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N, N'-di-[3- hydroxyl-4-(2- benzimidazole) phenyl] urea and application thereof as zinc ion fluorescent probe

A benzimidazole and fluorescent probe technology, applied in the field of fluorescent probes, can solve problems such as weak affinity, narrow working concentration range, and weak fluorescence, and achieve good reproducibility, high sensitivity and selectivity, and molecular plane good sex effect

Inactive Publication Date: 2010-12-15
DALIAN UNIVERSITY
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AI Technical Summary

Problems solved by technology

Fahrni et al. [6] first developed water-soluble Zn based on HBX fluorescent matrix in 2001. 2+ Fluorescent probes, Zhang et al. [7] introduced HBX into polymers and can also be used as Zn 2+ fluorescent probes, while HBX for Zn 2+ The affinity of Zn is usually weak, so Arai et al[8] introduced another molecule with Zn in the molecule containing the HBX functional group 2+ There are strong interaction sites for improving the Zn 2+ affinity, Tian et al. [9] designed a class of structurally symmetrical Zn containing two HBX functional groups 2+ fluorescent probes, these HBX-based Zn 2+ Fluorescent probe compounds are usually fluorescence-enhanced detection reagents, but the autofluorescence of HBX molecules is weak, making the above HBX-based fluorescent probes sensitive to Zn 2+ The working concentration range is usually narrow, about 10 -5 ~10 -3 mol / L

Method used

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  • N, N'-di-[3- hydroxyl-4-(2- benzimidazole) phenyl] urea and application thereof as zinc ion fluorescent probe
  • N, N'-di-[3- hydroxyl-4-(2- benzimidazole) phenyl] urea and application thereof as zinc ion fluorescent probe
  • N, N'-di-[3- hydroxyl-4-(2- benzimidazole) phenyl] urea and application thereof as zinc ion fluorescent probe

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Experimental program
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Effect test

Embodiment 14-D

[0024] Embodiment 14-DHBIU synthesis process

[0025] (1) Synthesis of 2-(4-amino-2-hydroxyphenyl)benzimidazole (4-AHBI)

[0026] Add 10.8g (0.1mol) of o-diphenylamine and 15.1g (0.1mol) of 4-aminosalicylic acid into 100mL of polyphosphoric acid (PPA), and stir at 180°C for 4h under nitrogen protection, the reaction solution After cooling, dilute with a large amount of ice water, and then use NaOH solution and Na 2 CO 3 The solution was adjusted to neutrality, and a large amount of precipitate was precipitated, which was filtered to obtain a light yellow crude product, and then the product was quickly passed through a silica gel column with an eluent of ethyl acetate / dichloromethane=3 / 1 (V / V). After purification, the yield of 4-AHBI was 84%.

[0027] (2) Synthesis of N, N'-di-[3-hydroxyl-4-(2-benzimidazole)phenyl]urea (4-DHBIU)

[0028] Add 0.225g (1mmol) 4-AHBI and 0.099g (0.6mmol) carbonylimidazole (CDI) into 20mL toluene, stir and reflux under the conditions of drying a...

Embodiment 2

[0030] Use a 250mL volumetric flask to prepare 5×10 -7 mol / L 4-DHBIU acetonitrile solution, then take 10mL of this solution and add it into 18 10mL volumetric flasks to prepare 4×10 -4 mol / L, 5×10 -4mol / L, 1×10 -3 mol / L, 2.5×10 -3 mol / L, 4×10 -3 mol / L, 5×10 -3 mol / L, 1×10 -2 mol / L, 2.5×10 -2 mol / L, 4×10 -2 mol / L, 5×10 -2 mol / L, 1×10 -1 mol / L, 2.5×10 -1 mol / L, 4×10 -1 mol / L, 5×10 -1 mol / L, 1.0mol / L, 2.5mol / L, 4.0mol / L, 5.0mol / L Zn 2+ Aqueous solution, 20μL each was added to 18 10mL 4-DHBIU acetonitrile solutions, so that Zn 2+ Concentrations were 8×10 -7 mol / L, 1×10 -6 mol / L, 2×10 -6 mol / L, 5×10 -6 mol / L, 8×10 -5 mol / L, 1×10 -5 mol / L, 2×10 -5 mol / L, 5×10 -5 mol / L, 8×10 -5 mol / L, 1×10 -4 mol / L, 2×10 -4 mol / L, 5×10 -4 mol / L, 8×10 -4 mol / L, 1×10 -3 mol / L, 2×10 -3 mol / L, 5×10 -3 mol / L, 8×10 -3 mol / L, 1×10 -2 mol / L, shake well and let it stand for half an hour to measure the fluorescence spectrum. Take the ratio of the fluorescence peak area at 395nm ...

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Abstract

The invention relates to N, N'-di-[3- hydroxyl-4-(2- benzimidazole) phenyl] urea and application thereof as a zinc ion fluorescent probe. A 1*10-9-1*10-6mol / L 4-DHBIU acetonitrile solution is prepared, and Zn<2+> water solution standard samples are added into the prepared solution to prepare 5 to 30 standard samples with the Zn<2+> concentration of 10-7-10-1mol / L. The fluorescence spectrum is determined. The strength of a fluorescence peak gradually reduces at 445 nanometre position with the increase of the concentration of the Zn<2+>, a new peak appears at 395 nanometre position, and the strength of fluorescence gradually increases. The ratio between the fluorescence peak area at 395 nanometre position and 445 nanometre position (A395 / A445) is taken as a vertical coordinate, and lg c(c is the molar concentration of the Zn<2+>) is taken as a horizontal coordinate to make a work curve. The compound 4-DHBIU has higher sensitivity and selectivity to the detection of the Zn<2+>, and has good repeatability. The invention is suitable for the detection of the Zn<2+> in the range of wide concentration.

Description

technical field [0001] The present invention relates to the field of fluorescent probes, in particular to an excited-state intramolecular proton transfer-urea derivative N, N'-di-[3-hydroxyl-4-(2-benzimidazole)phenyl]urea with novel structure (referred to as 4-DHBIU) structure, and this compound as a fluorescent probe in Zn 2+ Application in concentration detection. Background technique [0002] Excited state intramolecular proton transfer (ESIPT) compounds, due to the E- 1 E. * - 1 K * -K-E four-level transition behavior and large Stokes shift can be widely used in various fields such as laser dyes, electroluminescent materials, ultraviolet light stabilizers, chemical sensors, biochemistry, etc. Functional materials for use. In the past ten years, people have used the ESIPT properties of these compounds to successfully apply these compounds to the detection of anions and cations, and developed many fluorescent probes with excellent performance [1,2]. Given Zn 2+ It ...

Claims

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Application Information

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IPC IPC(8): C07D235/18C09K11/06G01N21/64
Inventor 贾颖萍吴玉防崔颖娜尹静梅
Owner DALIAN UNIVERSITY
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