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A preparation method based on intramolecular or intermolecular asymmetric organic molecular electrocatalyst and its application in zinc-air battery

An electrocatalyst and organic molecule technology, which is applied in the application field of zinc-air batteries, can solve the problems of inability to accurately synthesize and regulate catalytic active sites, and inability to further accurately design a material system with high catalytic activity. The effect of modulating catalytic activity

Active Publication Date: 2022-05-24
QINGDAO UNIV
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Problems solved by technology

Although researchers have carried out a lot of research on catalytic activity, they cannot precisely synthesize and regulate catalytic active sites, and cannot further accurately design material systems with high catalytic activity.

Method used

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  • A preparation method based on intramolecular or intermolecular asymmetric organic molecular electrocatalyst and its application in zinc-air battery
  • A preparation method based on intramolecular or intermolecular asymmetric organic molecular electrocatalyst and its application in zinc-air battery
  • A preparation method based on intramolecular or intermolecular asymmetric organic molecular electrocatalyst and its application in zinc-air battery

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of compound 2:

[0067] Under argon protection, 800.2 mg of compound 1 (preparation method reference: Polymer AcceptorBased on Double B← N Bridged Bipyridine (BNBP) Unit for High-Efficiency All-Polymer Solar Cells.Adv.Mater, 2016, 28(30) :6504-6508;Electron-DeficientBuilding Block Based on B←N Unit for Polymer Acceptor of All-Polymer SolarCells.Angew.Chem.Int.Ed.2016,55(4):1436-1440) soluble in dried dichloromethane (15mL), At the same time, 10 times the amount of boron trifluoride diethyl ether and 5 times the equivalent of triethylamine are slowly added to it, reflux at 50 ° C for 2h and then cooled to room temperature, the solvent is removed by distillation, the organic phase is extracted with n-hexane, and column chromatography is separated (dichloromethane: petroleum ether mobile phase) to give compound 2, yield: 570mg (67%). 1 H NMR(400MHz,CDCl 3 ,20℃):δ10.75-10.72(m,1H),8.09(d,J＝2.0Hz,1H),7.94(d,J＝2.0Hz,1H),7.41(d,J＝1.6Hz,1H),7.30(d,J＝2.0Hz,1H),3.39(d,J＝7...

Embodiment 2

[0079] Compound 4:

[0080] After dissolving 400.3 mg of compound 3 and 2 times the equivalent NaH in dried THF (10 mL) and refluxing at 70 °C for 2 h, add 3 times the equivalent C dropwise to the reaction 4 H 9 Br, after continuing to reflux at 70 °C for 24h, cooled to room temperature and added a small amount of water dropwise to quench the reaction, extracted with dichloromethane (150mL), column chromatography separation (dichloromethane: petroleum ether mobile phase) to give Compound 4, yield: 241mg (52%). 1 H NMR(400MHz,CDCl 3,20℃):δ9.41(s,1H),7.94(d,J＝2.0Hz,1H),7.86(d,J＝2.0Hz,1H),7.17(d,J＝2.0Hz,1H),7.11(d,J＝1.6Hz,1H),6.52(s,2H),3.18-3.13(m,2H),1.74-1.67(m,2H),1.52-1.46(m,2H),1.01-0.97(m, 3H).

[0081]

[0082] Compound 5:

[0083] 210.4 mg of compound 4 and 4 times the equivalent NaH were dissolved in dried THF (10 mL), reflux at 70 °C for 2 h, and then added 4 times the equivalent C to the reaction dropwise 16 H 33 I, continue at 70 °C after reflux for 24h, cooled to room...

Embodiment 3

[0095] as-BNT：

[0096] Under the protection of argon, 200.2 mg of compound 9,158.9 mg 2-tributylstannyl thiophene, 0.02 times equivalent tris (dibenzylacetone) dipalladium and 0.16 times equivalent of tri(o-methylphenyl) phosphorus were dissolved in dry toluene (20 mL). After reflux at 100 °C for 24h, it was cooled to room temperature, extracted with dichloromethane (150mL), separated by column chromatography (dichloromethane: petroleum ether mobile phase), and as-BNT was obtained, yield: 196mg (97%). 1 H NMR(400MHz,CDCl 3 ,20℃):δ8.41(d,J＝1.6Hz,1H),8.17-8.16(m,1H),7.68(d,J＝1.2Hz,1H),7.58-7.48(m,4H),7.21-7.18(m,1H),3.59-3.53(m,4H),1.71(d,J＝6Hz,2H),1.45-1.25(m,16H),0.97-0.86(m,12H).

[0097]

[0098] In order to explore the advantages of asymmetric structure small molecules in various properties, we synthesized and prepared small molecules with corresponding symmetrical structures according to the same method, and the synthesis route is as follows:

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Abstract

The invention relates to the field of oxygen reduction electrocatalysts, in particular to a method for preparing an electrocatalyst based on intramolecular or intermolecular asymmetric organic molecules and its application in zinc-air batteries. An asymmetric organic molecule oxygen reduction electrocatalyst has been prepared. The structure of the asymmetric organic molecule can be adjusted and the active site can be controlled, which can effectively avoid the inability to accurately synthesize the exact molecular structure by conventional carbonization or doping methods, resulting in heteroatoms / defective catalytic centers Problems with unclear understanding of the active site. Since the asymmetric molecular structure helps to break the integrity of the π-conjugated system, large-area redistribution of electrons occurs on the conjugated skeleton, which in turn affects the catalytic activity and the number of active sites of the material. Compared with the corresponding symmetrical organic molecules, the present invention significantly increases the catalytic activity of the oxygen reduction electrocatalyst under alkaline conditions by adjusting the degree of asymmetry of the organic molecules. Provide new ideas.

Description

Technical field [0001] The present invention relates to the technical field of oxygen reduction electrocatalysts, specifically relates to a preparation method based on intramolecular or intermolecular asymmetric organic molecular electrocatalysts and their applications in zinc-air batteries. Background [0002] Energy and the environment are an important support for human survival and development, and traditional fossil energy has always been the main source of energy supply for human society. With the rapid development of the global economy and the deepening of industrialization, the bottleneck constraints on energy resources are becoming increasingly prominent, and environmental constraints are also intensifying. Therefore, the development of highly efficient, pollution-free, stable and renewable new energy has become an important direction for future energy development. In recent years, among many energy conversion technologies, fuel cells, as a device that converts chemical e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01M4/88H01M4/90H01M12/06
CPCH01M4/8825H01M4/9008H01M4/9083H01M12/06H01M2004/8689
Inventor 龙晓静王彬彬王美龙宋伟琛赵子杰张乾坤
Owner QINGDAO UNIV
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