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Organic boron difluoride complex and preparation method thereof

A technology for boron difluoride and complexes, which is applied in the field of organic boron difluoride complexes and their preparation, can solve the problems of few and few studies on organic boron difluoride complexes, and achieve simple separation and purification of products, chemical Stable properties and large molar absorptivity

Inactive Publication Date: 2011-05-04
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there are relatively few studies on organic boron difluoride complexes containing N, O-bidentate ligands, which are isosteres of the above two, and there are few reports on species with luminescent properties.

Method used

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  • Organic boron difluoride complex and preparation method thereof
  • Organic boron difluoride complex and preparation method thereof
  • Organic boron difluoride complex and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] At room temperature, 2.81g (10mmol) of 2-(6,7-dimethoxy-2-quinolyl)phenol was placed in 15mL of toluene solution, and 4.2mL (30mmol) of triethylamine was added dropwise under stirring, 15 Minutes later, 2.8 mL (30 mmol) of boron trifluoride ether solution was added dropwise, and stirring was continued for 45 min after the addition was complete, gradually solid precipitated out. The solid was collected by filtration, washed repeatedly with anhydrous ether, and naturally dried to obtain complex 1 in the form of light yellow powder with a yield of 81%.

[0035] The infrared spectrum, proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the above-mentioned complex 1 are as follows:

[0036] IR(KBr): υ=1603, 1516, 1250, 1083, 849cm -1 .

[0037] 1 H NMR (DMSO-d 6 ): δ=4.02(s, 3H), 4.15(s, 3H), 7.02(t, J=8.0Hz, 1H), 7.07(s, 1H), 7.19(d, J=8.4Hz, 1H), 7.48 (t, J=8.0Hz, 1H), 7.83(d, J=8.0Hz, 1H), 7.94(d, J=8.8Hz, 1H), 8.29(m, 2H).

...

Embodiment 2

[0040]At room temperature, 2.56g (10mmol) of 2-(6-chloro-2-quinolyl)phenol was placed in 15mL of benzene solution, 3.7mL of triethylamine (27mmol) was added dropwise under stirring, and triethylamine was added dropwise after 15 minutes. Boron fluoride ether solution 4.2mL (45mmol), continue to stir for 45min after the addition, gradually solid precipitates out. The solid was collected by filtration, washed repeatedly with anhydrous ether, and naturally dried to obtain complex 2 in the form of yellow powder with a yield of 76%.

[0041] The infrared spectrogram, proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of above-mentioned complex 2 are as follows:

[0042] IR(KBr): υ=1614, 1517, 1358, 1265, 1165, 1099, 930, 847, 754cm -1 .

[0043] 1 H NMR (DMSO-d 6 ): δ=7.07(t, J=7.6Hz, 1H), 7.20(d, J=8.4Hz, 1H), 7.56(t, J=7.6Hz, 1H), 7.63(d, J=8.4Hz, 1H ), 7.84(d, J=8.8Hz, 1H), 7.90(d, J=8.4Hz, 1H), 8.15(d, J=8.8Hz, 1H), 8.47(d, J=8.8Hz, 1H...

Embodiment 3

[0046] At room temperature, 2.21g (10mmol) of 2-(2-quinolyl)phenol was placed in 10mL of ethyl acetate solution, and 2.9mL (21mmol) of triethylamine was added dropwise with stirring, and trifluorinated trifluoride was added dropwise after 15 minutes. Boron ether solution 2.8mL (30mmol), continue to stir for 45min after the addition, gradually a solid precipitates out. The solid was collected by filtration, washed repeatedly with anhydrous ether, and naturally dried to obtain complex 3 in the form of yellow powder with a yield of 86%.

[0047] The infrared spectrum, proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the above-mentioned complex 3 are as follows:

[0048] IR(KBr): υ=1609, 1560, 1523, 1481, 1265, 1085, 922, 760cm -1 .

[0049] 1 H NMR (DMSO-d 6 ): δ=7.06(t, J=7.6Hz, 1H), 7.21(d, J=8.4Hz, 1H), 7.54(t, J=8.0Hz, 1H), 7.69(t, J=7.6Hz, 1H ), 7.91 (m, 3H), 8.18 (d, J=8.8Hz, 1H), 8.52 (d, J=8.8Hz, 1H), 8.96 (d, J=8.8Hz, 1H)....

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Abstract

The invention discloses an organic boron difluoride complex which is a compound the structural formula I of which is shown in the specification, wherein R1 and R2 are OCH3, H or Cl independently respectively; R3 and R4 are H, NO2, Br, CH3 or OCH3 independently respectively; the complex has stable chemical properties, strong thermal stability, high fluorescence quantum yield and large molar absorption coefficient; furthermore, the complex not only has strong solution fluorescence, but also has significant solid fluorescence. The invention further discloses a preparation method of the organic boron difluoride complex, and the organic boron difluoride complex is prepared by carrying out room temperature or reflux reaction on a ligand and boron trifluoride diethyl etherate in an anhydrous organic solvent in the presence of organic base; and the method has the advantages of mild reaction conditions, short reaction time, high product yield and fastness and simpleness in separation and purification.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an organic boron difluoride complex and a preparation method thereof. Background technique [0002] Organic boron difluoride complexes are important fluorescent materials. As far as the coordination forms of boron atoms are concerned, the most important ones are N,N-bidentate ligands represented by pyrromethene and β-enolones. The 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, which are isosteres of the above two, and there are even fewer reports on species with luminescent prope...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06
Inventor 夏敏杨曦周宝成
Owner ZHEJIANG SCI-TECH UNIV
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