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Energy storage material based on 2,5-norbornadiene derivative and preparation method thereof

A technology of norbornol and derivatives, applied in the field of materials engineering, can solve the problems of unpreserved energy, low QC of recovery reaction, instability, etc., and achieve the effects of improving photon quantum yield, increasing energy density, and stable configuration.

Active Publication Date: 2018-11-23
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, after the NBD is converted into QC by light charging, the energy barrier of the recovery reaction is very low and the QC is very unstable, so the stored energy cannot be saved.

Method used

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  • Energy storage material based on 2,5-norbornadiene derivative and preparation method thereof
  • Energy storage material based on 2,5-norbornadiene derivative and preparation method thereof
  • Energy storage material based on 2,5-norbornadiene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1) Synthesis of ortho-disubstituted carboxyl 2,5-norbornadiene: Weigh 4.63g (70mmol) of butynedioic acid and dissolve it in 30mL deionized water, weigh 1.44g (10mmol) of refined cyclopentadiene and slowly It was added dropwise to the aqueous solution containing butynedioic acid, stirred and reacted at room temperature for 4 hours, and a white precipitate was obtained. The reaction solution was extracted with chloroform, and the solvent was distilled off to obtain a crude product.

[0038] 2) Purification: the crude product was dissolved in 1mol L -1 In aqueous NaOH solution, the aqueous layer was washed with chloroform, and then acidified with hydrochloric acid (pH=2) to obtain a white precipitate. The aqueous layer was extracted with dichloromethane, dried, and the solvent was removed by rotary evaporation. 0.984 g of the product was obtained with a yield of 72%.

[0039] 3) Synthesis of ortho-disubstituted azophenyl 2,5-norbornadiene: Weigh 0.700g (5mmol) disubstit...

Embodiment 2

[0042] 1) Synthesis of ortho-disubstituted carboxyl 2,5-norbornadiene: Weigh 7.00 g (106 mmol) of butynedioic acid and dissolve it in 40 mL of deionized water, weigh 1.72 g (15 mmol) of refined cyclopentadiene and slowly It was added dropwise to the aqueous solution containing butynedioic acid, stirred and reacted at room temperature for 4 hours, and a white precipitate was obtained. The reaction solution was extracted with chloroform, and the solvent was distilled off to obtain a crude product.

[0043] 2) Purification: the crude product was dissolved in 1mol L -1 In aqueous NaOH solution, the aqueous layer was washed with chloroform, and then acidified with hydrochloric acid (pH=2) to obtain a white precipitate. The aqueous layer was extracted with dichloromethane, dried, and the solvent was removed by rotary evaporation. 1.56 g of the product was obtained with a yield of 76%.

[0044] 3) Synthesis of ortho-disubstituted azophenyl 2,5-norbornadiene: Weigh 1.40g (10mmol) d...

Embodiment 3

[0047] 1) Synthesis of ortho-disubstituted carboxyl 2,5-norbornadiene: Weigh 23.15g (350mmol) of butynedioic acid and dissolve it in 100mL deionized water, weigh 5.70g (50mmol) of refined cyclopentadiene and slowly It was added dropwise to the aqueous solution containing butynedioic acid, stirred and reacted at room temperature for 4 hours, and a white precipitate was obtained. The reaction solution was extracted with chloroform, and the solvent was distilled off to obtain a crude product.

[0048] 2) Purification: the crude product was dissolved in 1mol L -1 In aqueous NaOH solution, the aqueous layer was washed with chloroform, and then acidified with hydrochloric acid (pH=2) to obtain a white precipitate. The aqueous layer was extracted with dichloromethane, dried, and the solvent was removed by rotary evaporation. 4.63 g of the product was obtained with a yield of 68%.

[0049] 3) Synthesis of ortho-disubstituted azophenyl 2,5-norbornadiene: Weigh 5.00g (37mmol) disubst...

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Abstract

The invention discloses an energy storage material based on a 2,5-norbornadiene derivative and a preparation method thereof. An esterification method is used for preparing an ortho grafted bisazo benzene 2,5-norbornadiene derivative; two azobenzene groups are introduced at 2,5-norbornadiene in an ortho manner, so that norbornadiene is obviously subjected to Einstein shift; the photon yield is effectively improved. 2,5-norbornadiene and the azobenzene groups are combined, so that the heat storage energy density can be effectively improved; the storage energy is increased. The material has excellent optical performance and is hopeful to be applied in the fields of light and heat conversion and energy storage.

Description

technical field [0001] The invention belongs to the technical field of material engineering, and more specifically relates to the preparation of an ortho-disubstituted azophenyl 2,5-norbornadiene, which has broad application prospects in the fields of solar energy storage, light drive and the like. Background technique [0002] Norbornadiene compounds (2,5-Norbornadiene, NBD for short) are the most extensively and deeply studied energy storage materials. The energy storage mechanism of this type of compound is: under the irradiation of ultraviolet light, NBD undergoes a diene cycloaddition reaction and converts into its photoisomer - Quadricyclane (QC for short) with extremely high tension. The solar energy is stored in the form of tension energy; under the irradiation of heating or catalyst (such as Co(II)-TPP) or another wavelength of ultraviolet light, QC reverses back to NB, and the tension energy is released in the form of heat at the same time. ( figure 1 ), effectiv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C07C51/353C07C61/29C09K5/10
CPCC07C51/353C07C245/08C09K5/10C07C61/29
Inventor 封伟董立奇冯奕钰阎清海符林霞
Owner TIANJIN UNIV
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