Organic boron difluoride complex containing N,O-bidentate ligand

A technology of boron difluoride and complexes, which is applied in the field of organic synthesis and achieves the effects of stable chemical properties, strong thermal stability and large molar absorption coefficient

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 t

Method used

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  • Organic boron difluoride complex containing N,O-bidentate ligand
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  • Organic boron difluoride complex containing N,O-bidentate ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] At room temperature (25°C), triethylamine (5mmol, 0.505g) was added dropwise to ethyl 2-(3-oxo-3,4-dihydroquinoxalinylidene)acetate (2mmol, 0.46g) In anhydrous dichloromethane (5 mL) solution, after stirring for 15 min, boron trifluoride diethyl ether (10 mmol, 1.42 g) was dropped into the above mixture to obtain a reaction liquid. The reaction solution was stirred at room temperature for 30 min and then concentrated on a rotary evaporator. The residue was poured into an appropriate amount of ether, and a pale yellow solid was precipitated under vigorous stirring. The resulting solid was filtered, dissolved with an appropriate amount of dichloromethane, and then separated and purified on a silica gel column chromatography using a mixture of petroleum ether / ethyl acetate (3:1, volume ratio) as the eluent, and the eluent was dried to obtain Complex 1 is light yellow powder, melting point: 220℃~221℃. Yield 73%.

[0042] Under the irradiation of 365nm ultraviolet light, t...

Embodiment 2

[0053] At room temperature, triethylamine (5mmol, 0.505g) was added dropwise to 3-[2-oxo-2-(2,6-dimethoxy)phenethylidene)]-3,4-dihydroquinone In a solution of oxalin-2-one (2mmol, 0.649g) in anhydrous dichloromethane (5mL), after stirring for 20min, boron trifluoride ether (10mmol, 1.42g) was added dropwise into the above mixture to obtain a reaction solution. The reaction solution was heated to reflux for 30 min, cooled to room temperature, concentrated on a rotary evaporator, and the residue was poured into an appropriate amount of ether, and an earthy red solid was precipitated under vigorous stirring. The resulting solid was filtered, dissolved with an appropriate amount of dichloromethane, and then separated and purified on a silica gel column chromatography using a mixture of petroleum ether / ethyl acetate (4:1, volume ratio) as the eluent, and the eluent was dried to obtain Complex 2 is earth red powder, melting point: 279°C~280°C. Yield 75%.

[0054] Under the irradia...

Embodiment 3

[0065] At room temperature, 3-[2-oxo-2-(2-methoxy)phenethylidene]-3,4-dihydroquinoxalin-2-one (0.588g, 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 solids precipitated . The resulting solid was filtered, washed several times with ether, and naturally dried to obtain complex 3 as a brown powder with a melting point of 267°C~268°C. Yield 87%.

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

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

[0068] UV (CH 2 Cl 2 ):λ max =449nm(ε=4.27×10 4 m -1 cm -1 );

[0069] FL(CH 2 Cl 2 ):λ max =518nm,Φ=0.32;

[0070] IR(KBr):v1688, 1601, 1580, 1566, 1521, 1493, 1386, 1250, 1164, 1105, 1044, 979, 750cm -1 ; ...

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Abstract

The invention discloses an organic boron difluoride complex containing an N,O-bidentate ligand. The complex is shown in the structural formula I in the specification, wherein R is 2,6-dimethoxyphenyl, oxethyl, 2-methoxyphenyl or 2-thienyl. 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 a N,O compound with 3-(2-oxo-2-substituted ethylidene)-3,4-dihydroquinoxalin-2-one derivative - Organic boron difluoride complexes with bidentate ligands. 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, 31, 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 iso...

Claims

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Application Information

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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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