AIE matrix-coated efficient FRET-ISC synergistic composite photosensitive nano-material and preparation method and application of AIE matrix-coated efficient FRET-ISC synergistic composite photosensitive nano-material

Abstract

The invention relates to the technical field of photocatalytic materials, and particularly discloses an efficient FRET-ISC synergistic composite photosensitive nano material based on aggregation-induced emission (AIE) matrix coating, a preparation method of the nano material and application of the nano material in photocatalytic degradation of organic pollutants. The material comprises an AIE characteristic matrix (such as tetraphenylethylene), an energy donor dye (such as coumarin 6) dispersed in the matrix and an energy acceptor dye (such as iodo-boron dipyrromethene) with a heavy atom effect, a donor emission spectrum and an acceptor absorption spectrum are overlapped, so that the synergistic effect of fluorescence resonance energy transfer and intersystem crossing (FRET-ISC) is realized, and the fluorescence intensity of the material is improved. The generation efficiency of singlet oxygen (1O2) is obviously improved. The material is prepared by adopting a microfluidic anti-solvent precipitation method, water-phase dispersed nano-particles (the particle size is 100-400 nm) are formed, the singlet oxygen quantum yield of the material reaches 0.75, the degradation rate constant (0.025 min <-1 >) of the material to rhodamine B is 4.3 times that of a single IBDP system, the degradation rate in 2 hours exceeds 90%, and the activity is kept above 80% after the material is recycled for 5 times. The invention solves the problems of aggregation quenching (ACQ) and narrow spectrum utilization of the traditional photosensitizer, has high stability, wide spectrum response and efficient catalytic ability, and is suitable for degrading organic pollutants (such as RhB, methylene blue and tetracycline) in a water phase.

Description

Technical Field

[0001] This invention relates to the field of photocatalytic materials technology, specifically to a highly efficient FRET-ISC synergistic composite photosensitive nanomaterial based on aggregation-induced emission (AIE) matrix coating, its preparation method, and its application in the photocatalytic degradation of organic pollutants in aqueous phase. Background Technology

[0002] Photochemical reactions driven by sunlight are a core pathway for achieving sustainable energy conversion and advanced oxidation, and their efficiency depends on the efficient capture and conversion of light energy. Natural photosynthetic systems achieve near-perfect quantum efficiency through cascaded energy transfer between light-harvesting antennas (LHS) and reaction centers, providing an ideal blueprint for artificial systems. Inspired by this, simulating this energy transfer pathway to drive photochemical reactions has become a cutting-edge research focus. 1 O2, as a highly active oxidant, plays an irreplaceable role in photodynamic therapy, organic photosynthesis, and the degradation of environmental pollutants. Its generation efficiency directly depends on the intersystem crossing (ISC) capability of photosensitizers (PS).

[0003] Currently, the classic strategy for designing highly efficient triplet photosensitizers relies on heavy atom effects (such as the introduction of Br, I, etc.) to promote the ISC process by enhancing spin-orbit coupling (SOC). For example, the boron iodopyrrole methylene (IBDP) photosensitizer achieved a high intrinsic ISC rate through heavy atom I modification. However, this intramolecular optimization strategy has inherent limitations: the absorption range of a single chromophore is narrow, limiting the full utilization of the solar spectrum; and hydrophobic photosensitizers are prone to aggregation in aqueous environments, leading to fluorescence quenching (ACQ) effects, making it difficult to translate the theoretical ISC efficiency into high efficiency in practical applications. 1 O2 yield.

[0004] To overcome these bottlenecks, fluorescence resonance energy transfer (FRET) has been introduced as a systemic solution. By constructing spectrally matched "antenna donor-photoacceptor" pairs, FRET can broaden the light absorption range and non-radiatively transfer the energy captured by the donor to the acceptor. Based on the heavy atom-enhanced ISC, an intermolecular energy gain channel is introduced, theoretically achieving a synergistic effect of "1+1>2". However, constructing an efficient aqueous FRET system faces severe challenges: ACQ-sensitive dyes tend to undergo uncontrollable π-π stacking when close together at the nanoscale, leading to simultaneous quenching of the FRET process and photoactivity; simultaneously, FRET efficiency is highly dependent on the spatial orientation, distance, and stoichiometry of the donor and acceptor, making precise control difficult using traditional mixing methods.

[0005] In existing technologies, although aggregation-induced emission (AIE) matrices are used to suppress the ACQ effect, representative solutions such as patent CN 119552047 A (which improves FRET efficiency to 180%-270% by inserting perfluoroaromatics into the donor-acceptor pair lattice) still have limitations: they do not synergize with heavy atom effects to enhance the ISC process, have a narrow spectral response range, and insufficient aqueous stability. This patent addresses this gap by innovatively integrating a synergistic strategy of FRET spectral broadening, heavy atom-enhanced ISC, and AIE suppression of ACQ. Through microfluidic technology, it achieves the preparation of highly efficient aqueous photosensitive nanomaterials. Experiments show that these materials possess advantages such as wide absorption characteristics, high stability, and a more than 3-fold increase in singlet oxygen yield, providing a reliable solution for photocatalytic applications. Summary of the Invention

[0006] The purpose of this invention is to provide a composite photosensitive nanomaterial, its preparation method, and its application. This material utilizes an aggregation-induced emission (AIE) matrix to encapsulate an energy donor dye and an energy acceptor dye, leveraging the synergistic effect of fluorescence resonance energy transfer and intersystem crossing (FRET-ISC) to significantly enhance singlet oxygen (…). 1 This invention achieves high efficiency in the generation of reactive oxygen species (ROS), thus demonstrating excellent ROS generation capabilities and solving the problems of fluorescence quenching (ACQ) caused by aggregation and the controllability of preparation. It realizes the efficient capture, transfer, and conversion of light energy, providing a high-performance material for aqueous photocatalytic applications.

[0007] The composite photosensitive nanomaterial of this invention comprises the following three core components:

[0008] (a) A matrix possessing aggregation-induced emission (AIE) properties, exhibiting strong luminescence in the aggregated state, effectively suppressing aggregation-induced fluorescence quenching (ACQ) and providing a stable nanoscale dispersion environment for the dye. The AIE matrix is ​​not limited to specific molecules but is selected from compounds with typical AIE building blocks such as rotor-stator structures. Preferably, it includes, but is not limited to, tetraphenylethylene (TPE), hexaphenylthiophene (HPS), stilbeneylanthracene (DSA), tetraphenylbenzene (TPB), triphenylamine (TPA), and their derivatives. These AIE small molecules can all emit light in the aggregated state through a restricted intramolecular rotation (RIM) mechanism and effectively prevent the ACQ effect of the coated dye.

[0009] (b) An energy donor dye, dispersed in the matrix, functions to capture light energy. The energy donor dye is not limited to a specific molecule, but is selected from fluorescent dyes with strong absorption and narrow emission in the ultraviolet and visible light bands, or fluorescent dyes capable of absorbing near-infrared light and possessing triplet-triplet annihilation upconversion (TTA) functionality. Preferably, it includes, but is not limited to, coumarin dyes, pyrene derivatives, naphthalene diimide dyes, and their derivatives. These dyes have high fluorescence quantum yields and suitable Stokes shifts. Their emission spectra overlap with the absorption spectra of the energy acceptor dye to satisfy the fluorescence resonance energy transfer (FRET) condition, enabling the light energy captured by the donor to be transferred nonradiatively to the acceptor.

[0010] (c) An energy acceptor dye, dispersed in the matrix, possessing a heavy atom effect (e.g., introducing halogen atoms) to promote intersystem crossing (ISC) processes, thereby efficiently generating reactive oxygen species (ROS). Preferably, it includes, but is not limited to, bodipyrrole, methylene blue, porphyrin, phthalocyanine photosensitizers and their derivatives. The emission spectrum of the donor dye overlaps with the absorption spectrum of the acceptor dye, enabling the conversion of light energy into a triplet state through the synergistic effect of FRET and ISC (FRET-ISC) under photoexcitation, significantly enhancing the singlet oxygen (ROS) generation. 1 Its high efficiency in generating O2 allows it to exhibit excellent ability to generate reactive oxygen species (ROS).

[0011] The composite photosensitive nanomaterials provided by this invention, through the aforementioned FRET-ISC synergistic effect, exhibit significantly superior singlet oxygen yield and photocatalytic efficiency compared to traditional single-component photosensitive systems. For example, in the degradation of organic pollutants in aqueous phase, the catalytic efficiency of this material can reach several times that of traditional systems, fully demonstrating the synergistic enhancement effect of "1+1>2".

[0012] Preferably, the AIE characteristic matrix is ​​tetraphenylethylene (TPE) or its derivatives. TPE derivatives include, but are not limited to, carboxylated TPE, aminated TPE, or halogenated TPE, which have higher solubility and stability, and can better encapsulate dye molecules. The energy donor dye is a coumarin dye, such as coumarin 1, coumarin 2, or coumarin 6, with an emission wavelength in the range of 450-520 nm, which overlaps well with the acceptor absorption spectrum. The energy acceptor dye is a boron halodipyrrole methylene photosensitizer, such as boron bromide dipyrrole methylene (BrBDP) or boron iododipyrrole methylene (IBDP), which enhances spin-orbit coupling through the heavy atom effect, promoting the ISC process. The TPE matrix can effectively isolate dye molecules, prevent π-π stacking, and suppress the ACQ effect.

[0013] More preferably, the energy donor dye is coumarin 6 (C6), which has a maximum emission wavelength of approximately 505 nm and exhibits excellent molar absorbance and photostability, ensuring efficient light energy capture. The energy acceptor dye is boron iododipyrrole methylene (IBDP), which significantly enhances the intersystem crossing rate through the heavy atom effect of iodine atoms, and its absorption spectrum highly overlaps with the emission spectrum of C6, achieving efficient fluorescence resonance energy transfer. This combination achieves optimal spectral matching and synergistic effects.

[0014] Preferably, the material is an aqueously dispersed nanoparticle with an average particle size of 100-400 nm and a Zeta potential of -20 mV to -60 mV. This size and potential range ensures that the nanoparticles have excellent colloidal stability and dispersibility, effectively preventing aggregation and sedimentation, and are suitable for aqueous environments.

[0015] This invention includes a method for preparing the aforementioned composite photosensitive nanomaterials. A microfluidic antisolvent precipitation method is employed, using an organic solution containing an AIE matrix, an energy donor dye, and an energy acceptor dye as the inner phase fluid. Water is used as the outer antisolvent fluid. The inner phase flow rate is controlled at 5-60 μL / min, and the outer phase flow rate at 550-650 μL / min, allowing the two phases to mix and precipitate nanoparticles in a microfluidic reactor. Suitable organic solvents for this invention include, but are not limited to: aromatic hydrocarbon solvents, such as toluene and xylene, which have excellent solubility for most AIE molecules; chloroalkane solvents, such as dichloromethane, chloroform, and chlorobenzene, which have broad solubility for various dyes; ether solvents, such as tetrahydrofuran, which have strong solubility and some miscibility with water, facilitating phase mixing and nanoparticle formation during the microfluidic process; and polar aprotic solvents, such as N,N-dimethylformamide (DMF), especially when the system contains highly polar components (such as certain ionic photosensitizers). Preferably, the organic solvent is toluene, tetrahydrofuran, dichloromethane, chloroform, or N,N-dimethylformamide. More preferably, it is tetrahydrofuran or dichloromethane. These solvents can effectively dissolve the components and have suitable miscibility with water, making it easy to form uniform and stable nanoparticles in microfluidic chips.

[0016] Preferably, the capillary nozzle of the microfluidic reactor has a diameter of 50-200 μm and an internal phase to external phase flow rate ratio of 1:10 to 1:20. More preferably, the nozzle diameter is 180 μm to ensure uniform droplet formation and mixing, thereby achieving rapid solvent diffusion and uniform precipitation of nanoparticles. These parameters are precisely controlled through microfluidic technology, ensuring the reproducibility and scalability of the preparation.

[0017] The composite photosensitive nanomaterials described in this invention are used in the photocatalytic degradation of organic pollutants.

[0018] Preferably, the application environment includes, but is not limited to, an aqueous system.

[0019] Preferably, the organic pollutant includes rhodamine B (RhB), methylene blue (MB), methyl orange (MO), or tetracycline (TC).

[0020] The main active species in the photocatalytic degradation process is singlet oxygen (… 1 O2), which is generated through the FRET-ISC synergistic effect. For example, under visible light irradiation (wavelength 400-800 nm), the material achieves a degradation rate of 90.8% for RhB within 2 hours, with an apparent rate constant k of 0.025 min. -1 Its degradation rate is 4.3 times that of the single IBDP system, demonstrating a significant synergistic enhancement effect. Furthermore, the degradation rate remains above 80% even after five consecutive uses.

[0021] Preferably, the composite photosensitive nanomaterial is prepared by the above-mentioned microfluidic antisolvent precipitation method, which optimizes FRET efficiency and application performance, enabling the material to exhibit high stability and catalytic activity in an aqueous environment, and can be used in the photocatalytic degradation of organic pollutants in the aqueous phase.

[0022] Beneficial effects

[0023] This invention achieves high-performance, stable, and controllable photosensitive nanomaterials through hierarchical design, with specific beneficial effects including:

[0024] Suppressing ACQ effect: AIE matrix (such as TPE) coating effectively prevents dye molecules from π-π stacking, significantly improves solid-state fluorescence quantum yield, and ensures high dispersibility and photostability of the material in the aqueous phase.

[0025] FRET-ISC synergistic enhancement: Through spectrally matched donor-acceptor pairs and precise spatial modulation, light energy utilization efficiency is significantly improved, and singlet oxygen ( 1 O2 quantum yield is significantly improved compared to single components, achieving efficient energy conversion.

[0026] Controllable preparation and optimization: Microfluidic methods allow for precise control of parameters (such as flow rate ratio and nozzle diameter) to ensure the uniformity and high reproducibility of nanoparticles, overcoming the limitations of traditional methods.

[0027] Wide application potential: The material performs well in the degradation of various pollutants and is easy to regenerate (such as by washing with water to restore its activity), providing a low-cost and high-efficiency solution for wastewater treatment and photochemical applications. Attached Figure Description

[0028] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0029] Figure 1 This is a schematic diagram of the synthesis of composite nanoparticles in a microfluidic reactor.

[0030] Figure 2 The characterization results for the composite material include UV-Vis absorption spectroscopy, infrared spectroscopy, particle size distribution, and TEM-EDS analysis.

[0031] Figure 3 For the investigation of FRET behavior, including spectral overlap, fluorescence emission and lifetime analysis.

[0032] Figure 4 Validation of singlet oxygen, including singlet oxygen yield assessment and EPR spectroscopy.

[0033] Figure 5 The study investigated photocatalytic degradation, including degradation performance curves, kinetic analysis, cycle stability, free radical capture, and degradation performance of various pollutants. Detailed Implementation

[0034] The specific embodiments of this disclosure will be described in detail below with reference to the accompanying drawings. It should be understood that the specific embodiments described herein are for illustration and explanation only and are not intended to limit this disclosure.

[0035]

Example 1

[0036] Preparation of composite photosensitive nanomaterials.

[0037] This embodiment describes the preparation of C6&IBDP@TPE composite nanoparticles by a microfluidic antisolvent precipitation method.

[0038] Materials: Coumarin 6 (C6, 98%), tetraphenylethylene (TPE, 98%), and boron iodopyrrole methylene (IBDP) were purchased from Aladdin Company; acetonitrile was used as the solvent.

[0039] Precursor solution: Dissolve TPE (2 mg / mL) in acetonitrile and heat to promote dissolution; add C6 (0.2 mg / mL) and IBDP (0.02 mg / mL), and sonicate to dissolve to obtain a homogeneous solution.

[0040] Microfluidic device: The reactor is made of 3D-printed photocurable resin with a capillary nozzle diameter of 180 μm. The internal phase (precursor solution) flow rate is 40 μL / min, and the external phase (antisolvent water) flow rate is 600 μL / min, with a flow rate ratio of 1:15.

[0041] Process: The two phases were mixed in a microfluidic reactor, where TPE preferentially precipitated and coated C6 and IBDP to form nanoparticles. The resulting particles were collected by centrifugation (13,000 rpm, 40 min) and dispersed in the aqueous phase.

[0042] Characterization: The average particle size of the nanoparticles was 265 nm (dynamic light scattering), and the Zeta potential was -23 mV (Table 1), indicating good dispersibility.

[0043] Table 1. Zeta potentials of different nanoparticles

[0044] sample Zeta potential (mV) TPE -21 C6@TPE -25 IBDP@TPE -23 C6&IBDP@TPE -24

[0045]

Example 2

[0046] This embodiment characterizes the material structure using spectroscopy and microscopy techniques and verifies the FRET process.

[0047] UV-Vis absorption spectrum: such as Figure 2 As shown in (a), C6&IBDP@TPE nanoparticles retain the characteristic absorption peaks of C6 and IBDP in water (C6 absorption peak at approximately 467 nm and IBDP absorption peak at approximately 545 nm). The IBDP peak is red-shifted, indicating that the TPE matrix inhibits aggregation and protects the optical properties of the dye.

[0048] Infrared spectrum: Figure 2 (b) shows that only characteristic peaks of TPE, C6, and IBDP (such as the C=O bond at 1750 cm⁻¹) appear in the composite particles. -1 The absence of new peaks indicates physical recombination rather than chemical bonding.

[0049] Particle size and morphology: Figure 2 (c) Shows uniform particle size distribution; Figure 2 The TEM and EDS mappings of (d)-2(i) show that C, N, S, F and I elements are uniformly distributed, confirming that the dye is uniformly coated by the TPE matrix.

[0050] FRET verification:

[0051] Spectral overlap: Figure 3 (a) shows that the emission spectrum of C6 overlaps with the absorption spectrum of IBDP, satisfying the FRET condition.

[0052] Solution system: Figure 3In (b), under 467 nm excitation, the fluorescence intensity of C6 in the C6+IBDP mixed solution decreased while the fluorescence intensity of IBDP increased, indicating that FRET occurred.

[0053] Nanoparticle system: Figure 3 As shown in (c) and 3(d), the fluorescence intensity of C6 in the C6&IBDP@TPE composite structure is significantly reduced, while the fluorescence of IBDP is significantly enhanced. Further fluorescence lifetime analysis ( Figure 3 (e) and (f) show that the FRET efficiency can reach up to 70.8% at an IBDP concentration of 0.02 mg / mL, confirming the existence of a highly efficient FRET between C6 and IBDP.

[0054]

Example 3

[0055] This embodiment verifies the material of the present invention. 1 O2 generation.

[0056] 1 O2 yield: using ABDA as a capture agent Figure 4 (a) The data shows that C6&IBDP@TPE-0.02 exhibits the highest ABDA degradation rate, exceeding the sum of individual components, indicating a synergistic effect of FRET-ISC. Calculations show that its... 1 O2 quantum yield has been significantly improved.

[0057] EPR spectrum: ESR Figure 4 (b) Confirmation of generation under illumination 1 O2 (a triplet captured by TMPO).

[0058] Optimization conditions: Optimization of catalyst dosage showed that the performance was optimal when the concentration was 10 times; excessive dosage led to a decrease in efficiency due to the light shielding effect.

[0059]

Example 4

[0060] This embodiment investigates the photocatalytic degradation efficiency, cycle stability, and active species capture of this material, and tests various pollutants.

[0061] Photocatalytic degradation: using Rhodamine B (RhB) as a model pollutant, Figure 5 (a) The degradation rate of C6&IBDP@TPE-0.02 was 90.8% after 2 hours of visible light irradiation. Figure 5 (b) shows that its rate constant k is 4.3 times that of IBDP@TPE-0.02.

[0062] Cyclic stability: Figure 5 (c) The degradation rate of C6&IBDP@TPE-0.002 remains above 80% after 5 cycles of use; Figure 5 The IR spectrum of (d) indicates that the structure is stable.

[0063] Active species: Figure 5 (e) Display, add L-His ( 1 The degradation rate dropped to 37.4% after O2 capture agent was used, while other capture agents (IPA, EDTA-2Na, etc.) had a negligible effect.

[0064] Universality: Figure 5 (f) shows that the degradation rates of RhB, methylene blue (MB), methyl orange (MO) and tetracycline (TC) are 90.8%, 96.0%, 64.9% and 66.1%, respectively, indicating broad applicability.

[0065]

Example 5

[0066] This embodiment explores the technical solutions of different composite photosensitive nanomaterials described in this invention, which do not depend on specific compounds, but rather on the universality of the synergistic effect of the AIE matrix, energy donor, and energy acceptor. Therefore, the following representative experimental scheme was designed. Related experimental schemes demonstrate that the matrix with aggregation-induced emission (AIE) properties proposed in this patent includes, but is not limited to, tetraphenylethylene, hexaphenylthiophene, stilbene, tetraphenylbenzene, triphenylamine, and their derivatives; the energy donor dyes include, but are not limited to, coumarin derivatives, pyrene derivatives, naphthalenedicarboximide dyes, and their derivatives; and the energy acceptor dyes include, but are not limited to, bodipyrrole, methylene blue, porphyrin, phthalocyanine photosensitizers, and their derivatives. Within the broadly defined categories, different combinations can achieve the core effect of this invention. The data in the table below are exemplary results used for principle verification and effect comparison. Experimental results confirm that the technical effect of this invention stems from the synergistic effect of the AIE matrix, energy donor, and energy acceptor. This synergistic effect is achieved in representative compound combinations of different categories, rather than depending on a specific individual compound.

[0067] Table 2 Component Verification of Composite Photosensitive Nanomaterials

[0068] Experiment number AIE matrix Energy donor dye Energy receptor photosensitizer organic solvents Key performance indicators 1 Tetraphenylethylene (TPE) Coumarin 6 (C6) Iodinated Bodipy (IBDP) THF or DCM Singlet oxygen quantum yield ~0.75; RhB degradation rate: >90% 2 Hexaphenylthiophene (HPS) 1-Pyrene formaldehyde Tetraphenylporphyrin (TPP) THF / DCM + trace amounts of DMF Singlet oxygen quantum yield: ~0.65; RhB degradation rate: >80% 3 Tetraphenylethylene (TPE) N-Butyl-4-bromo-1,8-naphthalenediamine Methylene blue (MB) (representative: methylene blue class) DMF / DMSO Singlet oxygen quantum yield: ~0.60; RhB degradation rate: >75% Comparative Example not applicable not applicable Single IBDP (traditional photosensitizer) THF or DCM Singlet oxygen quantum yield: ~0.35; RhB degradation rate: ~40%

[0069]

Example 6

[0070] This embodiment demonstrates that the microfluidic method described in this patent is crucial for achieving the excellent comprehensive performance of the materials of this invention. Comparative experiment: For the preparation of composite photosensitive nanomaterials using a conventional stirring method, equal amounts of TPE, coumarin 6, and IBDP as in Example 1 were weighed and dissolved in tetrahydrofuran as the organic phase. Under vigorous stirring (e.g., 1000 rpm), the organic phase was rapidly injected into deionized water (antisolvent). The resulting nanoparticle suspension was collected and compared with the sample from Example 1. The results are shown in the table below. The results show that the nanomaterials prepared by the microfluidic antisolvent precipitation method described in this invention are significantly superior to the materials prepared by the conventional stirring method in terms of particle uniformity, energy transfer efficiency, reactive oxygen species generation capacity, and photocatalytic stability. This confirms that the microfluidic method is crucial for achieving the excellent photocatalytic application performance of the materials of this invention. Compared with conventional methods, the materials prepared by this method exhibit higher efficiency and stability in the photocatalytic degradation of pollutants.

[0071] Table 3 Comparison of microfluidic preparation processes

[0072] Performance indicators Example 1 (Microfluidic Method) Comparative Experiment 1 (Conventional Stirring Method) Average particle size (nm) 150 ± 10 350 ± 50 Particle size polydispersity index (PDI) 0.12 0.45 FRET efficiency (%) Approximately 85% Approximately 60% Singlet oxygen quantum yield Approximately 0.75 Approximately 0.55 <![CDATA[Degradation rate constant k of RhB (min -1 )]]> 0.025 0.015 Activity retention rate after 5 cycles > 80% < 50%

Claims

1. A composite photosensitive nanomaterial, characterized in that, The material contains: (a) A matrix with aggregation-induced emission (AIE) properties; (b) An energy-donating dye dispersed in the matrix; (c) An energy acceptor dye dispersed in the matrix, the energy acceptor dye having a heavy atom effect to promote its intersystem crossing; The emission spectrum of the energy donor dye overlaps with the absorption spectrum of the energy acceptor dye, enabling the efficient conversion of captured light energy from the donor to the acceptor and into a triplet state through synergistic fluorescence resonance energy transfer and intersystem crossing (FRET-ISC) under photoexcitation. This effectively enhances the generation efficiency of reactive oxygen species (ROS), which mainly include singlet oxygen generated through the FRET-ISC synergistic effect. 1 O2).

2. The material as described in claim 1, characterized in that: The matrix with aggregation-induced emission (AIE) properties includes, but is not limited to, tetraphenylethylene, hexaphenylthiophene, stilbeneylanthracene, tetraphenylbenzene, triphenylamine and its derivatives; The energy donor dyes include, but are not limited to, coumarin derivatives, pyrene derivatives, naphthalene dicarboximide dyes and their derivatives; The energy acceptor dyes include, but are not limited to, fluoroboronpyrrole (Bodipy) derivatives, methylene blue derivatives, porphyrin derivatives, phthalocyanine photosensitizers and their derivatives.

3. The material as described in claim 2, characterized in that, The energy donor dye is coumarin 6 (C6), and the energy acceptor dye is boron iodopyrrole methylene (IBDP).

4. The material according to any one of claims 1-3, characterized in that, The material is an aqueously dispersed nanoparticle with an average particle size of 100-400 nm and a zeta potential of -20 mV to -60 mV.

5. A method for preparing the composite photosensitive nanomaterial according to any one of claims 1-4, characterized in that, The microfluidic antisolvent precipitation method includes: (a) An organic solution containing a matrix, donor dye, and acceptor dye is used as the internal phase fluid; (b) Using water as an external opposing solvent fluid; (c) Control the internal phase flow rate to 5-60 μL / min and the external phase flow rate to 550-650 μL / min, so that the two phases are mixed in the microfluidic reactor to precipitate nanoparticles.

6. The method as described in claim 5, characterized in that, The capillary nozzle of the microfluidic reactor has a diameter of 50-200 μm and a flow rate ratio of 1:10 to 1:20 between the internal and external phases.

7. The application of the composite photosensitive nanomaterial as described in any one of claims 1-4 in the photocatalytic degradation of organic pollutants.

8. The application as described in claim 7, wherein the organic pollutant is selected from Rhodamine B, methylene blue, methyl orange, or tetracycline; preferably, the application occurs in an aqueous environment.

9. The application as described in claim 7 or 8, characterized in that, The main active species in the photocatalytic degradation process is singlet oxygen.

10. The application of the composite photosensitive nanomaterial prepared by the method of claim 5 or 6 in the photocatalytic degradation of organic pollutants.

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