Preparation and application of visible light photosensitizer
By designing easy-to-synthetic visible light photosensitizers, the problems of UV photosensitizers being harmful to health and the small and complex types of long-wavelength photosensitizers are solved, and high-efficiency photopolymerization under visible light is achieved, with commercial potential.
Patent Information
- Application Number
- CN202510577039.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-05-06
- Publication Date
- 2025-08-08
AI Technical Summary
Most of the existing photosensitizers are ultraviolet photosensitizers, which have problems such as harmful to human health, expensive equipment and limited UV penetration ability. There are few types of long-wavelength visible light photosensitizers, complex structure, difficult to synthesize and are toxic.
A class of visible light photosensitizers that are easy to synthesize, are cheap and absorb long wavelengths are designed. By increasing the number of carbon-carbon double bonds of the chromophore and the length of the alkyl chain, the absorption wavelength of the compound is adjusted. The structure is simple and non-toxic, and it is used in photopolymerization, photocatalysis or photolithography.
It has achieved efficient luminopolymerization under visible light, short curing time of monomers, in line with the concept of green chemistry, and has commercial potential.
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Figure CN120441467A_ABST
Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of functional materials, and in particular to a preparation method of a photosensitizer with photopolymerization ability and application thereof. Background Art
[0002] Photosensitizers are molecules that, upon photoexcitation, transition from the ground state to the singlet state, generating a photoactive species or inducing a co-initiator to generate an active species, thereby initiating monomer polymerization. In recent years, the initiation of photopolymerization under low-intensity and visible light conditions has been a highly active area of research. Currently, most commercially available photosensitizers are UV-absorbing. However, UV light is detrimental to human health and can easily cause conditions like skin cancer. Furthermore, UV irradiation equipment is expensive and has limited UV penetration. Reports of long-wavelength photosensitizers, particularly those that absorb red light, are limited, and most suffer from structural complexity, difficulty in synthesis, high cost, and biotoxicity. Therefore, the synthesis of commercially viable, simple-structured, long-wavelength visible light photosensitizers is of profound significance for advancing scientific and technological development. In recent years, photopolymerization has shown broad application prospects in various fields, such as 3D printing, manufacturing, and healthcare, due to its advantages of high speed, high precision, and environmental friendliness. Summary of the Invention
[0003] The first objective of the present invention is to provide a type of visible light photosensitizer that is easy to synthesize, low-cost, and has a long absorption wavelength. The second objective is to provide a method for preparing the above-mentioned visible light photosensitizer. The third objective is to provide the application of the above-mentioned visible light photosensitizer in the field of photopolymerization.
[0004] The technical solution of the present invention is: a visible light photosensitizer molecule, the structure of which is shown in general formula (1):
[0005]
[0006] wherein R1 is selected from hydrogen, aryl, and C1-C10 alkyl; R2 is selected from aryl and C1-C10 alkyl;
[0007] A is selected from the following structures:
[0008]
[0009] R4 is selected from hydrogen, aryl, C1-C10 alkyl; R5 is selected from oxygen or sulfur;
[0010] for:
[0011]
[0012] R6 or R7 are each independently selected from hydrogen, aryl, C1-C10 alkyl; Y is -H, C1-C10 alkyl, -NO2, halogen, sulfonic acid, carboxyl, -CN.
[0013] Further, R1 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl;
[0014] R2 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl; phenyl, naphthyl.
[0015] Furthermore, R4 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl; and R5 is oxygen.
[0016] Furthermore, R6 or R7 are each independently selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, and 3-methylbutyl.
[0017] Furthermore, Y is halogen.
[0018] Furthermore, the structure of the photosensitizer molecule is:
[0019] 、 、 、 .
[0020] The above-mentioned photosensitizer molecules are used in photopolymerization, photocatalysis or photolithography.
[0021] Furthermore, the photosensitizer molecules undergo photopolymerization, photocatalysis or photolithography under visible light.
[0022] A method for preparing a photosensitizer molecule having photopolymerization ability, the reaction formula and reaction steps of the method are as follows:
[0023] The synthesis was carried out according to the following reaction formula:
[0024]
[0025] The synthesis of intermediate 1, the specific synthesis scheme is:
[0026] Under a nitrogen atmosphere, POCl₃ (0.4 mL, 4.2 mmol) was slowly added to anhydrous DMF (4 mL) in an ice-water bath. The mixture was stirred at 50°C for 45 min. C-0 (3 mmol) dissolved in anhydrous DMF (3 mL) was then added, and the mixture was stirred at 60°C for 2 h. After completion, 100 mL of ice water was added, and the mixture was stirred for 1 hour until an orange precipitate formed. The precipitate was filtered and rinsed twice with water. The crude product was co-evaporated with Et₂O under vacuum twice to obtain an orange amorphous powder.
[0027] The synthesis of intermediate 3, the specific synthesis scheme is:
[0028] Under a nitrogen atmosphere, sodium methoxide (25% methanol, 7.6 mL, 33.6 mmol), compound 2 (13.6 mmol), and (1,3-dioxazol-2-ylmethyl)triphenylphosphonium bromide (17.6 mmol) were added to 80 mL of tetrahydrofuran and stirred at 78°C for 12 hours. Saturated ammonium chloride solution was then added. After the reaction was completed, the reactants were extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was added to 40 mL of tetrahydrofuran solution, followed by hydrochloric acid. The mixture was stirred at room temperature for 1 hour, neutralized with sodium hydroxide solution (2 M), extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The mixture was vacuum distilled and purified by column chromatography (petroleum ether / dichloromethane = 5 / 1) to obtain solid compound 3.
[0029] The synthesis of intermediate 4, the specific synthesis scheme is:
[0030] Under a nitrogen atmosphere, compound 1 (1.84 mmol), 4-diethylaminobenzaldehyde (13.6 mmol), and ((1,3-dioxazol-2-yl)methyl)triphenylphosphonium bromide (17.6 mmol) were added to 80 ml of tetrahydrofuran and stirred at 78°C for 12 hours. Saturated ammonium chloride solution was then added. After the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was added to 40 ml of tetrahydrofuran solution, followed by the addition of hydrochloric acid. The mixture was stirred at room temperature for 1 hour, neutralized with 2 M sodium hydroxide solution, extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum.
[0031] The synthesis of intermediate 5, the specific synthesis scheme is:
[0032] Under a nitrogen atmosphere, 1-ethyl-3,3′-dimethylindole iodide (1.12 mmol), compound 1 (0.87 mmol), and a catalytic amount of piperidine (0.4 ml) were stirred in 25 mL of anhydrous ethanol at 78°C. The reaction mixture was refluxed for 5 hours. The mixture was evaporated under reduced pressure and column chromatography was performed with a methanol:dichloride ratio of 1:50 to obtain the product as a brown solid.
[0033] The synthesis of compound 7, the specific synthesis scheme is:
[0034] Under a nitrogen atmosphere, compound 4 (1.3 mmol) and 1-ethyl-3,3′-dimethylindole iodide (1.56 mmol) were stirred in 25 mL of anhydrous ethanol at 78°C. The reaction mixture was refluxed for 5 hours. The precipitated solid was filtered, washed with ethanol, dried, and recrystallized from ethanol to yield a brown solid.
[0035] The synthesis of compound 8, the specific synthesis scheme is:
[0036] Under a nitrogen atmosphere, 1-ethyl-3,3′-dimethylindole iodide (0.89 mmol) and compound 3 (0.74 mmol) were stirred in 25 mL of anhydrous ethanol at 78°C. The reaction mixture was refluxed for 5 hours. Evaporation under reduced pressure and column chromatography with a methanol to dichloride ratio of 1:50 yielded the product as a brown solid.
[0037] The synthesis of compound 6, the specific synthesis scheme is:
[0038] Compound 5 (0.38 mmol) was dissolved in methanol to prepare a saturated solution. Compound NB (0.76 mmol) was dissolved in an appropriate amount of methanol to prepare a saturated solution. The saturated solutions were mixed thoroughly and stirred at room temperature overnight. Finally, 10 mL of deionized water was added and stirred again until a precipitate formed. The dark blue precipitate was filtered to obtain a dark blue solid. The product was washed with methanol in small amounts several times, analyzed by TLC, and dried under vacuum at 60°C for 5 h.
[0039] The beneficial effects of the present invention are as follows: the absorption wavelength of the compound is adjusted by increasing the number of carbon-carbon double bonds connecting the chromophore and the length of the alkyl chain connected to the chromophore, so that the ultraviolet absorption range of the compound can reach 500 nm-750 nm, and the molar extinction coefficient exceeds , has good photopolymerization ability; the monomer curing time is 15-18s.
[0040] The present application provides a method for synthesizing a visible light photosensitizer that can efficiently initiate monomer polymerization. The method is simple to prepare, has a high yield, and both the synthesis steps and the product are non-toxic, which is in line with the concept of green chemistry. The photosensitizer shows good performance in photopolymerization and achieves the purpose of completing polymerization under white light. Therefore, the present application has certain practical and economic value in terms of synthesizing photosensitizers and photopolymerization. It solves the problems of existing visible light photosensitizers, especially red light absorbing photosensitizers, such as a small number of types, complex structures, difficult synthesis, and toxicity. The photosensitizer is simple to synthesize and has a high yield, is environmentally friendly, has a lower cost, and is more conducive to commercialization. BRIEF DESCRIPTION OF THE DRAWINGS
[0041] Figure 1 Schematic diagram of the UV absorption spectra of compounds C-2, C-3, and C-1-NB;
[0042] Figure 2 This is a diagram of monomer polymerization initiated by compounds C-2, C-3, and C-1-NB.
[0043] Figure 3 The double bond conversion rate of TMPTA polymerization initiated by compounds C-2, C-3, and C-1-NB changes with the illumination time DETAILED DESCRIPTION
[0044] This application also provides a method for preparing the above-mentioned molecule, which is described in detail below in conjunction with specific examples. This example is implemented based on the technical solution of the present invention, and provides a detailed implementation method and specific operation process, but the scope of protection of the present invention is not limited to the following examples. The method comprises the following steps:
[0045] Example
[0046] The synthesis of compound 1, the specific synthesis scheme is:
[0047] Under a nitrogen atmosphere, POCl3 (0.4 mL, 4.2 mmol) was slowly added to anhydrous DMF (4 mL) in an ice-water bath. The mixture was stirred at 50°C for 45 min, followed by the addition of 7-diethylaminocoumarin (600 mg, 3 mmol) dissolved in anhydrous DMF (3 mL). The mixture was stirred at 60°C for 2 h. After completion, 100 mL of ice water was added and stirred for 1 hour until an orange precipitate appeared. The precipitate was filtered and rinsed twice with water. The crude product was co-evaporated with Et2O under vacuum twice to obtain compound 1 (663.8 mg, 98% yield) as an orange amorphous powder.
[0048] The synthesis of compound 4, the specific synthesis scheme is:
[0049] Under a nitrogen atmosphere, compound 1 (500 mg, 1.84 mmol), 4-diethylaminobenzaldehyde (2 g, 13.6 mmol), and ((1,3-dioxazol-2-yl)methyl)triphenylphosphonium bromide (7.6 g, 17.6 mmol) were added to 80 ml of tetrahydrofuran and stirred at 78°C for 12 hours. Saturated ammonium chloride solution was then added. After the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was added to 40 ml of tetrahydrofuran solution, followed by the addition of hydrochloric acid. The mixture was stirred at room temperature for 1 hour, neutralized with 2 M sodium hydroxide solution, extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum.
[0050] The synthesis of compound C-2, the specific synthesis scheme is:
[0051] Under a nitrogen atmosphere, compound 4 (350 mg, 1.3 mmol) and 1-ethyl-3,3′-dimethylindole iodide (490 mg, 1.56 mmol) were stirred in 25 mL of anhydrous ethanol at 78°C. The reaction mixture was refluxed for 5 hours. The precipitated solid was filtered, washed with ethanol, dried, and recrystallized from ethanol to yield a brown solid (365 mg, 49% yield).
[0052] Example 2
[0053] The synthesis of compound 3, the specific synthesis scheme is:
[0054] Under a nitrogen atmosphere, sodium methoxide (25% methanol, 7.6 mL, 33.6 mmol), 4-diethylaminobenzaldehyde (2 g, 13.6 mmol), and (1,3-dioxazol-2-ylmethyl)triphenylphosphonium bromide (7.6 g, 17.6 mmol) were added to 80 mL of tetrahydrofuran and stirred at 78°C for 12 hours. Saturated ammonium chloride solution was then added. After the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was added to 40 mL of tetrahydrofuran solution, followed by hydrochloric acid. The mixture was stirred at room temperature for 1 hour, neutralized with sodium hydroxide solution (2 M), extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The mixture was vacuum distilled and purified by column chromatography (petroleum ether / dichloromethane = 5 / 1) to obtain solid compound 3 in an 88% yield.
[0055] The synthesis of compound C-3, the specific synthesis scheme is:
[0056] Under a nitrogen atmosphere, 1-ethyl-3,3′-dimethylindole iodide (280 mg, 0.89 mmol) and compound 3 (150 mg, 0.74 mmol) were stirred in 25 mL of anhydrous ethanol at 78°C. The reaction mixture was refluxed for 5 hours. Evaporation under reduced pressure and column chromatography with a methanol:dichloride ratio of 1:50 afforded the product as a brown solid (102 mg, 28% yield).
[0057] Example 3
[0058] The synthesis of intermediate C-1, the specific synthesis scheme is:
[0059] Under a nitrogen atmosphere, 1-ethyl-3,3′-dimethylindole iodide (350 mg, 1.12 mmol), 7-diethylamino-3-formylcoumarin (200 mg, 0.87 mmol), and a catalytic amount of piperidine (0.4 ml) were stirred in 25 mL of anhydrous ethanol at 78°C. The reaction mixture was refluxed for 5 hours. The mixture was evaporated under reduced pressure and column chromatography was performed using a methanol:dichloride ratio of 1:50 to obtain the product as a brown solid (322 mg; 83% yield).
[0060] The synthesis of compound C-1-NB, the specific synthesis scheme is:
[0061] Compound C-1 (200 mg, 0.38 mmol) was dissolved in methanol to prepare a saturated solution. Compound NB (541 mg, 0.76 mmol) was dissolved in an appropriate amount of methanol to prepare a saturated solution. The saturated solutions were mixed thoroughly and stirred at room temperature overnight. Finally, 10 mL of deionized water was added and stirred again until a precipitate formed. The dark blue precipitate was filtered to obtain the product. The product was washed with methanol in small amounts several times, analyzed by TLC, and dried under vacuum at 60°C for 5 h. The product was obtained as a dark blue solid (74 mg, 14% yield).
[0062] MALDI-TOF high-resolution accurate mass calibration, the target molecular formula of C-2 is C 30 H 33 IN2O2, the theoretical mass-to-charge ratio is 441.2537, and the measured mass-to-charge ratio is 441.2584. The target molecular formula of C-3 is C 28 H 33 IN2, the theoretical mass-to-charge ratio is 373.2638, and the measured mass-to-charge ratio is 373.2642. The target molecular formula of C-1-NB is C 53 H 62 BCl3N2O2, the theoretical mass-to-charge ratio is 415.2380, and the measured mass-to-charge ratio is 415.2383.
[0063] The UV absorption spectrum of the target molecule is as follows Figure 1As shown, C-2 and C-1-NB exhibit central absorption bands at 370 nm, 384 nm, and 370 nm, respectively, representing the absorption bands of indole. The structural absorption bands between 500 and 750 nm are characteristic of coumarins. For compounds C-2 and C-3, the increased number of double bonds alters the conjugated structure of the molecules, resulting in a significant red-shift in the absorption spectra to approximately 646 nm.
[0064] Example 4
[0065] The mixture of the polymerizable component and the photoinitiator system of the present invention was heated by a 35 W xenon lamp (white light intensity: 80 mW / cm 2 ) for light curing.
[0066] Compound C-2 is used as a photosensitizer:
[0067]
[0068] The total weight of the photopolymerizable composition is 100 wt %, and the weight of the photosensitizer accounts for 0.5 wt % of the weight of the photopolymerizable composition.
[0069] In some embodiments, the photoinitiator further comprises a second photoinitiator or an additive, wherein the additive comprises at least one of a colorant, an alkali-soluble resin, an adhesion promoter, a surfactant, and a dispersant.
[0070] In the photopolymerization experiments, a co-initiator system was formed using 0.5 wt% of C-2 with 0 wt% and 2.0 wt% of tetrabutylammonium tris(3-chloro-4-methylphenyl)hexylborate (NB), respectively. Each system was divided into two small sample vials, dissolved in 0.12 mL of N,N-dimethylformamide solution, and then 1 mL of trimethylolpropane triacrylate (TMPTA) monomer was added. The system was protected from light and deoxygenated, and mixed thoroughly. Each system was irradiated with a 35 W xenon lamp, and the time it took for the monomer to fully cure was recorded.
[0071] The changes of the sample before and after irradiation with a 35 W xenon lamp are shown as follows: Figure 2 As shown in the figure, when no NB is added, that is, when the NB concentration is 0 wt%, the monomer cannot be cured. When the photosensitizer concentration is 0.5 wt%, the monomer is fully cured in 15 s.
[0072] Example 5
[0073] The mixture of the polymerizable component and the photoinitiator system of the present invention was heated by a 35 W xenon lamp (white light intensity: 80 mW / cm 2 ) for light curing.
[0074] Compound C-3 was used as a photosensitizer:
[0075]
[0076] The total weight of the photopolymerizable composition is 100 wt %, and the weight of the photosensitizer accounts for 0.5 wt % of the weight of the photopolymerizable composition.
[0077] Furthermore, the photoinitiator further comprises a second photoinitiator or an additive, wherein the additive comprises at least one of a colorant, an alkali-soluble resin, an adhesion promoter, a surfactant, and a dispersant.
[0078] In the photopolymerization experiments, a co-initiator system was formed using 0.5 wt% of C-3 with 0 wt% and 2.0 wt% of tetrabutylammonium tris(3-chloro-4-methylphenyl)hexylborate (NB), respectively. Each solution was then divided into two small sample vials. 0.12 mL of N,N-dimethylformamide solution was added to dissolve the solution. Subsequently, 1 mL of trimethylolpropane triacrylate (TMPTA) monomer was added. The mixture was then mixed thoroughly, shielded from light and deoxygenated. Each vial was irradiated with a 35 W xenon lamp, and the time it took for the monomer to fully cure was recorded.
[0079] The changes of the sample before and after irradiation with a 35 W xenon lamp are shown in the figure below. Figure 2 As shown in the figure, when no NB is added, that is, when the NB concentration is 0 wt%, the monomer cannot be cured. When the photosensitizer concentration is 0.5 wt%, the monomer is fully cured in 17 s.
[0080] Example 6
[0081] The mixture of the polymerizable component and the photoinitiator system of the present invention was heated by a 35 W xenon lamp (white light intensity: 80 mW / cm 2 ) for light curing.
[0082] Using compound C-1-NB:
[0083]
[0084] The total weight of the photopolymerizable composition is 100 wt %, and the weight of the photosensitizer accounts for 0.5 wt % of the weight of the photopolymerizable composition.
[0085] In the photopolymerization experiment, 0.5 wt% C-1-NB was dissolved in 0.12 mL of N,N-dimethylformamide solution, followed by the addition of 1 mL of trimethylolpropane triacrylate (TMPTA) monomer. The mixture was then mixed thoroughly in the dark to remove oxygen. The mixture was then irradiated with a 35 W xenon lamp, and the time it took for the monomer to fully cure was recorded.
[0086] The changes of the sample before and after irradiation with a 35 W xenon lamp are shown in the figure below. Figure 2 The monomer fully cured in 18 s.
[0087] In summary, this application provides a method for synthesizing a visible light photosensitizer that can efficiently initiate monomer polymerization. This method is simple to prepare, has a high yield, and both the synthesis steps and the product are non-toxic, conforming to the concept of green chemistry. More importantly, the photosensitizer exhibits good performance in photopolymerization and achieves the goal of completing polymerization under white light. Therefore, this application has certain practical and economic value in the synthesis of photosensitizers and photopolymerization.
[0088] Example 7
[0089] The mixture of the polymerizable component and the photoinitiator system of the present invention was heated by a 35 W xenon lamp (white light intensity: 80 mW / cm 2 ) for photocuring and measure the double bond conversion rate of the monomer (TMPTA) in the photopolymerization system.
[0090] The kinetic curve of the photopolymerization process was continuously tracked using real-time infrared spectroscopy (Thermo Scientific Nicolet iS20). The corresponding LED light source was selected according to the absorption wavelength intensity of the compound, with an irradiation intensity of 10 mW / cm 2 The deoxygenated photosensitizer, monomer, and initiator mixture was spread on the surface of the instrument, covered with glass and the mixture, and N2 was used for purging during the entire mixing process.
[0091] System 1: 0.1% C-2, 0.82% NB, 1 mL TMPTA, 0.12 mL NVP
[0092] System 2: 0.5% C-3, 0.44% NB, 1 mL TMPTA, 0.12 mL NVP
[0093] System 3: 0.75% C-1-NB, 1 mL TMPTA, 0.12 mL NVP
[0094] C=O(1760 ) is the internal standard, and the center position of the C=C stretching vibration absorption peak is 1630 The change of , determines the change of dual-band conversion (DC) over time. The calculation formula is as follows:
[0095]
[0096] Where A0, A t are the ratios of the relative absorption band areas before photopolymerization and at photopolymerization time t, respectively.
[0097] See Figure 3The double bond conversion rates of TMPTA photopolymerization initiated by C-2, C-3, and C-1-NB were 48%, 30%, and 82%, respectively. This indicates that C-2, C-3, and C-1-NB are very effective red light photosensitizers.
[0098] Of course, the above embodiments of the present invention are merely examples for illustrating the present invention and are not intended to limit the specific implementation methods of the present invention. Those skilled in the art will appreciate that other variations or modifications can be made based on the above examples. It is not possible to provide detailed examples of all implementation methods here. Any obvious variations or modifications arising from the technical solutions of the present invention remain within the scope of protection of the present invention.
Claims
1. A visible light photosensitizer molecule, characterized in that: The structure of the photosensitizer molecule is shown in general formula (1): ； wherein R1 is selected from hydrogen, aryl, and C1-C10 alkyl; R2 is selected from aryl and C1-C10 alkyl; A is selected from the following structures: ； R4 is selected from hydrogen, aryl, C1-C10 alkyl; R5 is selected from oxygen or sulfur; for: ； R6 or R7 are each independently selected from hydrogen, aryl, C1-C10 alkyl; Y is -H, C1-C10 alkyl, -NO2, halogen, sulfonic acid, carboxyl, -CN.
2. The photosensitizer molecule according to claim 1, characterized in that: R1 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl; R2 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl; phenyl, naphthyl.
3. The photosensitizer molecule according to claim 1, characterized in that: R4 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl; R5 is oxygen.
4. The photosensitizer molecule according to claim 1, characterized in that: R6 or R7 are each independently selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl.
5. The photosensitizer molecule according to claim 1, characterized in that: Y is halogen.
6. The photosensitizer molecule according to claim 1, characterized in that: 、 、 、 。 7. The photosensitizer molecule according to any one of claims 1 to 6 is used in photopolymerization, photocatalysis or photolithography.
8. The use according to claim 7, characterized in that: The photosensitizer molecules undergo photopolymerization, photocatalysis or photolithography under visible light.