Alkyne-ketone intermediate based conjugated high-molecular polymer as well as preparation method and application thereof

A conjugated polymer and polymer technology, which is applied in the field of organic polymer optoelectronic materials to achieve the effects of high polymer yield, high regional and stereoselectivity, and high molecular weight

Active Publication Date: 2015-04-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is not possible with traditional olefin polymerization

Method used

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  • Alkyne-ketone intermediate based conjugated high-molecular polymer as well as preparation method and application thereof
  • Alkyne-ketone intermediate based conjugated high-molecular polymer as well as preparation method and application thereof
  • Alkyne-ketone intermediate based conjugated high-molecular polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A conjugated high molecular polymer, its structural formula is as shown in P1:

[0044]

[0045] The conjugated high-molecular polymer is prepared by multi-component series polymerization reaction using acetylenic ketone oligomer as an intermediate, and the reaction equation is as formula (1):

[0046]

[0047] Wherein, the monomer M1 is diethynyltetraphenylethylene, which can be prepared according to the disclosed method of the document [Polym.Chem.2012,3,1481]; the monomer M2 is terephthaloyl chloride, which can be purchased from the market. In this example, it was purchased from Alfa Aesar Company; the monomer M3 is butanethiol, which can be purchased from the market, and in this example, it was purchased from TCI Company.

[0048] The specific preparation steps of the conjugated polymer are as follows:

[0049] (1) the catalytic amount of palladium catalyst Pd (PPh 3 ) 2 Cl 2 and CuI, and diethynyltetraphenylethylene and terephthaloyl chloride at a molar r...

Embodiment 2

[0060] A conjugated high molecular polymer, its structural formula is as shown in P2:

[0061]

[0062] The conjugated high-molecular polymer is prepared by taking acetylenic ketone oligomer as an intermediate through multi-component series polymerization reaction, and the reaction equation is as formula (2):

[0063]

[0064] Among them, the monomer M2 terephthaloyl chloride was purchased from Alfa Aesar Company; the monomer M4 diethynylbenzene was purchased from Anaiji Company; the monomer M5 o-phenylenediamine was purchased from Bailingwei Company.

[0065] The specific preparation steps of the conjugated polymer are as follows:

[0066] (1) the catalytic amount of palladium catalyst Pd (PPh 3 ) 2 Cl 2 and CuI, and diethynylbenzene and terephthaloyl chloride with a molar ratio of 1:1 were added to the polymerization tube, vacuumed and replaced with nitrogen for 3 times, and redistilled THF was injected into a syringe to dissolve, and then 1.05 equivalents of tris ...

Embodiment 3

[0070] A conjugated high molecular polymer, its structural formula is as shown in P3:

[0071]

[0072] The conjugated high-molecular polymer is prepared by taking acetylenic ketone oligomer as an intermediate through multi-component series polymerization reaction, and the reaction equation is as formula (3):

[0073]

[0074] Wherein, monomer M6 dibromoterephthaloyl chloride is prepared according to the disclosed method of document [Macromolecules 1992,25,7107]; Monomer sodium sulfide nonahydrate (Na 2 S·9H 2 O) purchased from Bailingwei Company.

[0075] The specific preparation steps of the conjugated polymer are as follows:

[0076] (1) the catalytic amount of palladium catalyst Pd (PPh 3 ) 2 Cl 2 and CuI, and diethynyltetraphenylethylene and 2,5-dibromoterephthaloyl chloride in a molar ratio of 1:1 were added to the polymerization tube, vacuumed and replaced with nitrogen for 3 times, and redistilled THF was injected with a syringe Dissolve, then add 1.05 equi...

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Abstract

The invention belongs to the technical field of organic high-molecular photoelectric materials and discloses an alkyne-ketone intermediate based conjugated high-molecular polymer as well as a multi-component tandem polymerization based preparation method and application thereof. The preparation method of the conjugated high-molecular polymer comprises the following steps: carrying out coupling reaction on aryl diyne and aryl diacyl chloride under the co-catalysis of Pd and Cu (I) and the presence of an acid-binding agent to generate an alkyne-ketone oligomer; then adding a nucleophile in situ, and carrying out tandem reaction to generate a conjugated polymer in the second step; and settling the polymer solution obtained after reaction in a poor solvent, collecting, and drying to obtain the conjugated high-molecular polymer. The preparation method provided by the invention has the advantage of mild polymerization reaction condition, and the polymerization reaction can be carried out in room temperature efficiently. In addition, the polymerizing monomers are simple and are easy to obtain, and the polymer is high in yield and molecular weight and has high stereoselectivity, high atom economy and good film forming performance. The obtained conjugated high-molecular polymer has special photoelectric performance and can be widely applied to the field of biological and chemical fluorescence detection.

Description

technical field [0001] The invention belongs to the technical field of organic polymer optoelectronic materials, and in particular relates to a conjugated polymer based on an acetylenic ketone intermediate and a preparation method and application of multi-component series polymerization thereof. Background technique [0002] The development of polymer synthesis methods is the basis of polymer materials science. Olefins are traditional polymer synthesis monomers, and their synthesis methodology has been extensively studied. The polymer product obtained by olefin polymerization has a saturated main chain and belongs to general polymer materials. In the mid-1970s, the discovery of conductive polymer materials pushed alkyne polymers with special photoelectric properties onto the stage of history, making them promising functional polymer materials. Alkyne monomers contain C≡C triple bonds, which have richer chemical properties than the C=C double bonds of alkenes; polymers obta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C08G61/02
Inventor 唐本忠郑超胡蓉蓉秦安军赵祖金
Owner SOUTH CHINA UNIV OF TECH
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