Polyphenylene vinylene derivatives with supramolecular action regulating helical conformation and preparation method thereof

A technology of polyphenylene vinylene and helical conformation is applied in the field of polyphenylene vinylene derivatives and their preparation, which can solve problems such as restricting applications, and achieve the effects of widening applications, excellent temperature-sensitive properties, and excellent temperature-sensitivity.

Active Publication Date: 2021-11-05
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its application is limited because the process takes place in organic solvents rather than in water

Method used

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  • Polyphenylene vinylene derivatives with supramolecular action regulating helical conformation and preparation method thereof
  • Polyphenylene vinylene derivatives with supramolecular action regulating helical conformation and preparation method thereof
  • Polyphenylene vinylene derivatives with supramolecular action regulating helical conformation and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0033] Embodiment one: the present invention relates to the preparation of PPA.

[0034]1. Synthesis of monomeric PA-G1

[0035] Dissolve the first-generation dendritic alkoxyether group after amino modification and p-alkynyl benzoic acid in DCM at a molar ratio of 1:1.5, and add N,N-diisopropyl ethyl Amine (DIEA), 1-hydroxybenzotriazole (HOBt) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC•HCl), the amount of which is one generation of dendrimer 3 times, 1.2 times and 1.5 times of the alkoxy ethers; stir until the reaction is complete, and wash with saturated saline and NaHCO 3 Solution washing, DCM extraction of aqueous phase, anhydrous MgSO 4 The organic phase was dried and the DCM was removed to obtain a crude product, which was separated and purified by column chromatography to obtain the monomer PA-G1. 1 HNMR (500 MHz, D 2 O): δ =1.11-1.18 (m,9H,CH 3 ), 3.51-3.90 (m, 37H, CH 2 ), 4.51 (s,2H,CH 2 ), 6.76 (s, 2H, Ar-H), 7.63-7.66 (d,2H, Ar-H), 7...

Embodiment 2

[0041] The turbidity of the polymer was tested by UV spectrophotometer. The polymer PPA has a characteristic amphiphilic structure, which has a hydrophilic branched alkoxy ether unit and a hydrophobic polyphenylene vinylene main chain. It can be completely dissolved in water at low temperature and presents a clear and transparent state. The chain collapses and aggregates, and the solution presents a cloudy state, such as Figure 4 As shown, the phase transition temperature of the polyphenylene vinylene derivative T cp is 49.1 o C, the temperature will vary slightly with the actual copolymerization ratio of the two monomers. Therefore, the polyphenylene vinylene derivative has excellent temperature-sensitive properties.

Embodiment 3

[0043] The helical structure of polymer PPA was characterized by circular dichroism spectrometer. Through the variable temperature CD diagram of PPA in aqueous solution (20-80 o C) It can be seen that the Cotton effect is obvious in the wavelength range of 230-400nm, and there are two negative and positive Cotton effect absorption peaks at 360nm and 340nm respectively, indicating that the PPA main chain presents a left-handed helical conformation. Moreover, the helical conformation of the main chain has a great relationship with temperature, such as Figure 5 As shown, as the temperature increases, the helical signal of the polymer PPA gradually weakens until it flips, and then stabilizes, showing a right-handed helical conformation. During this process, there is no red shift and no change in UV absorption, which indicates that this conformational reversal is carried out directly without other intermediate processes, and when the solution returns to the initial temperature, t...

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Abstract

The invention relates to a polyphenylene vinylene derivative whose helical conformation is regulated by supramolecular action and a preparation method thereof. The structural formula of the polyphenylene vinylene derivative is: wherein: x=0.95-0.5, y=1-x; X=Me or Et; n=5, 6 or 7. The present invention utilizes the general-soldier principle and uses a small amount of phenylacetylene-cyclodextrin monomer to induce the helical conformation of the main chain. This kind of polyphenylene vinylene derivatives not only has excellent temperature-sensitive properties, but also can regulate its helical conformation by adding different guest molecules, that is, supramolecular action regulates the helical conformation. The invention of this new type of polyphenylene vinylene derivatives provides a new idea for the preparation of stimuli-responsive chiral materials, and expands the application prospects of polyphenylene vinylene derivatives in the field of smart materials.

Description

technical field [0001] The invention relates to a polyphenylene vinylene derivative whose helical conformation is regulated by supramolecular action and a preparation method thereof, belonging to the field of intelligent helical polymers. Background technique [0002] The spiral structure exists in every part of the living body. In life and nature, the spiral structure can be seen everywhere. The importance of the spiral structure to our human beings, it can be said that life originated from the spiral. Since the discovery of the helical structure, it has explained the life structure of human beings and nature very well, and gradually opened the history of helical polymers. [0003] As a widely used linear conjugated polymer, polyphenylene vinylene has a main chain with alternating single and double bonds, which endows its structure with semi-rigidity, making the helical structure formed by it dynamic, with controllable conformation and side group modification, etc. charac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F251/00C08F238/00C08B37/16
CPCC08B37/0012C08F251/00C08F238/00
Inventor 张阿方周聪聪肖莉仲国强陈佩芸任亮璇张夏聪刘坤李文
Owner SHANGHAI UNIV
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