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Beta-dione compounds with terminal vinyl group

A technology of compound and diketone, which is applied in the field of β-diketone compound, can solve the problems that there is no polymerization active center and cannot be used to prepare polymer light-emitting materials.

Inactive Publication Date: 2009-01-07
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, there is no polymerization active center in the above-mentioned β-diketone compound, so it cannot be used to prepare polymer luminescent materials

Method used

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  • Beta-dione compounds with terminal vinyl group
  • Beta-dione compounds with terminal vinyl group
  • Beta-dione compounds with terminal vinyl group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of 1-(9,9-dihexyl-2-fluorenyl)-12-tridecene-1,3-dione

[0035] 1.1 Synthetic route: the present invention is implemented with reference to the following synthetic route

[0036]

[0037]

[0038] 1.2 Synthesis steps

[0039] (1) Synthesis of 9,9-dihexylfluorene

[0040] Under nitrogen protection, add 10.00g fluorene and 200mL dimethyl sulfoxide to a 500mL three-necked flask, stir to dissolve, then add 25.3mL of 50% sodium hydroxide solution and 1.58g of tetrabutylammonium bromide. After stirring at room temperature for five minutes, 27.90 g of n-bromohexane was added dropwise. After the dropwise addition, the mixture was heated to 40° C. for 5 hours, and then naturally cooled to room temperature. Pour into 200mL of dichloromethane, stir and let stand, separate the organic phase and wash with water until neutral, dry with anhydrous magnesium sulfate, filter, concentrate the mother liquor, use petroleum ether as eluent, and separate by silica ...

Embodiment 2

[0056] Example 2: Synthesis of 1-(9,9-dihexyl-2-fluorenyl-7-octene-1,3-dione

[0057] 2.1 Synthesis

[0058] The operating steps of this example are basically the same as those in Example 1, except that hexyl hexenoate is used to replace hexyl undecylenate in the Claisen condensation reaction.

[0059] 2.2 Structure identification

[0060] Infrared spectrum (KBr, cm -1 ): 3070 (C=C-H); 1710 (C=O); 1590, 1470, 1449, 740 (fluorene ring); 2916, 2843, 1375 (-CH-).

[0061]NMR spectrum: δ(ppm), 16.20(s, 1H); 7.79-7.84(m, 2H); 7.55-7.59(m, 2H); 7.28-7.42(m, 3H); 6.70(s, 1H); 5.70 -5.78(m, 1H); 5.03-5.11(m, 1H); 4.93-4.98(m, 1H); 2.90-2.96(m, 2H); 1.93-1.98(m, 2H); 4H); 1.44-1.51 (m, 2H); 1.33-1.39 (m, 4H); 1.19-1.30 (m, 12H); 0.90-0.98 (m, 6H).

[0062] Elemental Analysis: C 33 h 44 o 2

[0063] Calculated value (%): C83.85, H9.38, O6.77;

[0064] Measured value (%): C83.78, H9.29, O6.71.

[0065] Mass Spectrum: 472(M + ).

[0066] The above data confirm that the compou...

Embodiment 3

[0069] Example 3: Synthesis of 1-(9,9-dihexyl-2-fluorenyl)-10-undecene-1,3-dione

[0070] 3.1 Synthesis

[0071] The operating steps of this example are basically the same as those in Example 1, except that hexyl nonenoate is used to replace hexyl undecylenate in the Claisen condensation reaction.

[0072] 3.2 Structural identification

[0073] Infrared spectrum (KBr, cm -1 ): 3075 (C=C-H); 1708 (C=O); 1598, 1476, 1450, 748 (fluorene ring); 2923, 2845, 1370 (-CH-).

[0074] NMR spectrum: δ(ppm), 16.25(s, 1H); 7.80-7.84(m, 2H); 7.53-7.58(m, 2H); 7.20-7.28(m, 3H); 6.70(s, 1H); 5.70 -5.75(m, 1H); 5.03-5.08(m, 1H); 4.91-4.97(m, 1H); 2.98(m, 2H); 1.89-1.96(m, 2H); 1.80-1.85(m, 4H) ; 1.37-1.40 (m, 2H); 1.28-1.33 (m, 6H); 1.21-1.25 (m, 16H); 0.91-0.96 (m, 6H).

[0075] Elemental Analysis: C 36 h 50 o 2

[0076] Calculated value (%): C83.99, H9.79, O6.22;

[0077] Measured value (%): C83.95, H9.71, O6.31.

[0078] Mass Spectrum: 514(M + ).

[0079] The above data confirm ...

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Abstract

The invention discloses a beta-diketone compound with terminal alkenes, which has a structural formula (1) shown in the drawing, wherein the structure of R is shown in the drawing; and n is an integer from 3 to 10. The beta-diketone compound with terminal alkenes is a blue-violet light-emitting material, and can be used as a ligand for preparing an organic fluorescent complex, an organic phosphorescent complex, a rear earth complex and a polymer light-emitting material.

Description

technical field [0001] The present invention relates to a β-diketone compound, in particular to a terminal ene β-diketone compound. Background technique [0002] The application of β-diketone compounds in the fields of metal-organic liquid crystals, extraction reagents, chemical shift reagents, and anti-counterfeiting materials has attracted widespread attention. With unique photochemical properties, it can be widely used as functional materials such as photostability and photoetching. [0003] The tautomers of β-diketone compounds, because the hydrogen in the enol hydroxyl group has strong acidity, it is easy to be replaced by metals, and the carbonyl group can be used as an electron donor, so it can interact with most heavy metal ions and rare earth metals Ions form stable complexes, which are one of the most typical metal chelating agents, and are widely used in the synthesis of electroluminescent materials such as organic fluorescent complexes, organic phosphorescent co...

Claims

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Application Information

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IPC IPC(8): C07C49/798C07C45/72C07D209/86C09K11/06
Inventor 徐茂梁王歌扬周瑞
Owner XIAN MODERN CHEM RES INST
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