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Carbon dioxide/photodimerization dual-response polymer and preparation method thereof

A carbon dioxide, dual-response technology, applied in the field of photopolymerization, can solve problems such as no research precedent, and achieve the effect of mild reaction conditions

Inactive Publication Date: 2020-07-24
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no research precedents at home and abroad for materials that respond to these two stimuli at the same time.

Method used

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  • Carbon dioxide/photodimerization dual-response polymer and preparation method thereof
  • Carbon dioxide/photodimerization dual-response polymer and preparation method thereof
  • Carbon dioxide/photodimerization dual-response polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Add 7-methyl-4-hydroxycoumarin, potassium hydroxide and acetone into the three-necked flask, and drip epichlorohydrin into the three-necked flask under the protection of nitrogen atmosphere, and react at 40 °C for 20 h. After cooling down, the reaction solution was suction filtered, the solvent was removed by rotary evaporation, the product was dissolved in chloroform, washed three times with ultra-pure water, the water was removed by anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and recrystallized from ethanol to obtain coumarin derivatives.

[0022] The coumarin derivatives with epoxy groups were dissolved in ethanol, dropped into ethylenediamine and reacted at 78 °C for 10 h. The solvent was removed by rotary evaporation, dissolved in ultrapure water, extracted with ethyl acetate, washed three times with saturated brine, and rotary evaporated to finally obtain the product of Example 1 as a yellow solid.

[0023] Proton NMR s...

Embodiment 2

[0026]

[0027] 7-Hydroxy-4-methylcoumarin and 2-chloroethanol were dissolved in DMF and mixed evenly, then added into a three-neck flask, then potassium carbonate was added, and nitrogen gas was introduced for protection. The temperature was raised to 85 °C after 30 min of nitrogen gas, and cooled to room temperature after 8 h of reaction. The reaction solution was slowly dropped into ice water for precipitation. After standing for 24 h, the precipitate was filtered off. The filtered solid was recrystallized again from ethyl acetate. 7-(2-Acrylateethoxy)-4-methylcoumarin is finally obtained. Under the protection of nitrogen atmosphere, dissolve 7-(2-acrylate ethoxy)-4-methylcoumarin coumarin and potassium hydroxide in acetone, add it to a three-necked flask, and raise the temperature to 40 °C Add epichlorohydrin to the three-neck flask and react for 20 h. After cooling down, the reaction solution was suction filtered, the solvent was removed by rotary evaporation, the ...

Embodiment 3

[0029]

[0030] 7-Hydroxy-4-methylcoumarin and 4-chlorobutanol were dissolved in DMF and mixed evenly, then added to a three-necked flask, then potassium carbonate was added, and nitrogen gas was introduced for protection. The temperature was raised to 85 °C after 30 min of nitrogen gas, and cooled to room temperature after 8 h of reaction. The reaction solution was slowly dropped into ice water for precipitation. After standing for 24 h, the precipitate was filtered off. The filtered solid was recrystallized again from ethyl acetate. Finally, 7-(4-acrylatebutoxy)-4-methylcoumarin is obtained. Under the protection of a nitrogen atmosphere, dissolve 7-(4-acrylate butoxy)-4-methylcoumarin coumarin and potassium hydroxide in acetone, add it to a three-necked flask, and raise the temperature to 40 °C Add epichlorohydrin to the three-neck flask and react for 20 h. After cooling down, the reaction solution was suction filtered, the solvent was removed by rotary evaporation, t...

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Abstract

The invention relates to a carbon dioxide / photodimerization dual-response polymer and a preparation method thereof. The invention provides an aminoalkyl substituted coumarin derivative with both carbon dioxide stimuli-responsiveness and photodimerization activity. Primary amino forms a carbamic acid ammonium salt bridge under the condition of introducing carbon dioxide, i.e., intermolecular physical crosslinking is formed, and physical crosslinking is opened under the condition of heating or introducing carbon dioxide; when the coumarin compound is irradiated by light with lambda larger than 300 nm, a photocyclization addition reaction can occur, and when the coumarin compound is irradiated by light with lambda less than 260 nm, a photolysis reaction can occur. A response system capable ofrealizing multi-step on-demand regulation can be realized on the basis of the two responsibilities, and the method is expected to be used for preparing a multi-regulation molecular size screening system.

Description

technical field [0001] The invention relates to the technical field of photopolymerization, in particular to a photodimerization system. It can be used as a double corresponding polymer of light and carbon dioxide to realize multi-level and multi-condition regulation on demand. Background technique [0002] The properties of photoresponsive materials mainly depend on the introduced photosensitive groups. The photosensitive groups are only dependent on the light of a specific band, and the corresponding photoreaction can only occur under the irradiation of light of a specific band. Photoresponsiveness includes changes in refractive index, changes in redox potential, changes in geometry, changes in dielectric constant, and the like. Photoresponsive materials can be used in self-healing materials, shape memory materials, drug release, microfluidic chip light-controlled switches, etc. [0003] In the photoresponsive system, the photoinduced cis-trans isomerization mechanism is...

Claims

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Application Information

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IPC IPC(8): C07D311/16C07D311/18
CPCC07D311/16C07D311/18
Inventor 何勇李星洲李捷鑫刘岱隆姚淼聂俊
Owner BEIJING UNIV OF CHEM TECH
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