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Spiral polyallylene containing azobenzene dipoles and preparation method thereof

A technology of azobenzene and polypropyne, which is applied in the field of helical polypropyne and its preparation, can solve the problems of limiting the application range of helical polyacetylene and unstable helical structure, and achieves the effect of stabilizing the helical structure and facilitating the helical structure.

Inactive Publication Date: 2014-05-07
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the helical structure of most polyacetylenes is unstable. As the temperature increases or the polarity of the solvent increases, their helical structure will gradually disappear and become a random structure, which greatly limits the application range of helical polyacetylenes.

Method used

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  • Spiral polyallylene containing azobenzene dipoles and preparation method thereof
  • Spiral polyallylene containing azobenzene dipoles and preparation method thereof
  • Spiral polyallylene containing azobenzene dipoles and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] The synthesis of poly(N-ethyl-N-ethylpentanoate) phenylazobenzamide-L-alanine propynylamide is as follows:

[0040] a. In a 100 mL three-necked flask, add 3.3 g (20 mmol) N-ethyl-N-hydroxyethylaniline, 2.75 mL (30 mmol) valeric acid, and 30 mL treated anhydrous DMF in sequence. Under nitrogen protection, stir under ice bath to dissolve, then add 0.366g (3mmol) DMAP, 6.18g (30mmol) DCC, and stir overnight at room temperature. The solvent was distilled off under reduced pressure, a small amount of water was added to the residue to wash it several times, and the white insoluble solid was filtered off after dissolving with dichloromethane, and the filtrate was concentrated under reduced pressure and separated by silica gel column chromatography (methanol / dichloromethane=1 : 30 (V / V)), the component with the highest concentration was collected, and the solvent was distilled off under reduced pressure to obtain 4.01 g of light yellow product N-ethyl-N-pentanoic ac...

Embodiment 2

[0047]

[0048] Synthesis of poly(N-ethyl-N-ethyl pentanoate) phenylazobenzamide-L-alanine propynyl ester: the preparation conditions in steps a-c are the same as in Example 1, steps d, e as follows:

[0049] d, the difference from Example 1 is that the propyne compound is propynyl alcohol, the quality of N-ethyl-N-pentanoic acid ethyl) phenyl azobenzamide-L-alanine and DMF The ratio is 1:9, and the molar ratio of (N-ethyl-N-ethylpentanoate) phenylazobenzamide-L-alanine to propynyl alcohol and DCC is 1:1.2:1.8. Other conditions are the same as in Example 1. 1 HNMR (CDCl 3 , 400MHz) δ (ppm): 0.89 (t, 3H, CH 3 ), 1.23(t, 3H, CH 3 ), 1.29-1.36 (m, 2H, CH 2 ), 1.52(t, 3H, CH3), 1.56-1.61(m, 2H, CH2), 2.27(s, 1H, CH), 2.32(t, 2H, CH 2 ), 3.51(q, 2H, CH 2 ), 3.67(t, 2H, CH 2 ), 3.88 (s, 2H, CH 2 ), 4.25(t, 2H, CH 2), 4.88-4.91 (m, 1H, CH), 6.79-6.81 (m, 3H, NH, Ar-H), 7.85-7.97 (m, 6H, Ar-H). IR (KBr, cm -1 ): 3300~3495(N-H), 3327(≡C-H), 2169(C≡C), 1656(C=O), 1448(N=N...

Embodiment 3

[0052]

[0053] Synthesis of poly(N-ethyl-N-(N-acetylglycinate ethyl))phenylazobenzamide-L-alanine propynyl ester:

[0054] A, the difference with embodiment 1 is that raw material carboxylic acid is N-acetylglycine, condensing agent, additive are EDCI and HOBT, and the mass ratio of N-ethyl-N-hydroxyethylaniline and anhydrous DMF is: 1:19, the molar ratio of EDCI to HOBT is: 10:1. Other conditions are the same as in Example 1.

[0055] b. The difference from Example 1 is that the raw material N-ethyl-N-carboxylate ethyl aniline is (N-ethyl-N-(N-acetylglycine ethyl)) aniline, N-ethyl The molar ratio of base-N-(N-acetylglycine ethyl)aniline to p-aminobenzoic acid is: 1:1.2, after the diazonium salt of benzoic acid is added dropwise, the reaction is continued for 2h to obtain (N-ethyl-N- (N-acetylglycine ethyl carboxyl))phenylazobenzoic acid. Other conditions are the same as in Example 1.

[0056] c. The difference from Example 1 is that the raw material azobenzoic acid i...

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Abstract

The invention discloses a spiral polyallylene containing azobenzene dipoles and a preparation method thereof. The preparation method comprises the following steps: by taking N-ethyl-N-ethoxyl aniline as an initial raw material, carrying out polystep reaction to obtain a series of allylene derivative monomers containing azobenzene dipoles and chiral centers; and under the effect of a rhodium ligand catalyst, polymerizing the allylene derivative monomers to obtain a spiral polymer with a highly ordered main chain, wherein the lateral group of the polymer contains the chiral center which is able to induce a polymer chain to form a spiral structure, and the lateral group contains multiple amido bonds and azobenzene dipoles in large size to form hydrogen-bond interaction, space repulsion and electrostatic interaction, thus, the spiral structure of the polymer is stabilized.

Description

technical field [0001] The invention relates to a class of polypropyne and a preparation method thereof, in particular to a helical polypropyne containing azobenzene dipoles and a preparation method thereof. Background technique [0002] Helical structures are ubiquitous in biopolymers (such as proteins and nucleic acids) and play an important role in life systems. Helical polymers have attracted extensive attention because of their excellent properties that ordinary polymers do not possess, such as unique functions such as molecular recognition, chiral catalysis, and optical activity. They can be applied in materials science, chemical sensing, and enantioselective catalysis, and the regulation of the helicity of helical polymers is an attractive research direction. Under appropriate conditions, polymers such as polyaldehydes, polysilanes, polyisocyanates, polyurethanes, and some oligomers can form helical structures. Among the synthesized helical polymers, substituted alk...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F138/00C08F4/80C07C245/08
Inventor 黄炜任晓张清忠
Owner EAST CHINA NORMAL UNIV
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