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S-triazacoronene compound and synthesis method and application thereof

A technology for the synthesis of s-triazepines, which is applied in chemical instruments and methods, organic chemistry, electrical components, etc., can solve the problems of low yield, scientific research development, long design route, harsh conditions, etc., and achieve good thermal stability and chemical stability, convenient operation, and mild reaction conditions

Inactive Publication Date: 2012-07-04
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are only two methods for the synthesis of azapine, and the design route is long, the steps are cumbersome, the conditions are harsh, the temperature even reaches 350°C, and the yield is low. Unfavorable conditions restrict the development of scientific research in this field

Method used

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  • S-triazacoronene compound and synthesis method and application thereof
  • S-triazacoronene compound and synthesis method and application thereof
  • S-triazacoronene compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Taking the synthesis of 2,3,6,7,10,11-hexamethoxy-4,8,12-triphenyl-1,5,9-triazepine as an example, its structural formula is as follows:

[0029]

[0030] The raw materials used and their synthetic methods are:

[0031] 1. Synthesis of 2,3,6,7,10,11-hexamethoxytriphenylene

[0032] Dissolve 23.00g of phthalic dimethyl ether in a flask filled with 500mL of dichloromethane, add 81.00g of anhydrous ferric chloride and 1.60g of concentrated sulfuric acid, and mix phthalic dimethyl ether with dichloromethane and anhydrous trichloride The molar ratio of iron and sulfuric acid was 1:16:3:0.04, stirred and reacted at 25°C for 4 hours, filtered, washed with methanol until the solid was off-white, and dried in a vacuum oven at 100°C for 5 hours to prepare 2,3, 6,7,10,11-hexamethoxytriphenylene with a yield of 89%.

[0033] 2. Synthesis of 1,5,9-trinitro-2,3,6,7,10,11-hexamethoxytriphenylene

[0034] Dissolve 3.0g of 2,3,6,7,10,11-hexamethoxytriphenylene in a mixture of 15.0...

Embodiment 2

[0046] Taking the synthesis of 2,3,6,7,10,11-hexamethoxy-4,8,12-three-(p-methoxyphenyl)-1,5,9-triazepine as an example, its structural formula as follows:

[0047]

[0048] The raw materials used and their synthetic methods are:

[0049] In step 4 of the present embodiment, benzaldehyde is replaced with equimolar p-methoxybenzaldehyde, and the volume ratio of ethyl acetate and petroleum ether is a mixed solution of 1:5 as a developing agent to separate the product by column chromatography, Recrystallize with acetone or tetrahydrofuran, and the other steps of this step are the same as in Example 1. The other steps are the same as in Example 1, and the yellow needle-like solid 2,3,6,7,10,11-hexamethoxy-4,8,12-tri-(p-methoxyphenyl)-1,5 , 9-triazepine, the yield is 66%, and the melting point is 287-289°C.

[0050] The spectral data of the resulting product are as follows:

[0051] 1 H NMR (300MHz, CDCl 3 +TMS)δ(ppm): 7.16(d, J=6.9Hz, 6H), 7.95(d, J=6.9Hz, 6H), 4.57(s, 9H...

Embodiment 3

[0057] Taking the synthesis of 2,3,6,7,10,11-hexamethoxy-4,8,12-tri-(p-bromophenyl)-1,5,9-triazepine as an example, its structural formula is as follows:

[0058]

[0059] The raw materials used and their synthetic methods are:

[0060] In step 4 of this embodiment, benzaldehyde is replaced by equimolar p-bromobenzaldehyde, and column chromatography is performed with a mixed solution of chloroform, ethyl acetate, and petroleum ether in a volume ratio of 1:1:5 as a developing solvent. The product was isolated by method and recrystallized with tetrahydrofuran. The other steps of this step were the same as in Example 1. The other steps are the same as in Example 1, and the yellow flake solid 2,3,6,7,10,11-hexamethoxy-4,8,12-tri-(p-bromophenyl)-1,5,9 - Triazepines with a yield of 54% and a melting point greater than 300°C.

[0061] The spectral data of the resulting product are as follows:

[0062] 1 HNMR (300MHz, CDCl 3 +TMS) δ (ppm): 7.80 (d, J = 7.83Hz, 6H), 7.75 (d, J...

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Abstract

The invention relates to an s-triazacoronene compound the structural formula of which is shown in the specification. In the invention, a triamine substance is prepared from low-price available dimethoxybenzene as a raw material, and the triamine substance is catalyzed or promoted under a protonic acid to obtain various substituted triazacoronene compounds. The reaction condition is mild, the operation is convenient and the yield is moderate. The compound has stronger fluorescence in an organic solvent the fluorescence emission spectrum of which is within the range of 450-510nm, has high heat stability and chemical stability and can be used for a blue luminescent material in an organic electroluminescence device.

Description

technical field [0001] The invention belongs to the technical field of polycyclic aromatic hydrocarbon compounds, in particular to s-triazepine compounds. Background technique [0002] Due to their unique molecular structure and outstanding electronic properties, polycyclic aromatic hydrocarbons are widely used in field effect transistors, organic semiconductor materials, photovoltaic cells and photodiodes. Kelenium is a very important polycyclic aromatic hydrocarbon, which was synthesized by Barth and Lawton in 1932. It is very promising to have D 6h Symmetrical nanographene. Afterwards, a series of studies on perone showed that this compound has a good photoluminescence effect, and it has been found to be an excellent organic material for making UV-CCD (Ultraviolet Charge Coupled Device) in recent years. [0003] When nitrogen atoms replace the carbon atoms in the perone structure, this structure is called azacone. With the introduction of nitrogen atoms, not only the p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/16C09K11/06H01L51/54
Inventor 魏俊发韩波李明张朋韩亚军高艳妮常健石先莹王文亮魏妮
Owner SHAANXI NORMAL UNIV
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