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Polymer containing cyclic azobenzene-dinaphthalene structure on side chain as well as preparation method and application of polymer

A technology of cyclic azobenzene and polymers, which is applied in the field of chiral optical polymers and can solve problems such as blanks

Active Publication Date: 2015-08-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at this stage, there are almost blank research reports on polymers containing cyclic azobenzene-binaphthyl structures in the side chains used as chiral optical switches.

Method used

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  • Polymer containing cyclic azobenzene-dinaphthalene structure on side chain as well as preparation method and application of polymer
  • Polymer containing cyclic azobenzene-dinaphthalene structure on side chain as well as preparation method and application of polymer
  • Polymer containing cyclic azobenzene-dinaphthalene structure on side chain as well as preparation method and application of polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1: Synthesis of azobenzene donor.

[0093] 1. Synthesis of azophenol intermediate (compound 1).

[0094] Add 18.8g (0.16mol) m-aminophenylacetylene, 100mL deionized water and 40.5mL concentrated hydrochloric acid into a 500mL beaker, and stir in an ice-salt bath. When the temperature drops to 0~5°C, add dropwise an aqueous solution of sodium nitrite (prepared by dissolving 12.35g (0.18mol) of sodium nitrite in 100mL of deionized water), keep the system temperature at 0~5°C, and complete the dropwise addition Afterwards, the reaction was continued for 20 minutes to obtain a diazonium salt solution.

[0095] Add 41.72g (0.24mol) of p-bromophenol, 300mL of deionized water and 12.85g (0.32mol) of sodium hydroxide into a 1000mL beaker, and stir in an ice-water bath. When the temperature drops to 0-5°C, add sodium bicarbonate to adjust the pH value to 9. The above-mentioned diazonium salt solution was slowly dropped into the system, and the reaction was continued f...

Embodiment 2

[0100] Example 2: Synthesis of binaphthyl donor.

[0101] 1. Synthesis of brominated binaphthyl intermediate (compound 3).

[0102] Add 2.9g (21mmol) of potassium carbonate and a catalytic amount of potassium iodide to a 1000mL three-necked flask, and dissolve them fully with 700mL of acetone. 2.86g (10mmol) of 2,2'-binaphthol was added under stirring, and while the temperature was raised, 2.66g (11mmol) of 1,6-dibromohexane in acetone was added dropwise, and refluxed at 80°C for 100 minutes. TLC tracking (the ratio of developer is n-hexane: ethyl acetate = 10:1) shows that by-products are formed in about 1.5 hours, and the heating should be stopped at this time. Natural cooling at room temperature, precipitation, rotary evaporation of acetone solution, purification by column chromatography with a mixed solvent of n-hexane and ethyl acetate (the ratio of developing solvent is n-hexane: ethyl acetate = 10:1), and spin-dried to obtain 1.87g target product.

[0103]

[0104...

Embodiment 3

[0110] Example 3: CuAAC ring-closing reaction between two donors.

[0111] 1. Synthesis of compound 6 (the first CuAAC reaction between an alkyne group and an azide group for linking two donors).

[0112] Take 0.2g (0.3mmol) of compound 5 and 0.16g (0.3mmol) of compound 2 into a three-necked flask, and then add 5mL of dichloromethane into it to dissolve. After passing argon for 30 minutes, 1 mg (7 μmol) of cuprous bromide and 6 ml (7 μmol) of pentamethyldiethylenetriamine (PMDETA) were added, and refluxed at 30°C for 40 minutes in an argon atmosphere. After the solvent was evaporated to dryness in vacuo, 0.30 g of the target product (compound 6) was obtained by column chromatography (developing solvent ratio: n-hexane: ethyl acetate = 4:1).

[0113]

[0114] 2. Synthesis of compound 7 (azidation reaction, used to introduce another azido group).

[0115] The process of compound 7 synthesized from compound 6 through azidation reaction can refer to the synthesis process of c...

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Abstract

The invention discloses a polymer containing a cyclic azobenzene-dinaphthalene structure on a side chain as well as a preparation method and application of the polymer. Specifically, the polymer has a structure shown by a formula I, and is prepared by the method comprising the following steps: (1) obtaining two types of donors; (2) connecting the two types of donors and performing closed-loop reaction; (3) synthesizing a cyclic monomer; and (4) synthesizing the polymer. The polymer disclosed by the invention is relatively good in product processability and mechanical property, and relatively narrow in molecular weight distribution; meanwhile, a general free radical polymerization method is adopted to synthesize asymmetrical monomers into a chiral optical polymer, and the experimental operation is simple and feasible, so that a new idea is provided for designing and synthesizing polymer chiral optical switches; and moreover, the chemical reagents used in the method disclosed by the invention are stable in the air, and the method is simple and convenient to operate, is high in efficiency and is convenient for industrial production.

Description

technical field [0001] The invention belongs to the field of chiral optical polymers, and relates to a polymer whose side chain contains a cyclic azobenzene-binaphthyl structure, a preparation method and an application thereof. Background technique [0002] On the one hand, due to their high sensitivity to external stimuli (such as pH, light, temperature, enzymes, and electric fields, etc.), smart responsive materials have gradually been favored by researchers in recent years. In particular, photoresponsive azobenzene compounds have been widely used in logic gates, molecular switches, and drug loading, all due to the special responsiveness of azobenzene groups to ultraviolet and visible light, which can be stimulated by light. Reversible cis-trans isomerization can occur and is accompanied by a size change between 9.0 Å (trans) and 5.5 Å (cis). On the other hand, since the 2,2'-substituted binaphthyl group has a stable chiral conformation, and the dihedral angle between two...

Claims

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Application Information

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IPC IPC(8): C08F212/32C07D498/18
Inventor 朱秀林陆金杰周年琛张正彪朱健张伟潘向强
Owner SUZHOU UNIV
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