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Phosphorescent ionic type iridium complex probe and preparation method and application thereof

An iridium complex and ionic technology is applied in the field of preparation of phosphorescent iridium complex materials, which can solve problems such as harm to organisms, and achieve the effects of high selectivity, fast response and remarkable detection effect.

Inactive Publication Date: 2014-02-05
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the production of ROS is essential for life in the normal cellular environment, they can also be harmful to the organism when they are produced in excess under exogenous stimuli

Method used

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  • Phosphorescent ionic type iridium complex probe and preparation method and application thereof
  • Phosphorescent ionic type iridium complex probe and preparation method and application thereof
  • Phosphorescent ionic type iridium complex probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: When N^N ligand is (Biquinoline), the preparation of iridium complex Ir-1 containing aldehyde group (CHO):

[0025] Complex Ir-1: Weigh 4-(2-pyridyl)benzaldehyde (2.5mmol) and IrCl 3 ·3H 2 O (1 mmol) was mixed and put into a three-necked bottle, and the double-row tube was vacuumized-nitrogen-gas-vacuumized, and the cycle was repeated three times, and finally the whole reaction system was protected by nitrogen gas. A mixture of ethylene glycol ether and water with a volume ratio of 3:1 was injected into the reaction system, the temperature was raised to 110° C., and the reaction was performed under magnetic stirring for 24 hours. After the reaction, the system was cooled to room temperature, the precipitate was filtered, and washed with ethanol and water. The obtained solid product was pyridylbenzaldehyde iridium dichloro bridge, which could be directly put into the next reaction.

[0026] Weigh the C^N ring metal ligand dichloro bridge (1mmol) and biq...

Embodiment 2

[0028] Example 2: Preparation of complex Ir-2 containing oxime group (C=N-OH):

[0029] Preparation of complex Ir-2: Weigh iridium complex Ir-1 (1mmol) and hydroxylamine hydrochloride (5mmol) into a double-neck flask, vacuumize on the double-row tube - nitrogen gas - vacuum, cycle back and forth three times, and finally Nitrogen was used to protect the entire reaction system. Inject 5 mL of distilled ethanol solution and 5 mmol of distilled triethylamine, and mix and stir at 60° C. for 4 hours. After the reaction was completed, it was concentrated and purified. The red solid product obtained is the iridium complex Ir-2. Yield: 81%. 1 H NMR (400MHz, DMSO): δ=11.14(s,1H),10.53(s,9H),10.36(s,2H),9.03–9.00(m,1H),8.94–8.91(m,1H),8.18 (s,1H),8.10(s,1H),7.88(d,J=10.4Hz,2H),7.85(s,1H),7.83(d,J=4.0Hz,2H),7.82(s,1H) ,7.57(t,J=7.4Hz,2H),7.15(t,J=9.0Hz,3H),7.08(t,J=6.5Hz,2H),6.47(s,1H); 13 CNMR(101MHz,DMSO)δ=166.19,160.22,150.95,148.76,148.72,148.58,147.72,144.89,144.40,141.89,139.3...

Embodiment 3

[0031] Embodiment 3: the ultraviolet-visible absorption spectrum of probe Ir-2 is to ClO - Responsiveness:

[0032] Dissolve the iridium complex Ir-2 in CH 3 OH / H 2O (v / v, 2:1, pH7.2) mixed solution, adding ClO - CH 3 OH / H 2 O mixed solution, each drop of ClO - After that, heat and stir in a constant temperature water bath at 37°C for 5 minutes to make the ClO - Fully react with the iridium complex Ir-2, and then test its ultraviolet absorption intensity. like figure 1 As shown, with ClO - The addition of , the absorption spectrum of the iridium complex Ir-2 solution changed immediately, accompanied by ClO - The concentration of dropwise increases, when ClO - When the equivalent of the dropping concentration reaches 30eq., the titration reaches the end point, and then continue to drop ClO - , the spectrum does not change.

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Abstract

The invention discloses a phosphorescent ionic type iridium complex probe and a preparation method and application thereof, and particularly relates to a phosphorescent iridium complex for detecting hypochlorite (ClO<->) and containing an oxime group (C=N-OH) and an application thereof. The material of the complex consists of a ring metal ligand containing an oxime group, a metal center and an N^N ligand, and the structural general formula is shown in the specification. The synthesis steps of the material are simple, the conditions are mild, and the material has very good application prospects in hypochlorite detection, cell imaging and bio-labeling.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials. It specifically relates to a preparation method of a kind of phosphorescent iridium complex material and its application in hypochlorite detection, cell imaging and biomarker. Background technique [0002] Molecular oxygen is an essential component for all oxygen-consuming organisms to maintain their life activities. Reactive oxygen species (ROS) is a type of molecular oxygen produced during human metabolism, including peroxides, hydroxyl groups, peroxyl radicals, peroxidation Hydrogen, singlet oxygen and hypochlorous acid / hypochlorite. The reactive oxygen species ROS in the human body is mainly oxygen produced through the process of mitochondrial respiration. At the same time, it can also be induced by external disturbances, such as exogenous chemicals, infectious agents and ultraviolet rays. ROS are involved in a wide range of physiological and pathological ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00G01N21/64C12Q1/02
Inventor 赵强黄维于海霞许文娟刘淑娟唐艳
Owner NANJING UNIV OF POSTS & TELECOMM
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