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Asymmetric near-infrared squaraine dye, preparation method thereof and application thereof

An asymmetric and foreign technology, applied in the field of analytical chemistry, can solve the problems of poor water solubility and limited biomedical applications, and achieve the effects of good stability, improved solubility, and excellent optical properties

Inactive Publication Date: 2015-10-28
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most current squaraine dyes have poor water solubility, which limits their application in biomedicine.

Method used

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  • Asymmetric near-infrared squaraine dye, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The specific steps of synthesis:

[0034] Add m-aminophenol (0.196 g, 1.80 mmol) into a clean 50 mL three-neck flask, (0.988 g, 3.60 mmol), sodium carbonate (0.267 g, 2.52 mmol), and then add 30 mL of isopropanol-water mixture (1:1, v / v) to dissolve, mix well, stir and heat to 85°C, then reflux for 48 hours, TLC tracking until the raw material point completely disappears, which is the end of the reaction. After the reaction, the isopropanol in the reaction mixture was removed by rotary evaporation. Then the resultant was transferred to a 100 mL separatory funnel, a small amount of saturated saline was added, and then extracted three times with 30 mL of dichloromethane, and the organic layers were combined. Dry the organic layer with anhydrous magnesium sulfate, let it stand, filter to remove magnesium sulfate, and remove excess dichloromethane by rotating the mother liquor. The resulting substance was purified with a silica gel column. First, petroleum ether: ethyl...

Embodiment 2

[0036] The specific steps of synthesis:

[0037] Add m-aminophenol (1.96 g, 18.0 mmol), sodium carbonate (2.76 g, 26.0 mmol), bromoethane (3.92 g, 36.0 mmol) into a clean 100 mL three-necked flask, and then add 60 mL of isopropanol-water The mixed solution (1:1, v / v) was dissolved, mixed evenly, stirred and heated to 85°C under the protection of nitrogen, and then refluxed for 24 hours, followed by TLC until the raw material point completely disappeared, which was the end of the reaction. After the reaction, the isopropanol in the reaction mixture was removed by rotary evaporation. Then the resultant was transferred to a 250 mL separatory funnel, a small amount of saturated saline was added, and then extracted three times with 30 mL of dichloromethane, and the organic layers were combined. Dry the organic layer with anhydrous magnesium sulfate, let it stand, filter to remove magnesium sulfate, and then rotary evaporate to remove excess dichloromethane. The obtained substan...

Embodiment 3

[0039] Asymmetric near-infrared squaraine dyes The specific preparation method is as follows:

[0040] Squaric acid was added to a 100 mL three-necked bottle (43.3 mg, 0.38 mmol), 30 mL of n-butanol and 15 mL of benzene, heated to reflux for about 1 hour under the protection of nitrogen, when there was no obvious separation of water in the water trap, slowly add a small amount of n-butanol dissolved (81.5 mg, 0.26 mmol), after reacting for 20 minutes, add a small amount of n-butanol to dissolve (84.3 mg, 0.51 mmol), under the condition of stirring, the water was separated and refluxed for 2 hours, the reaction was stopped, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. elution with dichloromethane:methanol (100:1, v / v) to obtain 57.5 mg of the target product with a yield of 40% and a melting point of 154-156 °C. 1 H NMR (400 MHz, CDCl 3 ): δ 12.13(s,1H), 11.43(s,1H), 7.89(s,2H), 6.41(dd, J =9.2, 2.4 Hz, 1H), 6....

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Abstract

The invention discloses an asymmetric near-infrared squaraine dye, a preparation method thereof and an application thereof. According to the invention, an m-aminophenol derivative and the squaric acid are mixed to dissolve in an appropriate solvent, and then are subjected to the backflow water-diversion treatment in the nitrogen protection environment. After that, the resultant obtained reaction mixture is cooled to be at the room temperature and subjected to the decompression treatment to remove the solvent. The resultant crude product is purified through the silica gel column chromatography process to prepare the asymmetric near-infrared squaraine dye. According to the technical scheme of the invention, through introducing an oxygen-ether chain, the dissolvability of the squaraine dye in an aqueous solution can be effectively improved. The obtained asymmetric near-infrared squaraine dye is good in stability and excellent in optical performance, which can be used as a protein biomarker for dual responses of fluorescence reaction and colorimetric reaction. The asymmetric near-infrared squaraine dye can be applied in multiple fields of biological molecule marking, analyzing, separating, and the like.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to an asymmetric near-infrared squarylium dye and a preparation method and application thereof. Background technique [0002] The emission wavelength of near-infrared fluorescent dyes is between 650-900 nm. In this range, the autofluorescence of biomolecules is weak, which can avoid the interference of biological background and obtain high analytical sensitivity (Shi Feng; Li Hongyang; Peng Xiaojun. Bioanalysis Near Research progress of infrared fluorescent dyes. Fine Chemicals 2003, 20 (5) , 268-272.), and red light with a wavelength >650 nm can penetrate animal skin and tissues, therefore, the application of near-infrared dyes as fluorescent probes in biological analysis and cell imaging has attracted extensive attention. [0003] Squaric acid dyes are 1,3-disubstituted derivatives produced by the condensation of squaryl acid with electron-rich aryl c...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06G01N21/64
Inventor 傅南雁王桂美
Owner FUZHOU UNIV
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