Phenyl s-triazine ligand for metallic organic frame complex and synthesizing process therefor

A technology of metal-organic frameworks and synthesis methods, applied in organic chemistry and other fields, can solve the problems of rare ligand research, long reaction time, and low yield, and achieve the effects of high yield, low cost, and simple synthesis process

Inactive Publication Date: 2008-09-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Carboxyl-containing phenyl-s-triazine compounds have high thermal stability and are easy to coordinate with metal ions to form a three-dimensional structure with large pores. They are a class of organic ligands with great application prospects. Ligands ar

Method used

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  • Phenyl s-triazine ligand for metallic organic frame complex and synthesizing process therefor
  • Phenyl s-triazine ligand for metallic organic frame complex and synthesizing process therefor
  • Phenyl s-triazine ligand for metallic organic frame complex and synthesizing process therefor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] R in the structural formula of phenyl-s-triazine ligand 1 for hydrogen, R 2 For carboxyl.

[0021] The synthetic route of this phenyl-s-triazine ligand is as follows:

[0022]

[0023] The synthesis method is:

[0024] (1) Add 500ml of water and 2mol of concentrated hydrochloric acid to 1mol of 5-aminoisophthalic acid, and slowly add 200ml of NaNO with a molar concentration of 4mol / L at 0°C 2 aqueous solution for diazotization reaction. After reacting for 20 minutes, crushed ice and sodium carbonate were added to adjust the pH to 3-4 to obtain a diazonium salt solution.

[0025] (2) Take another beaker and add 1 mol of cuprous cyanide and 1 mol of sodium cyanide, and add a sufficient amount of water, after completely dissolving, add 2 mol of sodium carbonate, and cool to 0°C. Add the diazonium salt solution obtained in step (1) slowly, and react at 0° C. for 30 minutes under stirring, and then react at 50° C. for 5 hours.

[0026] (3) Add the reaction solution ...

Embodiment 2

[0032] R in the structural formula of phenyl-s-triazine ligand 1 is the carboxyl group, R 2 for hydrogen.

[0033] The synthetic route of this phenyl-s-triazine ligand is as follows:

[0034]

[0035] The synthesis method is:

[0036] 1. Add 500ml of water and 4mol of concentrated hydrochloric acid to 1mol of 5-aminophthalic acid, and slowly add 200ml of NaNO with a molar concentration of 7mol / L at 5°C 2 aqueous solution for diazotization reaction. After reacting for 40 minutes, crushed ice and sodium carbonate were added to adjust the pH to 3-4 to obtain a diazonium salt solution.

[0037] 2. Take another beaker and add 1 mol of cuprous cyanide and 3 mol of sodium cyanide, and add sufficient amount of water. After completely dissolving, add 4 mol of sodium carbonate and cool to 0°C. Add the diazonium salt solution obtained in step (1) slowly, and react at 0° C. for 100 min under stirring, and then react at 90° C. for 2 h.

[0038] 3. Add the reaction liquid obtained ...

Embodiment 3

[0042] R in the structural formula of phenyl-s-triazine ligand 1 is methyl, R 2 for hydrogen.

[0043] The synthetic route of this phenyl-s-triazine ligand is as follows:

[0044]

[0045] The synthesis method is:

[0046] 1. Add 500ml of water and 3mol of concentrated hydrochloric acid to 1mol of 2-methyl-5-aminobenzoic acid, and slowly add 200ml of NaNO with a molar concentration of 5mol / L at 2°C 2 aqueous solution for diazotization reaction. After reacting for 30 minutes, crushed ice and sodium carbonate were added to adjust the pH to 3-4 to obtain a diazonium salt solution.

[0047] 2. Take another beaker and add 1 mol of cuprous cyanide and 2 mol of sodium cyanide, and add a sufficient amount of water. After completely dissolving, add 3 mol of sodium carbonate and cool to 0°C. Add the diazonium salt solution obtained in step (1) slowly, and react at 0° C. for 60 minutes under stirring, and then react at 70° C. for 3 hours.

[0048] 3. Add the reaction liquid obtain...

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Abstract

The present invention discloses a phenyl triazine ligand that is used for the complexes of a metal organic framework and has a structural formula as shown in the formula (1). In the formula, R1 is carboxyl, hydrogen or methyl; R2 is hydrogen, methyl or carboxyl. At first, the derivative of aminobenzoic acid is used for synthesizing the aromatic nitrile intermediate; then the aromatic nitrile intermediate has trimerization reaction to prepare the carboxyl-containing triazine ligand. The synthetic method has the advantages of simple process, low cost, high yield, easily available raw materials and mild reaction conditions. The phenyl triazine ligand can coordinate with metal ions through the thermal reaction of the solvent so as to form the complexes of the metal organic framework. And the phenyl triazine ligand can practically applied in the small-molecule detection, catalysis, hydrogen storage and other fields.

Description

technical field [0001] The invention relates to a phenyl-s-triazine ligand for metal organic framework complexes and a synthesis method thereof. Background technique [0002] With the rapid development of science and technology and the continuous improvement of human living standards, the diagnosis and prevention of diseases at the molecular level is an inevitable demand for human health care. The rapid development of industry and the discharge of waste have also brought unprecedented challenges to the living environment of people. A large number of heavy metal ions and deadly organic substances contained in industrial waste pose a great threat to the survival of people themselves and various organisms in the environment. Timely detection and prevention of the diffusion of these metal ions and organic substances into the environment has become extremely important. Therefore, the demand and variety of sensing probes used in fields such as environmental monitoring, medical d...

Claims

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Application Information

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IPC IPC(8): C07D251/24
Inventor 钱国栋崔元靖郑倩高俊阔王智宇樊先平王民权
Owner ZHEJIANG UNIV
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