Preparation and applications of water-soluble phosphorescnet iridium complex
A technology of iridium complex and phosphorescence emission, which is used in compounds containing elements of Group 8/9/10/18 of the periodic table, organic chemistry, biological testing, etc. problem, to achieve the effect of improving emission wavelength tunability, reducing cytotoxicity, and reducing toxicity
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Embodiment 1
[0022] Embodiment 1, the preparation of functional N^N ligand:
[0023] Compound 1: Preparation of 5-nitro-1,10-phenanthroline
[0024] Add 5g of 1,10-phenanthroline hydrate into a round bottom flask, add 30mL of concentrated sulfuric acid to dissolve, then add 15mL of fuming nitric acid dropwise, heat the solution to keep its temperature at 160-170°C, and reflux for 2 hours. After the reaction was complete, it was allowed to cool to room temperature, after which the solution was poured into ice water. The pH was adjusted to 3 by adding 10% sodium hydroxide solution. The precipitated yellow precipitate was the product, which was filtered off with suction, washed with water and dried in vacuo. Yield 5 g (88%) of a pale yellow solid. GC-MS (EI-m / z): 225 (M + )
[0025] Compound 2: Preparation of 5-amino-1,10-phenanthroline
[0026] Dissolve 1.889g of 5-nitro-1,10-phenanthroline in 150mL of absolute ethanol, add 0.378g of 5% Pd / C catalyst, heat to 70°C under nitrogen protec...
Embodiment 2
[0030] Embodiment 2: the preparation of iridium complex containing hydrophilic group:
[0031] Compound 1: Iridium complex [Ir(dfppy) 2 cpa] + PF 6 - preparation of
[0032] Weigh iridium dichloro bridge compound 121mg and N^N ligand (cpa) 68mg and join in the double-necked bottle, then add 15mL CH 2 Cl 2 Mixed solvent with methanol (2:1, v / v), reflux under magnetic stirring. After 4 hours, it was cooled to room temperature, and 5 times the equivalent of potassium hexafluorophosphate (KPF 6 ), after continuing to stir for about 1 hour, the solvent was removed by rotary evaporation under reduced pressure, and the resulting solid mixture was redissolved in about 10 mL of CH 2 Cl 2 , the insoluble matter was removed by filtration, and the filtrate was rotary evaporated under reduced pressure to remove the solvent, and the solid obtained was separated by column chromatography (dichloromethane / acetone) to obtain a pure product. Yield: 63%, 1 HNMR (400MHz, CDCl 3 )9.32(s,...
Embodiment 3
[0037] Example 3: Live cell imaging experiment:
[0038] The iridium complex was prepared into a 10 mmol solution, and 20 uL of the solution was pipetted into 2000 uL of PBS buffer solution to dilute the concentration to 10 μM. Take 2 mL of the solution and incubate the cells for 30 minutes, then wash the cells with PBS buffer for 3-5 times, and use a wavelength of 405 nm to excite the cells for confocal imaging and Z-scan. The test data shows that the water-soluble iridium complex has good cell penetration and is distributed in the cytoplasmic area.
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