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Molecular synthesis method acrylic acid type functional monomer containing supermolecule quadrupolar hydrogen bond structure

A technology of quadruple hydrogen bonds and functional monomers, applied in organic chemistry and other fields, to achieve the effects of easy polymerization, high activity, and simple post-processing

Inactive Publication Date: 2016-07-06
XINJIANG INST OF ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the selection of functional monomers is crucial to the imprinting efficiency of molecularly imprinted polymers. Acrylic acid and its derivatives are widely used in molecular imprinting as functional monomers. The structural units containing UPy have been seen in supramolecular science research. reported that UPy, a supramolecular quadruple hydrogen bond structure unit, was embedded into molecularly imprinted functional monomer molecules through organic synthesis to obtain multi-site strong hydrogen bond interactions with template molecules, and acrylic acid Molecules like these are easy to polymerize and form novel structures that are not available in cross-linked polymers, which have not been reported yet.

Method used

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  • Molecular synthesis method acrylic acid type functional monomer containing supermolecule quadrupolar hydrogen bond structure
  • Molecular synthesis method acrylic acid type functional monomer containing supermolecule quadrupolar hydrogen bond structure
  • Molecular synthesis method acrylic acid type functional monomer containing supermolecule quadrupolar hydrogen bond structure

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] a. Dissolve 125 mg of 2-amino-4-hydroxy-6-picoline and 310 mg of methacryloyloxyethyl isocyanate in 6 mL of pyridine solution, and react at a temperature of 100 ° C for 16 hours;

[0031] b. Separation and purification of the reaction system obtained in step a: naturally cool the reaction solution to room temperature, a white solid is precipitated, suction filtered, and the filter cake is collected to obtain a white solid, and the white solid is recrystallized by volume ratio of 1:1 chloroform: acetone , and vacuum-dried to obtain a white solid supramolecular quadruple hydrogen-bonded acrylic functional monomer molecule.

[0032] 1 HNMR (400MHz, CDCl 3 )δ12.97(s,1H),11.92(s,1H),10.48(s,1H),6.18(s,1H),5.78(s,1H),5.55(s,1H),4.27(s,2H ),3.59(s,2H),2.20(d,J=26.8Hz,3H),1.94(s,3H). 13 CNMR (400MHz, CDCl 3 )δ172.58(s),167.30(s),156.79(s),154.92(s),148.25(s),136.07(s),125.78(s),106.49(s),63.09(s),38.80( s),19.16(s),18.30(s).MS(ESI):C 12 h 16 N 4 o 4 M=280.

Embodiment 2

[0034] a. Dissolve 125 mg of 2-amino-4-hydroxy-6-picoline and 388 mg of methacryloyloxyethyl isocyanate in 6 mL of pyridine solution, and react at a temperature of 100 ° C for 16 hours;

[0035] b. Separation and purification of the reaction system obtained in step a: naturally cool the reaction solution to room temperature, a white solid is precipitated, suction filtered, and the filter cake is collected to obtain a white solid, and the white solid is recrystallized by volume ratio of 1:1 chloroform: acetone , and vacuum-dried to obtain a white solid supramolecular quadruple hydrogen-bonded acrylic functional monomer molecule.

[0036] 1 HNMR (400MHz, CDCl 3 )δ12.97(s,1H),11.92(s,1H),10.48(s,1H),6.18(s,1H),5.78(s,1H),5.55(s,1H),4.27(s,2H ),3.59(s,2H),2.20(d,J=26.8Hz,3H),1.94(s,3H). 13 CNMR (400MHz, CDCl 3 )δ172.58(s),167.30(s),156.79(s),154.92(s),148.25(s),136.07(s),125.78(s),106.49(s),63.09(s),38.80( s),19.16(s),18.30(s).MS(ESI):C 12 h 16 N 4 o 4 M=280.

Embodiment 3

[0038] a. Dissolve 125 mg of 2-amino-4-hydroxy-6-picoline and 465 mg of methacryloyloxyethyl isocyanate in 6 mL of pyridine solution, and react at a temperature of 100 ° C for 16 hours;

[0039] b. Separation and purification of the reaction system obtained in step a: naturally cool the reaction solution to room temperature, a white solid is precipitated, suction filtered, and the filter cake is collected to obtain a white solid, and the white solid is recrystallized by volume ratio of 1:1 chloroform: acetone , and vacuum-dried to obtain a white solid supramolecular quadruple hydrogen-bonded acrylic functional monomer molecule.

[0040] 1 HNMR (400MHz, CDCl 3 )δ12.97(s,1H),11.92(s,1H),10.48(s,1H),6.18(s,1H),5.78(s,1H),5.55(s,1H),4.27(s,2H ),3.59(s,2H),2.20(d,J=26.8Hz,3H),1.94(s,3H). 13 CNMR (400MHz, CDCl 3 )δ172.58(s),167.30(s),156.79(s),154.92(s),148.25(s),136.07(s),125.78(s),106.49(s),63.09(s),38.80( s),19.16(s),18.30(s).MS(ESI):C 12 h 16 N 4 o 4 M=280.

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Abstract

The invention relates to a method for synthesizing an acrylic functional monomer containing a supramolecular quadruple hydrogen bond structure. The optimization of reaction solvent and reaction time can obtain acrylate functional monomers with supramolecular quadruple hydrogen bond structure. The synthesized acrylate functional monomer molecule containing supramolecular quadruple hydrogen bond structure contains terminal double bonds substituted by acrylic acid methyl group in the structure, so that the functional monomer molecule has high activity and is easy to polymerize. The molecular structure also contains a supramolecular quadruple hydrogen bond unit that can form a self-complementary structure, which can reduce the generation of non-specific recognition sites. The molecular structure contains ureido-pyrimidinone supramolecular quadruple hydrogen bond structure units, which can form multiple hydrogen bond structures with high multi-site binding constants with template molecules, which can significantly improve the recognition efficiency of template molecules and the effect of molecular imprinting. The method has the advantages of simple operation, short reaction time and simple post-processing.

Description

technical field [0001] The invention relates to a synthesis method of an acrylic functional monomer molecule containing a supramolecular quadruple hydrogen bond structure. Background technique [0002] The ureidopyrimidinone (Upy) structural unit is a quadruple hydrogen bond with self-recognition function (Science. A series of ureidopyrimidone unit compounds with different substituents, the reaction raw materials are cheap and easy to obtain, the reaction route is short, and it is easy to derivatize, so that the quadruple hydrogen bond structure of ureidopyrimidone has been widely used in the field of supramolecular chemistry and Research (Adv. Mater. 2000, 12, 874-878). [0003] Supramolecular chemistry refers to high molecular polymers formed by self-assembly of small molecular monomers or low molecular polymers through non-covalent bonds (Chem. Rev. 2009, 109, 5687-5754), which mainly studies two or Multiple molecules through weak non-covalent interactions between molec...

Claims

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Application Information

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IPC IPC(8): C07D239/47
CPCC07D239/47
Inventor 张亚刚王璐璐尹兆明吾满江·艾力郅轲轲姜莹芳张岚
Owner XINJIANG INST OF ENG
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