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Thienyl and selenophenyl viologen derivatives, and synthesis method and application thereof

A synthetic method, viologen technology, applied in electrochemical generators, regenerative fuel cells, fuel cells, etc., can solve the problems of low electron transfer rate, low solubility, low conjugation, etc., and achieve outstanding kinetic performance, Improve solubility and conductivity, and effect of charge balance

Pending Publication Date: 2021-08-06
XI AN JIAOTONG UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to overcome the above-mentioned shortcoming of the prior art, the present invention provides a class of thienyl, selenophene base viologen derivatives and their synthesis methods and applications, which solve the problem of viologen derivatives with low conjugative properties and low electron transfer rates. The problem of low solubility and low capacity can effectively improve the application performance of the viologen system in the field of neutral aqueous organic redox flow batteries, and can further expand the application field of viologen derivatives

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  • Thienyl and selenophenyl viologen derivatives, and synthesis method and application thereof
  • Thienyl and selenophenyl viologen derivatives, and synthesis method and application thereof
  • Thienyl and selenophenyl viologen derivatives, and synthesis method and application thereof

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preparation example Construction

[0066] 1, the synthetic method of a class of thienyl viologen derivatives of the present invention comprises the following steps:

[0067] 1): Precursor A of thienyl viologen derivatives synthesized by Suzuki coupling reaction;

[0068] Under an argon protective atmosphere, take 2,5-dibromothiophene (4.13mmol), 4-pyridine borate (10.33mmol), and tetrakistriphenylphosphine palladium (0.21mmol) in a pressure-resistant tube. Phenylphosphine palladium is used as a reaction catalyst, and the molar ratio of the three is 1:2.5:0.05. Add methyl trioctyl ammonium chloride (phase transfer catalyst), 40mL oxygen-free potassium carbonate solution (2M) and 60mL freshly steamed toluene (anhydrous and oxygen-free toluene as solvent), the volume ratio of potassium carbonate solution and toluene is 2:3. Stir well and heat the reaction at 130°C for 3d.

[0069] Post-treatment process: Cool the reaction mixture to room temperature, take the organic matter in the upper layer after liquid separa...

Embodiment 1

[0096] 1, the synthetic method of a class of thienyl viologen derivatives of the present invention comprises the following steps:

[0097] 1): Precursor A of thienyl viologen derivatives synthesized by Suzuki coupling reaction;

[0098] Take a 100mL branch bottle and a 250mL pressure tube to dry, and use a pump to cool it for later use. Prepare 40 mL of potassium carbonate solution (2M) and bubble for 20 minutes. Take 1g of 2,5-dibromothiophene (4.13mmol), 2.12g of 4-pyridine borate (10.33mmol), the molar ratio of the two is 1:2.5, add it to the 250mL pressure tube prepared in advance, and put it in the glove box Weigh 260 mg tetrakistriphenylphosphine palladium (0.21 mmol) in it as a reaction catalyst. Under argon atmosphere, 1 mL of methyltrioctylammonium chloride (phase transfer catalyst), 40 mL of potassium carbonate solution (2M), 60 mL of freshly distilled toluene were added. Stir well and heat the reaction at 130°C for 3d.

[0099] Post-treatment process: Cool the r...

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Abstract

The invention relates to thienyl and selenophenyl viologen derivatives, and a synthesis method and application thereof. An ideal electron acceptor material is obtained by combining a viologen compound with an electron donating thiophene group and a selenophenyl group, so that the conjugacy and the stability of the viologen derivatives are widened, rapid intramolecular electron transfer is realized, and the viologen derivatives have outstanding dynamic performance; and by introducing quaternary ammonium salt, the reduction threshold value of the material is greatly reduced, the solubility and the conductivity are improved, multi-electron charging and discharging can be performed, and the capacity is further improved. Single-electron charging and discharging can be performed by introducing hydroxyl, so that the structural stability is further improved; after bromide ions of the corresponding viologen derivative are converted into chloride ions, when the electrode material is applied to a neutral aqueous organic redox flow battery, the ions in the electrode material and ions in an electrolyte are kept consistent, and charges are balanced; and the molecular weight is reduced, the solubility is improved, and the influence of bromide ion electricity on an electrochemical test can be eliminated.

Description

technical field [0001] The invention belongs to the technical field of electrode materials for liquid flow batteries, and specifically relates to a class of thienyl and selenophene based viologen derivatives and their synthesis methods and applications. Background technique [0002] Energy shortage and environmental problems have become two major problems faced by human beings. The use of clean and efficient energy represented by solar energy and wind energy has become a world development trend. However, solar and wind power generation has strong fluctuations and intermittences, which pose a huge challenge to the stable output of traditional power grids. Efficient storage and transportation of such power has become a hot research issue at present. But at present, because the existing fossil fuel-based energy infrastructure cannot meet the requirements of sustainable social development, improving energy supply capacity and energy security are facing severe challenges. To ad...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D421/14H01M4/86H01M8/18
CPCC07D409/14C07D421/14H01M4/86H01M8/188H01M2004/8684Y02E60/50
Inventor 何刚刘旭张旭日张冰洁张思坤李国平杨小东
Owner XI AN JIAOTONG UNIV
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