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Preparation method of quinoline heptamethine cyanine dye

A technology of quinoline heptamethine and dyes, which is applied in the field of preparation of quinoline heptamethine dyes, can solve the problems of short maximum absorption wavelength and fluorescence emission wavelength, low sensitivity, etc., achieve good photostability, simple synthesis method, The effect of mild conditions

Inactive Publication Date: 2018-08-17
成都驷博生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The quinoline dyes currently used have shorter maximum absorption wavelength and fluorescence emission wavelength, and the sensitivity of fluorescence detection is lower.

Method used

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  • Preparation method of quinoline heptamethine cyanine dye
  • Preparation method of quinoline heptamethine cyanine dye
  • Preparation method of quinoline heptamethine cyanine dye

Examples

Experimental program
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Effect test

Embodiment 1

[0035] (1) Weigh 3 g of 4-methylquinoline in a 100 ml flask, add 50 ml of dry acetonitrile. After dissolving, 2.26 g of ethyl bromide was added, and the mixture was reacted under reflux for 6 hours. After the reaction was completed, most of the acetonitrile was removed under vacuum distillation, and the product was dropped into anhydrous ether, and a yellow solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain a pure product with a yield of 95%.

[0036] (2) Weigh 0.8 grams of the product in step (1), N-[(3-(anilinomethylene)-2-chloro-1-cyclohexen-1-yl)methylene]aniline hydrochloride 0.5 grams, 0.9 grams of sodium acetate, dissolved in 50 ml of ethanol. After solvent removal, the mixture was reacted under reflux for 12 hours. After the reaction was complete, the solvent was evaporated, and the product was purified by column chromatography (dichloromethane:methanol=95:5), dissolved again in dichloromethane, an...

Embodiment 2

[0040] (1) Weigh 3 g of 4-methylquinoline in a 100 ml flask, add 50 ml of dry acetonitrile. After dissolving, 3.9 g of ethyl iodide was added, and the mixture was reacted under reflux for 6 hours. After the reaction was completed, most of the acetonitrile was removed under vacuum distillation, and the product was dropped into anhydrous ether, and a yellow solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain a pure product with a yield of 96%.

[0041] (2) Weigh 0.8 grams of the product in step (1), N-[(3-(anilinomethylene)-2-chloro-1-cyclohexen-1-yl)methylene]aniline hydrochloride 0.5 grams, 0.9 grams of sodium acetate, dissolved in 50 ml of ethanol. After solvent removal, the mixture was reacted under reflux for 12 hours. After the reaction was complete, the solvent was evaporated, and the product was purified by column chromatography (dichloromethane:methanol=95:5), dissolved again in dichloromethane, and ...

Embodiment 3

[0043] (1) Weigh 3 g of 4-methylquinoline in a 100 ml flask, add 50 ml of dry acetonitrile. After dissolving, 5.24 g of dodecane bromide was added, and the mixture was reacted under reflux for 6 hours. After the reaction was completed, most of the acetonitrile was removed under vacuum distillation, and the product was dropped into anhydrous ether, and a yellow solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain a pure product with a yield of 95%.

[0044] (2) Weigh 0.8 grams of the product in step (1), N-[(3-(anilinomethylene)-2-chloro-1-cyclohexen-1-yl)methylene]aniline hydrochloride 0.5 grams, 0.9 grams of sodium acetate, dissolved in 50 ml of ethanol. After solvent removal, the mixture was reacted under reflux for 12 hours. After the reaction was complete, the solvent was evaporated, and the product was purified by column chromatography (dichloromethane:methanol=95:5), dissolved again in dichloromethane,...

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Abstract

The invention relates to near infrared quinoline type heptamethine cyanine dye and a preparation method thereof and belongs to the field of chemical organic dye synthesis. Synthetic near infrared dyehas the advantages of excellent optical performance such as in a near infrared region 2, large compound Stokes shift, high photostability, few synthesis step and convenience for purification. The mostobvious characteristics of the dye include high absorptivity in the near infrared zone 2, excellent penetrability to environment and biological tissue and high quantum yield in an organic solvent like dichloromethane. The dye can be used in the field of biomolecular marking and fluorescence imaging. A probe preparation method is simple and easy to implement, low in cost, good in economic benefitand suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic dye synthesis, and in particular relates to a preparation method of quinoline heptamethine dye. Background technique [0002] Polymethine cyanine dyes are fluorescent dyes that often end in various heterocycles such as indole, pyridine, quinoline, thiazole, and pyrrole. The molecule of cyanine dye contains a conjugated chain composed of methine (also known as methine group), and the two ends or the middle of the conjugated chain are connected with heterocycles, aromatic ring compounds, cycloalkenes, etc. and the conjugated chain to form a large conjugated chain. In the yoke system, the hydrogen inside the molecule can be replaced by a certain number of various substituents. Quinoline cyanine dyes are an important branch of cyanine dyes. This kind of dyes has a high molar extinction coefficient, the fluorescence emission wavelength is easy to adjust, and the maximum absorption wavelength can be tuned in a l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10C09K11/06C07D215/12
Inventor 裴照卿
Owner 成都驷博生物科技有限公司
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