Aggregation-induced luminescence photosensitizer with near-infrared emission and high singlet oxygen yield, and preparation method and application thereof
A technology of aggregation-induced luminescence and singlet oxygen, which is applied in the preparation of organic compounds, medical preparations containing active ingredients, luminescent materials, etc., can solve problems such as performance degradation, and achieve high diagnostic accuracy, low cost, and small side effects. Effect
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Embodiment 1
[0037] The synthetic process of the target product of the present embodiment is as follows:
[0038]
[0039] (1) Synthesis of intermediate M3
[0040] Raw material M1 (0.3g, 0.67mmol), M2 (0.25g, 0.8mmol) and catalyst tetrakis (triphenylphosphine) palladium (5mol% of M2) were added to the reaction flask, sealed and then vacuumed and then passed through argon , and so on three times. Then use a syringe to add 8 mL of deoxygenated tetrahydrofuran, 2M K 2 CO 3 1.7 mL, the resulting mixture was heated to 70 °C and stirred for 12 h. After the mixture in the reaction flask was cooled to room temperature, dichloromethane was added to dilute it and washed twice with water. After separation, the organic layer was washed with anhydrous Na 2 SO 4 Dry and filter. After the obtained solid was rotary evaporated to remove the solvent, the residue was purified by silica gel column chromatography, the eluent was petroleum ether / ethyl acetate (v / v, 8 / 1). Finally, a total of 0.30 g of...
Embodiment 6
[0051] Using the compound of formula I prepared in Example 1 as the photosensitive material and the amphiphilic polymer DSPE-PEG2000 as the encapsulating material, the composite fluorescent nanoparticles were prepared by nanoprecipitation method: 1 mg of the compound of formula I and 2 mg of DSPE-PEG2000 were dissolved in 1 mL of THF , the resulting solution was added to 10 mL of ultrapure water and sonicated immediately for 30 min. The mixed solution was then stirred at room temperature overnight until the THF was completely evaporated. The mixed solution was filtered through a 0.22 μm filter membrane, and the filtrate was concentrated by ultrafiltration, centrifuged, and washed three times. The obtained nanoparticle (AIE-NPs) solution was stored at 4°C for later use.
[0052] An appropriate amount of AIE-NPs solution was taken for dynamic light scattering test, and the results were as follows Figure 4 shown. From this, it can be determined that the particle size of the AI...
Embodiment 7
[0054] Measurement of Singlet Oxygen Quantum Yield
[0055] Using 9,10-anthracenediyl-bis(methylene)dicarboxylic acid (ABDA) as the singlet oxygen indicator, and commercial rose bengal (RB) as the photosensitizer reference, the ABDA reference concentrations of 5μg / mL were prepared respectively. ratio solution, ABDA+RB mixed solution, ABDA+AIE-NPs mixed solution. The three solutions were treated with white light (400-700nm, 100mW / cm 2 ) irradiated for 7 minutes, and the absorption spectrum of the solution and the change of the absorption value at 378 nm were recorded every 1 minute. The results are as follows Figure 5 shown. After calculation, it is found that the singlet oxygen yield of AIE-NPs is more than 3 times that of RB.
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