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Antipyrine derivative probe material for naked eye detections and identifications of Cr3+ and Cu2+ as well as preparation method thereof

A technology for aminoantipyrine and derivatives, which is applied in the measurement of color/spectral properties, organic chemistry, etc., can solve the problems of high cost, poor reagent selectivity, complicated equipment and other problems, and achieves high yield and simple and convenient post-processing. , the effect of a simple synthesis route

Inactive Publication Date: 2014-03-19
ANHUI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] All along, for Cu 2+ and Cr 3+ The detection methods of ions mainly include atomic absorption method, spectrophotometry, high performance liquid phase analysis method and electrochemical analysis method, etc., but in the above methods, some reagents have poor selectivity, and when used for the analysis of some complex samples, often need With proper pretreatment; some instruments and equipment are complex and costly, and they are not ideal for identifying and detecting Cu in organisms. 2+ 、Cr 3+ As a simple, effective and economical method, the colorimetric and fluorescence analysis methods of ions are becoming one of the most widely used methods in the biological world with high sensitivity and the ability to identify them with the naked eye.

Method used

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  • Antipyrine derivative probe material for naked eye detections and identifications of Cr3+ and Cu2+ as well as preparation method thereof
  • Antipyrine derivative probe material for naked eye detections and identifications of Cr3+ and Cu2+ as well as preparation method thereof
  • Antipyrine derivative probe material for naked eye detections and identifications of Cr3+ and Cu2+ as well as preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of compound (3)

[0035] (1) Weigh 4g (24mmol) carbazole, add 20mL of anhydrous DMF, stir at room temperature until completely dissolved, then add 1g NaH in batches, seal in oil, continue stirring at room temperature for 20min, then add 4mL (28mmol) bromhexine dropwise with a constant pressure funnel Alkanes in DMF (10mL) solution, after dropping, reflux in 80°C water bath for 3 hours to stop the reaction, pour it into water after cooling, adjust the pH value to neutral with hydrochloric acid with a volume ratio of 1:1, let it stand still, precipitate the crude product, pump Filter and recrystallize from ethanol to obtain 4.59 g of white needle-like crystals, with a yield of about 76.1%. FT-IR (KBr, cm -1 ):3049(=C-H),2856-2953(-CH 2 ,-CH 3 ), 1459 (-CH 3 ), 1323 (-CH 2 -),1621-1594(structure of carbozle). 1 H-NMR (CDCl 3 ,400Hz):δ H 8.09(d, J=7.60Hz, 2H), 7.38~7.48(m, 4H), 7.21(d, J=8.00Hz, 2H), 4.28(t, 2H), 1.86(m, 2H), 1.33(m ,6H)...

Embodiment 2

[0038] Embodiment 2: The ultraviolet-visible absorption spectrometry of compound (3)

[0039] Accurately weigh the test sample compound (3) (4.7mg), dissolve it and transfer it to a 10mL volumetric flask, use acetonitrile solvent to make up the volume, and prepare a concentration of 1.0×10 -3 mol / L stock solution. Accurately pipette the stock solution for the next step of dilution, and prepare to a concentration of 1.0×10 -5 mol / L test solution. The ultraviolet-visible spectrum and fluorescence spectrum were measured respectively.

[0040] Take 3mL concentration as 1.0×10 -5 mol / L of the sample to be tested in a quartz cuvette (the thickness of the quartz cuvette is 1cm), and then add 30 μL of the concentration of 1.0×10 -3 mol / L stock solution of various metal ions, shake well and place for a certain period of time, and measure its influence on the probe absorption spectrum and fluorescence spectrum.

[0041] Various metal cations in the acetonitrile solution of compound...

Embodiment 3

[0042] Embodiment 3: The determination of the ultraviolet-visible absorption spectrum titration experiment and detection limit of compound (3)

[0043] Cr 3+ and Cu 2+ The ultraviolet absorption spectroscopic titration experiment of the ion-pair probe compound (3) (as attached figure 2 shown), with Cr 3+ With the addition of ions, the acetonitrile solution of compound (3) gradually changed from colorless to yellow, and the absorbance of the shoulder peaks at 286nm and 293nm gradually increased, and the absorption peak gradually blue-shifted, and after the blue shift, it was still a shoulder peak (274nm and 287nm ), while the absorbance at 346nm gradually weakens, and the absorption peak gradually blue-shifts until the blue shifts to 322nm; with Cu 2+ With the addition of ions, the acetonitrile solution of compound (3) gradually changed from colorless to light yellow, and the absorbance of the shoulder peaks of compound (3) at 286nm and 293nm gradually increased, and the ab...

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Abstract

The invention discloses a colorimetric probe compound containing carbazole-antipyrine Schiff base for detecting Cr3+ and Cu2+ as well as identifying naked eyes and preparation method thereof. The Schiff base derivative containing carbazole group is obtained by condensation reaction of aldehyde group based on carbazole and amino group in 4-amino antipyrine, and the molecular characteristic is that the Schiff base compound structure contains N-substituted antipyrine group and -C=N group and carbazole group; the probe compound comprises Schiff base derivatives containing C=N structure, simultaneously the molecule contains O and N and other coordination atoms, which can form coordination molecules with some metal ions, thereby generating special UV and fluorescence phenomenons. The compound can realize identifications of Cu2+ / Cr3+ ions and quantitative determination by UV-visible spectrophotometry method, and can be used as a colorimetric probe for identifications of Cu2+ / Cr3+ according to obvious color changes, moreover, with the existences of other ions, the product has the advantages of good interference resistance, high selectivity and sensitivity.

Description

technical field [0001] The invention relates to the field of metal ion detection and selective colorimetric identification, in particular to a Cu 2+ 、Cr 3+ Synthesis of probe molecules containing carbazole-antipyrine Schiff base derivatives for naked-eye recognition and detection and their ion recognition properties. Background technique [0002] In recent years, transition metal ions play an important role in the environment and life sciences, so designing and synthesizing probe molecules that can selectively recognize transition metal ions has attracted more and more attention. Among many transition metal ions and heavy metal ions, copper ions are closely related to our life. Copper is one of the essential trace heavy metal elements in animals and plants. There are about 20 kinds of functions that require the participation of copper ions, such as cytochrome oxidase, superoxide dismutase and tyrosinase. However, if the content of copper ions in the body is too high, the ...

Claims

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Application Information

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IPC IPC(8): C07D403/12G01N21/31
CPCC07D403/12G01N21/33
Inventor 朱维菊李村方敏杨莲莲黄强
Owner ANHUI UNIVERSITY
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