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Water-soluble cationic iridium complex phosphorescence probe and preparation method

A water-soluble cation and iridium complex technology, applied in the field of phosphorescent chemical probes, can solve the problems of cell damage, no hydrophilic group, high rigidity, etc., and achieve the effect of eliminating interference and improving detection sensitivity.

Inactive Publication Date: 2010-07-28
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the phosphorescent probes reported in the literature have good fat solubility, but because their organic ligands are insoluble in water, very rigid, and have no hydrophilic groups, their water solubility is generally poor. can not enter the cell, or enter the cell concentration is very small
This greatly affects their application range, and also causes a certain degree of damage to cells.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0052] 2-Phenylpyridine iridium dichloro bridge complex (Ir 2 (ppy) 4 Cl 2 ) preparation: weigh IrCl 3 ·3H 2 O (5.52mmol) and 2,4-difluorophenylpyridine (11.04mmol) were added in the three-necked flask, and then the mixed solution of 2-ethylene glycol ether and water was added, and the volume ratio of the two was 4:1; then The reaction mixture was heated to 110° C. and stirred for 30 hours. After the reaction was completed, it was cooled to room temperature (25° C.), and a yellow precipitate was formed. The resulting precipitate was washed with water and ethanol, respectively, and dried in vacuo to obtain a bright yellow solid 2,4-difluorophenylpyridine iridium dichloro bridge complex, Ir 2 (dfppy) 4 Cl 2 .

Embodiment 2

[0054] The preparation of 3,8-diethynyl o-phenanthroline: under nitrogen protection, 3,8-dibromophenanthroline 10.68mmol, Pd (pph 3 ) 4 0.54mmol, 5mol%, CuI 1.50mmol, 14mol% were mixed in 160mL of degassed tetrahydrofuran and triethylamine degassed (v / v 8:1) mixed solution, and then added 42.72mmol of trimethylsilylacetylene. After heating to reflux for 18 hours, it was cooled, and the solid was removed by filtration, and an appropriate amount of dichloromethane was added to the filtrate. Then it was washed with water three times, dried over anhydrous magnesium sulfate, and the solvent was spun out; the obtained solid was dissolved in 90 mL of methanol, and excess potassium fluoride was added, and stirred at room temperature for 25 hours. After the reaction, it was washed with water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, and purified by spin-drying column chromatography to obtain a white solid product.

[0055] 1 H NMR: (400MHz, CDCl 3 ), ...

Embodiment 3

[0057] Preparation of 3,8-diethynyl-phenanthroline iridium 2-phenylpyridine complex: Accurately weigh 0.25 mmol of 2-phenylpyridine-iridium dichloro bridge complex and 3,8-diethynyl-phenanthroline Add 0.75mmol into a three-neck flask; add 60mL of a mixed solution of dichloromethane and methanol, the volume ratio of which is 5:1; heat to 45°C, and stir for 26 hours. After the reaction, the reaction solution was spin-dried, and the red solid product was obtained by chromatography.

[0058] 1 H NMR: (400MHz, CDCl 3 ), δ(ppm): 8.98(s, 2H), 8.64(s, 2H), 8.19(d, 2H, J=1.6Hz), 7.95(d, 2H, J=8.4Hz), 7.78(t, 2H , J=7.6Hz), 7.73(d, 2H, J=6.8Hz), 7.32(d, 2H, J=5.6Hz), 7.08(t, 2H, J=7.4Hz), 6.97(m, 4H), 6.35 (d, 2H, J = 7.2 Hz), 3.47 (s, 2H).

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Abstract

The invention relates to the technology of phosphorescence chemical probe, in particular to a water-soluble cationic iridium complex phosphorescence probe and a preparation method. Iridium metal is not used for cell marking in the prior art. The structural formula of the water-soluble cationic iridium complex phosphorescence probe of the invention is as shown in the attached figure. The preparation of the invention is as follows: preparing 2-phenylpyridine iridium dichlorendic complex Ir2 (ppy) 4Cl2; preparing 3, 8-diacetylene o-phenanthroline; preparing 3, 8-diacetylene o-phenanthroline iridium 2-phenylpyridine complex; and preparing the objective complex. The invention has the advantages that with good water solubility and lipid solubility, the complex can quickly enter cells; and with long luminescent lifetime of iridium complex, the interference of the background fluorescence can be effectively eliminated through the time-resolved fluorescence technique, and thereby improving the detection sensitivity can be improved.

Description

technical field [0001] The invention belongs to the phosphorescent chemical probe technology, in particular to a water-soluble cationic iridium complex phosphorescent probe and a preparation method. Background technique [0002] With the rapid development of cell labeling technology, the requirements for fluorescent dyes are getting higher and higher. Existing technologies such as organic dyes, fluorescent proteins, etc., all have many shortcomings, such as the emission wavelength of organic dyes is not easy to adjust; Stokes (Stokes) ) displacement is small; the source range of fluorescent protein materials is narrow; and the operation is cumbersome; it is not easy to modify it; the emission wavelength range is narrow, and it is seriously interfered by background fluorescence. Phosphorescent heavy metal complexes have superior photophysical properties, the main features are: the emission wavelength changes with the environment; compared with organic phosphorescent materials...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
Inventor 杨红李刘涛杨仕平
Owner SHANGHAI NORMAL UNIVERSITY
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