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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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 i

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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

Examples

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Example Embodiment

[0034] Example 1: Synthesis of compound (3)

[0035] (1) Weigh 4g (24mmol) of carbazole, add 20mL of anhydrous DMF, stir at room temperature until it is completely dissolved, add 1g of NaH in batches, oil seal, continue to stir at room temperature for 20 minutes, then add 4mL (28mmol) of bromide in a constant pressure funnel. DMF (10mL) solution of alkane, after dripping, reflux in a water bath at 80°C for 3 hours to stop the reaction. After cooling, pour it into water, adjust the pH to neutral with hydrochloric acid with a volume ratio of 1:1, leave it to stand, and precipitate the crude product. After filtration and ethanol recrystallization, 4.59 g of white needle-like crystals were obtained, 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),0.86(t,3H).

[0036] (2) W...

Example Embodiment

[0038] Example 2: Ultraviolet-visible absorption spectrum measurement of compound (3)

[0039] Accurately weigh the compound (3) (4.7 mg) of the sample to be tested, and transfer it to a 10 mL volumetric flask after dissolution, and use acetonitrile solvent to make the volume constant to a concentration of 1.0×10 -3 mol / L stock solution. Accurately pipette the stock solution for the next step of dilution, and make a constant volume to a concentration of 1.0×10 -5 mol / L test solution. Measure its ultraviolet-visible spectrum and fluorescence spectrum respectively.

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

[0041] In the acetonitrile solut...

Example Embodiment

[0042] Example 3: Ultraviolet-visible absorption spectrum titration experiment of compound (3) and determination of detection limit

[0043] Cr 3+ And Cu 2+ Ion-pair probe compound (3) UV absorption spectrum titration experiment (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. The absorbance of the shoulder peak at 286nm and 293nm gradually increased, and the absorption peak gradually shifted to blue. After the blue shift, there is still a shoulder peak (274nm and 287nm). ), while the absorbance at 346nm gradually weakened, the absorption peak gradually blue shifted until the blue shift to 322nm; with Cu 2+ With the addition of ions, the acetonitrile solution of compound (3) gradually changed from colorless to light yellow. The absorbance of the shoulder peaks of compound (3) at 286nm and 293nm gradually increased, and the absorption peak gradually shifted to blue until the blu...

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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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