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2,2'-(1,2-phenyl)bis(1h-imidazole-4,5-dicarboxylic acid), its synthesis method and its application

A synthesis method and technology of dicarboxylic acid, applied in the field of 2,2'-bis and its synthesis, can solve the problems that have not been reported in the synthesis and performance research, and achieve the effect of increasing stability and good sensing performance

Active Publication Date: 2018-09-14
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) (H 6 Phbidc) synthesis and performance studies have not been reported yet

Method used

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  • 2,2'-(1,2-phenyl)bis(1h-imidazole-4,5-dicarboxylic acid), its synthesis method and its application
  • 2,2'-(1,2-phenyl)bis(1h-imidazole-4,5-dicarboxylic acid), its synthesis method and its application
  • 2,2'-(1,2-phenyl)bis(1h-imidazole-4,5-dicarboxylic acid), its synthesis method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid)

[0035] 1. Synthesis of 1,2-bis(2-benzimidazolyl)benzene

[0036] 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. The blue-green solid was recrystallized with a mixture of methanol and dimethylformamide (DMF) (volume ratio 1:1.5) to obtain white needle-like crystals, which were filtered, washed, and dried in vacuo to obtain 2.16 g of 1,2- Bis(2-benzoimidazolyl)benzene (OBMB), yield: 76.59%.

[0037] 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 t...

Embodiment 2

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

[0041] 1. Hydrogen nuclear magnetic resonance

[0042] 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. 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).

[0043] 2. Elemental analysis

[0044] The elemental analysis of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) obtained in Example 1 was carried out by using an American Thermo FLASH EA 1112 elemental analyzer. The measured values ​​(%) of C, H and N are respectively: C 49.65, H2.71, N 14.62; according to molecular formula C 16 h 10 o 8 N 4 (M r =386.27) calculation, the theoretical values ​​(%) of C, H, N are respectively: C49.75, H 2.61, N 14.50. It can be known from the elemental analysis results that the target compound 2,2'-(1...

Embodiment 3

[0045] Example 3 Sensing performance detection of 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid)

[0046] Experimental instrument: Fluorescence spectrophotometer, model F7000, produced by Hitachi, Japan.

[0047] Preparation of reagents:

[0048] 1. Sample solution

[0049] 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.

[0050] 2. Metal ion storage solution

[0051] 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.

[0052] Cd 2+ The preparation method of stock solution: weigh Cd(NO 3 ) 2 4H 2 O 0.154...

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Abstract

The invention discloses 2, 2'-(1, 2-phenyl)bis(1H-imidazole-4, 5-dicarboxylic acid) and a synthesis method and use thereof. The 2, 2'-(1, 2-phenyl)bis(1H-imidazole-4, 5-dicarboxylic acid) is synthesized by a two-step method, and the first step comprises that o-phenylenediamine and phthalic acid as raw materials undergo an addition-condensation reaction under the action of phosphoric acid to produce an intermediate product 1, 2-bis(2-benzimidazolyl)benzene and the second step comprises that in the presence of concentrated sulfuric acid, H2O2 is slowly added into the intermediate product and the mixture undergoes an oxidation ring opening reaction to produce 2, 2'-(1, 2-phenyl)bis(1H-imidazole-4, 5-dicarboxylic acid). The 2, 2'-(1, 2-phenyl)bis(1H-imidazole-4, 5-dicarboxylic acid) contains a plurality of carboxyl groups and nitrogen atoms and has a strong coordination ability. The benzimidazolyl group of the molecule of the 2, 2'-(1, 2-phenyl)bis(1H-imidazole-4, 5-dicarboxylic acid) has a rigid plane and can increase the stability of the complex. The 2, 2'-(1, 2-phenyl)bis(1H-imidazole-4, 5-dicarboxylic acid) has good metal ion sensing properties.

Description

technical field [0001] The invention relates to a compound with metal ion sensing properties, in particular to 2,2'-(1,2-phenyl)bis(1H-imidazole-4,5-dicarboxylic acid) and its synthesis method and application. Background technique [0002] Imidazole carboxylic acid and its derivatives are an important class of heterocyclic compounds, which show unique properties in many fields such as high-performance composite materials, electronic chemicals, metal anti-corrosion, photosensitive materials, etc., and have a wide range of applications; benzimidazole carboxylic acid Acid derivatives have rigid planes and π-electron conjugated systems, which are easy to generate fluorescence, and have potential application value in fluorescence sensors. Imidazole carboxylic acid also has significant biological activity and is an important class of pharmaceutical intermediates. For example, it is used to produce drugs for anti-cancer, anti-fungal, blood sugar regulation and treatment of physiol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/90C09K11/06G01N21/64C07F3/08A61K31/555A61P35/00
CPCA61K31/555C07B2200/13C07D233/90C07F3/003C09K11/06G01N21/6428G01N2021/6432
Inventor 刘艳菊邢爱萍程迪李晓飞杨怀霞
Owner HENAN UNIV OF CHINESE MEDICINE