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Polyphenylene vinylene derivatives with reversible regulation of temperature-induced helical conformation and preparation methods thereof

A technology of polyphenylene vinylene and helical conformation, applied in the direction of organic chemistry, etc., to achieve the effect of broadening the application field, reversible process, and broadening the application.

Inactive Publication Date: 2017-11-10
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, some progress has been made in the research on the regulation of the helical conformation of polyphenylene vinylene, but there are few reports on the temperature-responsive helical polyphenylene vinylene. The work of changing the temperature to control the inversion of the helical conformation has not been reported

Method used

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  • Polyphenylene vinylene derivatives with reversible regulation of temperature-induced helical conformation and preparation methods thereof
  • Polyphenylene vinylene derivatives with reversible regulation of temperature-induced helical conformation and preparation methods thereof
  • Polyphenylene vinylene derivatives with reversible regulation of temperature-induced helical conformation and preparation methods thereof

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Embodiment 1

[0027] Embodiment 1: The present invention relates to the preparation of PPA-OEt.

[0028] 1. Synthesis of monomers

[0029] (a) The first-generation alkoxyether dendron with benzyl hydroxyl as its core (G1-CH 2 OH) was dissolved in DCM, weighed L-alanine (1.3 equivalents), 4-dimethylaminopyridine (DMAP, 0.3 equivalents) were dissolved in DCM and added to the above solution, and 1.5 equivalents of EDC was added under the protection of nitrogen in an ice-salt bath. HCl, under the protection of nitrogen in an ice-salt bath, continue to stir until the reaction is complete; use saturated KHSO 4 solution and saturated Na 2 CO 3 Solution washing, DCM extraction of aqueous phase, anhydrous MgSO 4 The organic phase was dried, and the DCM was spin-dried, and the crude product was purified by column chromatography with DCM / MeOH (40:1) to obtain product A.

[0030] (b) Dissolve A in DCM, add trifluoroacetic acid (TFA, 10 equivalents), and react at room temperature for 2 h. After the...

Embodiment 2

[0035] The aqueous solution of polymer PPA-OEt was observed by circular dichroism spectroscopy. as attached image 3 As shown, at low temperature, the main chain of the polymer has a CD signal absorption peak, showing a one-handed helical structure. When heated above the phase transition temperature, the CD signal reverses; when the temperature drops below the LCST, the secondary structure of polyphenylene vinylene recovers. to the original state. It shows that the dehydration and aggregation of temperature-sensitive elements can change the main role of stabilizing the helical conformation, such as hydrogen bonding, and lead to the inversion of the helical conformation of polyphenylene vinylene.

[0036] The monomer has been confirmed by NMR and mass spectrometry. There is only one monomer during polymerization, so the NMR characterization can be confirmed, and the peak shape of the NMR spectrum of the polymer is obviously broadened, and the hydrogen of the main chain has cha...

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Abstract

The invention relates to a polyphenylene vinylene derivative with temperature-induced helical conformation reversible regulation and a preparation method thereof. Firstly, L-alanine with a first-generation alkoxyether dendron is obtained, and then reacted with p-ethynylbenzoic acid active ester to obtain a polymer monomer, and the rhodium metal complex catalyzes the polymerization of the monomer to obtain polyphenylene vinylene . This type of polyphenylene vinylene exhibits excellent temperature-sensitive characteristics and one-handed helical conformation in aqueous solution; by changing the temperature, not only the helical conformation is reversed, but also can be completely restored, and the whole process is fast and reversible; in addition, the alkoxy ether end group Different, in addition to adjusting the minimum critical temperature of this type of polymer, it can also change its dominant helical conformation, and also realize the reversible regulation of temperature-induced helical conformation, which has important theoretical research value and potential in the preparation of biomimetic and functional materials. The application value has expanded the application prospect of intelligent helical polymers in the field of biomedicine.

Description

technical field [0001] The invention relates to a class of polyphenylene vinylene derivatives with temperature-induced helical conformation reversible regulation and a preparation method thereof. Background technique [0002] Helical polymers with a secondary ordered structure have great applications in the fields of materials science, chemical induction, asymmetric synthesis, and separation of counterparts. According to the size of the helical transformation barrier, helical polymers can be divided into those with high rotational resistance Static helical polymers and dynamic helical polymers with low rotational resistance. Designing and synthesizing helical polymers with adjustable optical rotation properties has become a current research hotspot. Among the helical polymers with different main chain structures that have been reported, polyphenylene vinylene and its derivatives have excellent electrical conductivity, liquid crystallinity, and luminescence. , helicity, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F138/00C07C233/83
Inventor 张阿方王芳许安球陈卢青鲁琴华代玉堂刘坤
Owner SHANGHAI UNIV
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