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Polyimidazole compound, in-situ preparation method and applications thereof

An in-situ preparation and compound technology, which is applied in the field of polyimidazole compounds and their in-situ preparation, can solve the problems of limited polymerization performance, restricted development of polyimidazole compounds, etc., and achieves high polymerization efficiency, excellent stereoselectivity, and operation. convenient effects

Inactive Publication Date: 2017-07-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although document 1 (Hiroyuki Ohno et al.Macromolecules 2006,39,6924-6927) discloses a polymer containing imidazole groups in the main chain, it can be used to prepare polymers containing imidazole rings in the main chain. There are very few types of monomers in the compound, and the polymerization performance is also very limited, which greatly limits the development of polyimidazole compounds.

Method used

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  • Polyimidazole compound, in-situ preparation method and applications thereof
  • Polyimidazole compound, in-situ preparation method and applications thereof
  • Polyimidazole compound, in-situ preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The polyimidazole compound of preparation structural formula as shown in PII:

[0078]

[0079] 1) Firstly, monomer 3 was synthesized through reaction formula (1), that is, the above-mentioned monomer wherein R is (V-2).

[0080]

[0081] Formula (1)

[0082] The specific preparation process of the monomer 3 is as follows:

[0083] (1) Under the protection of inert gas, compound 1 (potassium isocyanoacetate) and compound 2 (1,6-dibromohexane) were mixed at a ratio of 1:0.45, and fully reacted in DMF solvent at 50°C for 8 hours .

[0084] (2) After the reaction, the reaction solvent DMF was removed, and the final product was separated by column chromatography using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 1:1 as the eluent to obtain monomer 3.

[0085] Utilize monomer 3 to prepare polymer PII by reaction formula (two), concrete steps are as follows:

[0086] 1) Under the protection of an inert gas, add the monomer 3 and the ...

Embodiment 2～5

[0097] Embodiment 2~5 investigated the influence of different reaction temperatures on reaction conditions. Wherein, the preparation of polymerized monomers and the steps of using monomers to prepare polymers are the same as in Example 1, the difference lies in the polymerization reaction temperature. The specific polymerization conditions are shown in Table 1.

[0098] Table 1. Effect of polymerization reaction temperature on the polymerization of monomer 3 a

[0099]

[0100] a Reaction in acetonitrile in air; reaction time 2h; [M] 0 = 0.5M.

[0101] b T = reaction temperature.

[0102] c Determined by GPC with linear polystyrene as the calibration substance and DMF as the mobile phase.

[0103] It is completely soluble in common organic solvents such as DMF (dimethylformamide) and DMSO (dimethyl sulfoxide).

[0104] It can be seen from Table 1 that the polymerization activity is very high, and polymers with relatively high molecular weight can also be generated...

Embodiment 6～8

[0106] Examples 6-8 investigated the influence of different monomer concentrations on the reaction conditions. The preparation of polymerized monomers and the steps of using monomers to prepare polymers are the same as in Example 1, except that the concentration of monomers in the polymerization is different. , the specific reaction conditions and results are shown in Table 2.

[0107] Table 2. Effect of monomer concentration on polymerization of monomer 3 a

[0108]

[0109] a Reaction in acetonitrile in air; reaction time 2h; temperature at room temperature (25°C).

[0110] b Determined by GPC with linear polystyrene as the calibration substance and DMF as the mobile phase.

[0111] It is completely soluble in common organic solvents such as DMF and DMSO.

[0112] It can be seen from Table 2 that too high or too low monomer concentration is not conducive to the occurrence of polymerization reaction, and too low concentration will cause the probability of collision be...

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Abstract

The present invention discloses a polyimidazole compound, an in-situ preparation method and applications thereof, wherein a binary isocyano compound is subjected to a cyclization polymerization reaction in an organic solvent under the action of a cyclization polymerization catalyst to obtain the polyimidazole compound. According to the present invention, the imidazole unit in the prepared polyimidazole compound is formed by carrying out in-situ polymerization on the imidazole-unit-free monomer so as to make up the gaps in the prior art; the cyclization polymerization reaction is the one-component polymerization reaction, the monomer ratio is not required to be considered, the process is simple, the reaction raw materials and the catalyst are easy to obtain, the polymerization reaction conditions are mild, the polymerization can be performed at the room temperature, and the energy source is saved; and the polymerization efficiency of the polymerization reaction is high, the high molecular weight polymer can be obtained after the reaction is performed for a short time, the polymerization reaction has excellent region selectivity and excellent stereoselectivity, no by-product is generated during the polymerization process, and the atom economy is met.

Description

technical field [0001] The invention relates to the technical field of polymer preparation, in particular to a polyimidazole compound and its in-situ preparation method and application. Background technique [0002] The imidazole ring is a five-membered aromatic heterocycle containing two meta-nitrogen atoms in the molecular structure. Organic compounds containing the imidazole ring structure have been widely used in the fields of catalysis, biology, and optoelectronics. In addition to imidazole small molecule compounds, polymers containing imidazole groups have also been reported, and have been widely used in the fields of catalysis and optoelectronics. [0003] At present, the method of synthesizing imidazole group-containing polymers with relatively large molecular weight is relatively simple, mainly through free radical living polymerization of vinyl monomers containing imidazole groups (D.Mecerreyes.Progress in Polymer Science36(2011)1629–1648 ; J. Yuan, M. Antonietti....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/08
CPCC08G73/08
Inventor 唐本忠程天宇秦安军胡蓉蓉赵祖金
Owner SOUTH CHINA UNIV OF TECH
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