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A kind of iridium (Ⅲ) complex and its preparation method and application

A complex and reaction technology, applied in indium organic compounds, chemical instruments and methods, platinum group organic compounds, etc., can solve the problems of poor photostability, concentration quenching, small Stokes shift, etc., and achieve a short synthesis route. , the process is simple, the effect of large Stokes displacement

Active Publication Date: 2019-12-10
NANJING TECH UNIV
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some common disadvantages of traditional biological probes are poor photostability, small Stokes shift, and concentration quenching effect.

Method used

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  • A kind of iridium (Ⅲ) complex and its preparation method and application
  • A kind of iridium (Ⅲ) complex and its preparation method and application
  • A kind of iridium (Ⅲ) complex and its preparation method and application

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preparation example Construction

[0036] The present invention provides a preparation method for the iridium (III) complex described in the above technical scheme, comprising the following steps:

[0037] (1) Under anhydrous and oxygen-free conditions, under the action of organic palladium catalysts and basic substances, 2-bromo-4-formic acid ethyl pyridine and phenylboronic acid derivatives are subjected to Suzuki coupling reaction in an organic solvent to obtain 2-Phenylisonicotinic acid ethyl ester derivatives;

[0038] (2) Under anaerobic conditions, carry out the first coordination reaction with the 2-phenylisonicotinic acid ethyl ester derivative obtained in step (1) and iridium trichloride hydrate in a solvent to obtain a bridge chlorine complex; Said solvent is the mixed solvent of organic solvent and water;

[0039] (3) Under anhydrous and oxygen-free conditions, the bridge chlorine complex obtained in step (2) and 3,6-di-tert-butyl-9-(4-(4,5-dimethyl-2-( Pyridin-2-yl)-1H-imidazol-1-yl)butyl)-9H-car...

Embodiment 1

[0068] Synthesis of Ligand 2-(3,5-Dimethoxyphenyl)isonicotinic acid ethyl ester

[0069]

[0070] In a 100mL two-necked flask, 2.10g of ethyl 2-bromo-4-carboxylate pyridine, 2.01g of 3,5-dimethoxyphenylboronic acid, 4.86g of potassium carbonate, 0.66g of tetrakis(triphenylphosphine)palladium, toluene 60mL, heated at 110°C for 20 hours. After cooling to room temperature, the solution was washed with water (3 x 60 mL). The organic layer was washed with anhydrous MgSO 4 Dry, filter and remove solvent under reduced pressure. Purification by column chromatography (eluent: petroleum ether / ethyl acetate=80:1) gave 1.47 g of white product with a yield of 56%.

[0071] Adopt nuclear magnetic resonance (NMR) to measure the product obtained, the obtained result is: 1 H NMR (400MHz, CDCl 3 )δ8.82(d, J=4.9Hz, 1H), 8.26(s, 1H), 7.79(dd, J=5.0, 1.2Hz, 1H), 7.22(d, J=2.2Hz, 2H), 6.56( t, J=2.2Hz, 1H), 4.45(d, J=7.1Hz, 2H), 3.89(s, 6H), 1.44(t, J=7.1Hz, 3H). 13 C NMR (100MHz, CDCl 3...

Embodiment 2

[0073] Synthesis of Ligand 2-(3,5-Dimethylphenyl)isonicotinic acid ethyl ester

[0074]

[0075] The preparation method is the same as in Example 1, except that 3,5-dimethoxyphenylboronic acid is replaced by 3,5-dimethylphenylboronic acid. A white solid was obtained by column chromatography with a yield of 46%.

[0076] Adopt nuclear magnetic resonance (NMR) to measure the product obtained, the obtained result is: 1 H NMR (400MHz, CDCl 3 )δ8.82(d,J=5.0Hz,1H),8.28(s,1H),7.84–7.74(m,1H),7.67(s,2H),7.10(s,1H),4.45(m,2H ),2.42(s,6H),1.45(dd,J=13.4,6.3Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ165.34, 158.72, 150.24, 138.40, 131.14, 124.85, 120.96, 119.80, 61.82, 21.39, 14.26; test results proved that the obtained product was ethyl 2-(3,5-dimethylphenyl)isonicotinate.

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Abstract

The invention provides an iridium (III) complex. A 2-phenylethyl isonicotinate derivative is used as the main ligand, and 3,6-di-tert-butyl -9-(4-(4,5)-dimethyl-2-(pyrid-2-yl)-1H-imidazol-1-yl) butyl)-9H-carbazole is used as the auxiliary ligand. The iridium (III) complex has good light stability, large Stokes shift, high luminous efficiency and aggregation-induced emission property, and can be applied to the field of cell imaging.

Description

technical field [0001] The invention relates to the field of organic photoelectric functional materials, in particular to an iridium (III) complex and its preparation method and application. Background technique [0002] Biological probes can effectively help us to monitor the internal environment of organisms in real time or effectively trace drugs, and have become very important tools in the biomedical field of life sciences. However, some common disadvantages of traditional biological probes are poor photostability, small Stokes shift, and concentration quenching effect. In recent years, octahedral iridium complexes have attracted widespread attention due to their high quantum yield, easily adjustable emission wavelength, large Stokes shift and relatively long lifetime. [0003] In 2010, Li Fuyou's research group published the research on five cationic iridium complexes with tunable emission color as phosphorescent dyes for cell imaging. The emission wavelength and phos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0033C09K11/06C09K2211/185G01N21/6428G01N2021/6439
Inventor 刘睿黎杨施红朱红军朱森强唐猛陆佳鹏
Owner NANJING TECH UNIV
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