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A class of ortho-positioned azobenzene derivatives containing charge-withdrawing groups for solar thermal storage and preparation method thereof

An azobenzene derivative, solar thermal technology, applied in heat exchange materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of reduced energy density, large steric hindrance, short service life, etc. , the preparation method is simple, the effect of high yield

Active Publication Date: 2019-02-22
TIANJIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, azobenzene also has disadvantages due to its own chemical structure limitation, (1) the standard free energy ΔH is small, the experimental measurement is only 41.4KJ / mol, and the ΔH obtained by theoretical calculation is only 56.9KJ / mol
(2) The thermal recovery barrier ΔEa is small, so that the time for cis to revert to trans is short, that is, the service life is short, and the half-life is generally less than 2 minutes
[0004] In 2011, G.Andrew Woolley synthesized azobenzene derivatives substituted with ortho-permethoxy groups. It was found that the half-life of the cis structure was prolonged due to the large steric hindrance of the ortho-position groups. to 2.4 days, but its energy density is greatly reduced

Method used

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  • A class of ortho-positioned azobenzene derivatives containing charge-withdrawing groups for solar thermal storage and preparation method thereof
  • A class of ortho-positioned azobenzene derivatives containing charge-withdrawing groups for solar thermal storage and preparation method thereof
  • A class of ortho-positioned azobenzene derivatives containing charge-withdrawing groups for solar thermal storage and preparation method thereof

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preparation example Construction

[0031] 1) Preparation of diazonium salt: prepare 0.3-0.6 mol / L 4-amino-3-fluoro (chloro, bromo) benzoic acid aqueous solution in a beaker, and mix a 37.5% HCl solution (HCl with the moles of the above-mentioned drugs) in a beaker ratio of 1:4) into it, and kept stirring until the 4-amino-3-fluoro(chloro, bromo)benzoic acid was fully dissolved, and it was kept in an ice bath (0-5°C); weighed NaNO 2 (1:1 molar ratio to 4-amino-3-fluoro(chloro, bromo)benzoic acid) was dissolved in distilled water and poured into the above solution; kept stirring under ice bath conditions to obtain a diazonium salt solution.

[0032] 2) Coupling reaction of diazonium salt and 3,5-dimethoxyaniline: weigh 3,5-dimethoxyaniline (1:1 molar ratio to diazonium salt) in distilled water; drop into beaker Add the HCl solution that mass fraction is 37.5%, (HCl and above-mentioned drug molar ratio are 1:4) edge dropwise stirring, until completely dissolving and keep it under ice-bath condition; And above-men...

Embodiment 1

[0036] 1) Preparation of diazonium salt: weigh 4-amino-3-fluorobenzoic acid of 0.93g weight in a beaker and pour 20ml of distilled water into it, and measure 2ml of 37.5% HCl solution in mass fraction, without Stir continuously until the 4-amino-3-fluorobenzoic acid is fully dissolved, and keep it in an ice bath (0-5°C); weigh 0.40g of NaNO 2 In a beaker, add 10ml of distilled water to dissolve completely and pour it into the above solution; keep stirring for 1h under ice bath conditions to obtain a diazonium salt solution.

[0037] 2) Coupling reaction of diazonium salt and 3,5-dimethoxyaniline: Weigh 0.92 g of 3,5-dimethoxyaniline (1:1 molar ratio to diazonium salt) in a beaker, Pour 50ml of distilled water into the volume; dropwise add 2ml of concentrated HCl solution with a mass fraction of 37.5% in the beaker, stir while adding dropwise, until completely dissolved and keep it under ice bath conditions; and the above-mentioned diazonium salt solution Slowly added dropwise...

Embodiment 2

[0042]1) Preparation of diazonium salt: weigh 4-amino-3-chlorobenzoic acid of 1.02g weight in a beaker and pour 20ml of distilled water into it, and measure 2ml of HCl solution with a mass fraction of 37.5%. Stir continuously until the 4-amino-3-chlorobenzoic acid is fully dissolved, and keep it in an ice bath (0-5°C); weigh 0.40g of NaNO 2 In a beaker, add 10ml of distilled water to dissolve completely and pour it into the above solution; keep stirring for 1h under ice bath conditions to obtain a diazonium salt solution.

[0043] 2) Coupling reaction of diazonium salt and 3,5-dimethoxyaniline: Weigh 0.92 g of 3,5-dimethoxyaniline (1:1 molar ratio to diazonium salt) in a beaker, Pour 50ml of distilled water into the volume; dropwise add 2ml of concentrated HCl solution with a mass fraction of 37.5% in the beaker, stir while adding dropwise, until completely dissolved and keep it under ice bath conditions; and the above-mentioned diazonium salt solution Slowly added dropwise t...

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Abstract

The invention relates to an ortho-position azobenzene derivative containing electron drawing groups for solar heat storage and a preparation method of the derivative. The preparation method includes the steps: 1) preparing diazonium salt; 2) performing coupling reaction for the diazonium salt and 3, 5-dimethoxyaniline; 3) adjusting pH (potential of hydrogen); 4) purifying to obtain the azobenzene derivative. The obtained azobenzene derivative is provided with the electron drawing groups and large-space steric hindrance groups at ortho-position, cis-vinylene restoring half-life period of azobenzene can be prolonged, carboxyl replaced at para-position can form intermolecular hydrogen bonding, energy storage density can be improved, and the azobenzene derivative can be applied to solar heat storage.

Description

technical field [0001] The invention relates to a class of azobenzene derivatives containing electric-absorbing groups in the ortho position for solar thermal storage and a preparation method thereof, in particular to a class of azobenzene derivatives with electric-absorbing groups, steric hindrance and intermolecular hydrogen bonds Preparation of azobenzene derivatives and their application in solar heat storage. Background technique [0002] Stimuli-responsive materials refer to materials whose physical and chemical properties change correspondingly under the action of specific external stimuli (such as light temperature, electric field, and ionic strength, etc.). Light irradiation has the advantages of being clean, easy to control, and does not change the surrounding environment of the analyte, so it has attracted much attention in the preparation of stimuli-responsive materials. Azobenzene has cis-trans isomerism under light irradiation, and its cis-trans isomers can ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/08C09K5/16
CPCC07C245/08C09K5/16
Inventor 封伟曹晨冯奕钰李瑀
Owner TIANJIN UNIV
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