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A kind of method for preparing 1,5-stereoregular polytriazole mediated by phosphazene base

A stereoregular, polytriazole technology, applied in the field of polymer preparation, can solve the problems of poor product solubility, difficult metal catalysts, differences in luminescence properties, mechanical properties, crystallization behavior, etc., to achieve high yield, reaction The effect of easy availability of raw materials and less impurities

Active Publication Date: 2019-04-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the residual metal catalysts in polymers are difficult to completely remove, which not only makes the solubility of the obtained products poor, but also affects their optical and electrical properties
In addition, polytriazoles prepared by click polymerization catalyzed by monovalent copper are mainly 1,4-isomers, and slight differences in polymer structures may lead to differences in their luminescent properties, mechanical properties, and crystallization behavior. A huge difference
However, there are few reports on the synthesis methods of 1,5-isomer-based or single polytriazoles. Therefore, it is particularly necessary to explore the synthesis of 1,5-isomer-based polytriazoles without metal catalysis.

Method used

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  • A kind of method for preparing 1,5-stereoregular polytriazole mediated by phosphazene base
  • A kind of method for preparing 1,5-stereoregular polytriazole mediated by phosphazene base
  • A kind of method for preparing 1,5-stereoregular polytriazole mediated by phosphazene base

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Experimental program
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Effect test

Embodiment 1

[0037] This embodiment utilizes phosphazene base t-BuP 4 The preparation of polytriazole (P1) by mediating binary azido compound (1a) and binary alkynyl compound (2a) is as follows:

[0038]

[0039] Wherein, the synthesis method of the binary azido-based compound, that is, the monomer 1a, is according to the published literature (Yuan, W.Z., Mahtab, F., Gong, Y.Y., et al. Synthesis and self-assembly of tetraphenylethene andbiphenyl based AIE-active triazoles [J].J.Mater.Chem., 2012,22,10472) synthetic method; the synthetic method of binary alkynyl compound, namely monomer 2a, is according to the published literature (Yao, B.C., Mei, J., Li, J., etal.Catalyst-Free Thiol–Yne Click Polymerization: A Powerful and FacileTool for Preparation of Functional Poly(vinylene sulfide)s[J].J.Mater.Chem.2011,21,4056; Macromolecule 2014,47 , 1325) synthetic method.

[0040] phosphazene base t-BuP 4 A method for preparing a polytriazole (P1) mediated by a binary azido compound (1a) and ...

Embodiment 2

[0043] This embodiment utilizes phosphazene base t-BuP 4 Mediating binary azido compound (1a) and binary alkynyl compound (2b) to prepare polytriazole P2, the synthetic route is as follows:

[0044]

[0045] The synthetic method of binary azido-based compound, that is, monomer 1a, is according to published literature (Yuan, W.Z., Mahtab, F., Gong, Y.Y., et al. Synthesis and self-assembly of tetraphenyle theneand biphenyl based AIE-active triazoles[ J].J.Mater.Chem., 2012,22,10472) is synthesized by the synthetic method; The synthetic method of binary alkynyl compound is monomer 2a according to published literature (Yao, B.C., Mei, J., Li , J., etal.Catalyst-Free Thiol–Yne Click Polymerization: A Powerful and Facile Tool for Preparation of Functional Poly(vinyle ne sulfide)s[J].J.Mater.Chem.2011,21,4056; Macromolecule 2014, 47,1325) synthetic method.

[0046] phosphazene base t-BuP 4 A method for preparing a polytriazole (P2) by mediating a binary azido compound (1a) and ...

Embodiment 3

[0052] This embodiment utilizes phosphazene base t-BuP 4 Mediating binary azido compound (1a) and binary alkynyl compound (2c) to prepare polytriazole P3, the synthetic route is as follows:

[0053]

[0054] Wherein the synthetic method of binary azido-based compound, that is, monomer 1a, is according to published literature (Yuan, W.Z., Mahtab, F., Gong, Y.Y., et al. Synthesis and self-assembly of tetraphenylethene andbiphenyl based AIE-active triazoles[ J].J.Mater.Chem., 2012,22,10472) synthetic method; the synthetic method of binary alkynyl compound, namely monomer 2c, is according to the published literature (Zhao, E.G., Li, H.K., Wu, H.Q., etal.Structure-dependent emission of polytriazoles[J].Polym.Chem., 2014,5,2301) synthetic method.

[0055] phosphazene base t-BuP 4 The method for preparing polytriazole P3 by mediating a binary azido compound (1a) and a binary alkynyl compound (2c) comprises the following steps:

[0056] Add 23.6 mg (0.1 mmol) of monomer 1a and 4...

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Abstract

The invention belongs to the field of high-molecular polymer preparation and discloses a method for preparing 1,5-steric regular polytriazole under a mediating effect of phosphine nitrile alkali. The method comprises the following steps: performing clicking polymerization reaction on binary alkynyl compound and binary azide group compound in an organic solvent under the mediating effect of phosphine nitrile alkali under the inert gas shielding, and then performing subsequent treatment, thereby acquiring the 1,5-steric regular polytriazole. The structure of the 1,5-steric regular polytriazole is shown as formula (I), n in the formula is an integer of 2-200 and R1 and R2 are same or different organic groups. The method provided by the invention is simple; the reaction raw materials are easily acquired; the yield of the product is high; no side product is generated in the polymerization process; the polytriazole taking 1,5-isomer as a main or unique component can be prepared according to the method provided by the invention.

Description

technical field [0001] The invention belongs to the field of polymer preparation, and in particular relates to a method for preparing 1,5-stereoregular polytriazole mediated by a phosphazene base. Background technique [0002] Since 2002, the Meldal and Sharpless research groups have independently discovered that monovalent copper catalyzes the cycloaddition reaction of azide and terminal alkyne ( C.W.,Christensen,C.,Meldal,M..Peptidotriazoles on SolidPhase:[1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides[J].J.Org .Chem.,2002,67,3057; Kolb,H.C.,Finn,M.G.,Sharpless,K.B..Click Chemistry: Diverse Chemical Function from a Few Good Reactions[J].Angew.Chem.Int.Ed.,2001,40,2004 ). As a typical click reaction, this reaction has been widely concerned and applied because of its mild reaction conditions, strong functional group tolerance, less impurities and easy purification of the product, and strong stereoselectivity....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/08
CPCC08G73/08
Inventor 唐本忠李白雪秦安军赵祖金胡蓉蓉
Owner SOUTH CHINA UNIV OF TECH
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