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Methacrylate containing ortho-tetrafluoroazobenzene structure, polymer thereof, and preparation method and application thereof

A technology of methacrylate and tetrafluoroazobenzene is applied in the fields of methacrylate containing ortho-tetrafluoroazobenzene structure, its polymer, preparation and use, and can solve the problem of affecting the optical properties of materials, biological Harm, application limitation, etc., to avoid light loss, avoid loss, and improve stability

Inactive Publication Date: 2015-09-16
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, azobenzene polymers are not perfect in practical applications
General azobenzene polymers can only undergo trans→cis isomerization under ultraviolet light, and ultraviolet light is very harmful to organisms, which greatly limits its application
In addition, with the increase of illumination time and frequency or the enhancement of excitation light intensity, the N=N bond of azobenzene chromophore may appear fatigue fracture (photodecomposition) during multiple cis-trans isomerization cycles, thereby affecting The overall optical properties of the material

Method used

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  • Methacrylate containing ortho-tetrafluoroazobenzene structure, polymer thereof, and preparation method and application thereof
  • Methacrylate containing ortho-tetrafluoroazobenzene structure, polymer thereof, and preparation method and application thereof
  • Methacrylate containing ortho-tetrafluoroazobenzene structure, polymer thereof, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Example 1: Synthesis of methacrylate containing ortho-tetrafluoroazobenzene structure (TFAzoMMA).

[0081] (1) Synthesis of compound 2:

[0082] Add 2,6-difluoroaniline (compound 1) (1.94g, 15.00mmol) into a 100mL beaker, add hydrochloric acid (4.95mL concentrated hydrochloric acid + 4.95mL deionized water) and deionized water (30mL) under stirring, at room temperature Stir well until 2,6-difluoroaniline is dissolved; then place the beaker in an ice-water bath and continue stirring, and when the temperature drops to 0~5°C, slowly add NaNO dropwise to the system 2 aqueous solution (17.25mmol NaNO 2 Dissolved in 15mL deionized water), keep the reaction temperature at 0~5℃ during the dropwise addition; after the dropwise addition, continue to stir at 0~5℃ for 20 minutes, then add a small amount of sulfamic acid to destroy the excess NaNO 2 , and continued to stir at 0~5°C for 20 minutes to obtain an aqueous solution of compound 2.

[0083]

[0084] (2) Synthesis of c...

Embodiment 2

[0094] Example 2: Using EBiB as an ATRP initiator to synthesize a methacrylate-type homopolymer (PTFAzoMMA) with a side chain containing an ortho-tetrafluoroazobenzene structure.

[0095] Add TFAzoMMA (500.0 mg, 1.14 mmol), CuBr ( 3.3mg, 0.023mmol), EBiB (4.4mg, 0.023mmol), PMDETA (9.5μL, 0.046mmol), with THF (2mL) as the solvent, the double row tube was filled with argon three times, and the tube was sealed under an oxygen-free atmosphere. The sealed ampoule was placed in a constant temperature oil bath at 70°C for 23 hours. After the reaction, take out the sealed tube, cool it with cold water immediately, open the sealed tube, add a small amount of THF to dilute, pour it into 100 mL of ice-free methanol, put it in the refrigerator overnight, filter it with suction, and dry it to obtain PTFAzoMMA (300 mg).

[0096]

[0097] The H NMR spectrum of the homopolymer PTFAzoMMA is as follows: figure 2 shown. According to the hydrogen integral value in the terminal methoxy gro...

Embodiment 3

[0099] Embodiment three: with PEG 50 -Br is the ATRP initiator for the synthesis of amphiphilic block copolymers (PEG 50 - b -PTFAzoMMA 31 ).

[0100] By n(TFAzoMMA):n(PEG 50 -Br):n(CuBr):n(PMDETA)=50:1:3:6 molar ratio, TFAzoMMA (250.0mg, 0.57mmol), CuBr (5.0mg, 0.034mmol), CuBr (5.0mg, 0.034mmol), PEG 50 -Br (58.8mg, 0.011mmol), PMDETA (15.0μL, 0.068mmol), THF (2mL) was used as solvent, the double row tube was filled with argon three times, and the tube was sealed under an oxygen-free atmosphere. The sealed ampoule was placed in a constant temperature oil bath at 70°C for 20 h. After the reaction, take out the sealed tube, cool it with cold water immediately, open the sealed tube, add a small amount of THF to dilute, pour it into 100ml of anhydrous ether, filter it with suction, and dry it to obtain PEG 50 - b -PTFAzoMMA 31 (115 mg).

[0101]

[0102] Block copolymer PEG 50 - b -PTFAzoMMA 31 The H NMR spectrum of Figure 4 shown. According to the integral va...

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PUM

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Abstract

The invention discloses methacrylate containing ortho-tetrafluoroazobenzene structure, a polymer thereof, and a preparation method and an application thereof. According to the invention, an ortho-tetrafluoroazobenzene structure-containing methacrylate monomer represented by a formula I is successfully prepared through the steps of (1) diazonium salt synthesis, (2) ortho-tetrafluoroazo phenol synthesis, (3) ortho-tetrafluoroazobenzene-containing alcohol synthesis, and (4) monomeric compound synthesis; the monomer is adopted as a basis, and a corresponding methacrylate-type homopolymer and an amphiphilic block copolymer are prepared through an ATRP polymerization reaction. The ATRP method adopted by the invention has active / controllable polymerization characteristics, such that the homopolymer and the block copolymer with side chains containing the ortho-tetrafluoroazobenzene structure and with double light responses can be synthesized. The homopolymer and the block copolymer have controllable molecular weights and narrow molecular weight distribution.

Description

technical field [0001] The invention belongs to the field of optical polymer materials, and relates to a preparation method and application of a methacrylate and a polymer thereof, in particular to a methacrylate containing an ortho-tetrafluoroazobenzene structure, and a side chain containing an ortho-tetrafluoro Methacrylate homopolymer with azobenzene structure and amphiphilic block polymerization composed of hydrophobic side chain polymer segment containing ortho-tetrafluoroazobenzene structure and hydrophilic polyethylene glycol segment The preparation method and use of the substance. Background technique [0002] Stimuli-responsive materials refer to materials whose physical and / or chemical properties change accordingly under the action of specific external stimuli (such as light, temperature, pH value, electric field, and ionic strength, etc.). Due to the advantages of being clean, easy to control, and not changing the surrounding environment of the measured object, l...

Claims

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Application Information

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IPC IPC(8): C07C245/08C08F120/36C08F293/00C08F220/36G02B1/04
Inventor 周年琛夏爱游陆金杰王健朱健张正彪朱秀林
Owner SUZHOU UNIV
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