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Light-sensitive luminous europium complex and light-sensitive ligand molecular and their synthesizing method

A europium complex and photosensitive technology, applied in the field of photosensitive luminescent europium complexes, can solve the problems of low yield and difficult product separation, and achieve high yield, high rare-earth ion fluorescence quantum yield, and large two-photon absorption cross-section. Effect

Inactive Publication Date: 2007-11-14
北京纳材科技有限公司
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  • Abstract
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Problems solved by technology

Because tripolychlorazine attacks the diethylamine group of reactant simultaneously, the reaction generates a large amount of by-products, adopts the intermediate product N of this synthetic method gained, the productive rate of N-diethylamine phenyl-dichlorotriazine is low at 25%
Simultaneously, because there is a large amount of excess tripolychlorazine in the reaction system, product separation is difficult, so the productive rate of final target product dpbt is lower, about 20%

Method used

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  • Light-sensitive luminous europium complex and light-sensitive ligand molecular and their synthesizing method
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  • Light-sensitive luminous europium complex and light-sensitive ligand molecular and their synthesizing method

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preparation example Construction

[0049] The synthesis method of the organic photosensitive molecule of the present invention may specifically comprise the following steps:

[0050] 1) P-N, N-dialkylamino-2,6-dimethylphenyllithium or p-N, N-dialkylamino-2-methylphenyllithium and tripolychlorazine (cyanide Uric acid chloride, cyanuric chloride) reaction, makes the substitution triazine compound shown in formula IV;

[0051] 2) reacting the substituted triazine compound obtained in step 1) with the pyrazole or substituted pyrazole anion shown in formula V to prepare the photosensitized organic ligand compound shown in formula I;

[0052] The synthetic method of europium complex of the present invention, its reaction process is described below

[0053]

[0054] Wherein, R in formula I, formula VI 1 , R 2 is an alkyl group with 1-4 carbon atoms, R 3 =R 4 =R 5 =R 6 is methyl or H, R 7 is methyl, R 8 is methyl or H.

Embodiment 1

[0055] Example 1, 2-(N,N-diethyl-2,6-dimethylanilino-4-yl)-4,6-bis(3,5-dimethylpyrazol-1-yl)- 1,3,5-triazine (C 25 h 32 N 8 , formula VIII, that is, R in formula I 1 =R 2 =H 3 CH 2 C-, R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H 3 C-) Synthesis of Photosensitive Ligand Molecular Compound

[0056] Take 4 mmol of N,N-diethyl-2,6-dimethyl-p-bromoaniline, dissolve it in dried tetrahydrofuran, pass through argon to remove oxygen, place it in a dry ice acetone bath at -78°C, and Under protection, add 6.4mmol n-BuLi, slowly warm up to room temperature, continue stirring for 30min, add it to 5.4mmol tripolychlorazine frozen at -78°C, slowly warm up to room temperature, continue stirring for 60min. After removal of the solvent, the product was chromatographed on a silica gel column with dichloromethane as the eluent. The obtained crude product was recrystallized in petroleum ether to obtain 2-(N,N-diethyl-2,6-dimethylaniline-4-yl)-4,6-dichloro-1,3,5- Triazine yellow needle crystal ...

Embodiment 2

[0059] Embodiment 2, europium complex [Eu (tta) 3 VIII] (EuC 49 h44 N 8 f 9 o 6 S 3 )Synthesis

[0060] Under argon protection, 10mL Eu(tta) 3 ·3H 2 O (0.03 mmol) in tetrahydrofuran was added dropwise to 10 mL of the compound of formula VIII (0.03 mmol) prepared in Example 1 in tetrahydrofuran, and stirred at room temperature for 30 min. Remove the solvent, dissolve and filter with a small amount of ether, use n-hexane as a precipitant to precipitate a solid, wash it, and dry it to obtain 27 mg of a yellow powder.

[0061] The obtained yellow powder was subjected to mass spectrometry analysis, and the mass spectrometry (MALDI-TOF MS) characterization showed that the molecular ion peak M / Z=1260; elemental analysis (mass percentage): C, 46.80% (46.71%); H, 3.43% (3.52%); N, 9.01% (8.89%), is theoretical value in brackets; NMR analysis shows that product is [Eu(tta) 3 VIII], its structure is shown in formula XIV.

[0062] The complex [Eu(tta) 3 VIII] Dissolved in tolue...

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Abstract

This invention relates to a photosensitive shining Europium complex and its photosensitive ligand molecule, also relates to the synthetic method. The Europium complex structure is showd as VI: the R1, R2 is alkyl with 1 to 4 carbon atoms, R3, R4, R5, and R6 are same and are methyl or H, the R8 is methyl or H. The organic photosensitive ligand molecule structural formula is showd as I: the R1, R2 is alkyl with 1 to 4 carbon atoms, R3, R4, R5, and R6 are same and are methyl or H, the R8 is methyl or H. The photoallergy molecule possess fine long wave photoactivate Europium ion luminance. The new style Europium complex possess width activating window, at the same time possess large two-photon absorption acting section and / or high rare earth ion fluorescence quanta yield, is useful for preparing excellent bioluminescence probe stuff, possess comprehensive application prospects.

Description

technical field [0001] The invention relates to photosensitive luminescent europium complexes, photosensitive ligand molecules and their synthesis methods. Background technique [0002] Unique electronic structures of rare earth ions, especially their 5P 6 6S 2 The shielding effect of electrons on the 4f orbital makes its compound have many special spectral properties. They have important application value in light-emitting devices (energy-saving lamps, light-emitting diodes, displays), optical fibers, optical amplifiers, lasers, biosensing, bioimaging, and fluorescent immunoassays. The sharp line emission of rare earth ions in the visible or near-infrared region and the long luminescent state lifetime (ms level) can reduce the fluorescence interference generated by the biological material itself, so that the detection has high sensitivity and efficiency, and at the same time avoids the use of radioactive element bands. A series of questions to come. [0003] Since the f...

Claims

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Application Information

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IPC IPC(8): C07D403/04C07F5/00C09K11/06
Inventor 王远郝锐马严
Owner 北京纳材科技有限公司
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