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Rare earth europium fluorescent chelating agent and preparation method thereof

A chelating agent and fluorescent technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as poor optical properties

Active Publication Date: 2010-06-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Due to the Eu used for immunolabeling 3+ The molecular structure of chelating agent (Michael P., etal.Analyst, 1984,109,1449-1450) is still under study, so far has not obtained ideal fluorescence intensity with practical value, currently used in molecular biology, genomics , Proteomic analysis still uses organic dyes with poor optical properties

Method used

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  • Rare earth europium fluorescent chelating agent and preparation method thereof
  • Rare earth europium fluorescent chelating agent and preparation method thereof
  • Rare earth europium fluorescent chelating agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] (1) Preparation of 2-bromo-6-picoline

[0102] Dissolve 70g of 2-amino-6-picoline in 330ml of HBr solution with a mass concentration of 40%, keep it at 0°C, and add 100ml of Br with a concentration of 0.02mol / ml dropwise 2 , then dropwise add 175ml of aqueous solution containing sodium nitrite 0.66g / ml, stir for 30min, continue to dropwise add 265ml of aqueous solution containing NaOH 0.95g / ml, stir for another 30min, extract with dichloromethane, and use MgSO 4 After absorbing water and drying, vacuum distillation collected 103 g of distillate 2-bromo-6-picoline at 4 mmHg at 62 ° C, bp 129-130 ° C, yield 72%.

[0103] (2) add 2-bromo-6-picoline 88g in the reactor, sodium formate dihydrate 82.0g, be the palladium carbon catalyst 3.2g of 5% with mass concentration, benzyltriethylammonium chloride 21.2g (0.08 mol), mass concentration is 32% NaOH solution 53ml, H 2 O 130ml, stirred, heated to reflux reaction 48h, added 3.8g sodium formate dihydrate, 0.8g palladium carbon...

Embodiment 2

[0122] (1) Preparation of 2-bromo-6-picoline

[0123] Dissolve 73g of 2-amino-6-picoline in 330ml of HBr solution with a mass concentration of 40%, keep it at -8°C, and add 100ml of Br with a concentration of 0.02mol / ml dropwise 2 , then dropwise add 175ml of aqueous solution containing sodium nitrite 0.66g / ml, stir for 30min, continue to dropwise add 265ml of aqueous solution containing NaOH 0.95g / ml, stir for another 30min, extract with dichloromethane, and use MgSO 4 After absorbing water and drying, vacuum distillation collected 103 g of distillate 2-bromo-6-methylpyridine at 4 mmHg at 63°C, bp 129-130°C, yield 71%.

[0124] (2) Preparation of 6,6'-dimethyl-2,2'-bipyridine

[0125] Add 2-bromo-6-picoline 90g in reactor, sodium formate dihydrate 82.0g, be 5% palladium carbon catalyst 3.2g, benzyltriethylammonium chloride 21.2g (0.08mol) with mass concentration, Mass concentration is 32% NaOH solution 53ml, H 2 O 130ml, stirred, heated to reflux reaction for 48h, added ~5...

Embodiment 3

[0140] (1) Preparation of 2-bromo-6-picoline

[0141] Dissolve 75g of 2-amino-6-picoline in 330ml of HBr solution with a mass concentration of 40%, keep it at -15°C, and add 100ml of Br with a concentration of 0.02mol / ml dropwise2 , then dropwise add 175ml of aqueous solution containing sodium nitrite 0.66g / ml, stir for 30min, continue to dropwise add 265ml of aqueous solution containing NaOH 0.95g / ml, stir for another 30min, extract with dichloromethane, and use MgSO 4 After absorbing water and drying, vacuum distillation collected 103 g of distillate 2-bromo-6-methylpyridine at 4 mmHg at 65 °C, bp129-130 °C, yield 70%.

[0142] (2) Preparation of 6,6'-dimethyl-2,2'-bipyridine

[0143] Add 2-bromo-6-picoline 92g in reactor, sodium formate dihydrate 82.0g, be 5% palladium carbon catalyst 3.2g, benzyltriethylammonium chloride 21.2g (0.08mol) with mass concentration, Mass concentration is 32% NaOH solution 53ml, H 2 O 130ml, stirred, heated to reflux reaction 48h, added 11.5g ...

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Abstract

The invention relates to a rare earth europium fluorescent chelating agent and a preparation method thereof. The rare earth europium fluorescent chelating agent is 4,4'-dibromo-6,6'-bis(N,N-bis(ethoxycarbonyl methyl)aminomethyl)-2,2'-bipyridine; and the rare earth europium fluorescent chelating agent can form 4,4'-dibromo-6,6'-bis(N,N-bis(ethoxycarbonyl methyl)aminomethyl)-2,2'-bipyridine-Eu3+fluorescent chelating agent having fluorescence characteristics of europium ions and fluorescence lifetime with trivalent europium ions by hydrolysis. Detection is carried out on a fluorescence time-resolved spectroscopy and a fluorescence lifetime measurement instrument: a new fluorescence spectrum with the characteristic peak of the europium ions is formed at 615nm under the excitation of a light source of 337nm, and the fluorescence lifetime thereof is about 610 microseconds.

Description

technical field [0001] The invention relates to a rare earth europium fluorescent chelating agent and a preparation method thereof. Background technique [0002] The preparation of rare earth ion chelating agents is based on the requirements of spin symmetry matching. After organic molecules absorb light energy, electronic transitions occur between electronic vibration levels with the same spin; in addition, electronic transitions should also meet the requirements of orbital symmetry matching. . After the molecule absorbs light energy, the electrons are excited to the singlet excited state corresponding to the light energy of the excitation light, and the lifetime of the high-energy singlet excited state is very short (10 -10 ~10 -6 s), generally very quickly non-radiatively migrate to a low-energy singlet excited state, and then radiatively drop to the ground state and emit a fluorescent photon. The transition of electrons between the singlet excited state and the triple...

Claims

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Application Information

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IPC IPC(8): C07D213/61C09K11/06
Inventor 潘利华李俊玲徐经伟马世盐郑经康谢文兵
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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