Method for preparing unsymmetrical rhodamine

An asymmetric, ketoacid technology, applied in the field of preparation of organic fluorescent dyes, can solve the problem of not finding naphthalenediol, etc., and achieve the effects of simple equipment, high fluorescence intensity and low price

Inactive Publication Date: 2012-01-18
EAST CHINA UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there have been many research reports on the synthesis of rhodamine esters, but no research report on asymmetric rhodamine with a naphthalene diol structure has been found. This structure is easy to synthesize, and has a certain Stokes shift and a high Fluorescence intensity, good photostability, can be used as a new type of rhodamine-based fluorescent dyes, widely used in laser dyes, fluorescent probes, fluorescent labels, etc.

Method used

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  • Method for preparing unsymmetrical rhodamine
  • Method for preparing unsymmetrical rhodamine
  • Method for preparing unsymmetrical rhodamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation and purification of asymmetric rhodamine I:

[0032] Add 9.9g of N,N-diethylm-aminophenol and 9.0g of phthalic anhydride in a 250ml three-neck flask equipped with magnetic stirring, dissolve with 150ml of toluene, N 2 Protect, stir, stop the reaction after heating to reflux for 8 hours, suction filter after cooling to room temperature, and recrystallize the filter cake with water to obtain 11.7 g of light yellow columnar crystals, namely keto acid, with a yield of 62.5%.

[0033] Add 3.1 g of keto acid, 4.6 g of ethyl naphthalene diol formate, and 1.3 g of zinc chloride into a 100 mL round bottom flask equipped with magnetic stirring. Heated and stirred at 120°C for 6h. The obtained mixture was put into 200ml of water to precipitate a precipitate, filtered with suction, and the filter cake was dried to obtain a crude product.

[0034] 3 g of the obtained crude product was dissolved in 100 ml of absolute ethanol, and 5 ml of concentrated sulfuric acid was a...

Embodiment 2

[0039] Preparation and purification of asymmetric rhodamine II:

[0040] Add 9.9g of N,N-diethylm-aminophenol and 9.0g of phthalic anhydride in a 250ml three-neck flask equipped with magnetic stirring, dissolve with 150ml of toluene, N 2 Protect, stir, stop the reaction after heating to reflux for 8 hours, suction filter after cooling to room temperature, and recrystallize the filter cake with water to obtain 11.7 g of light yellow columnar crystals, namely keto acid, with a yield of 62.5%.

[0041] Add 3.1 g of keto acid, 4.6 g of ethyl naphthalene diol formate, and 10 ml of methanesulfonic acid into a 100 mL round bottom flask equipped with magnetic stirring. Heated and stirred at 100°C for 10h. The obtained mixture was put into 200ml of water to precipitate a precipitate, filtered with suction, and the filter cake was dried to obtain a crude product.

[0042] 3 g of the obtained crude product was dissolved in 100 ml of absolute ethanol, and 5 ml of concentrated sulfuric a...

Embodiment 3

[0047] A method for preparing asymmetric rhodamine, its technological process is as follows image 3 As shown, the method includes the following steps:

[0048] (1) Preparation of intermediate keto acid: take N, N-diethyl m-aminophenol and its equimolar phthalic anhydride as raw materials, dissolve with 10 times the mass of toluene, stir under nitrogen protection conditions, and heat Reflux for 5 hours, and suction filter after cooling to obtain the intermediate ketoacid;

[0049] (2) The preparation of asymmetric rhodamine: get the intermediate ketoacid prepared by step (1), the naphthalenediol ethyl formate and catalyst zinc chloride of equal molar weight, the weight of zinc chloride and intermediate ketoacid The ratio is 1:4, heated to 100°C and reacted for 10 hours, the obtained mixture is put into 40-80 times the mass of water to precipitate a precipitate, filtered by suction, and dried to obtain a crude product;

[0050] (3) Esterification of asymmetric rhodamine crude...

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Abstract

The invention relates to a method for preparing unsymmetrical rhodamine. The method comprises the following steps of: reacting N,N-diethyl m-aminophenol with phthalic anhydride to prepare an intermediate ketonic acid; reacting the ketonic acid with the corresponding binaphthol structure under the action of a catalyst to generate the unsymmetrical rhodamine; directly performing ethyl esterification on the crude products and performing column chromatography; and recrystallizing to obtain unsymmetrical rhodamine dye which meets the requirements and has different structures. Compared with the prior art, the method has the advantages of low requirement on equipment, low production cost and high production efficiency and is easy to operate. The obtained novel rhodamine has good fluorescence property and high stability and can be widely applied.

Description

technical field [0001] The invention relates to a preparation method of an organic fluorescent (laser) dye, in particular to a preparation method of an asymmetric rhodamine. Background technique [0002] Rhodamine-based compounds are basic xanthene dyes based on xanthene. Due to their special structure and corresponding fluorescent properties, rhodamine-based fluorescent dyes are widely used in information science, fluorescent labeling, and laser dyes. Compared with other commonly used fluorescent dyes, rhodamine dyes have the advantages of good photostability and high fluorescence quantum yield. [0003] There are many synthetic methods of rhodamine compounds, which can be divided into two categories: direct condensation method and stepwise condensation method from the synthesis steps, and can be divided into parent ring modification, bottom ring modification and Synthesis of multichromophore rhodamine-based fluorescent dyes. Since the molecular structure contains conjuga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78C09K11/06C09B57/00
Inventor 常顺周张金龙陈日升张薇张志忠田宝柱田志丹黄伟
Owner EAST CHINA UNIV OF SCI & TECH
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