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Method for preparing quadri [4-(1- imidazolyl) phenyl] methane

A technology of imidazolyl and methane, which is applied in the field of preparation of tetrakis [4-phenyl] methane, can solve the problems of unfavorable industrial production, complex post-treatment, long reaction time, etc. short time effect

Active Publication Date: 2015-03-25
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above scheme uses the traditional solution method, the reaction time is long, and it needs to be refluxed for 2 days; at the same time, the reaction process uses toxic organic solvents such as dimethyl sulfoxide and dichloromethane, which is harmful to the environment and the post-treatment is complicated, which is not conducive to industrial production.

Method used

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  • Method for preparing quadri [4-(1- imidazolyl) phenyl] methane
  • Method for preparing quadri [4-(1- imidazolyl) phenyl] methane
  • Method for preparing quadri [4-(1- imidazolyl) phenyl] methane

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment one: the synthesis of tetrakis [4- (1-imidazolyl) phenyl] methane

[0033] Specific steps are as follows:

[0034] Add 0.636g (1mmol) of tetrakis(4-bromophenyl)methane, 0.076g (0.4mmol) of cuprous iodide, 0.828g (6mmol) of potassium carbonate and 0.68g (10mmol) of imidazole into the crucible, grind it with a glass rod Put it into an ordinary household microwave oven after mixing it evenly, and heat it in a microwave for 90 seconds with a power of 720w. It is detected by TLC (thin layer chromatography) method, and it is found that the point of the raw material tetrakis (4-bromophenyl) methane disappears, and the reaction is complete. Crude product 1;

[0035] Add 10mL of water, 0.117g (0.4mmol) of ethylenediaminetetraacetic acid (0.4mmol) and 0.15mL of 25% ammonia water to the crude product 1, soak for 5 hours, filter, and wash the precipitate with water 3 times (10mL / time) to obtain the crude product 2;

[0036] The crude product 2 was recrystallized ...

Embodiment 2

[0041] Embodiment two: four [4- (1-imidazolyl) phenyl] the synthesis of methane

[0042] Specific steps are as follows:

[0043] Add 0.636g (1mmol) of tetrakis(4-bromophenyl)methane, 0.076g (0.4mmol) of cuprous iodide, 0.828g (6mmol) of potassium carbonate and 0.544g (8mmol) of imidazole into the crucible, grind it with a glass rod Put it into an ordinary household microwave oven after mixing it evenly, and heat it in a microwave for 90 seconds with a power of 720w. It is detected by TLC (thin layer chromatography) method, and it is found that the point of the raw material tetrakis (4-bromophenyl) methane disappears, and the reaction is complete. Crude product 1;

[0044] Add 10mL of water, 0.117g (0.4mmol) of ethylenediaminetetraacetic acid (0.4mmol) and 0.15mL of 28% ammonia water to the crude product 1, soak for 6 hours, filter, and wash the precipitate with water 3 times (10mL / time) to obtain the crude product 2;

[0045] The crude product 2 was recrystallized with...

Embodiment 3

[0046] Example 3: Synthesis of imidazole-based coordination polymers

[0047] Take zinc nitrate hexahydrate Zn(NO 3 ) 2 · 6H 2 O (0.15 g, 0.5 mmol), isophthalic acid (0.13 g, 0.5 mmol) and tetrakis[4-(1-imidazolyl)phenyl]methane (0.14 g, 0.25 mmol) were placed in an 8 mL pyrex tube , adding 3 mL of acetonitrile / water mixed solvent with a mass ratio of 1:1 and blocking. React in an oven at a constant temperature of 150°C for 2 days, then slowly cool down to room temperature at a rate of 5°C / hour to obtain a yellow crystal, which is the product imidazole-based coordination polymer, and the molecular formula is C 53 h 3 N 8 o 8 Zn 2 . Product is carried out infrared analysis, and result is as follows:

[0048] IR:v(KBr) / cm -1 3447m, 3136w, 1613s, 1561w, 1523s, 1373s, 1313w, 1270w, 1126w, 1068m, 966m, 827m, 762s, 656m, 561m.

[0049] attached Image 6 It is the crystal structure diagram of the above-mentioned imidazolyl coordination polymer, by the attached Image 6 ...

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Abstract

The invention discloses a method for preparing quadri [4-(1-imidazolyl) phenyl] methane. The method comprises the following specific steps of: uniformly mixing quadri[4-bromophenyl]methane, cuprous iodide, potassium carbonate and imidazole to obtain a mixture, putting the mixture in a vessel, and heating to react to obtain a crude product 1; then adding water, ethylenediamine tetraacetic acid and ammonia water to the crude product 1, soaking for 4-6 hours, filtering and washing to obtain a crude product 2; and recrystallizing the crude product 2 to obtain light yellow crystals, namely the quadri[4-(1-imidazolyl) phenyl] methane. The quadri [4-(1-imidazolyl) phenyl] methane prepared by using the method has an excellent fluorescence property and can be used for preparing a fluorescent material. The method disclosed by the invention is low in cost, mild in reaction condition, short in reaction time, simple in posttreatment of reaction, beneficial to purification and high yield of the quadri [4-(1-imidazolyl) phenyl] methane; and in addition, compared with the prior art, the method has the advantages that use of a reaction solvent is avoided, and the preparation process is environment-friendly and easy for industrial operation.

Description

technical field [0001] The invention relates to the preparation of organic ligands containing imidazole groups, in particular to a preparation method of tetrakis[4-(1-imidazolyl)phenyl]methane. Background technique [0002] Coordination polymers containing imidazole-based ligands have unique optical properties, magnetism, catalysis, and biological activity, and have the characteristics of complexes and polymers. They have broad applications in new materials, molecular recognition, and supramolecular self-assembly. application prospects. [0003] The organic ligands containing multiple imidazole groups are polydentate imidazole ligands, which have the characteristics of many coordination sites, strong coordination ability, and rich coordination modes. Because the imidazole group has good fluorescence, ultraviolet and other characteristics, and the coordination polymer formed by the multidentate imidazole ligand and metal ion has good magnetic properties, adsorption and other...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/58C09K11/06
Inventor 郎建平李端秀程洪见任志刚
Owner SUZHOU UNIV
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