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Carbazole porous polymer containing 8-hydroxyquinoline group as well as preparation method and application of carbazole porous polymer

A porous polymer, hydroxyquinoline technology, used in instruments, analytical materials, measuring devices, etc., can solve the problems of expensive precious metals, increased detection costs, poor stability, etc.

Active Publication Date: 2021-07-06
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Using the surface-enhanced Raman effect of noble metal nanostructures can effectively improve the detection signal, but noble metals are expensive and have poor stability, which increases the detection cost and limits its application and promotion to a certain extent.

Method used

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  • Carbazole porous polymer containing 8-hydroxyquinoline group as well as preparation method and application of carbazole porous polymer
  • Carbazole porous polymer containing 8-hydroxyquinoline group as well as preparation method and application of carbazole porous polymer
  • Carbazole porous polymer containing 8-hydroxyquinoline group as well as preparation method and application of carbazole porous polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040](1) Synthesis of 5-chloromethyl-8-hydroxyquinoline hydrochloride: take 8-hydroxyquinoline (10mmol, 1.45g) and join in the there-necked flask containing 20ml paraformaldehyde, magnetic stirring and heating to 80°C, 10ml of concentrated hydrochloric acid (38% HCl, 120mmol) was slowly added dropwise to the reaction liquid, kept at 80°C for 6h after the dropwise addition, cooled naturally to room temperature, filtered with suction to obtain a filter cake, washed three times with 50ml of acetone, and vacuumed at 45°C Dry to obtain a yellow powder with a yield of 63%.

[0041] (2) Synthesis of 5-(N-methylenecarbazole)-8-hydroxyquinoline: Weigh carbazole (5mmol, 0.835g) and NaH (10mmol, 0.24g) and dissolve it in 20mlDMSO, stir at room temperature until No bubbles were generated. After the mixture was filtered, the reaction solution was filtered and placed in a three-necked flask. KOH (10 mmol, 0.56 g) was added to the filtrate, and magnetically stirred for 30 minutes. Weigh 5-...

Embodiment 2

[0053] Embodiment 2 and embodiment 1 are prepared identically, and difference is: the mol ratio of 8-hydroxyquinoline and hydrochloric acid (HCl, mass fraction 36%) is 1:10 in the step (1), and reaction temperature is 65 ℃, time is 5h; the mol ratio of 5-chloromethyl-8-hydroxyquinoline and carbazole in step (2) is 1:1.5, the mol ratio of carbazole and NaH, KOH is 1:1:1, and the reaction temperature is 80 ℃, the heating reaction time is 5h; in step (3), the molar ratio of 5-(N-methylenecarbazole)-8-hydroxyquinoline and trichlorotriazine to cyanuric chloride is 2:2, and the reaction temperature is 100 ℃, the reaction time is 72h, the molar ratio of 5-(N-methylenecarbazole)-8-hydroxyquinoline and methanesulfonic acid is 1:5.

Embodiment 3

[0055] Embodiment 3 and embodiment 1 are prepared identically, and difference is: the mol ratio of 8-hydroxyquinoline and hydrochloric acid (HCl, mass fraction 38%) is 1:20 in step (1), and reaction temperature is 80 ℃, time is 5h; the mol ratio of 5-chloromethyl-8-hydroxyquinoline and carbazole in step (2) is 1:1.2, the mol ratio of carbazole and NaH, KOH is 1:3:3, and the reaction temperature is 80 ℃, the heating reaction time is 2h; the molar ratio of 5-(N-methylenecarbazole)-8-hydroxyquinoline and trichlorotriazine cyanuric chloride in step (3) is 3:2, and the reaction temperature is 150 ℃, the reaction time is 12h, the molar ratio of 5-(N-methylenecarbazole)-8-hydroxyquinoline and methanesulfonic acid is 1:80.

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Abstract

The invention discloses a carbazole porous polymer containing an 8-hydroxyquinoline group as well as a preparation method and application of the carbazole porous polymer. The carbazole porous polymer containing the 8-hydroxyquinoline group is formed by polycondensation of 5-(N-methylenecarbazole)-8-hydroxyquinoline and cyanuric chloride under the catalysis of strong acid. According to the invention, the 5-(N-methylenecarbazole)-8-hydroxyquinoline prepared with carbazole and 8-hydroxyquinoline as raw materials has good solubility in dichloromethane, chloroform, toluene and other solvents, and the 5-(N-methylenecarbazole)-8-hydroxyquinoline and the cyanuric chloride are subjected to high-temperature polycondensation under the catalysis of methanesulfonic acid to obtain the porous polymer; and the porous polymer contains an active 8-hydroxyquinoline group and a triazine electron-rich structural unit, and can be applied to ion detection and Raman detection.

Description

technical field [0001] The invention relates to the field of porous polymers, in particular to a carbazole porous polymer containing 8-hydroxyquinoline groups and its preparation method and application. Background technique [0002] Porous polymers (POPs) are constructed from purely organic frameworks, interconnected by covalent bonds, with open channels and permanent pores. Due to the diversity of organic chemical synthesis methods, a wealth of synthetic routes and construction methods are provided for the construction of organic molecular stacking and molecular networks. The pure organic microporous materials that have emerged in recent years have been widely used in many fields due to their rich structures and excellent properties, and have become important research topics in the fields of materials chemistry and organic chemistry. Carbazole-based polymers are widely used semiconductor materials. Carbazole porous polymers are mostly formed by oxidative coupling of ferric...

Claims

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Application Information

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IPC IPC(8): C08G61/12G01N21/65
CPCC08G61/124C08G61/122G01N21/658C08G2261/124C08G2261/143C08G2261/3221C08G2261/3241C08G2261/94
Inventor 孔凡贾雪莉付国东丁收年邱腾
Owner SOUTHEAST UNIV
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