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Compound (2z)-2-((4-bromophenyl)hydrazono)acenaphthyl-1-one and its preparation method and application

A technology of a compound, bromophenyl, applied in the field of compound (2Z)-2-((4-bromophenyl)hydrazono)acenaphthyl-1-one and its preparation and application, which can solve the problem of low product yield, Complex reaction conditions, high cost of raw materials, etc., to achieve the effect of safe and reliable operation, mild reaction temperature, easy control, and low cost

Active Publication Date: 2016-04-20
常熟紫金知识产权服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this reaction, the cost of raw materials is relatively high, the reaction conditions are relatively complicated, and the yield of products is relatively low, so it is not suitable for industrial production of organic small molecule materials with photoelectric activity.

Method used

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  • Compound (2z)-2-((4-bromophenyl)hydrazono)acenaphthyl-1-one and its preparation method and application
  • Compound (2z)-2-((4-bromophenyl)hydrazono)acenaphthyl-1-one and its preparation method and application
  • Compound (2z)-2-((4-bromophenyl)hydrazono)acenaphthyl-1-one and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 100mL round-bottomed flask, add 1.82g (10.0mmol) acenaphthenequinone, 2.57g (11.5mmol) p-bromophenylhydrazine hydrochloride and 1g anhydrous sodium sulfate in sequence, 50mL ethanol as a solvent, nitrogen protection, and magnetic stirring Heat to about the boiling point of ethanol, reflux for 5 hours, cool to room temperature, filter with suction, wash the filter cake with an appropriate amount of water, and drain to obtain an orange-yellow solid, which is recrystallized to obtain 1.78 g of orange-yellow crystals. Yield 50.6%. 1H-NMR (400MHz, CDCl3, 25°C, TMS): δ=12.56(s, 1H); 8.12(d, J=8.0Hz, 1H); 8.01(d, J=8.0Hz, 1H); 7.85( d,J=8.0Hz,1H);7.80(d,J=8.0Hz,1H);7.73(t,J=8.0Hz,1H);7.66(t,J=8.0Hz,1H);7.47(d, J=8.8Hz,2H);7.29(d,J=8.8Hz,2H).MS(ESI):m / z=350.01,352.00,351.01,353.01(M+;Abundance ratio=5:5:1:1); calcdforC18H11BrN2O[M+Na]+:372.84,374.85,373.84,375.84(Abundance ratio=5:5:1:1).Elem.Anal.Calcd.forC18H11BrN2O(351.2):C,61.56;H,3.16;Br,22.75; N,7.98;O,4.56.Found:...

Embodiment 81

[0042] In a 100mL round bottom flask, add 1.82g (10.0mmol) of acenaphthenequinone, 1.14g (5.1mmol) of p-bromophenylhydrazine hydrochloride and 1g of anhydrous potassium sulfate, 50mL of ethanol as a solvent, nitrogen protection, and heating under magnetic stirring To the boiling point of ethanol, reflux for about 12 hours, cool to room temperature, filter with suction, wash the filter cake with an appropriate amount of water, and drain to obtain an orange-yellow solid, which is recrystallized to obtain 1.66 g of orange-yellow crystals. Yield 92.6%.

[0043] Examples 82–96:

[0044] The reaction solvent, reaction time and other operations were the same as in Example 81, but the molar ratio of the reactants was changed, and the quality and yield of the final product are shown in Table 6 below.

[0045] Table 6 ethanol as solvent, product quality and its productive rate under the situation of different molar ratios of reactant

[0046] Example

82

83

84

...

Embodiment 161

[0064] In a 100mL round-bottomed flask, add 1.82g (10.0mmol) acenaphthenequinone, 2.57g (11.5mmol) p-bromophenylhydrazine hydrochloride and 1g anhydrous sodium sulfate in sequence, 50mL ethanol as a solvent, nitrogen protection, and magnetic stirring Heated to about 60°C, refluxed for 12 hours, cooled to room temperature, filtered with suction, washed the filter cake with an appropriate amount of water, and dried to obtain an orange-yellow solid, which was recrystallized to obtain 2.27 g of orange-yellow crystals. Yield 64.6%.

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PUM

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Abstract

The invention discloses a compound (2Z)-2-((4-bromophenyl) hydrazono) acenaphthene-1-ketone with photoelectric activity as well as a preparation method and application thereof. According to the preparation method, acenaphthene quinone and para-bromophenylhydrazine hydrochloride are taken as raw materials, low-carbon alcohols is taken as a solvent, a dehydrating agent is added when the raw materials and the solvent are stirred, and a heating reaction is performed under the condition that air is separated so as to prepare the compound. The obtained compound has definite photoelectric activity, the production cost is low, and the reaction technology is simple and feasible.

Description

technical field [0001] The invention relates to a compound that can be used as a photoelectric material, in particular to (2Z)-2-((4-bromophenyl)hydrazono)acenaphthyl-1-one and its preparation method and application. Background technique [0002] Acenaphthoquinone is a relatively cheap product with almost no obvious optical, electrical or pharmaceutical activities, but its derivatives are widely used in the fields of pharmaceuticals, optoelectronic materials, and biochemistry. [0003] With the rapid development of science and technology, some materials with photoelectric activity play an increasingly important role, because their molecules contain π-conjugated systems, so they have very ideal physical and chemical properties. Such organic small molecule optoelectronic materials can be applied in many fields, such as transistors, switch sensors, photovoltaic cells, etc. Compared with conductive polymers and inorganic materials, organic small molecule optoelectronic material...

Claims

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Application Information

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IPC IPC(8): C07C251/84C07C249/16C09K11/06H01L51/30H01L51/46H01L51/54
CPCY02E10/549
Inventor 张超智胡鹏李世娟沈丹张骁
Owner 常熟紫金知识产权服务有限公司
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