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Dinuclear cyclic metal iridium complex as well as preparation method and application thereof

A technology of iridium complexes and ring metals, which is applied in the direction of indium organic compounds, platinum group organic compounds, chemical instruments and methods, etc., to achieve the effect of strong lipophilicity

Active Publication Date: 2016-09-21
苏州纳凯科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Cyclometallic iridium(III) complexes with dual-emission properties are mainly formed by coupling with other luminescent molecules, while dual-emission probes directly composed of pure iridium(III) complexes have not been reported yet.

Method used

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  • Dinuclear cyclic metal iridium complex as well as preparation method and application thereof
  • Dinuclear cyclic metal iridium complex as well as preparation method and application thereof
  • Dinuclear cyclic metal iridium complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The present embodiment provides 6-chlorophenanthridine (structural formula is: ) synthetic route, such as figure 1 As shown, specifically:

[0046] 6(5H)-phenanthridone (5.11g, 26.2mmol) and phosphorus pentachloride (6.12g, 29.4mmol) were placed in a 250ml one-necked flask, 50ml of phosphorus oxychloride was added, and refluxed at 100°C for 2 hours under nitrogen protection ; Cool to room temperature, add 50ml of toluene to dilute the reaction solution, then spin off most of the excess phosphorus oxychloride, slowly pour the residual liquid into 2mol / L ammonia water, and extract the separated solid 3 times with 100ml of ethyl acetate; wash with water , dried over anhydrous magnesium sulfate and spin-dried to obtain 5.1 g of light yellow product. The resulting crude product was separated by silica gel column chromatography (EA:PE=2:3, v / v, the same below) to obtain 4.93 g of yellow flaky solid with a yield of 88.1%. figure 1 shown.

Embodiment 2

[0048] Present embodiment also provides 6-chlorophenanthridine (structural formula is: ) synthetic route, specifically:

[0049] Under nitrogen protection, 6(5H)-phenanthridinone (7.68g, 39.3mmol) was dissolved in 20ml SOCl 2 medium (0.5ml DMF as catalyst) at 85°C for 3 hours; after the reaction, spin dry excess SOCl 2 . Add dichloromethane to dissolve the residual solid, wash with saturated sodium bicarbonate solution three times, dry and spin dry, and put on a silica gel column; use DCM:PE=2:1 as the eluent to wash the column to separate the second component to obtain light yellow Flaky solid 5.49g, yield 65.3%. GC-MS: m / z (M + ) calcd 213.0, found 213.0. 1 H NMR (400MHz, CDC 3 )δ8.60(d,J=8.3Hz,1H),8.55-8.45(m,2H),8.09(dd,J=8.1,1.0Hz,1H),7.90(ddd,J=8.3,7.1,1.3Hz ,1H),7.79-7.65(m,3H).

Embodiment 3

[0051] The present embodiment provides 6-(2-benzo[b]thienyl)phenanthridine (BTPhen, the structural formula is: ) synthetic route, specifically:

[0052] Add 6-chlorophenanthridine (5.16g, 24.1mmol), 2-benzothiophene boronic acid (6.56g, 36.9mmol), Pd(PPh 3 ) 4 (1.47g, 1.27mmol) and anhydrous sodium carbonate (5.17g, 48.78mol), 24ml of water, 40ml of absolute ethanol and 80ml of toluene were added successively, and nitrogen replacement was performed three times after stirring evenly; then stirred and refluxed at 90°C for 12 hours; Cool to room temperature after the reaction, separate the toluene layer, extract the water phase with 100ml dichloromethane three times and merge into the toluene phase; spin dry and separate by silica gel column chromatography (DCM:PE=1:1) to obtain 6.84g white fine needles like crystals with a yield of 91.0%. GC-MS: m / z([M-H] + ) calcd 310.1, found 310.1. 1 H NMR (400MHz, CDCl 3 )δ8.70(d, J=8.3Hz, 1H), 8.65(d, J=8.3Hz, 1H), 8.59(d, J=7.8Hz, 1...

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Abstract

The invention relates to a dinuclear cyclic metal iridium complex as well as a preparation method and application thereof. A chemical structure formula of the complex is shown in the description, wherein a form I and a form II shown in the description are bidentate ligands taking C and N atoms as ligand atoms and mutually independently have the following structures: formula I, formula II, formula III, formula IV, formula V, formula VI or formula VII shown in the description, wherein R is a hydrogen atom, alkyl, alkoxy, alkyl sulphanyl, alkyl amino, aryl, aryloxy, arylthio, aryl amino, aryl alkyl, aryl alkoxy, aryl alkyl sulphanyl, aryl alkyl amino, acyl, acyloxy, acylamino, imino or carboxyl; X is Cl, Br, I, PF6, BF4 or (CF3SO2)2N; n and m are mutually independently and are integers of 1 to 6. The dinuclear cyclic metal iridium complex is a single-excitation and double-emission phosphorescent probe, and absorption and luminescent properties of two phosphorescent groups are kept very well; the dinuclear cyclic metal iridium complex is hopeful to be used for phosphorescent ratio type O2 sensing and imaging, has relatively strong lipotropy and can be used for mitochondrial location.

Description

technical field [0001] The invention belongs to the field of biological imaging and relates to a dinuclear cyclometal iridium complex, in particular to a dinuclear cyclometal iridium complex and a preparation method and application thereof. Background technique [0002] With the development of microscope technology, cell and in vivo imaging has increasingly become a routine research method in life science, chemical biology and biomedicine. Finding new bioimaging probes and materials has always been one of the most important topics in cell and in vivo imaging. The luminescent imaging agents or probes used in cell and in vivo imaging reported so far are various and complicated, and can be roughly divided into three categories: nanoprobes, macromolecular probes and small molecule probes. [0003] Small molecule probes are the earliest studied, most diverse, and most widely used biological probes. According to the excitation method, they can be divided into photoluminescence pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0033C09K11/06C09K2211/185G01N21/6456
Inventor 刘扬张庆庆周明
Owner 苏州纳凯科技有限公司
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