Ionic type iridium complex with double phosphorescence emission properties as well as preparation method and application of ionic type iridium complex

A technology of phosphorescent emission and iridium complexes, which is applied in the direction of indium organic compounds, platinum group organic compounds, and compounds containing elements of Group 8/9/10/18 of the periodic table, etc., which can solve the problem of no concentration and difficulty in controlling the concentration of complexes , the concentration of the complex affects the detection results of the analyte, etc., to achieve the effects of reduced interference, accurate quantification, and reliable detection results

Inactive Publication Date: 2017-12-01
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The concentration of complexes in cells or in vivo is difficult to control, and there is currently no simple and effective method

Method used

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  • Ionic type iridium complex with double phosphorescence emission properties as well as preparation method and application of ionic type iridium complex
  • Ionic type iridium complex with double phosphorescence emission properties as well as preparation method and application of ionic type iridium complex
  • Ionic type iridium complex with double phosphorescence emission properties as well as preparation method and application of ionic type iridium complex

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0036] Example 1:

[0037] (1) Synthesis of 4-methyl-4'-acetamide-2,2'-bipyridine

[0038]

[0039] Synthesis of 4-methyl-4’-aldehyde-2,2’-bipyridine: Weigh 5.27g (28mmol) of 4,4’-dimethyl-2,2’-bipyridine, SeO 2 3.84g (34.6mmol), add 260mL of 1,4-dioxane, vacuum, react at 102°C under nitrogen protection for 24h, and then weigh hot filtered; spin the filtrate to dryness and dissolve it in 500mL of ethyl acetate, then Filter again to remove insoluble solids to obtain a yellow solution, use 1.0M Na 2 CO 3 (2×100mL) Extract twice, take the organic phase; then use 0.3M (3×100mL) Na 2 S 2 O 5 Take the inorganic phase and use Na 2 CO 3 Adjust the pH of the inorganic phase to 10, then use CH 2 Cl 2 Extract (4×100 mL) and spin dry to obtain 2.5 g of white solid with a yield of 45%. 1 H NMR (400MHz, CDCl3, δ): 10.1 (1H, s), 8.80 (1H, d), 8.73 (1H, s), 8.49 (1H, d), 8.18 (1H, s), 7.63 (1H, d) ), 7.11 (1H, d), 2.37 (3H, s).

[0040] Synthesis of 4-methyl-4'-carboxy-2,2'-bipyridine: Weigh 198.2m...

Example Embodiment

[0051] Example 2

[0052] (1) Synthesis of 4,4’-Dibutyramide-2,2’-Bipyridine:

[0053]

[0054] 1) Synthesis of 4,4'-dicarboxy-2,2'-bipyridine: Weigh 1.0g (5.4mmol) of 4,4-dimethyl-2,2,-bipyridine into the reaction flask and slowly drop it Add 18 mL of concentrated sulfuric acid and stir. A large amount of heat is released during the process. When the solution is cooled to room temperature, 3.3 g (11.3 mmol) of potassium dichromate is added. At this time, the solution turns dark green, and then reacts at 65° C. for 6 hours. After the reaction is over, cool to room temperature, add the reactant to 1000 mL of water. At this time, a large amount of white flocculent precipitate is generated. Filter by suction, and wash the white precipitate with water and methanol successively until the filtrate is clear, and then dry in a vacuum drying cabinet at 60°C for 18 hours. The yield was 98%.

[0055] Synthesis of dimethyl 4,4'-dicarboxylate-2,2'-bipyridine: Weigh 500mg (2.05mmol) of 4,4'-dica...

Example Embodiment

[0066] Example 3

[0067] (1) Synthesis of 4,4’-Dibutyramide-2,2’-Bipyridine:

[0068]

[0069] 1) Synthesis of 4,4'-dicarboxy-2,2'-bipyridine: Weigh 1.0g (5.4mmol) of 4,4-dimethyl-2,2,-bipyridine into the reaction flask and slowly drop it Add 18 mL of concentrated sulfuric acid and stir. A large amount of heat is released during the process. When the solution is cooled to room temperature, 3.3 g (11.3 mmol) of potassium dichromate is added. At this time, the solution turns dark green, and then reacts at 65° C. for 6 hours. After the reaction is over, cool to room temperature, add the reactant to 1000mL of water. At this time, a large amount of white flocculent precipitate is generated, suction filter, and wash the white precipitate with water and methanol successively until the filtrate is clear, and then dry it in a vacuum drying oven at 60°C for 18h. The yield was 98%.

[0070] Synthesis of dimethyl 4,4'-dicarboxylate-2,2'-bipyridine: Weigh 500mg (2.05mmol) of 4,4'-dicarboxy-2,2...

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Abstract

The invention belongs to the technical field of organic photoelectric functional materials, and particularly relates to an ionic type iridium complex with double phosphorescence emission properties as well as a preparation method and an application of the ionic type iridium complex. The complex comprises a metal center and cyclometalated ligands. The preparation method comprises steps as follows: dichloro bridge is prepared from a phenylpyridine derivative and iridium(III) chloride trihydrate through a coordination reaction, and the ionic type iridium complex with the double phosphorescence emission properties is prepared from dichloro bridge and a dipyridyl derivative or sodium carbonate through coordination reaction. The ionic type iridium complex with the double phosphorescence emission properties can be applied to the fields of biological detection and biological imaging for hypoxic oxygen-enriched conditions; a diagnosis and treatment integrated multifunctional probe based on the ionic type iridium complex with the double phosphorescence emission properties has great potential in further biomedicine application.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and specifically relates to an ion-type iridium complex with dual phosphorescent emission properties, its preparation method and application. Background technique [0002] The history of life on Earth is a chronicle of oxygen production and utilization. About 2.5 billion years ago, primitive photosynthetic organisms acquired an amazing skill: capturing the sun's energy and storing it in chemical bonds within glucose; about 1.5 billion years ago, they acquired another remarkable skill: fully oxidizing glucose into carbon dioxide and water; about 1 billion years ago, plants and animals were differentiated: one group (plants) specialized in photosynthesis of glucose, while the other (animals) specialized in consuming oxygen produced by plants and other organisms; about 500 million years To this day, animals learn to obtain oxygen from the atmosphere. [0003] Mol...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0033C09K11/06C09K2211/185G01N21/6408G01N2021/641G01N2021/6415
Inventor 张寅张太伟孙光兰高鹏丽陈晓娇赵强刘淑娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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