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1,5,9-Triazapine compound and its synthesis method

A synthesis method and compound technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of unfavorable conjugated system derivation and expansion, harsh conditions, rare raw materials, etc., and achieve good thermal and chemical stability , mild reaction conditions and short synthesis steps

Inactive Publication Date: 2017-02-01
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, unfavorable conditions such as rare raw materials, long design route, cumbersome steps, harsh conditions and low yield restrict the development of this field.
In 2010, Wei Junfa’s research group synthesized 2,3,6,7,10,11-hexamethoxy-s-triazepine compound ( Angew. Chem. Int. Ed. , 2010, 49 , 8209 –8213), but this method can only synthesize hexaalkoxy-substituted triazepine compounds, but cannot synthesize unalkoxy-substituted s-triazepine compounds
Due to the presence of alkoxy groups, some intrinsic properties of s-triazepine compounds will inevitably be changed. For example, the solid accumulation of this type of compound lacks strong intermolecular π force, and this force is stronger. Cycloaromatic hydrocarbons are an extremely important prerequisite for electronic materials, which limits their application in molecular devices; at the same time, these alkoxy groups are also not conducive to the derivation and extension of further conjugated systems

Method used

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  • 1,5,9-Triazapine compound and its synthesis method
  • 1,5,9-Triazapine compound and its synthesis method
  • 1,5,9-Triazapine compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0042] Example 2: Taking the synthesis of 4,8,12-tri-(p-methylphenyl)-1,5,9-triazapine as an example, its structural formula is as follows:

[0043]

[0044] The raw materials and synthesis methods used are:

[0045] In step 3 of this embodiment, benzoyl chloride is replaced with equimolar p-toluyl chloride, and other steps in this step are the same as those in embodiment 1. The other steps were the same as in Example 1, and the yellow solid 4,8,12-tris-(p-methylphenyl)-1,5,9-triazapine was prepared, the yield was: 73%, and the melting point was: > 300 o C.

[0046] The spectral data of the obtained product are as follows: 1 H NMR (500 MHz, CDCl 3 : CF 3 COOD = 0.5 mL : 10 μL): δ 9.64 (d, J = 9.1 Hz, 3H), 9.58 (d, J = 9.1 Hz, 3H), 8.12 (d, J = 7.7Hz, 6H), 7.70 (d, J = 7.65 Hz, 6H), 2.66 (s, 9H). 13 C NMR (125 MHz, CDCl 3 :CF 3 COOD = 0.5 mL : 10 μL): δ 163.5, 144.0, 141.0, 133.4, 131.7, 130.7, 130.0, 127.3, 126.1, 121.1, 115.1, 21.9. HRMS: m / z calcd for C ...

Embodiment 3

[0047] Example 3: Taking the synthesis of 4,8,12-tri-(p-methoxyphenyl)-1,5,9-triazapine as an example, its structural formula is as follows:

[0048]

[0049] The raw materials and synthesis methods used are:

[0050] In step 3 of this embodiment, benzoyl chloride is replaced with equimolar p-methoxybenzoyl chloride, and other steps in this step are the same as those in embodiment 1. The other steps were the same as in Example 1, and the yellow solid 4,8,12-tris-(p-methoxyphenyl)-1,5,9-triazapine was prepared, the yield was: 67%, and the melting point was :> 300 o C.

[0051] The spectral data of the obtained product are as follows:

[0052] 1 H NMR (500 MHz, CF 3 COOD): δ 9.82 (d, J = 9.1 Hz, 3H), 9.58 (d, J =9.1 Hz, 3H), 8.27 (d, J = 8.2 Hz, 6H), 7.49 (d, J = 8.3 Hz, 6H), 4.06 (s, 9H). 13 C NMR (125 MHz, CDCl 3 : CF 3 COOOD = 0.5 mL : 0.1 mL): δ 166.5, 164.0, 138.6, 136.9, 134.9, 128.6, 123.8, 121.8, 121.0, 117.0, 115.4, 56.4.

[0053] HRMS: m / z calcd for ...

Embodiment 4

[0054] Example 4: Taking the synthesis of 4,8,12-tri-(p-chlorophenyl)-1,5,9-triazapine as an example, its structural formula is as follows:

[0055]

[0056] The raw materials and synthesis methods used are:

[0057] In step 3 of this embodiment, benzoyl chloride is replaced with equimolar p-chlorobenzoyl chloride, and in step 4, it is washed with dichloromethane, and other steps in this step are the same as those in embodiment 1. The other steps were the same as in Example 1, and 4,8,12-tris-(p-chlorophenyl)-1,5,9-triazapine was prepared as an earthy yellow solid, the yield was: 74%, and the melting point was: > 300 o C.

[0058] The spectral data of the obtained product are as follows: 1 H NMR (500 MHz, CDCl 3 : CF 3 COOD = 0.4 mL : 30 μL): δ 9.73 (d, J = 8.8 Hz, 3H), 9.69 (d, J = 8.6 Hz, 3H), 8.17 (d, J = 7.5Hz, 6H), 7.70 (d, J = 7.7 Hz, 6H). 13 C NMR (125 MHz, CDCl 3 : CF 3 COOD = 0.6 mL : 40 μL): δ 163.0, 141.7, 139.6, 134.8, 132.8, 130.7, 128.5, 127....

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Abstract

The invention relates to a 1, 5, 9-triazanaphthalene coronene compound and a synthetic method thereof. The compound has a structural formula as shown in the description, wherein R represents any one of hydrogen, alkyl, aryl, heterocyclic aryl, trifluoromethyl and perfluoroalkyl. The synthetic method disclosed by the invention comprises the following steps of: utilizing cheap 2, 3- dichloronitrobenzene which is easy to obtain as a raw material to prepare trinitro type substances; reducing the trinitro type substances so as to obtain triamine type substances; enabling the triamine type substances to react with acyl chloride or anhydride so as to obtain triamide type compounds; and cyclizing the triamide compounds so as to obtain substituted 1, 5, 9-triazanaphthalene coronene compounds in novel structures. The synthetic method is few in synthetic steps, mild in reaction conditions, convenient to operate and high in yield. The fluorescence emission spectrum of the triazanaphthalene coronene compound in an organic solvent has stronger fluorescence within the range of 420-550nm; the triazanaphthalene coronene compound has favorable heat stability and chemical stability, and can be used for preparing luminescent materials of organic light-emitting diodes and organic semiconductor materials.

Description

technical field [0001] The invention relates to a polycyclic aromatic hydrocarbon compound and a preparation method thereof, in particular to a 1,5,9-triazapinene compound and a preparation method thereof. Background technique [0002] As an important organic functional material, PAH molecules have unique and tunable molecular structures, optoelectronic properties and self-assembly behaviors, and are widely used in field-effect transistors, organic semiconductor materials, solar cells, and organic light-emitting diodes. Pinidine, also known as superbenzene, was first synthesized in 1932 and is a very important polycyclic aromatic hydrocarbon with perfect D 6h Symmetry, which can be seen as nanographene, has broad application prospects. Subsequently, a series of tests on pinium showed that it has a good photoluminescence effect and is a class of organic semiconductor materials with important prospects. [0003] At present, an important research trend of polycyclic aromatic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/16C09K11/06
CPCC07D471/16C09K11/06C09K2211/1029
Inventor 谭启涛陈欢欢夏怀达刘秉新许斌
Owner SHANGHAI UNIV
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