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

Abstract

The application discloses a cationic phthalocyanine-benzophenone photothermal photodynamic synergistic antibacterial agent and a preparation method thereof. The compound has excellent photothermal conversion performance and photodynamic antibacterial performance. The structure of the antibacterial finishing agent is shown in the following formula: the preparation method of the antibacterial agent comprises the following steps: introducing 3,3',4,4'-benzophenone tetracarboxylic dianhydride and a quaternary ammonium salt group on a phthalocyanine to synthesize a cationic phthalocyanine-benzophenone compound. The compound shows excellent photothermal conversion performance under red light, ultraviolet light and visible light. The antibacterial test results show that the prepared cationic phthalocyanine compound can show high bactericidal effect on staphylococcus aureus and escherichia coli under different light sources. In addition, the compound has good water solubility and multi-band light absorption capacity, and is suitable for various antibacterial application scenarios.

Description

Technical Field

[0001] The present 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 inevitably come into contact with a variety of microorganisms, which pose a threat to human health. Consequently, research on antimicrobial agents and antimicrobial materials has garnered widespread attention in recent years. Using sunlight for antimicrobial treatment offers a number of advantages over traditional chemical antimicrobial agents. These agents suffer from a narrow antimicrobial spectrum, high dosage requirements, and safety concerns. Using photodynamic therapy to generate reactive oxygen species on material surfaces offers highly effective antimicrobial efficacy and is a key development direction for antimicrobial products. Its advantages are embodied in the following aspects: 1. High efficiency: Photodynamic therapy can kill a wide range of pathogens, including bacteria, fungi, and viruses, in a short period of time. Traditional inorganic compound antimicrobial agents typically require large dosages and a long time to be effective, and their antimicrobial spectrum is narrow. 2. Low drug resistance: Bacteria have a low resistance to photodynamic therapy. Long-term use of traditional antimicrobial agents, such as silver ions and quaternary ammonium salts, can lead to bacterial resistance. 3. Controllability: By adjusting the light intensity and exposure time, the antimicrobial effect of photodynamic therapy can be precisely controlled, minimizing side effects. However, dosage control is relatively difficult with traditional antimicrobial agents. ④ Environmentally friendly: The photosensitizers used in photodynamic antimicrobial technology are typically organic molecules, which are less polluting to the environment than some inorganic antimicrobial agents, such as heavy metal compounds. In general, photodynamic antimicrobial technology utilizes light energy to convert into chemical energy for antimicrobial effects, combining both physical and chemical mechanisms of action. It offers advantages such as high efficiency, safety, controllability, and environmental friendliness, and holds broad application prospects in antimicrobial therapy.

[0003] Current research in photodynamic antimicrobial treatment primarily uses photocatalysts for disinfection under the action of ultraviolet light. Japan is a leader in this field. Toshiba has developed a leading-edge next-generation photocatalyst product, photodynamic functional fibers, and has launched a significant marketing campaign, promoting the slogan "Bacteria can be eliminated anywhere with light." my country's research has only begun since 2000, with photodynamic materials, such as titanium dioxide, being widely used in antimicrobial research and indoor environmental purification due to their excellent photocatalytic oxidation properties. However, photocatalysts such as titanium dioxide primarily operate in the ultraviolet (254-380 nm) region, resulting in a narrow spectrum and low antimicrobial efficiency. Phthalocyanine and its derivatives, organic compounds with large π-conjugated structures, are widely used in photodynamic therapy and antimicrobial applications. However, traditional phthalocyanine compounds often suffer from poor water solubility and a narrow absorption band, limiting their application in antimicrobial applications. 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 and photodynamic synergistic antibacterial agent, comprising:

[0006] (1) At room temperature, an organic solvent, aminophenol, and anhydrous sodium carbonate were added to a reaction flask in sequence. After stirring under nitrogen for 1 hour, 4-nitrophthalonitrile was added and the reaction was continued at room temperature. After the reaction was completed, the reaction solution was poured into deionized water, filtered, and 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′-dibenzophenonetetracarboxylic dianhydride in sequence, stir and react in an ice bath 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, wash the filter cake with water, and then dry it after recrystallization.

[0008] (3) In another reaction flask, N,N-dimethylformamide, 4-nitrophthalonitrile, N,N-dimethylethanolamine, and potassium carbonate were added in sequence and reacted at room temperature under nitrogen protection. After the reaction was completed, the organic phase was extracted and collected, and the water was removed with anhydrous sodium sulfate, and the filtrate was 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 the 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. to continue the reaction. After the reaction was completed, the product was dropped into n-hexane and stirred. Solid precipitated, and the filter cake was filtered. Impurities were removed by ethanol washing and N,N-dimethylformamide hot washing to obtain a filtrate. Ethyl acetate was added to the filtrate. Solid precipitated, and the filter cake was filtered and dried.

[0010] (5) Add N,N-dimethylformamide, the product obtained in step (4), and bromobutane 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 and photodynamic synergistic antibacterial agent and its preparation method 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, 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 commonly 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 number 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 used in 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 agents in Example 1 and Example 2 under (a) red light, (b) ultraviolet light, and (c) visible light irradiation;

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

[0033] Figure 9 The following are photos of the antibacterial effect of different concentrations of the antibacterial agent of Example 1 on Escherichia coli under (a) red light and darkness; (b) violet light and visible light conditions;

[0034] Figure 10 The antibacterial effect of different concentrations of the antibacterial agent of Example 1 on Staphylococcus aureus under (a) red light and darkness; (b) violet light and visible light conditions are shown;

[0035] Figure 11 These are photos of the antibacterial effect of different concentrations of the antibacterial agent of Example 2 on Escherichia coli under (a) red light and darkness; and (b) violet light and visible light conditions;

[0036] Figure 12 The following are photos of the antibacterial effect of different concentrations of the antibacterial agent of Example 2 on Staphylococcus aureus under (a) red light and darkness; and (b) violet light and visible light. DETAILED DESCRIPTION

[0037] The following will clearly and completely describe the technical solutions in the embodiments of the present invention in conjunction with the accompanying drawings. 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 making creative efforts are within the scope of protection of the present invention.

[0038] Example 1

[0039] (1) p-Aminophenol (2.40 g, 22.00 mmol) and anhydrous potassium carbonate (6.04 g, 32.00 mmol) were weighed, added to 30 mL of DMF, and stirred under nitrogen for 1 h. 4-Nitrophthalonitrile (3.46 g, 20.00 mmol) was added, and the mixture was stirred at 25°C for 4 h. The reaction progress was monitored by TLC. After the reaction was completed, the reaction solution was poured into deionized water to precipitate a white powder, which was filtered, washed with water, and dried 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 temperature was then raised to 60°C. Acetic anhydride (0.20 g, 2.00 mmol) and pyridine (0.16 g, 2.00 mmol) were then added and stirred for 4 h. After the reaction was completed, the reaction solution was poured into deionized water. A grayish-white precipitate was precipitated, which was filtered 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 with a yield of 91.45%.

[0041] (3) 4-Nitrophthalonitrile (2.00 g, 11.56 mmol) was weighed, 20 mL of DMF was added, and the mixture was stirred at room temperature. N,N-dimethylethanolamine (1.03 g, 11.56 mmol) and K2CO3 (2 g, 14.50 mmol) were added in sequence. The mixture was reacted at 25°C under nitrogen for 24 h. After the reaction was completed, the reaction solution was extracted with dichloromethane:water = 3:1 (v / v) and the organic phase was collected. Anhydrous sodium sulfate was added to remove moisture from the organic phase. The mixture was filtered and the filtrate was evaporated to obtain 2.03 g of an 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), and 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. Heat the mixture to 50°C under nitrogen protection for reaction. Stir the reaction for 2 h and then heat the mixture to 137°C to 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 then with 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 0.32 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 and dissolved in 5 mL of DMF. After stirring and dissolving, bromobutane (1.26 g, 1.00 mmol) was added, and 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 a 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 is attached Figure 2 , see the attached H NMR spectrum Figure 3 .

[0045] Example 2

[0046] (1) m-Aminophenol (2.40 g, 22.00 mmol) and anhydrous potassium carbonate (6.04 g, 32.00 mmol) were weighed, added to 30 mL of DMF, and stirred under nitrogen for 1 h. 4-Nitrophthalonitrile (3.46 g, 20.00 mmol) was added, and the mixture was stirred at 25°C for 4 h. The reaction progress was monitored by TLC. After the reaction was completed, the reaction solution was poured into deionized water to precipitate a white powder, which was filtered, washed with water, and dried 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 temperature was then raised to 60°C. Acetic anhydride (0.20 g, 2.00 mmol) and pyridine (0.16 g, 2.00 mmol) were then added and stirred for 4 h. After the reaction was completed, the reaction solution was poured into deionized water. A grayish-white precipitate was precipitated, which was filtered 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 with a yield of 83.01%.

[0048] (3) 4-Nitrophthalonitrile (2.00 g, 11.56 mmol) was weighed, 20 mL of DMF was added, and the mixture was stirred at room temperature. N,N-dimethylethanolamine (1.03 g, 11.56 mmol) and K2CO3 (2 g, 14.50 mmol) were added in sequence. The reaction was allowed to proceed at 25°C under nitrogen for 24 h. After the reaction was completed, the reaction solution was extracted with dichloromethane:water = 3:1 (v / v) and the organic phase was collected. Anhydrous sodium sulfate was added to remove moisture from the organic phase, and the mixture was filtered and rotary evaporated to obtain 1.96 g of an oily product with a yield of 77.74%.

[0049] (4) 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) were weighed, and 5 mL of n-pentanol, DBU (0.60 g, 1.94 mmol), and zinc acetate dihydrate (0.22 g, 0.65 mmol) were added in sequence. 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 added dropwise into n-hexane and stirred. Solid precipitated and filtered. The filter cake was washed with ethanol and hot washed with DMF to remove impurities to obtain a filtrate. Ethyl acetate was added to the filtrate. Solid precipitated and filtered to 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 and dissolved in 5 mL of DMF. After stirring and dissolving, bromobutane (1.26 g, 1.00 mmol) was added, and 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 a 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 is attached Figure 5 , see the attached H NMR spectrum Figure 6 .

[0052] Test Example 1

[0053] Weigh 0.10 g of the antibacterial powders of 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 closed light box using a FLIR thermal imager from the American company Filier. An 8W red light / ultraviolet light / visible light flashlight was used to illuminate the product 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 photothermal conversion performance.

[0054] Test Example 2

[0055] The antimicrobial agents prepared in Example 1 and Example 2 were subjected to an active oxygen generation test. The generation of active oxygen by the antimicrobial agents was detected by spectrophotometry.

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

[0057] To a 50 mL centrifuge tube, 20 mL of a solution containing 40 μmol / L p-NDA and 1 mmol / L L-histidine was added. A certain concentration of the antibacterial agent described in Example 1 or Example 2 was then added. The solution was irradiated under different light sources for different periods of time. The absorbance of the solution at 438 nm was measured, and the reactive oxygen species production 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 30 min of irradiation.

[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 red light, ultraviolet light and visible light irradiation.

[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. 0.1 mL of the diluted 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 resulting solution and continuously dilute it 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 number of bacteria reduced can be calculated based on the number of surviving bacterial groups 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 Figure 9 The antibacterial rates of different concentrations of the antibacterial agent of Example 1 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 Figure 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 Figure 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 irradiation are shown in Table 4, and the antibacterial photos are attached. Figure 12 .

[0067] At a concentration of 0.20 mmol / L, the antimicrobial agent in Example 1 demonstrated an antibacterial rate of 55.27% against Escherichia coli and 58.72% against Staphylococcus aureus in the dark. After 30 minutes of irradiation with red light, ultraviolet light, and visible light, PC-BP-N achieved an antibacterial rate of 99.99% against both E. coli and Staphylococcus aureus. PC-BJ-N also exhibited similar antibacterial properties. Test data demonstrates that the cationic phthalocyanine-benzophenone antimicrobial agent of the present invention possesses excellent 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 agents 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, add DMF, aminophenol, and anhydrous potassium carbonate to a reaction flask in sequence. Stir and react for 1 hour under nitrogen. Then add 4-nitrophthalonitrile and react at room temperature. After the reaction, pour the reaction solution into deionized water, filter, wash the filter cake with water, and dry. 2) In another clean reaction flask, add N,N-dimethylformamide, the product obtained in step 1), and 3,3′,4,4′-benzophenonetetracarboxylic dianhydride in sequence. Stir the mixture in an ice bath for 2 hours, then raise the temperature to 60°C. Add acetic anhydride and pyridine in sequence and stir the mixture. After the reaction is complete, pour the reaction mixture into deionized water, filter, wash the filter cake with water, recrystallize, and dry. 3) In another reaction flask, add N,N-dimethylformamide, 4-nitrophthalonitrile, N,N-dimethylethanolamine, and potassium carbonate in sequence and react at room temperature under nitrogen. After the reaction, extract and collect the organic phase, remove water with anhydrous sodium sulfate, filter, and evaporate the filtrate; 4) The product obtained in step 2), the product obtained in step 3), n-pentanol, DBU, and zinc acetate were added to a reaction flask in sequence. 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 complete, the product was added dropwise to n-hexane and stirred. Solid precipitated, which was filtered. The filter cake was washed with ethanol and then with hot N,N-dimethylformamide to remove impurities to obtain a filtrate. Ethyl acetate was added to the filtrate. Solid precipitated, which was filtered and dried. 5) Add N,N-dimethylformamide, the product obtained in step 4), and bromobutane to the reaction flask in sequence, and raise the temperature 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 and photodynamic synergistic antibacterial agent according to claim 2, characterized in that: The reaction time in step 1) is 3 to 5 hours.

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

Images