Imidazolecarboxylic acid complex and synthesis method and application thereof

A technology of imidazole carboxylic acid and synthesis method, which is applied in the field of coordination chemistry and achieves the effects of mild reaction conditions, simple synthesis method and high yield

Active Publication Date: 2017-03-22
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid)(H 2 Phbidc) has not been reported on the construction of metal ion complexes as ligands.

Method used

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  • Imidazolecarboxylic acid complex and synthesis method and application thereof
  • Imidazolecarboxylic acid complex and synthesis method and application thereof
  • Imidazolecarboxylic acid complex and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Synthesis of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid)

[0041] 1. Synthesis of 1,2-bis(2-benzimidazolyl)benzene

[0042]Mix 4.758g (0.044mol) of o-phenylenediamine and 3.3226g (0.02mol) of phthalic acid, then add 40ml of 85% phosphoric acid (mass fraction), intermittently heat up to 180°C, stir and reflux for 6h, cool to room temperature, and then Pour into 160ml of ice water, leave at room temperature for 6h, and filter with suction to obtain a blue-green solid. Recrystallize the blue-green solid with a mixture of methanol and dimethylformamide (DMF) (volume ratio 1:1.5) to obtain white needle-like crystals, filter, wash, and dry in vacuo to obtain 2.16 g of 1,2- Bis(2-benzoimidazolyl)benzene (OBMB), yield: 76.59%.

[0043] The intermittent temperature rise is as follows: from room temperature to 140°C, every time the temperature rises by 10°C, keep warm for 5 minutes (when the temperature rises to 140°C for the last time, if the temperature...

Embodiment 2

[0046] Example 2 Structural characterization of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid)

[0047] 1. NMR spectrum

[0048] Adopt NMR spectrometer Avance III (500MHz), TMS is internal standard, measure the 2,2'-(1,2-phenyl) bis(1H-imidazole-4,5-dicarboxylic acid) that embodiment 1 obtains Hydrogen spectrum, the analysis result is: 1 H NMR (500 MHz, DMSO) δ 7.97 (dd, J=5.8, 3.3 Hz, 2H), 7.78 (dd, J=5.8, 3.3 Hz, 2H).

[0049] 2. Elemental analysis

[0050] The elemental analysis of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) obtained in Example 1 was carried out with an American Thermo FLASH EA 1112 elemental analyzer, and the analysis result was : The measured value (%) of C, H, N is respectively: C49.65, H 2.71, N 14.62; According to molecular formula C 16 h 10 o 8 N 4 (M r =386.27) The theoretical values ​​(%) of C, H, and N obtained by calculation are respectively: C 49.75, H 2.61, N 14.50. It can be known from the elemental analysis resu...

Embodiment 3

[0051] Example 3 Sensing performance detection of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid)

[0052] Test instrument: Fluorescence spectrophotometer, model F7000, produced by Hitachi, Japan.

[0053] Preparation of reagents:

[0054] 1. Sample solution

[0055] 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) solution: weigh 0.0386g 2,2'-(1,2-phenyl)bis(1H- imidazole-4,5-dicarboxylic acid) in a beaker, add 20ml dimethyl sulfoxide (DMSO), stir to dissolve, then transfer to a 100ml volumetric flask, dilute to volume with DMSO, and prepare a concentration of 1×10 -3 mol / l 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) solution.

[0056] 2. Metal ion storage solution

[0057] Zn 2+ The preparation method of stock solution: weigh Zn(NO 3 ) 2 ·6H 2 O 0.1487g, dissolved in DMSO, formulated as Zn 2+ The concentration is 5×10 -2 mol / l solution.

[0058] Cd 2+ The preparation method of stock solution: weigh Cd(NO 3 ) 2 4H 2 O 0.1542g, diss...

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Abstract

The invention discloses an imidazolecarboxylic acid complex and a synthesis method and application thereof. The chemical formula of the imidazolecarboxylic acid complex is [Cd(L)<1/2>.2H2O]n, wherein a ligand L is 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid). The brand new imidazolecarboxylic acid complex is obtained by taking 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) as a bridging ligand and constructing a coordination polymer by means of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) and metal ions Cd<2+>. According to the method, Cd(Ac)2.2H2O and 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) react through a hydrothermal method, the ligand and the corresponding metal ions are subjected to coordination, and then the brand new imidazolecarboxylic acid complex is obtained. The synthesis method is simple, convenient to operate, safe, mild in reaction condition, high in yield and purity and beneficial for subsequent testing.

Description

technical field [0001] The invention relates to an imidazole carboxylic acid complex, a synthesis method and an application thereof, belonging to the field of coordination chemistry. Background technique [0002] As a new type of functional material, complexes have become a hot spot in material chemistry and other related scientific research. Coordination polymers constructed from nitrogen-containing heterocyclic organic carboxylic acid molecules and metal ions not only have a variety of topological structures, but also show potential applications in the fields of optics, magnetism, adsorption separation, catalysis, and medicine. Imidazole carboxylic acid and its derivatives are an important class of pharmaceutical intermediates, which have N / O coordination atoms and significant biological activity. At the same time, their skeleton is relatively stable, with strong coordination ability and flexible coordination mode. As a better organic carboxylic acid bridging ligand and m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00A61P35/00
CPCC08G83/008
Inventor 刘艳菊程迪邢爱萍孟祥茹段宛露杨怀霞
Owner HENAN UNIV OF CHINESE MEDICINE
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