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Synthetic and purifying method of near-infrared indole hepatmethine cyanine dye

A technology of indole heptamethyl cyanine and synthesis method, applied in the directions of methine/polymethine dyes, chemical instruments and methods, organic dyes, etc., can solve the problems of increasing the cost of analytical reagents, expensive reagents, and limiting wide application. , to achieve the effect of reducing synthesis cost, high cost and difficult purification

Inactive Publication Date: 2012-07-04
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The separation and purification of traditional indole heptamethine dyes mostly use simple chromatographic column separation and purification, the purification efficiency is low, and a large amount of solvent is used in the separation process, which increases the cost of analytical reagents, makes the reagents expensive, and limits further extensive applications

Method used

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  • Synthetic and purifying method of near-infrared indole hepatmethine cyanine dye
  • Synthetic and purifying method of near-infrared indole hepatmethine cyanine dye
  • Synthetic and purifying method of near-infrared indole hepatmethine cyanine dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (Type 2 dye 2a: R 1 = SO 3 H, R 2 =benzyl)

[0017] Accurately weigh 20mmol of 2-chloro-1-formyl-3-hydroxymethylenecyclohexene, N-benzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid potassium 40mmol was added to a 100mL round-bottomed flask with 50mL ethanol solvent, under nitrogen protection, stirred and refluxed for 5h, the solution gradually changed from light red to dark red, and finally green. After the reaction was completed, it was allowed to stand for cooling, and 8.5 g of green crystals were obtained by suction filtration. The pure substance can be obtained by recrystallization with ethanol.

Embodiment 2

[0019] (Type 2 dye 2b: R 1 = SO 3 H, R 2 =CH 3 )

[0020] Accurately weigh 20 mmol of 2-chloro-1-formyl-3-hydroxymethylenecyclohexene, N-methyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid potassium 40mmol was added to a 100mL round-bottomed flask with 50mL ethanol solvent, under nitrogen protection, stirred and refluxed for 5h, the solution gradually changed from light red to dark red, and finally green. After the reaction was completed, it was allowed to stand for cooling, and 7.1 g of green crystals were obtained by suction filtration. The pure substance can be obtained by recrystallization with ethanol.

Embodiment 3

[0022] (type 2 dye 2c: R 1 = SO 3 H, R 2 =CH 2 CH 3 )

[0023] Accurately weigh 20mmol of 2-chloro-1-formyl-3-hydroxymethylenecyclohexene, N-ethyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid potassium 40mmol was added to a 100mL round-bottomed flask with 50mL ethanol solvent, under nitrogen protection, stirred and refluxed for 5h, the solution gradually changed from light red to dark red, and finally green. After the reaction was completed, it was allowed to stand for cooling, and 7.5 g of green crystals were obtained by suction filtration. The pure substance can be obtained by recrystallization with ethanol.

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Abstract

The invention discloses a synthetic and purifying method of a near-infrared indole hepatmethine cyanine dye. The method does not need any catalyst, only adopts ethanol as a solvent, allows a 1-type intermediate of N-methyl (or ethyl, benzyl)-2,3,3-trimethyl-3H indole-5 potassium sulfonate quaternary ammonium salt to react with a condensing agent of 2-chloro-1-formoxyl-3-hydroxyl methylene cyclohexene through a one-step method to obtain the 2-type serial near-infrared indole hepatmethine cyanine dye; no traditional column chromatography separation and purification is adopted, and a solvent recrystallization method is adopted which can obtain the serial near-infrared indole hepatmethine cyanine dye with high efficiency. The invention not only has mild reaction conditions, is simple in separation and purification, is green and environment-friendly, but also has great industrial production value.

Description

technical field [0001] The invention relates to the technical field of synthetic chemistry and biological analysis of chemical high-tech products (functional dyes). Background technique [0002] Indole heptamethine dyes are an important branch of cyanine dyes. Because of its large molar extinction coefficient, good fluorescence performance, increased fluorescence efficiency after combining with the matrix, and a large tunable range of the maximum absorption wavelength, it is widely used in spectral sensitization, infrared laser dyes, optical disc recording media, LB films, Electrophotography, optical nonlinear materials, solar cells, trace metal ion detection, etc. With the rapid development of biotechnology and fluorescent labeling technology, cyanine dyes have become the main fluorescent probes used in the analysis and detection of DNA, protein and nucleic acid, especially the indole heptamethine dye, whose maximum absorption and emission wavelengths are at 600 The near-...

Claims

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Application Information

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IPC IPC(8): C09B23/08C09B67/10
Inventor 陈秀英牛艳明郭琳
Owner JIANGNAN UNIV
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