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

Active Publication Date: 2014-03-26
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the heavy metal complexes reported for bioimaging have poor water solubility, and a mixed solvent of water and organic solvents such as dimethyl sulfoxide is necessary for imaging experiments
Although biogenesis was successfully achieved on the basis of mixed solvents, organic solvents are toxic to cells

Method used

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  • Preparation and applications of water-soluble phosphorescnet iridium complex
  • Preparation and applications of water-soluble phosphorescnet iridium complex
  • Preparation and applications of water-soluble phosphorescnet iridium complex

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention belongs to the technical field of the organic photoelectric material and particularly relates to a preparation method of a water-soluble phosphorescnet iridium complex and applications of the complex in the fields of cell marking, imaging and organic photoelectronic devices. The complex material consists of ring metal ligands, a metal center and phenanthroline ligands. The structural general formula of the complex is shown as below. The material has simple synthesis steps and mild conditions; and triethylamine is used for the quaternization of the N^N ligand, thus the obtained complex has water-solubility and then has good application prospect in the cell imaging field. The C^N ligand is 2-(2',4'-difluorophenyl)pyridine, 2-phenylpyridine, 2-(2'-thienyl)quinoline, 2-phenylquinoline, 2-fluorenylisoquinoline, 1-phenylisoquinoline or 2-(2'-benzothienyl)pyridine.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a preparation method of a water-soluble iridium complex and its application in the fields of cell labeling, imaging and organic optoelectronic devices. Background technique [0002] In recent years, with the continuous development of life sciences, the research on active species in cells, cell signal transduction and cell apoptosis has become more and more in-depth. Fluorescent labeling and imaging analysis is an effective visual analysis technique widely used in live cell analysis. Most of the fluorescent probes currently used for live cell labeling and imaging analysis are organic fluorescent dye molecules, which provide effective fluorescent probes for live cell analysis. [0003] Phosphorescent heavy metal complexes have excellent photophysical properties, such as high triplet photon quantum efficiency at room temperature, long emission lif...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00G01N33/52H01L51/50H01L51/54
Inventor 黄维赵强马云刘淑娟杨会然
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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