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A class of boron-containing heteronuclear iridium complexes and their preparation methods and applications

An iridium complex and heteronuclear technology is applied in the field of preparation of new boron-containing heteronuclear iridium complexes, which can solve problems such as complex chemical reactions, limited development and application, and achieve simple synthesis steps, good cell staining effect, and mild conditions. Effect

Inactive Publication Date: 2015-09-02
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods generally involve relatively complex chemical reactions, which limits further development and application.

Method used

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  • A class of boron-containing heteronuclear iridium complexes and their preparation methods and applications
  • A class of boron-containing heteronuclear iridium complexes and their preparation methods and applications
  • A class of boron-containing heteronuclear iridium complexes and their preparation methods and applications

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of embodiment 1 iridium complex 1:

[0027] a. Synthesis of ligand (dfppy): difluorophenylboronic acid (5 mmol), Pd(PPh 3 ) 4 (4%) joins in the there-necked flask, vacuumizes-inflates nitrogen-vacuumizes on the double row pipe, circulates three times, finally protects the reaction system with nitrogen. Draw 2-bromopyridine (2 mL) into the reaction system with a syringe. Draw purified toluene (20mL), 2M potassium carbonate solution (10mL) and ethanol (10mL) into the reaction system with a syringe. Stir, and raise the temperature of the reaction system to 80°C, avoid light for reaction, and reflux for 24h. After the reaction, the solvent was removed, and DCM was used as the eluent, and the column was purified by column chromatography. Recrystallization (DCM / n-hexane) gave an oily product with a yield of 80%.

[0028]

[0029] b. at N 2 Under protective conditions, dissolve 1 equivalent of iridium trichloride and 2.2 equivalents of ligand (dfppy) i...

Embodiment 2

[0031] The preparation of embodiment 2 complex 2:

[0032] in N 2 Under protective conditions, dissolve 1 equivalent of iridium trichloride and 2.2 equivalents of ligand (ppy) in a mixture of 2-ethoxyethanol and water (3:1, v:v), and react under reflux for 24 hours ; After being cooled to room temperature, add a large amount of water, have precipitation to produce, suction filtration, dry under the infrared lamp to obtain the iridium dichloro bridge intermediate; 2 CO 3Dissolve in 2-ethoxyethanol, reflux and stir to react for 24 hours; after the reaction, suction filter, spin dry the filtrate under reduced pressure, add dichloromethane to dissolve, separate by column chromatography, and recrystallize to obtain the iridium complex intermediate; Then add boron trifluoride diethyl ether diluted with dichloromethane dropwise to the dichloromethane solution in which the iridium complex is dissolved, and stir at room temperature for 12 hours; after the reaction, the solvent is rem...

Embodiment 3

[0034] The preparation of embodiment 3 iridium complex 3:

[0035] a. Synthesis of ligand (thq): Add 2-nitrobenzaldehyde (3.8g, 25mmol), iron powder (10g, 178.5mmol), 85mL absolute ethanol, 85mL glacial acetic acid and 45mL deionized water into a three-necked flask , reflux reaction for half an hour. After the reaction was finished, filter with suction and collect the filtrate with CH 2 Cl 2 After extraction three times, the organic phase was washed three times with saturated aqueous sodium bicarbonate solution and deionized water, dried over anhydrous magnesium sulfate, and spin-dried to obtain anthranilaldehyde as a yellow oil. Yield 70%. Then, 5.9 g of diacetylthiophene, 2.8 g of NaOH, and 40 mL of ethanol were added to 5.7 g of anthranilaldehyde, and refluxed overnight. After the reaction was completed, it was cooled and filtered, and the obtained crude product was recrystallized from ethanol to obtain white needle-like crystals with a yield of 70%.

[0036]

[003...

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Abstract

The invention belongs to the technical fields of organic photovoltaic functional materials and biosensing, and in particular relates to a preparation method of a novel boracic heteronuclear iridium complex, and the application of the novel boracic heteronuclear iridium complex in organic electroluminescence and bioimaging field. The material is the heteronuclear complex designed with a novel iridium core including heavy metals and non-metal boron center, and the structural formula is shown in the specification. The martial is simple in synthesis steps and mild in synthesis conditions; and the photophysical property of the complex can be adjusted by changing different cyclometalated ligands and introducing four-coordinated boron, so that the material has great application prospect in the field of organic optoelectronic functional materials, and aspects of bio-labeling and cell-imaging.

Description

technical field [0001] The invention belongs to the field of photoelectric functional organic material technology and chemical / biological sensing. It specifically relates to a preparation method of a novel type of boron-containing heteronuclear iridium complex and its application in the fields of organic photoelectric functional devices and biological imaging. Background technique [0002] Due to their excellent photophysical properties, optoelectronic functional materials based on heavy metal iridium complexes are widely used in the fields of organic electroluminescence devices, light-emitting electrochemical cells, photocatalytic hydrogen production, chemical sensing, biomarkers and bioimaging. [0003] At the end of the 20th century, Tang of the Kodak Company of the United States and Burroughes of the University of Cambridge respectively proposed electroluminescent materials and devices based on organic and polymers. . Compared with traditional liquid crystal and cathod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C09K11/06G01N21/64H01L51/54
Inventor 黄维赵强杨丽娟孙会彬刘淑娟
Owner NANJING UNIV OF POSTS & TELECOMM
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