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Diisoindole iridium (III) complex and preparation method thereof

A technology of indole iridium and complexes, which is applied in the field of bisisoindole iridium complexes and their preparation, can solve the problems of difficulty in synthesis, short absorption wavelength of complexes, inability to reach near infrared rays and the like

Active Publication Date: 2021-09-10
THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a kind of bis-isoindole iridium (III) complex, aiming at solving the short absorption wavelength of the existing iridium (III) complex, which cannot Reaching near-infrared, limited application range and other technical problems
[0006] Another object of the present invention is to provide a method for preparing bisisoindole iridium (III) complexes, aiming to solve the problem of existing iridium (III) complexes The preparation method of this method has technical problems such as expensive raw materials, harsh reaction conditions, relatively difficult synthesis, and the synthesized complex has a short absorption wavelength and cannot reach near-infrared

Method used

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  • Diisoindole iridium (III) complex and preparation method thereof
  • Diisoindole iridium (III) complex and preparation method thereof
  • Diisoindole iridium (III) complex and preparation method thereof

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preparation example Construction

[0059] Correspondingly, the embodiment of the present invention also provides a preparation method of bisisoindole iridium (III) complex, comprising the following steps:

[0060] S10. Under the first protective gas atmosphere, obtain a mixed solution of isoindolinone compounds, pyrrole compounds and phosphorus oxychloride, and perform a first contact reaction to obtain a first product;

[0061] S20. Alkali treatment is performed on the first product to obtain bisisoindole ligand compound;

[0062] S30. Under the second protective gas atmosphere, after mixing the bisisoindole ligand compound, iridium (III) dimer and silver hexafluorophosphate with an organic solvent, perform a second contact reaction to separate and obtain bisisoindole Indole iridium(III) complexes.

[0063] The preparation method of the bis-isoindoline iridium (III) complex provided by the embodiment of the present invention is to carry out the first contact reaction of the isoindolinone compound and the pyrr...

Embodiment 1

[0078] A kind of synthesis of bisisoindole iridium (III) complex Ir-1:

[0079]

[0080] Under nitrogen protection, dissolve isoindolinone (100mg, 0.75mmol) and pyrrole (62μL, 0.90mmol) in anhydrous chlorobenzene (20mL), add phosphorus oxychloride (68μL, 0.75mmol), and mix The solution was heated to 110°C and stirred for 6h. TLC tracking spot plate, after the consumption of isoindolinone is complete, add sodium carbonate saturated solution containing potassium ferricyanide to the reaction system, continue stirring at room temperature for 2h, then transfer the reaction mixture to a separatory funnel, add dichloromethane Methane and water, extract, stand still, separate the organic phase, extract the corresponding aqueous phase with dichloromethane three times, and combine the organic layers. The organic phase was washed once with water, dried over anhydrous sodium sulfate, filtered, the solvent was concentrated in vacuo, and purified by silica gel column chromatography to o...

Embodiment 2

[0088] A kind of synthesis of bisisoindole iridium (III) complex Ir-2:

[0089]

[0090] Get the obtained bisisoindole ligand powder 54mg (0.15mmol), iridium (III) dimer Ir dimer2 (0.075mmol, 96mg) and silver hexafluorophosphate (0.15mmol, 38mg) in methanol and 1 , in a 1:1 system of 2-dichloroethane (total volume 20mL), stir at 80°C for 2h to obtain the target product, purify it with silica gel column chromatography, and then recrystallize it with dichloromethane and n-hexane to obtain Bisisoindole iridium(III) complex powder Ir-2, yield 47% (78mg).

[0091] The NMR data and high-resolution mass spectrometry data of the bisisoindole iridium (III) complex Ir-2 are as follows:

[0092] 1 H NMR (400MHz, CD 3 CN)δ9.27(s,2H),8.67(dd,J=6.5,3.5Hz,2H),8.55(d,J=7.9Hz,2H),8.21(d,J=6.4Hz,2H),8.10 (d,J=8.1Hz,2H),7.95(d,J=7.9Hz,2H),7.86(dd,J=6.5,3.2Hz,2H),7.76–7.66(m,7H),7.52(t, J=7.7Hz, 2H), 7.35(d, J=6.4Hz, 2H), 7.01(t, J=7.6Hz, 2H), 6.89(s, 2H), 6.78(t, J=7.4Hz, 2H) ,6.48(s,2H...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a diisoindole iridium (III) complex which is characterized in that the structural general formula of the diisoindole iridium (III) complex is as shown in a formula I defined in the description, wherein R1, R2 and R3 are respectively and independently selected from one of H, alkyl with the carbon atom number of 1-12 and naphthenic base with the carbon atom number of 3-12; and Ar1 and Ar2 are each independently selected from a group containing an aromatic ring. The diisoindole iridium (III) complex has structural diversity and high molar absorption coefficient, the maximum absorption wavelength can reach a near-infrared region, and the diisoindole iridium (III) complex has good application prospects in the fields of biomedicine, material science and the like as a photosensitizer, an imaging reagent, a strong near-infrared absorber and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a bisisoindole iridium (III) complex and a preparation method thereof. Background technique [0002] Metal iridium(III) complexes are widely used in organic electroluminescence, biomedical imaging, sensing, catalysis, etc. field has potential application prospects. Different main ligands and auxiliary ligands play an important role in the iridium(III) complexes, and the interaction between iridium(III) and the complexes exhibits different electronic transition properties. [0003] However, in the current prior art, the main ligands of iridium(III) complexes are mostly bipyridyl systems and their derivatives, and their preparation generally involves metal-catalyzed preparation, and there are expensive raw materials, harsh reaction conditions, and relatively difficult synthesis. shortcoming. Moreover, the absorption wavelength of the electron-deficient bipyridine syste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00
CPCC07F15/0033C07B2200/13
Inventor 黄维扬于长江
Owner THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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