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A kind of iridium complex containing (hydrazinocarbonyl) ferrocene ligand and preparation method and application thereof

A technology of hydrazinocarbonyl and iridium complexes, applied in the field of fluorescent materials, can solve the problems of less research, achieve high sensitivity, reduce the proportion of side reactions, and shorten the production cycle

Active Publication Date: 2019-07-30
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Previous studies have focused on the synthesis of iridium metal complexes with good fluorescence quantum yields, and less research has been done on iridium metal complexes for the targeted detection of hypochlorous acid

Method used

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  • A kind of iridium complex containing (hydrazinocarbonyl) ferrocene ligand and preparation method and application thereof
  • A kind of iridium complex containing (hydrazinocarbonyl) ferrocene ligand and preparation method and application thereof
  • A kind of iridium complex containing (hydrazinocarbonyl) ferrocene ligand and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0038] The method for preparing the iridium complex containing (hydrazinocarbonyl) ferrocene ligand in this embodiment consists of the following steps:

[0039] (1) Preparation of chlorine-bridged dimers

[0040] Under nitrogen protection, 0.3528g (1mmol) of IrCl 3 ·3H 2 O was added to the mixed solvent of 2-ethoxyethyl ether and water, 2-ethoxyethanol: water (V:V) = 30:10mL, magnetically stirred for 15min, after stirring evenly, 0.4792g (2.2mmol) 2-Phenylbenzothiazole, heated to 120°C, refluxed, stirred for 24 hours, then stopped the reaction, cooled to room temperature, and filtered with suction to obtain a precipitate, which was washed with 30mL of secondary deionized water, 30mL of ethanol and 30mL of n-hexane , vacuum drying in a drying oven at 50°C for 12 hours to dryness to obtain an orange-red powdery chlorine-bridged dimer;

[0041] (2) Preparation of 4'-methyl-2,2'-bipyridine-4-(hydrazinocarbonyl)ferrocene

[0042] Under anhydrous and oxygen-free conditions, add 21...

Embodiment 2

[0048] The method for preparing the iridium complex containing (hydrazinocarbonyl) ferrocene ligand in this embodiment consists of the following steps:

[0049] (1) Preparation of chlorine-bridged dimers

[0050] Under nitrogen protection, 0.3528g (1mmol) of IrCl 3 ·3H 2 O was added to the mixed solvent of 2-ethoxyethyl ether and water, 2-ethoxyethanol: water (V:V) = 30:10mL, magnetically stirred for 15min, after stirring evenly, 0.4356g (2mmol) of 2-Phenylbenzothiazole, heated to 120°C, refluxed, stirred for 15 hours, then stopped the reaction, cooled to room temperature, and filtered with suction to obtain a precipitate, which was washed with 30mL secondary deionized water, 30mL ethanol and 30mL n-hexane respectively, Vacuum bake in a drying oven at 50°C for 12 hours to dryness to obtain an orange-red powdery chlorine-bridged dimer;

[0051] (2) Preparation of 4'-methyl-2,2'-bipyridine-4-(hydrazinocarbonyl)ferrocene

[0052] Under anhydrous and oxygen-free conditions, ad...

Embodiment 3

[0056] (1) Preparation of chlorine-bridged dimers

[0057] Under nitrogen protection, 0.3528g (1mmol) of IrCl 3 ·3H 2 O was added to the mixed solvent of 2-ethoxyethyl ether and water, 2-ethoxyethanol: water (V:V) = 30:10mL, magnetically stirred for 15min, after stirring evenly, 0.5445g (2.5mmol) 2-Phenylbenzothiazole, heated to 120°C, refluxed, stirred for 18 hours, then stopped the reaction, cooled to room temperature, and filtered with suction to obtain a precipitate, which was washed with 30mL of secondary deionized water, 30mL of ethanol and 30mL of n-hexane , vacuum drying in a drying oven at 50°C for 12 hours to dryness to obtain an orange-red powdery chlorine-bridged dimer;

[0058] (2) Preparation of 4'-methyl-2,2'-bipyridine-4-(hydrazinocarbonyl)ferrocene

[0059] Under anhydrous and oxygen-free conditions, add 214mg (1mmol) of 4'-methyl-2,2'-bipyridine-4-carboxylic acid into 50mL of thionyl chloride solvent, heat to reflux at 75°C, and stop after stirring for 3h ...

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Abstract

The invention relates to an iridium complex containing a (hydrazine carbonyl) ferrocene ligand and a preparation method thereof and application. Under nitrogen protection, chloro-bridged dimer and 4'-methyl-2,2'-dipyridyl-4-(hydrazine carbonyl) ferrocene are added into dichloromethane solvent to undergo thermal reaction, and an iridium complex containing the hydrazine carbonyl-ferrocene ligand is obtained. The hydrazine carbonyl ferrocene is introduced into the iridium complex for the first time, characteristics that hydrazine carbonyl can be specially cut by hypochlorous acid are combined with characteristics that ferrocene has intracellular quench fluorescent effects, so the fluorescence characteristic of the iridium complex is quenched by ferrocene, hydrazine carbonyl is specially cut by hypochlorous acid after being met with hypochlorite, switching on and switching off of light-emitting signals are achieved, and thus serving as a fluorescent probe for hypochlorite, the iridium complex achieves detection of content of hypochlorous acid in organisms and cells. Besides, the iridium complex has the advantages of high sensitivity, high selectivity, rapid fluorescence response, wide pH range and so on.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials, and in particular relates to an iridium complex containing (hydrazinocarbonyl) ferrocene ligand, a preparation method and application thereof. Background technique [0002] Iridium metal complexes have aroused great research interests of many scholars because of their good fluorescence quantum yield and luminous efficiency and good optical stability. Compared with ruthenium bipyridine complexes, iridium metal complexes have the advantages of high luminous efficiency, long lifetime, and high sensitivity, and have been favored by analytical chemists in recent years. Previous studies have focused on the synthesis of iridium metal complexes with good fluorescence quantum yields, and less research has been done on iridium metal complexes for the targeted detection of hypochlorous acid. Similar to other ROS / RNS, hypochlorous acid / hypochlorite plays an important physiological role in orga...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C09K11/06G01N21/64
CPCC07F17/02C09K11/06C09K2211/185C09K2211/187G01N21/6402G01N21/6486
Inventor 张成孝韩丹娟漆红兰
Owner SHAANXI NORMAL UNIV
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