Cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent and preparation method thereof

Abstract

The invention discloses a cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent and a preparation method thereof. The compound has excellent photothermal conversion performance and photodynamic antibacterial performance. The structural formula of the antibacterial finishing agent is shown as follows: a preparation method of a # imgabs0 # antibacterial agent comprises the following steps: introducing 3, 3 ', 4, 4'-benzophenone tetracarboxylic dianhydride and quaternary ammonium salt groups on phthalocyanine to synthesize a cationic phthalocyanine-benzophenone compound; the compound shows excellent photothermal conversion performance under the irradiation of red light, ultraviolet light and visible light. Staphylococcus aureus and Escherichia coli are used as model strains, and antibacterial test results show that the prepared cationic phthalocyanine compound can have an efficient sterilization effect on staphylococcus aureus and Escherichia coli under different light sources. In addition, the compound provided by the invention has good water solubility and multiband light absorption capability, and is suitable for various antibacterial application scenes.

Description

Technical Field

[0001] The invention belongs to the field of synthesis and application of organic compound antibacterial agents, and specifically relates to a cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent and a preparation method thereof. Background Art

[0002] In daily life, people will inevitably come into contact with various microorganisms, which are harmful to human health. Therefore, in recent years, the research on antibacterial agents and antibacterial materials has received widespread attention. Compared with traditional chemical antibacterial agents, the use of solar energy for antibacterial has a series of advantages. Traditional chemical antibacterial agents have a series of problems such as narrow antibacterial spectrum, large dosage, and unsafe. Using photodynamics to generate active oxygen on the surface of materials can effectively fight bacteria and is an important direction for the development of antibacterial functional products. Its advantages are specifically reflected in the following aspects: ① High efficiency: Photodynamic antibacterial can kill a variety of pathogenic microorganisms, including bacteria, fungi and viruses, in a short time. Traditional inorganic compound antibacterial agents usually require a large dosage and a long time to take effect, and the antibacterial spectrum is narrow. ② Low drug resistance: Bacteria have low resistance to photodynamic antibacterial. Traditional antibacterial agents, such as silver ions, quaternary ammonium salts, etc., may cause bacteria to develop drug resistance after long-term use. ③ Controllability: By adjusting the intensity and irradiation time of light, the photodynamic antibacterial effect can be accurately controlled to reduce side effects. Traditional antibacterial agents are relatively difficult to control in terms of dosage. ④ Environmentally friendly: The photosensitizers used in photodynamic antibacterial technology are usually organic molecules, which are less polluting to the environment than some inorganic antibacterial agents such as heavy metal compounds. In general, photodynamic antibacterial technology uses light energy to convert into chemical energy for antibacterial purposes, combines the dual action mechanisms of physics and chemistry, and has many advantages such as high efficiency, safety, controllability and environmental protection, and has broad application prospects in antibacterial treatment.

[0003] The current research on photodynamic antibacterial mainly uses photocatalysts for antibacterial disinfection under the action of ultraviolet rays. In this field, Japan is a leading country. Toshiba of Japan has developed a new generation of photocatalyst products with leading level, namely photodynamic functional fibers, and put forward the slogan "As long as there is light, sterilization can be done anywhere", which has a huge impact. my country has only started gradually since 2000. Photodynamic materials represented by titanium dioxide have been widely used in the study of antibacterial and indoor environment purification due to their excellent photocatalytic oxidation performance. However, photocatalysts represented by titanium dioxide are mainly used in the ultraviolet region (254-380nm), with a very narrow spectrum and low antibacterial efficiency. Phthalocyanine and its derivatives, as an organic compound with a large π conjugated structure, are widely used in photodynamic therapy and antibacterial fields. However, traditional phthalocyanine compounds usually have problems such as poor water solubility and a single absorption band, which limits their application in the antibacterial field. Summary of the invention

[0004] The technical problem to be solved by the present invention is to provide a cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent and a preparation method thereof. The antibacterial agent has a novel chemical structure and mild reaction conditions. The prepared antibacterial agent has the synergistic effect of photothermal conversion and photodynamics and has high-efficiency, long-lasting and broad-spectrum antibacterial properties.

[0005] The present invention provides a method for preparing a cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent, comprising:

[0006] (1) Under room temperature, an organic solvent, aminophenol, and anhydrous sodium carbonate were added to a reaction flask in sequence. After stirring and reacting for 1 hour under nitrogen protection, 4-nitrophthalonitrile was added and reacted at room temperature. After the reaction was completed, the reaction solution was poured into deionized water, filtered, the filter cake was washed with water, and dried.

[0007] (2) Take a clean reaction bottle, add N,N-dimethylformamide, the product obtained in step (1), and 3,3′,4,4′-benzophenonetetracarboxylic dianhydride in sequence, stir and react in an ice bath for 2 hours, then raise the temperature to 60° C., add acetic anhydride and pyridine in sequence, stir and react, after the reaction is completed, pour the reaction solution into deionized water, filter, wash the filter cake with water, and then dry it after recrystallization.

[0008] (3) In another reaction bottle, N,N-dimethylformamide, 4-nitrophthalonitrile, N,N-dimethylethanolamine, and potassium carbonate were added in sequence, and the mixture was reacted at room temperature under nitrogen protection. After the reaction was completed, the organic phase was extracted and the water was removed by using anhydrous sodium sulfate. The filtrate was then filtered and evaporated.

[0009] (4) The product obtained in step (2), the product obtained in step (3), n-pentanol, DBU, and zinc acetate dihydrate were added to a reaction flask in sequence, and the temperature was raised to 50° C. under nitrogen protection for reaction. After stirring for 2 h, the temperature was raised to 137° C. for further reaction. After the reaction was completed, the product was dropped into n-hexane and stirred. Solid precipitated and filtered. The filter cake was washed with ethanol and hot washed with N,N-dimethylformamide in sequence to remove impurities to obtain a filtrate. Ethyl acetate was added to the filtrate. Solid precipitated and filtered. The filtrate was dried.

[0010] (5) Add N,N-dimethylformamide, the product obtained in step (4), and butyl bromide to a reaction flask in sequence, and heat to 100° C. to react. After the reaction is completed, add ethyl acetate to the reaction solution to precipitate the product, and obtain an antibacterial agent after recrystallization.

[0011] The organic solvent in step (1) is preferably N,N-dimethylformamide, and the reaction time is 3 to 5 hours.

[0012] The aminophenol in step (1) is preferably p-aminophenol or m-aminophenol.

[0013] The reaction time in step (2) is 3 to 5 hours, and the recrystallization solvent is preferably ethanol.

[0014] The extractant in step (3) is dichloromethane / water (v / v=1-3:1).

[0015] The recrystallization solvent in step (5) is preferably water.

[0016] The chemical structure of the antimicrobial agent is shown below:

[0017]

[0018] The synthetic route of the antibacterial agent is:

[0019]

[0020] The beneficial effects of the present invention are as follows: compared with the prior art, the cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent and the preparation method thereof provided by the present invention have the following advantages:

[0021] (1) The compounds of the present invention have novel chemical structures, simple synthesis and preparation methods, are easy to operate, and have mild reaction conditions. There are no special requirements for reaction conditions such as temperature, air pressure, pH value, and reaction equipment, and they are easy to meet the requirements of industrial production. In addition, the raw materials used in the preparation process are all conventionally used, and the cost is low.

[0022] (2) The antibacterial agent prepared by the present invention has good water solubility;

[0023] (3) The antibacterial agent prepared by the present invention can generate a large amount of active oxygen free radicals under the irradiation of ultraviolet light, visible light and near-infrared light, can kill bacteria efficiently and persistently, and will not produce drug resistance. It is expected to be applied to the design and development of new medical and health materials.

[0024] (4) The antibacterial agent prepared by the present invention has good photothermal conversion performance and has a photothermal and photodynamic synergistic antibacterial effect. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is the UV-visible absorption spectrum of the antibacterial agent in Example 1;

[0026] Figure 2 is the infrared spectrum of the antibacterial agent in Example 1;

[0027] Figure 3 is the hydrogen nuclear magnetic resonance spectrum of the antibacterial agent in Example 1;

[0028] Figure 4 is the UV-visible absorption spectrum of the antibacterial agent in Example 2;

[0029] Figure 5is the infrared spectrum of the antibacterial agent in Example 2;

[0030] Figure 6 is the hydrogen nuclear magnetic resonance spectrum of the antibacterial agent in Example 2;

[0031] Figure 7 The photothermal conversion performance of the antibacterial agent in Example 1 and Example 2 under (a) red light, (b) ultraviolet light and (c) visible light;

[0032] Figure 8 is the amount of active oxygen generated by the antibacterial agent in Example 1 and Example 2 under (a) red light, (b) ultraviolet light and (c) visible light;

[0033] Fig. 9 The antibacterial photos of different concentrations of the antibacterial agent of Example 1 on Escherichia coli under (a) red light and darkness; (b) purple light and visible light conditions;

[0034] Fig.10 The antibacterial photos of different concentrations of the antibacterial agent of Example 1 against Staphylococcus aureus under (a) red light and darkness; (b) purple light and visible light conditions;

[0035] Fig.11 The antibacterial photos of different concentrations of the antibacterial agent of Example 2 against Escherichia coli under (a) red light and darkness; (b) purple light and visible light conditions;

[0036] Fig.12 The antibacterial photos of different concentrations of the antibacterial agent of Example 2 against Staphylococcus aureus under (a) red light and darkness; (b) purple light and visible light conditions are shown. DETAILED DESCRIPTION

[0037] 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.

[0038] Example 1

[0039] (1) Weigh p-aminophenol (2.40 g, 22.00 mmol) and anhydrous potassium carbonate (6.04 g, 32.00 mmol), add 30 mL of DMF and stir for 1 h under nitrogen protection. Add 4-nitrophthalonitrile (3.46 g, 20.00 mmol), stir for 4 h at 25 °C, and use TLC to monitor the reaction progress. After the reaction is completed, pour the reaction solution into deionized water to precipitate a white powder, filter it with suction, wash the filter cake with water, and dry it to obtain 4.43 g of product with a yield of 94.23%.

[0040] (2) The product obtained in step (1) (0.46 g, 2.00 mmol) and BPTCD (0.32 g, 1.00 mmol) were weighed, 5 mL of DMF was added, and the mixture was stirred in an ice bath for 2 h. The mixture was then heated to 60° C., acetic anhydride (0.20 g, 2.00 mmol) and pyridine (0.16 g, 2.00 mmol) were then weighed and added thereto. The mixture was stirred for 4 h. After the reaction was completed, the reaction solution was poured into deionized water. An off-white precipitate was precipitated. The precipitate was filtered off with suction, and the filter cake was washed with water several times. The crude product was recrystallized from ethanol to obtain 0.65 g of a light yellow product. The yield was 91.45%.

[0041] (3) Weigh 4-nitrophthalonitrile (2.00 g, 11.56 mmol), add 20 mL DMF, stir at room temperature, add N, N-dimethylethanolamine (1.03 g, 11.56 mmol), K2CO3 (2 g, 14.50 mmol) in sequence. React for 24 h at 25 °C under nitrogen protection. After the reaction is completed, extract the reaction solution with dichloromethane: water = 3:1 (v / v) and collect the organic phase. Add anhydrous sodium sulfate to remove the moisture in the organic phase, filter with suction, and rotary evaporate the filtrate to obtain 2.03 g of oily product with a yield of 80.52%.

[0042] (4) Weigh the product obtained in step (2) (0.28 g, 0.32 mmol) and the product obtained in step (3) (0.63 g, 1.94 mmol), add 5 mL of n-pentanol, DBU (0.60 g, 1.94 mmol), and zinc acetate dihydrate (0.22 g, 0.65 mmol) in sequence, and heat to 50°C under nitrogen protection for reaction. After stirring for 2 h, heat to 137°C and continue the reaction. After the reaction is completed, add the product dropwise into n-hexane and stir. Solid precipitates. Filter with suction. Wash the filter cake with ethanol and DMF hot wash to remove impurities to obtain a filtrate. Add ethyl acetate to the filtrate. Solid precipitates. Filter with suction and dry to obtain 0.32 g of a green product with a yield of 43.30%.

[0043] (5) The product obtained in step (4) (0.30 g, 0.13 mmol) was weighed, dissolved in 5 mL of DMF, stirred to dissolve, and bromobutyl (1.26 g, 1.00 mmol) was added, and then the temperature was raised to 100° C. After the reaction was completed, ethyl acetate was added to the reaction solution to precipitate the product, and the product was recrystallized with water to obtain 0.21 g of cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent, with a yield of 67.2%.

[0044] The UV-visible absorption spectrum of the antibacterial agent of this embodiment is shown in the attached Figure 1 , infrared spectrum see attached Figure 2 , see the attached H NMR spectrum Figure 3 .

[0045] Example 2

[0046] (1) Weigh m-aminophenol (2.40 g, 22.00 mmol) and anhydrous potassium carbonate (6.04 g, 32.00 mmol), add 30 mL of DMF and stir for 1 h under nitrogen protection. Add 4-nitrophthalonitrile (3.46 g, 20.00 mmol), stir for 4 h at 25 °C, and use TLC to monitor the reaction progress. After the reaction is completed, pour the reaction solution into deionized water to precipitate a white powder, filter it with suction, wash the filter cake with water, and dry it to obtain 4.16 g of product with a yield of 88.49%.

[0047] (2) The product obtained in step (1) (0.46 g, 2.00 mmol) and BPTCD (0.32 g, 1.00 mmol) were weighed, 5 mL of DMF was added, and the mixture was stirred in an ice bath for 2 h. The mixture was heated to 60° C., acetic anhydride (0.20 g, 2.00 mmol) and pyridine (0.16 g, 2.00 mmol) were then weighed and added thereto. The mixture was stirred for 4 h. After the reaction was completed, the reaction solution was poured into deionized water. An off-white precipitate was precipitated. The precipitate was filtered off with suction, and the filter cake was washed with water several times. The crude product was recrystallized from ethanol to obtain 0.59 g of a light yellow product. The yield was 83.01%.

[0048] (3) Weigh 4-nitrophthalonitrile (2.00 g, 11.56 mmol), add 20 mL DMF, stir at room temperature, add N, N-dimethylethanolamine (1.03 g, 11.56 mmol), K2CO3 (2 g, 14.50 mmol) in sequence. React for 24 h at 25 °C under nitrogen protection. After the reaction is completed, extract the reaction solution with dichloromethane: water = 3:1 (v / v) and collect the organic phase. Add anhydrous sodium sulfate to remove the moisture in the organic phase, filter with suction, and rotary evaporate the filtrate to obtain 1.96 g of oily product with a yield of 77.74%.

[0049] (4) Weigh the product obtained in step (2) (0.28 g, 0.32 mmol) and the product obtained in step (3) (0.63 g, 1.94 mmol), add 5 mL of n-pentanol, DBU (0.60 g, 1.94 mmol), and zinc acetate dihydrate (0.22 g, 0.65 mmol) in sequence, and heat to 50°C under nitrogen protection for reaction. After stirring for 2 h, heat to 137°C and continue the reaction. After the reaction is completed, add the product dropwise into n-hexane and stir. Solid precipitates. Filter with suction. Wash the filter cake with ethanol and DMF hot wash to remove impurities to obtain a filtrate. Ethyl acetate is added to the filtrate. Solid precipitates. Filter with suction and dry to obtain 0.49 g of a green product with a yield of 66.30%.

[0050] (5) The product obtained in step (4) (0.30 g, 0.13 mmol) was weighed, dissolved in 5 mL of DMF, stirred to dissolve, and bromobutyl (1.26 g, 1.00 mmol) was added, and then the temperature was raised to 100° C. After the reaction was completed, ethyl acetate was added to the reaction solution to precipitate the product, and the product was recrystallized with water to obtain 0.28 g of cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent, with a yield of 89.60%.

[0051] The UV-visible absorption spectrum of the antibacterial agent of this embodiment is shown in the attached Figure 4 , infrared spectrum see attached Figure 5 , see the attached H NMR spectrum Figure 6 .

[0052] Test Example 1

[0053] Weigh 0.10 g of the antibacterial powders in Example 1 and Example 2 respectively and spread them evenly over an area of ​​1.00 cm 2 The temperature change of the antimicrobial powder was recorded in a square grid using the Flir thermal imager of the American company Filier in a closed light box with an 8W red light / ultraviolet light / visible light flashlight at a distance of 5 cm for 5 minutes. The results are shown in the attached Figure 7 As can be seen from the figure, under the irradiation of red light, ultraviolet light and visible light, the temperature of the antibacterial agent in Example 1 and Example 2 increased significantly, showing good light-to-heat conversion performance.

[0054] Test Example 2

[0055] The antimicrobial agents prepared in Example 1 and Example 2 were tested for active oxygen generation. The generation of active oxygen in the antimicrobial agents was detected by spectrophotometry.

[0056] The reactive oxygen species generated by phthalocyanine-benzophenone compounds include hydroxyl radicals and singlet oxygen. With nitrosodimethylaniline (p-NDA) as an active oxygen scavenger, p-NDA is oxidized and decolorized by hydroxyl radicals. Singlet oxygen reacts with L-histidine to form an intermediate compound, which can also oxidize p-NDA. Therefore, the total production of reactive oxygen species can be determined based on the decolorization rate of p-NDA in the presence of L-histidine.

[0057] 20 mL of a solution of 40 μmol / L p-NDA and 1 mmol / L L-histidine was added to a 50 mL centrifuge tube, and then a certain concentration of the antibacterial agent in Example 1 or Example 2 was added. The solution was irradiated for different time periods under different light sources, and the absorbance at 438 nm of the solution was measured. The yield of active oxygen was calculated according to the following formula.

[0058] ΔC=C-Ct

[0059] p-NDA bleaching rate = ΔC / C

[0060] Where C is the initial concentration of p-NDA, and Ct is the concentration of p-NDA remaining in the solution after irradiation for 30 min.

[0061] See attached for the results Figure 8 As can be seen from the figure, the antibacterial agents in Example 1 and Example 2 can generate a large amount of active oxygen free radicals under the irradiation of red light, ultraviolet light and visible light.

[0062] Test Example 3

[0063] The photodynamic antibacterial properties of the antibacterial agents in Example 1 and Example 2 were tested according to the standard of AATCC100 and measured by the minimum inhibitory concentration method. The bacteria used were Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus. The diluted 0.1 mL of Escherichia coli solution and Staphylococcus aureus solution with a concentration of 105-106 (CFU) / mL were added to 0.9 mL of antibacterial solution of different concentrations. These solutions were placed in ultraviolet light, red light, visible light, and darkness for 30 minutes. Take 0.1 mL of the obtained solution and dilute it continuously to 103, 102 and 101 CFU / mL, drop 100 μL of each dilution on the agar plate, and then culture at 37°C for 10 hours. The final bacterial reduction number can be calculated based on the number of surviving bacterial colonies on the agar plate according to the following formula:

[0064] Bacterial reduction percentage (%) = (BA) / B*100

[0065] Where B is the number of bacteria on the blank agar plate, and A is the number of colonies on the agar plates of other samples.

[0066] The antibacterial rates of the antibacterial agent of Example 1 at different concentrations against Escherichia coli under dark, red light, ultraviolet light and visible light are shown in Table 1, and the antibacterial photos are shown in the attached Fig. 9 The antibacterial rates of the antibacterial agents of Example 1 at different concentrations against Staphylococcus aureus under dark, red light, ultraviolet light and visible light are shown in Table 2, and the antibacterial photos are shown in the attached Fig.10 The antibacterial rates of the antibacterial agents of Example 2 at different concentrations against Escherichia coli under dark, red light, ultraviolet light and visible light are shown in Table 3, and the antibacterial photos are shown in the attached Fig.11 The antibacterial rates of different concentrations of the antibacterial agent in Example 2 against Staphylococcus aureus under dark, red light, ultraviolet light and visible light are shown in Table 4, and the antibacterial photos are shown in the attached Fig.12 .

[0067] The antibacterial rate of the antibacterial agent in Example 1 with a concentration of 0.20mmol / L under dark conditions against Escherichia coli is 55.27%, and the antibacterial rate against Staphylococcus aureus is 58.72%. After irradiation with red light, ultraviolet light and visible light for 30 minutes, the antibacterial rate of PC-BP-N against Escherichia coli and Staphylococcus aureus can reach 99.99%. PC-BJ-N also exhibits similar antibacterial properties. The test data show that the cationic phthalocyanine-benzophenone antibacterial agent in the present invention has good photodynamic antibacterial properties.

[0068] Table 1 Antibacterial rate of different concentrations of the antibacterial agents in Example 1 against Escherichia coli under different conditions

[0069]

[0070] Table 2 Antibacterial rate of different concentrations of the antibacterial agents in Example 1 against Staphylococcus aureus under different conditions

[0071]

[0072] Table 3 Antibacterial rate of different concentrations of the antibacterial agents in Example 2 against Escherichia coli under different conditions

[0073]

[0074] Table 4 Antibacterial rate of different concentrations of the antibacterial agent in Example 2 against Staphylococcus aureus under different conditions

[0075]

Claims

1. A cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent, characterized in that: The structural formula of the antibacterial agent is as follows:

2. A method for preparing a cationic phthalocyanine-benzophenone photothermal and photodynamic synergistic antibacterial agent, characterized in that: The synthetic route of the antibacterial agent is as follows: The specific synthesis method of the antibacterial agent is as follows: 1) At room temperature, an organic solvent, aminophenol, and anhydrous sodium carbonate were added to a reaction flask in sequence, and stirred for reaction for 1 hour under nitrogen protection, and then 4-nitrophthalonitrile was added and reacted at room temperature; after the reaction, the reaction solution was poured into deionized water, filtered, the filter cake was washed with water, and dried; 2) Take another clean reaction bottle, add N,N-dimethylformamide, the product obtained in step 1), and 3,3′,4,4′-benzophenonetetracarboxylic dianhydride in sequence, react in an ice bath with stirring for 2 hours, then heat to 60° C., add acetic anhydride and pyridine in sequence, stir and react, after the reaction is completed, pour the reaction solution into deionized water, filter with suction, wash the filter cake with water, and then dry it after recrystallization; 3) In another reaction bottle, N,N-dimethylformamide, 4-nitrophthalonitrile, N,N-dimethylethanolamine and potassium carbonate were added in sequence, and the mixture was reacted at room temperature under nitrogen protection. After the reaction, the mixture was extracted, the organic phase was collected, the water was removed with anhydrous sodium sulfate, the mixture was filtered, and the filtrate was evaporated; 4) The product obtained in step 2), the product obtained in step 3), n-pentanol, DBU, and zinc acetate dihydrate were sequentially added to a reaction flask, and the temperature was raised to 50° C. under nitrogen protection for reaction. After stirring for 2 hours, the temperature was raised to 137° C. for further reaction. After the reaction was completed, the product was dripped into n-hexane and stirred. Solids were precipitated, and the product was filtered. The filter cake was washed with ethanol and hot washed with N,N-dimethylformamide to remove impurities to obtain a filtrate. Ethyl acetate was added to the filtrate. Solids were precipitated, and the product was filtered and dried. 5) Add N,N-dimethylformamide, the product obtained in step 4) and butyl bromide to the reaction flask in sequence, and heat to 100° C. for reaction; after the reaction is completed, add ethyl acetate to the reaction solution to precipitate the product, and obtain the antibacterial agent after recrystallization.

3. The method for preparing a cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent according to claim 2, characterized in that: The organic solvent in step 1) is N,N-dimethylformamide, and the reaction time is 3 to 5 hours.

4. The method for preparing a cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent according to claim 2, characterized in that: The aminophenol in step 1) is p-aminophenol or m-aminophenol.

5. The method for preparing a cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent according to claim 2, characterized in that: The reaction time in step 2) is 3 to 5 hours, and the recrystallization solvent is ethanol.

6. The method for preparing a cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent according to claim 2, characterized in that: The extractant in step 3) is dichloromethane / water, v / v=1-3:

1.

7. The method for preparing a cationic phthalocyanine-benzophenone photothermal-photodynamic synergistic antibacterial agent according to claim 2, characterized in that: The recrystallization solvent in step 5) is water.

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