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Europium complex with visible light sensitized light emitting performance and its synthesis process

A technology of europium complexes and synthesis methods, which is applied in the field of europium complexes and their synthesis, can solve the problems of strong background fluorescence, biological damage and large interference, and achieve excellent visible light-sensitized luminescent performance and excellent visible light-sensitized luminescent performance Effect

Inactive Publication Date: 2007-11-07
北京纳材科技有限公司
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Problems solved by technology

Although many rare earth complexes exhibit good luminescent properties under the excitation of ultraviolet light, ultraviolet light can cause great damage and interference to organisms, and also produce strong background fluorescence. Exciting the window and improving the luminous efficiency of rare earth complexes has become one of the important research directions (K.Kuningas, et al., Anal.Chem.2005, 77, 7348)

Method used

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  • Europium complex with visible light sensitized light emitting performance and its synthesis process
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  • Europium complex with visible light sensitized light emitting performance and its synthesis process

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preparation example Construction

[0029] The synthetic method of europium complex of the present invention, its specific steps are as follows:

[0030] The compound of formula III and the compound of formula II are reacted in an organic solution to obtain the photosensitive luminescent europium complex of formula I.

[0031] The above reaction can be carried out in many organic solvents, such as ether solvents such as tetrahydrofuran and diethyl ether, aromatic solvents such as benzene, toluene and xylene, and chlorinated solvents such as chloroform and methylene chloride.

Embodiment 1

[0033] Embodiment 1, synthetic structural formula is as the europium complex shown in formula IV (that is R in formula I 1 = R 2 =H 3 CH 2 C-, R 3 = R 4 = H, R 5 = R 6 = R 7 = R 8 =H 3 C-)

[0034] Take 4mmol of N,N-diethyl-p-bromoaniline, dissolve it in dried tetrahydrofuran, pass through argon to remove oxygen, put it in a dry ice acetone bath at -78°C, and add 6.4mmol of n-BuLi under the protection of argon. , after slowly warming up to room temperature, continue to stir for 30 min, add it to 5.4 mmol of tripolychlorazine frozen at -78°C, slowly warm up to room temperature, and continue stirring for 60 min. After removal of the solvent, the product was chromatographed on a silica gel column with dichloromethane as the eluent. The resulting crude product was recrystallized in petroleum ether to obtain 0.65 g of 2-(N,N-diethylanilin-4-yl)-4,6-dichloro-1,3,5-triazine yellow needle-like crystals . Under the protection of argon, add 1.25 mmol of freshly cut potassiu...

Embodiment 2

[0039] Example 2, the europium complex shown in the synthetic formula V (i.e. R in the formula I 1 = R 2 =H 3 C-, R 3 = R 4 = H, R 5 = R 6 = R 7 = R 8 =H 3 C-)

[0040] According to the synthesis method of Example 1, replace N, N-diethyl-p-bromoaniline with N, N-dimethyl-p-bromoaniline, and synthesize the obtained structure as shown in formula II (R 1 = R 2 =H 3 C-, R 3 = R 4 = H, R 5 = R 6 = R 7 = R 8 =H 3 C-) Ligand compounds.

[0041] Get structure as shown in formula III 0.05mmol is dissolved in the tetrahydrofuran of 30mL and make solution A, get structure as shown in formula II (R 1 = R 2 =H 3 C-, R 3 = R 4 = H, R 5 = R 6 = R 7 = R 8 =H 3 C-) 0.05 mmol of the ligand compound was dissolved in 30 mL of tetrahydrofuran to prepare solution I, and solution A was added dropwise to solution I. After stirring at 25°C for 1 h, the solvent was evaporated to dryness under reduced pressure to obtain 71.3 mg of an orange-yellow solid with the structure of...

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Abstract

The present invention discloses one kind of europium complex with visible light sensitized light emitting performance and its synthesis process. The europium complex of the present invention as one RE complex has structure as shown. The europium complex has excellent visible light sensitized light emitting performance, and may be applied in synthesizing biological fluorescent probe and other functional materials with excellent light emitting performance and possesses important application in biosensing, imaging, fluoresce immunoassay, etc.

Description

technical field [0001] The invention relates to a europium complex with visible light-sensitized luminescent performance and a synthesis method thereof. Background technique [0002] The unique electronic structure of rare earth ions makes its compounds 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-f transition of rare earth ions is limited by the electric dipole selection rate...

Claims

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Application Information

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