Binuclear ion-type phosphorescence iridium complex, preparation method and application thereof

An iridium complex, ionic technology is applied to a class of dual-nuclear ionic phosphorescent iridium complexes and their preparation and application fields, which can solve the problems of limited fluorescence characteristics, difficulty in completely eliminating background noise, and reduced fluorescence imaging sensitivity. Low toxicity, avoids photodamage and photobleaching problems, and achieves the effect of two-photon excitation

Inactive Publication Date: 2014-05-28
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although different techniques are used to separate background light, it is difficult to completely eliminate background noise due to the limitation of fluorescence characteristics, which reduces the sensitivity of fluorescence imaging

Method used

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  • Binuclear ion-type phosphorescence iridium complex, preparation method and application thereof
  • Binuclear ion-type phosphorescence iridium complex, preparation method and application thereof
  • Binuclear ion-type phosphorescence iridium complex, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: [(ppy) 2 Ir(tpphz)Ir(ppy) 2 ] 2+ (PF 6 - ) 2 (Ir1) Preparation

[0038]

[0039] 1,10-phenanthroline-5,6-dione: In a 250mL three-necked flask, add 1,10-phenanthroline (5g, 27.7mmol) and potassium bromide (25g, 16.8mmol), and mix well. Slowly add 100mL concentrated sulfuric acid and 50mL concentrated nitric acid at 0°C, slowly raise the temperature to 70-80°C, and reflux for 1-4 hours (absorb the generated tail gas with sodium hydroxide solution). After the reaction was completed and the tail gas was removed, the system was transferred to a 500mL beaker, and solid sodium hydroxide was added to neutralize the excess acid. Observed with pH test paper, when neutralized to neutral, a large amount of flocculent precipitates are produced in the solution. After filtration, 1,10-phenanthroline-5,6-dione was obtained as a light yellow solid, which was weighed after drying, and the yield was 72% to 79%.

[0040]

[0041] tpphz: Add 1,10-phenanthroline-5,6-...

Embodiment 2

[0048] Example 2: [(dfppy) 2 Ir(tpphz)Ir(dfppy) 2 ] 2+ (PF 6 - ) 2 (Ir2) Preparation

[0049]

[0050] 1,10-phenanthroline-5,6-dione: In a 250mL three-necked flask, add 1,10-phenanthroline (5g, 27.7mmol) and potassium bromide (25g, 16.8mmol), and mix well. Slowly add 100mL concentrated sulfuric acid and 50mL concentrated nitric acid at 0°C, slowly raise the temperature to 70-80°C, and reflux for 1-4 hours (absorb the generated tail gas with sodium hydroxide solution). After the reaction was completed and the tail gas was removed, the system was transferred to a 500mL beaker, and solid sodium hydroxide was added to neutralize the excess acid. Observed with pH test paper, when neutralized to neutral, a large amount of flocculent precipitates are produced in the solution. After filtration, 1,10-phenanthroline-5,6-dione was obtained as a light yellow solid, which was weighed after drying, and the yield was 72% to 79%.

[0051]

[0052] tpphz: Add 1,10-phenanthroline-...

Embodiment 3

[0059] Embodiment 3: [(ppy) 2 Ir(tpphz)Ir(ppy) 2 ] 2+ (Cl - ) 2 Preparation of (Ir5)

[0060]

[0061] 1,10-phenanthroline-5,6-dione: In a 250mL three-necked flask, add 1,10-phenanthroline (5g, 27.7mmol) and potassium bromide (25g, 16.8mmol), and mix well. Slowly add 100mL concentrated sulfuric acid and 50mL concentrated nitric acid at 0°C, slowly raise the temperature to 70-80°C, and reflux for 1-4 hours (absorb the generated tail gas with sodium hydroxide solution). After the reaction was completed and the tail gas was removed, the system was transferred to a 500mL beaker, and solid sodium hydroxide was added to neutralize the excess acid. Observed with pH test paper, when neutralized to neutral, a large amount of flocculent precipitates are produced in the solution. After filtration, 1,10-phenanthroline-5,6-dione was obtained as a light yellow solid, which was weighed after drying, and the yield was 72% to 79%.

[0062]

[0063] tpphz: Add 1,10-phenanthroline-5...

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Abstract

The invention discloses a novel binuclear ion-type phosphorescence iridium complex, a preparation method thereof, and an application of the complex in bio-imaging. The chemical structure of the complex can be represented by a formula I: [Ir(C^N)2(tpphz)Ir(C^N)2]+Y-2, wherein tpphz represents tetrapyridinophenazine, C^N ligand is phenylpyridine (ppy), 2,4-difluorophenylpyridine (dfppy), thiophene quinoline (tpq) and 2-(4-dimesitylborylphenyl)quinoline (bpq), and the counter ion Y is PF6<-> and Cl<->. The iridium complex has the advantages of long phosphorescence lifetime , large Stokes shift, good optical stability, low toxicity, and good biocompatibility, and is an excellent probe for cell imaging.

Description

technical field [0001] The invention relates to the preparation and application of a class of dinuclear ionic phosphorescent iridium complexes Background technique [0002] Using the combination of molecular probes and fluorescence microscopes to stain and image cells is one of the more efficient and convenient cell detection techniques today. However, fluorescent molecular probes face a series of problems in the process of cell imaging, such as poor water solubility, high toxicity, and easy photobleaching. Some commercial nuclear stains, such as 4',6-diamidino-2-phenylindole (DAPI) and Hoechst Stains, require excitation with UV light, which can be somewhat harmful to Cell damage. In addition, fluorescence has a short lifetime. In the process of fluorescence imaging, when excited by the excitation light, many substances in the organism will produce fluorescence. Although different techniques are used to separate background light, it is difficult to completely eliminate b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54G01N21/64
Inventor 赵强黄维梁花许文娟刘淑娟徐杭
Owner NANJING UNIV OF POSTS & TELECOMM
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