Squaric acid dye and application thereof in manufacturing colorimetric fluorescent dual-response copper ion probe

A copper ion and dye technology, applied in the field of analytical chemistry, can solve problems affecting human health, organ burden, etc., and achieve the effects of good linear relationship, low detection limit, and good anti-interference ability.

Inactive Publication Date: 2018-11-02
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Excess copper ions in humans can lead to serious health problems such as ischemic heart disease, kidney disease, anemia, and bone disease (Reddy, S.A.; Reddy, K. J.; Narayan, S. L.; Reddy A. V. Analytical Applications of 2,6- Diacetylpyridine Bis-4-phenyl-3-thiosemi-carbazone and Determination of Cu(II) in Food Samples. Food Chem. 2008, 109(3) , 654-659.), will also burden the organs in the body, thus affecting human health

Method used

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  • Squaric acid dye and application thereof in manufacturing colorimetric fluorescent dual-response copper ion probe
  • Squaric acid dye and application thereof in manufacturing colorimetric fluorescent dual-response copper ion probe
  • Squaric acid dye and application thereof in manufacturing colorimetric fluorescent dual-response copper ion probe

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Experimental program
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Embodiment 1

[0033] Aniline derivatives Preparation of:

[0034] In a 100 mL two-neck flask, add aniline derivative (2.71 g, 15 mmol), dissolved in 30 mL of dichloromethane, added triethylamine (4.54 g, 45 mmol), added dropwise acetyl chloride (3.53 g, 45 mmol) in an ice-water bath, controlled the temperature at 25°C, and added dropwise After stirring at room temperature for 2 hours, TLC monitoring, after the reaction was complete, filtered to remove Et 3 N.HCl, the filtrate was washed with 10% sodium carbonate, washed once with water, dried with anhydrous sodium carbonate, filtered, and the solvent was removed to obtain a dark brown liquid. The crude product was eluted by silica gel column chromatography with petroleum ether: ethyl acetate (6:1, v / v) to obtain 3.82 g of a yellow oil with a yield of 96%. FTIR(KBr): ν max 2961, 1740, 1600, 1506, 1381, 1232, 1196, 1038, 750 cm -1 .

[0035] The near-infrared squaraine dye Preparation of:

[0036] In a 100 mL round bottom flask, ad...

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Abstract

The invention discloses a squaric acid dye and application thereof in manufacturing a colorimetric fluorescent dual-response copper ion probe. The preparation method comprises the following steps: (1)mixing a phenylamine derivative with squaric acid to obtain a mixture, dissolving the mixture into a proper solvent, connecting to an upper water distributor, and performing decompressing inner ebullition and separating water for several hours under protection of N2; (2) cooling a reaction mixture obtained in step (1) to the room temperature, and removing the solvent under reduced pressure to obtain a crude product; and (3) performing chromatographic purification on the crude product through a silicagel column, thereby obtaining a near-infrared squaric acid dye product. The squaric acid dye is good in stability and is excellent in optical performance; a nitrogen atom and an oxygen atom on a side chain have relatively good bonding force with copper ions, and only copper ion in various added metal ions in the system causes fluorescence quenching of the dye, and the color of the solution is changed to colorless from blue color, and therefore, the dye can be taken as a colorimetric/fluorescent probe for copper ion detection, can be used for detecting copper ion in a water-containing medium, and shows relatively good detection sensitivity.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and in particular relates to a squarylium dye and its application in the preparation of a colorimetric fluorescence double-response copper ion probe. Background technique [0002] Copper ions are an essential trace element in life, widely distributed in biological tissues, copper ions have redox activity, so copper ions participate in the redox process of the body and scavenge free radicals (Uauy, R.; Olivares, M. ; Gonzalez, M. Essentiality of Copper in Humans. Am. J. Clin. Nutr. 1998, 67 , 952S-959S.). Copper ions are also components of some important enzymes in biology, such as cytochrome C, which plays an important role in maintaining the energy of cells, and another lysyl oxidase is involved in the cross-linking process of collagen and elastin to form connective tissue, Lysyl oxidase not only helps maintain the integrity and elasticity of connective tissue in the heart and blood vessel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00G01N21/64G01N21/78
CPCC09B57/007G01N21/64G01N21/6428G01N21/643G01N21/78G01N2021/6417G01N2021/6432G01N2021/6495
Inventor 傅南雁王桂美
Owner FUZHOU UNIV
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