]

[0057] The structural formula of the compound TBPPMF is:

[0058]

[0059] The structural formula of the compound TBPPM is:

[0060] Unless otherwise specified, the room temperature or normal temperature in the embodiments of the present invention refers to 25±3°C.

[0061] Example 1

[0062] A method for preparing an aggregation-induced emission material TBPPM comprises the following steps:

[0063] (1) Compound a (5 mmol), compound 1 (boric acid containing R1 substituent) (5 mmol), potassium carbonate (20 mmol) and tetrakistriphenylphosphine palladium (0.1 mmol) were added to a 500 mL double-necked round-bottom flask, and then 100 mL of distilled toluene and 30 mL of water were added, and then heated to reflux for 6 h under a nitrogen environment, cooled to room temperature, poured into water, and extracted three times with dichloromethane. The organic phase obtained after extraction was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound b;

[0064] (2) Compound b (2 mmol), tetrakistriphenylphosphine palladium (0.04 mmol), CuI (0.1 mmol), EtN3 (0.1 mmol) and compound 4 (2 mmol) were added to a 500 mL double-necked round-bottom flask, and THF was added. The mixture was heated to reflux for 6 h under a nitrogen atmosphere, cooled to room temperature, poured into water, and extracted three times with dichloromethane. The organic phase obtained after extraction was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, evaporated the solvent, and purified by silica gel column chromatography to obtain compound c;

[0065] (3) Sodium hydride (4 mmol) was dissolved in dry N,N-dimethylformamide, and compound 3 (raw material containing R3 substituent) (2 mmol) was added at 0°C for reaction for 30 min, and then carbon disulfide (8 mmol) was added and reacted at room temperature for 2 h to obtain a mixture. Compound c (0.4 mmol) obtained in step (1) was dissolved in dry N,N-dimethylformamide, added to the mixture, and stirred at 80°C overnight, then cooled to room temperature and poured into water, extracted three times with dichloromethane, and the organic phase obtained by extraction was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound d;

[0066] (4) Compound d (200 mg, 0.24 mmol) was dissolved in 30 mL of acetone, and then compound 2 (halogenated R2 compound) (142 mg, 1 mmol) was added, and the mixture was heated under reflux for 48 h under nitrogen. After the reaction was completed, the solvent was removed, and the obtained solid was dispersed in acetonitrile by stirring, and 50 mL of saturated NH4PF6 solution was added dropwise during the stirring and dispersion. After refluxing for 8 h, the precipitate was separated by vacuum filtration, and washed with deionized water at least 3 times, and the precipitate was collected and dried under high vacuum to obtain a reddish brown solid, i.e., the aggregation-induced emission material TBPPM.

[0067] The following are the name, yield, physical state and NMR data of the aggregation-induced emission material obtained in Example 1:

[0068] TBPPM: yield 60%, solid powder. 1 H NMR (500MHz, DMSO-d6): δ9.43 (s, 2H), 9.08 (d, 2H, J = 6Hz), 8.65 (d, 2H, J = 8.5Hz), 8.16 (t, 2H, J = 6.5Hz), 7.94-7. 92(m,3H),7.89-7.88(m,2H),7.55(d,2H,J=8.5Hz),7.32(m,2H),7.16(d,4H,J=8Hz),7.10(m,4H),4.45(s,6H). 13 CNMR (125MHz, CDCI3+DMSO-d6): δ177.0,153.4,152.5,149.7,148.1,146.9,146.5,145.5,142.1,136.0,135.9,135.3,13 0.4,129.8,128.3,126.5,125.9,124.7,123.3,123.1,122.7,120.4,112.4,112.2,107.7,100.2,94.3,85.1,84.3,48.8.

[0069] Example 2

[0070] A method for preparing an aggregation-induced emission light penetrator patch, such as Figure 1 As shown, the following steps are included:

[0071] A mixture containing TBPPM (2 μM) obtained in Example 1, hyaluronic acid methacryloyl (HAMA, 10%, w / v) and phenyl (2,4,6-trimethylbenzoyl) lithium phosphate LAP (photoinitiator, 0.25 wt% of the total weight) was ultrasonically treated to form a uniform mixed solution, and cast into a mold until the cavity was filled, and then centrifuged at room temperature and degassed in a vacuum oven for 3 times, each time drying for 3 hours, so that the dried mixture was concentrated at the needle tip of the mold, and then the mold containing the dried mixture was placed under ultraviolet light with a wavelength of 405 nm for 5 minutes, and finally the above-mentioned uniform mixed solution was repeatedly added to the mold after ultraviolet light irradiation, and then placed in a 40°C oven for 12 hours. After drying, the molded material was carefully separated from the mold to obtain an aggregation-induced luminescence light penetrator patch (TBPPM-VLP).

[0072] Example 3

[0073] A method for preparing an aggregation-induced emission material TBPPMF comprises the following steps:

[0074] (1) Compound a (5 mmol), compound 1 (boric acid with different substituents R1) (5 mmol), potassium carbonate (20 mmol) and tetrakistriphenylphosphine palladium (0.1 mmol) were added to a 500 mL double-necked round-bottom flask, and then 100 mL of distilled toluene and 30 mL of water were added, and then heated to reflux for 6 h under a nitrogen environment, cooled to room temperature, poured into water, and extracted three times with dichloromethane. The organic phase obtained after extraction was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated, and purified by silica gel column chromatography to obtain compound b;

[0075] (2) Compound b (2 mol), tetrakistriphenylphosphine palladium (0.04 mmol), CuI (0.1 mmol), EtN3 (0.1 mmol) and compound 4 (2 mmol) were added to a 500 mL double-necked round-bottom flask, and THF was added. The mixture was heated to reflux for 6 h under a nitrogen atmosphere, cooled to room temperature, poured into water, and extracted three times with dichloromethane. The organic phase obtained after extraction was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, evaporated the solvent, and purified by silica gel column chromatography to obtain compound c;

[0076] (3) Compound c (143 mg, 0.2 mmol) was dissolved in 30 mL of acetone, and then compound 2 (halogenated R2 compound) (56 mg, 0.4 mmol) was added, and the mixture was heated under reflux for 48 h under nitrogen. After the reaction was completed, the solvent was removed, and the obtained solid was dispersed in acetonitrile by stirring, and 50 mL of saturated NH4PF6 solution was dropped into the mixture during the stirring and dispersion. After reflux for 8 h, the precipitate was separated by vacuum filtration, and washed with deionized water at least 3 times. After the precipitate was collected, it was dried under high vacuum to obtain a reddish brown solid, i.e., the aggregation-induced emission material TBPPMF.

[0077] The following are the name, yield, physical state and NMR data of the aggregation-induced luminescence material obtained in Example 3:

[0078] TBPPMF: 1 H NMR (500MHz, DMSO-d6): δ9.53 (s, 2H), 9.07 (d, 2H, J = 6.3

[0079] Hz),8.55(d,2H,J=8.3Hz),8.14(t,2H,J=6.2Hz),7.94-7.90(m,3H),7.55(d ,2H,J=8.3Hz),7.30(m,2H),7.14(d,4H,J=7.8Hz),7.08(m,4H),4.43(s,6H).

[0080] Example 4

[0081] A method for preparing an aggregation-induced luminescence light penetrator patch is different from Example 2 only in that the TBPPM obtained in Example 1 is replaced with an equal amount of TBPPMF obtained in Example 3. The other process steps and parameters are the same as those in Example 2.

[0082] Example 5

[0083] A method for preparing an aggregation-induced luminescence light penetrator patch is different from Example 2 in that the TBPPM obtained in Example 1 is replaced with a mixed luminescent material obtained by mixing an equal amount of TBPPM obtained in Example 1 and TBPPMF obtained in Example 3 in a mass ratio of 1:1. Other process steps and parameters are the same as those in Example 2.

[0084] Technical effect:

[0085] Antibacterial activity test of the aggregation-induced luminescence light penetrator patch obtained in Example 2:

[0086] 1. Test bacteria: methicillin-resistant Staphylococcus aureus (MRSA).

[0087] 2. Sample preparation: Accurately weigh a certain amount of the test compound into a centrifuge tube, add 1 mL of sterile water to make a 2 μmol / L solution. Use 0.9% NaCl as a blank control.

[0088] 3. Preparation of solid culture medium: 7.5 g tryptone, 2.5 g soy peptone, 2.5 g NaCl, 7.5 g agar powder, add 500 ml deionized water, and adjust the pH to 5.5.

[0089] 4. Determination of antibacterial activity: The antibacterial activity was determined by plate colony counting method. 10 μg / ml was added to the AIL penetrator patch, the blank patch without AIL material, and vancomycin. 9 CPU / mL of bacterial solution was mixed and irradiated under white light (5mW / cm 2 ) for 1 minute and placed in a 37°C constant temperature and humidity incubator for culture. In addition, as a control experiment, the above experimental group operation was repeated, and the material was mixed with the bacterial solution, and then placed in a 37°C constant temperature and humidity incubator for culture without white light irradiation. Each of the above treatments was repeated three times. After culturing for 16 hours, the number of colonies was counted, and the antibacterial rate of each test compound was calculated according to the following formula.

[0090]

[0091] C is the colony count of the test group; C0 is the colony count of the blank control group.

[0092] The test results can be found in Figure 2 to Figure 4 , that is, the inhibitory activity of the aggregation-induced luminescence light penetrator patch on methicillin-resistant Staphylococcus aureus (3 μM). The results show that under light stimulation, at a concentration of 3 μM, the aggregation-induced luminescence light penetrator patch exhibited a certain inhibitory activity on methicillin-resistant Staphylococcus aureus. It can be seen that the aggregation-induced luminescence light penetrator patch involved in the present invention has a strong antibacterial activity against methicillin-resistant Staphylococcus aureus and has a potential use for preparing medical dressings for photodynamic therapy.

[0093] Specifically, by Figure 2 It can be seen that the AIL light penetrator patch has good light penetration, can penetrate 3mm of skin tissue, and the transmittance is as high as 86%. Figure 3 It can be seen that after 2 minutes of low-power white light illumination, the patch showed a significant inhibitory effect on methicillin-resistant Staphylococcus aureus, with an inhibition rate of more than 97%. The developed aggregation-induced luminescence light penetrator patch was used to treat mouse infection. Figure 4 The patch treatment was shown to be effective.

[0094] Antibacterial activity test of the aggregation-induced luminescence light penetrator patch obtained in Example 4:

[0095] The test results can be found in Figure 5 , that is, the inhibitory activity of the aggregation-induced luminescence light penetrator patch on methicillin-resistant Staphylococcus aureus (2 μM). The results show that under light stimulation, at a concentration of 2 μM, the aggregation-induced luminescence light penetrator patch exhibited a certain inhibitory activity on methicillin-resistant Staphylococcus aureus. It can be seen that the aggregation-induced luminescence light penetrator patch involved in the present invention has a strong antibacterial activity against methicillin-resistant Staphylococcus aureus and has a potential use for preparing medical dressings for photodynamic therapy.

[0096] The above are only preferred specific implementations of the present application, but the protection scope of the present application is not limited thereto. Any changes or substitutions that can be easily thought of by a person skilled in the art within the technical scope disclosed in the present application should be included in the protection scope of the present application. Therefore, the protection scope of the present application should be based on the protection scope of the claims.

Claims

1. An aggregation-induced emission material, characterized in that: Includes the following compounds: and / or Wherein, the R1 is selected from One or any of the following; The R2 is selected from One or any several of, wherein n=0-20; The R3 is selected from and / or R4 is selected from F, Cl, Br, I and One or any of the following; The X is selected from one or any combination of Cl, Br, I, PF6, OTf and CF3SO2O.

2. The aggregation-induced emission material according to claim 1, characterized in that: The synthesis method of the TBPPMF comprises the following steps: Compound a is reacted with a boronic acid containing an R1 substituent through Suzukii coupling reaction to obtain compound b, and then compound b is reacted with A compound c is obtained by a Suzukii coupling reaction, and then the compound c is reacted with a halogenated R2 compound in the presence of an ammonium salt by a Suzukii coupling reaction to obtain a compound TBPPMF; The structural formula of compound a is: The structural formula of the boronic acid containing the R1 substituent is The structural formula of compound b is The structural formula of compound c is 3. The aggregation-induced emission material according to claim 1, characterized in that: The preparation method of the TBPPM comprises the following steps: Compound a is reacted with a boronic acid containing an R1 substituent through Suzukii coupling reaction to obtain compound b, and then compound b is reacted with Compound c is obtained by Suzukii coupling reaction, and then compound c is reacted with a nitrile reagent containing an R3 substituent to obtain compound d, and then compound d is reacted with a halogenated R2 compound in the presence of an ammonium salt by Suzukii coupling reaction to obtain compound TBPPM; Wherein, the structural formula of compound a is: The structural formula of the boronic acid containing the R1 substituent is The structural formula of compound b is The structural formula of compound c is The structural formula of compound d is 4. Use of an aggregation-induced emission material as described in any one of claims 1 to 3 in a light penetrator patch.

5. An aggregation-induced emission light penetrator patch, characterized in that: The invention comprises the aggregation-induced emission material according to any one of claims 1 to 3.

6. The method for preparing an aggregation-induced emission light penetrator patch according to claim 5, characterized in that: The following steps are involved: The aggregation-induced luminescence material, hyaluronic acid methacryloyl and photoinitiator are mixed evenly and poured into a mold for drying. After irradiation with ultraviolet light, a mixed solution including hyaluronic acid methacryloyl and photoinitiator is continuously poured into the mold, and the mold is demolded after drying again to obtain the aggregation-induced luminescence light penetrator patch.

7. The method for preparing an aggregation-induced emission light penetrator patch according to claim 6, characterized in that: The mixed solution also includes the aggregation-induced emission material.

8. The method for preparing an aggregation-induced emission light penetrator patch according to claim 6, characterized in that: The photoinitiator is phenyl (2,4,6-trimethylbenzoyl) lithium phosphate.

9. The method for preparing an aggregation-induced emission light penetrator patch according to claim 6, characterized in that: The ultraviolet light irradiation is 5 minutes under ultraviolet light irradiation with a wavelength of 405nm.

10. Use of the aggregation-induced luminescence light penetrator patch as claimed in claim 5 in the preparation of medical dressings.

Citation Information

Patent Citations

  • AIE photosensitizer with different positive charges as well as preparation method and antibacterial application thereof

    CN112521381A

  • Fluorescent compound and application thereof

    CN113861224A

  • Photosensitive active aggregation-induced emission compound as well as preparation method and application thereof

    CN117143116A