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Organic boron difluoride complex

A technology of boron difluoride and complexes, applied in the field of organic boron difluoride complexes, to achieve the effects of large molar absorptivity coefficient, strong thermal stability, and stable chemical properties

Inactive Publication Date: 2013-03-27
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although some studies have been carried out on organic boron difluoride complexes with fluorescence in the prior art, and some organic boron difluoride complexes with special structures have also been disclosed, but there are still few reports from the reported situation, indicating that at present The research on organic boron difluoride complexes with fluorescence is still in the preliminary exploration stage, and further research is needed in order to provide a wider range of organic boron difluoride complexes with different fluorescent colors for the industrial field

Method used

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  • Organic boron difluoride complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] At room temperature (25°C), triethylamine (5mmol, 0.51g) was added dropwise to 6-methoxy-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxa Lin-2-one (2mmol, 0.556g) in anhydrous dichloromethane (5mL) was stirred for 20min, and boron trifluoride ether (10mmol, 1.420g) was added dropwise into the above mixture. The reaction solution was stirred at room temperature for 30 minutes and then filtered. The obtained solid was washed three times with ether, and dried naturally to obtain the product complex 1 as an orange-red powder, melting point: 262°C-263°C, yield 80%.

[0042] The fluorescence effect of the dichloromethane solution of complex 1 under the irradiation of 365nm ultraviolet light is yellow-green.

[0043] The detection data of the above complex 1 are as follows:

[0044] UV(acetone):λ max =466nm(ε=2.97×10 4 m -1 cm -1 , ε is the molar absorptivity);

[0045] FL(acetone):λ max =530nm, Φ=0.32 (Φ means quantum yield);

[0046] IR(KBr):ν2924,1684,1577,1527,1385...

Embodiment 2

[0053] At room temperature, 6,7-dimethoxy-3-[2-oxo-2-phenylethylidene]-3,4-dihydroquinoxalin-2-one (0.584g, 2mmol) was added to Toluene / acetic acid (1:1, volume ratio) mixed solution (10mL), after heating to slight boiling, drop boron trifluoride ether (10mmol, 1.42g) into the reaction solution, reflux for 30min and cool to room temperature, a large amount of Solid precipitated out. The resulting solid was filtered, washed several times with ether, and dried naturally to obtain product complex 2, which was iron red powder, melting point: 320°C-321°C. Yield 90%.

[0054] Under the irradiation of 365nm ultraviolet light, the fluorescence effect of the dichloromethane solution of complex 2 is yellow.

[0055] The detection data of the above complex 2 are as follows:

[0056] UV (CH 2 Cl 2 ):λ max =482nm(ε=4.11×10 4 m -1 cm -1 );

[0057] FL(CH 2 Cl 2 ):λ max =550nm,Φ=0.35;

[0058] IR(KBr):ν1677,1567,1514,1408,1279,1258,1159,1107,775cm -1 ;

[0059] 1 H-NMR(400MH...

Embodiment 3

[0065] At room temperature, 6,7-dimethoxy-3-[2-oxo-2-(4-hydroxy)phenethylidene]-3,4-dihydroquinoxalin-2-one (0.68g , 2mmol) was added to toluene / acetic acid (1:1, volume ratio) mixed solution (10mL), heated to a slight boil, boron trifluoride diethyl ether (10mmol, 1.42g) was added dropwise into the reaction solution, refluxed for 30min and then cooled At room temperature, a large amount of solid precipitated out. The resulting solid was filtered, washed several times with ether, and dried naturally to obtain product complex 3, which was ocher red powder, melting point: 316°C-318°C. Yield 93%.

[0066] The fluorescence effect diagram of the dichloromethane solution of complex 3 under 365nm ultraviolet light irradiation is shown in yellow.

[0067] The detection data of the above complex 3 are as follows:

[0068] UV(THF):λ max =480nm(ε=5.85×10 3 m -1 cm -1 );

[0069] FL(THF):λ max =540nm,Φ=0.28;

[0070] IR(KBr):ν3435, 1677, 1384, 1123, 1083cm -1 ;

[0071] 1 H-N...

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Abstract

The invention discloses an organic boron difluoride complex. The complex is shown in the structural formula I in the specification, wherein R1 is H or OCH3; and R2 is C6H5, 4-HOC6H4, 4-(CH3)2NC6H4 or 2-C4H4S. The complex can be used for preparing luminescent materials, fluorescent probes, fluorescent tracers, information storage media, laser dyes and photodynamic cancer treatment photosensitizers. The invention also discloses a preparation method of the complex. The complex is prepared through reaction of a corresponding ligand and boron trifluoride diethyl etherate. The complex has the advantages of mild reaction conditions, short reaction time, high product yield, rapidness, simpleness and convenience in separation and purification and high product purity.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an organic boron difluoride complex. Background technique [0002] Organic boron difluoride complexes are important fluorescent materials. As far as the coordination form of boron atoms is concerned, the most important ones are the N,N-bidentate ligand type represented by pyrromethene and the β-enolone Two types of O, O-bidentate ligands are represented, and the research on their performance and application has been quite in-depth and abundant (Chem.Rev., 2007, 107, 4891; Angew.Chem.Int.Ed., 2008, 47, 1184; New J. Chem., 2007, 3 1,496; J. Phys. Org. Chem. 1996, 9, 7; J. Am. Chem. Soc., 2007, 129, 8942; Tetrahedron, 2007, 63, 9354). [0003] However, there are relatively few studies on organic boron difluoride complexes containing N,O-bidentate ligands as the isosteres of the above two electrons. For example, morpholino-substituted 2-(2 -Quinolinyl)-1H-1,3(2H)-perylenedione as a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06
Inventor 夏敏姚起超马儒政周宝成
Owner ZHEJIANG SCI-TECH UNIV
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