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Lanthanide metal ether complex and preparation method and application thereof

A technology of lanthanide metals and complexes, which is applied in the field of lanthanide metal cryptate complexes and their preparation, and can solve the problems of short fluorescence lifetime, weak fluorescence intensity, poor stability, etc.

Inactive Publication Date: 2017-02-22
SUZHOU INST OF BIOMEDICAL ENG & TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned lanthanide compounds have disadvantages such as weak fluorescence intensity, short fluorescence lifetime, and poor stability, which limit their application as fluorescent markers.

Method used

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  • Lanthanide metal ether complex and preparation method and application thereof
  • Lanthanide metal ether complex and preparation method and application thereof
  • Lanthanide metal ether complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Example 1 The preparation of the intermediate shown in formula (Ⅳ)

[0102] References Helvetica Chimica Acta, 1992, 75, 1578.

[0103]

[0104]Under anhydrous and oxygen-free conditions, first take 1 mmol of 6,6-dimethyl-4,4-dimethyl ester-2,2-bipyridine (ie: the compound shown in formula (1-1)) and add it to In a 100mL two-necked flask, add about 40mL of anhydrous and oxygen-free toluene, heat to 80°C, add t-BuLi solution in t-BuOH dropwise; after the addition, continue to reflux for 30min to obtain compound 6,6- Methyl-4,4-di-tert-butyl-2,2-bipyridine (namely: the intermediate represented by formula (1-2)), the yield is 58%.

[0105] First take 0.5mmol of 6,6-dimethyl-4,4-di-tert-butyl-2,2-bipyridine (ie: the compound shown in formula (1-2)) into the round bottom flask, and then sequentially Join CCl 4 , 2.1mmol NBS and a catalytic amount of diethyl phosphite, under the conditions of anhydrous, anaerobic and argon protection, heated and refluxed overnight; af...

Embodiment 2

[0110] Example 2 The preparation of the intermediate shown in formula (Ⅴ)

[0111] References J.Am.Chem.Soc.2010, 132, 14334.

[0112]

[0113] Take 0.3mmol of the compound represented by formula (1-3), add it to 3mL of chloroform solution, heat to reflux until it becomes completely clear, then slowly add 0.66mmol of hexamethylenetetramine in chloroform solution (1.5mL×2) , and then continue to heat and reflux for 3h; after the reaction is over, let it stand, cool, filter, and the filter cake is washed with chloroform and vacuum filtered; then, add H to the filter cake 2 O: EtOH: 47% HBr aqueous solution with a volume ratio of 1.4:5.8:1.0 mixed solvent, heat and stir at 75°C until the solids are completely dissolved, and then the solution becomes clear; stop the reaction, cool and stand for 1h, then ice bath for 30min , pale yellow crystals were precipitated, filtered, the filter cake was washed with ethanol, and vacuum filtered to obtain the intermediate shown in formul...

Embodiment 3

[0118] Example 3 The preparation of the intermediate shown in formula (Ⅲ)

[0119]

[0120] In an anhydrous, anaerobic two-necked flask, add 300mL of acetonitrile, then sequentially add 20mmol of the compound shown in formula (IV), 10mmol of the compound shown in formula (V) and 0.26mmol of sodium carbonate, heat and reflux for 2 to 3 days , after the reaction was finished, let stand, cool, filter, the filtrate was concentrated under reduced pressure, and then washed with ether to obtain the intermediate shown in formula (Ⅲ), with a yield of 48%.

[0121] The structure confirmation data of the intermediate represented by formula (Ⅲ):

[0122] 1 H NMR (Acetone-d 6 ):8.73(s,1H,Hbpy),8.28(m,2H,Hbpy),7.76(s,2H,Hbpy),7.58(s,1H,Hbpy),3.95(s,9H,-OCH 3 ),1.54(s,9H,-C(CH 3 ) 3 );

[0123] MS: 557..23(C 60 h 66 NaN 8 o 12 +H + ) 2+ (M / z=557.23);

[0124] Elemental analysis (%): C, 62.68; H, 5.79; N, 9.75.

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Abstract

The invention belongs to the organic chemical field, and particularly relates to a lanthanide metal ether complex and preparation method and application thereof. The lanthanide metal ether complex, has the chemical structure equation shown in equation (I): (img file = 'DDA0001109726700000011.TIF' wi = '478' he = '663' / ). The invention designs a novel lanthanide metal ether complex, through selecting a designated substituent, enabling the prepared lanthanide metal ether complex to obtain an excitation spectrum excited using a wave length of 340nm fixed emission light, the intensity is relatively strong (reaching 400000), the florescent life is relatively long (larger than 0.2ms), the stability is relatively strong, therefore the complex has relatively good application prospect in fields of time resolution energy transfer and the like; the lanthanide metal ether complex has relatively short route, simple operation steps, and relatively high produce rate.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a lanthanide metal cryptate complex, a preparation method and application thereof. Background technique [0002] At present, the fluorescent markers that have been studied more can be divided into the following categories: organic compound fluorescent markers, fluorescent quantum dots, and rare earth complexes. Organic compound-type fluorescent markers have good biocompatibility, but there are disadvantages such as high quenching rate, instability under light conditions, sensitivity to pH value, and broad emission wave; fluorescent quantum dots as biomarkers have exciting The spectrum is wide and continuous, the emission spectrum is narrow and symmetrical, the luminous efficiency is high, the photochemical stability is good, and photobleaching is not easy to occur, but it has the disadvantage of too much cytotoxicity; It has the characteristics of low cytotoxicity and...

Claims

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Application Information

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IPC IPC(8): C07F5/00C09K11/06G01N21/64
CPCC07F5/00C09K11/06G01N21/64
Inventor 刘元忠王弼陡刘涛韩坤罗刚银程文播祝楠楠
Owner SUZHOU INST OF BIOMEDICAL ENG & TECH CHINESE ACADEMY OF SCI
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