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Hexa-aza-naphthalene derivative and preparation method and application thereof

A technology of hexaaza and derivatives, which is applied in the field of synthesis of electrode materials for water-based zinc-ion batteries, can solve the problems of high price, and achieve the effects of low cost, good reproducibility and high cycle stability

Active Publication Date: 2021-02-26
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, Wang Yonggang et al. reported pyrene-4,5,9,10-tetraketone (PTO) as the cathode material of aqueous zinc batteries and flexible aqueous zinc batteries. The excellent electrochemical performance and mechanical durability of flexible aqueous zinc batteries show However, the potential application value of this zinc battery in wearable electronic devices is regrettably used in the preparation of pyrene-4,5,9,10-tetraketone process to use expensive noble metal catalysts (Angew.Chem.Int.Ed.2018 ,57,11737–11741)

Method used

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  • Hexa-aza-naphthalene derivative and preparation method and application thereof
  • Hexa-aza-naphthalene derivative and preparation method and application thereof
  • Hexa-aza-naphthalene derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0077]In a 100mL three-necked flask was added 60mL of acetic acid, while adding 4,5-difluoro-1,2-phenylenediamine (0.690g, 4.8mmol), cyclohexanone octahydrate (0.499g, 1.6mmol), under nitrogen Under the protection, the reaction mixture was kept stirring under reflux. The reaction time was 24 hours. After the reaction, the heating was stopped, and acetic acid, deionized water and ethanol were added to wash several times. The solid was collected by suction filtration and dried under vacuum at 100°C for 6 hours to obtain the compound. A: 2,3,8,9,14,15-hexafluorohexaazanaphthalene, the yield was 84.3%.figure 1 Is the infrared spectrum,figure 2 Is the NMR spectrum,image 3 Is a solid nuclear magnetic carbon spectrum,Figure 4 It is a mass spectrum, which is used as the active material of the electrode material. According to the mass ratio of the active material: Ketjen Black: Binder (PVDF) = 30%: 60%: 10%, mix and grind, and then add the diffusing agent (NMP) dropwise. Grinding, coating on...

Embodiment 2

[0083]In a 100mL three-necked flask, add 30mL of acetic acid and 30mL of ethanol, and add 4,5-dichloro-o-phenylenediamine (0.85g, 4.8mmol), cyclohexanone octahydrate (0.499g, 1.6mmol) at the same time, under nitrogen protection The reaction mixture was continuously stirred under reflux status. The reaction time was 24 hours. After the reaction, the heating was stopped, and acetic acid, deionized water, and ethanol were added to wash several times. The solid was collected by suction filtration, and then the product was transferred to the flask and added 30% nitric acid (50 mL) was stirred and refluxed at 140°C for 3 hours. The solid was collected by filtration, the filter cake was thoroughly washed with deionized water and ethanol in sequence, and dried in vacuum to obtain compound B: 2,3,8,9,14,15-hexachlorohexaazin with a yield of 87%.Figure 22 Is the rate stability diagram of button battery;Figure 23 It is the charging and discharging curve diagram of the button cell under differe...

Embodiment 3

[0085]The experimental method is the same as in Example 1, except that 4,5-difluoro-1,2-phenylenediamine is added to the mass of reactants (1.380g, 9.6mmol) to obtain compound C: 1,2,3,4,7,8 ,9,10,13,14,15,16-Dodecafluorohexaazanaphthalene, the yield was 73%.

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Abstract

The invention belongs to the field of synthesis of aqueous zinc ion battery electrode materials, and particularly relates to a hexa-aza-naphthalene derivative and a preparation method and applicationthereof. The synthesis method of the hexa-aza-naphthalene derivative comprises the following synthesis steps that 3, 4-diamino-1, 6-phenyl derivative and cyclohexanone octahydrate are added into a reactor under the protection of inert gas and dissolved in an organic solvent; the reaction mixture is stirred continuously in the reflux state, after the reaction is over, heating is stopped, the aceticacid, the deionized water and the ethanol are added for washing, suction filtration is carried out, and the hexa-aza-naphthalene derivative is synthesized. The preparation method of the hexa-aza-naphthalene derivative is simple in process, low in cost, low in energy consumption, good in reproducibility and excellent in performance. The synthesized hexa-aza-naphthalene derivative material not onlycan solve the problem that organic material naphthoquinone derivatives are dissolved in electrolyte, but also is expected to obtain performance with high conductivity so as to guarantee rapid transmission of electrons in the electrochemical reaction process, and has wide application prospects in the field of aqueous zinc ion battery electrode materials.

Description

Technical field[0001]The invention belongs to the field of synthesis of electrode materials for water-based zinc ion batteries, and particularly relates to the synthesis and application of hexaazanaphthalene derivatives.Background technique[0002]With the progress of the times, the old battery system is gradually replaced by the new system. Therefore, it is an inevitable trend to design green, environmentally friendly and high-performance electrical energy storage devices for future electronic products. The development direction of today's electronic equipment is lightweight, portable, and long battery life. At the same time, it can meet the application on different devices, so the battery needs to be universal and safe. This undoubtedly poses a serious problem for the development of water-based batteries. For the time being, commercial batteries cannot solve this problem for the time being. And there are many elements that pollute the environment in commercial batteries. In addition...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14H01M4/60H01M10/36
CPCC07D487/14H01M4/60H01M10/36Y02E60/10
Inventor 刘琦苏豪祺马艳伟
Owner CHANGZHOU UNIV
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