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A kind of preparation method and application of fluorescent dye with carbazole-rhodamine hybrid structure

A fluorescent dye, carbazole technology, applied in the field of fluorescent dye preparation based on carbazole-rhodamine hybrid structure, can solve the problems of poor cell research effect, limited wide application, large interference, etc.

Inactive Publication Date: 2019-08-09
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the above-mentioned dyes, there are the following disadvantages in the structure: due to the limitation of the conjugated system structure of the dye itself, the phenolic hydroxyl group in the dye does not have the possibility of converting from a hydroxyl group to a ketone structure
At the same time, it is relatively disturbed by the sample background, the fluorescence quantum yield is reduced in the physiological environment of the organism, and it is sensitive to light. It is prone to photobleaching under strong light detection, has poor lipophilicity, and is not easy to penetrate into cells. Therefore, it is used in cells. Poor research effect and poor specific selectivity limit its wide application in biomolecular detection

Method used

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  • A kind of preparation method and application of fluorescent dye with carbazole-rhodamine hybrid structure
  • A kind of preparation method and application of fluorescent dye with carbazole-rhodamine hybrid structure
  • A kind of preparation method and application of fluorescent dye with carbazole-rhodamine hybrid structure

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1, the preparation of carbazole-rhodamine hybrid fluorescent dye 1

[0029] The preparation steps are as follows:

[0030] 1) Add 2-hydroxycarbazole (1.83g, 10mmol) and 2-(4-diethylamino-2-hydroxybenzoyl) benzoic acid (3.14g, 10mmol) into 60mL of methanesulfonic acid and stir in 60°C oil The reaction was heated in a bath for 5 hours, and then heated in an oil bath at 80° C. for 10 hours to obtain a product solution.

[0031] 2) Add 600mL water to the reacted product solution, add appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with dichloromethane to collect the organic phase, and washed with anhydrous Na 2 SO 4 After drying and filtering, the obtained solid crude product was passed through a silica gel column with dichloromethane and ethyl acetate to obtain carbazole-rhodamine hybrid fluorescent dye 1, 3.31 g of powder white solid powder, yield 72%, melting point: 238-242 ℃.

[0032] 1 H NMR (400MHz, CDCl 3 )δ=8.23...

Embodiment 2

[0033] Embodiment 2, the preparation of carbazole-rhodamine hybrid fluorescent dye 1

[0034] 1) Add 2-hydroxycarbazole (1.83g, 10mmol) and 2-(4-diethylamino-2-hydroxybenzoyl) benzoic acid (3.46g, 11mmol) into 50mL of methanesulfonic acid and stir in 65°C oil The reaction was heated in a bath for 5 h, and then heated in an oil bath at 85° C. for 5 h.

[0035] 2) Add 600mL water to the reaction solution, add appropriate amount of NaHCO 3The solid neutralized the reaction solution, extracted with dichloromethane to collect the organic phase, and washed with anhydrous Na 2 SO 4 After drying and filtering, the obtained solid crude product was passed through a silica gel chromatography column with dichloromethane and ethyl acetate to obtain carbazole-rhodamine hybrid fluorescent dye 1, 3.12 g of off-white solid powder, and the yield was 67.8%. Melting point: 238-242°C. Progen spectrum and carbon spectrum are the same as embodiment 1.

Embodiment 3

[0036] Embodiment 3, the preparation of carbazole-rhodamine hybrid fluorescent dye 1

[0037] 1) Add 2-hydroxycarbazole (1.83g, 10mmol) and 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (3.76g, 12mmol) into 50mL of methanesulfonic acid and stir in 80°C oil The reaction was heated in a bath for 10 h, and then heated in an oil bath at 95° C. for 5 h.

[0038] 2) Add 600mL water to the reaction solution, add appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with dichloromethane to collect the organic phase, and washed with anhydrous Na 2 SO 4 After drying and filtering, the obtained solid crude product was passed through a silica gel chromatography column with dichloromethane and ethyl acetate to obtain carbazole-rhodamine hybrid fluorescent dye 1, 3.22 g of powdery white solid powder, and the yield was 70.0%. Melting point: 238-242°C. Progen spectrum and carbon spectrum are the same as embodiment 1.

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Abstract

The invention provides a preparation method and application of fluorescent dye of carbazole-rhodamine hybrid structures. The method has the advantages that the designed and synthesized novel carbazole-rhodamine fluorescent dye sufficiently uses the various good properties of carbazole in the field of a photoelectric material as a structure base element and good optical physical and optical chemical properties of rhodamine dye. Through such a hybrid design, the dye shows a greater molar absorption coefficient, longer fluorescence emission wavelength, more flexible and controllable adsorption and fluorescence emission wavelength and the like than the carbazole base element structure. A fluorescence probe designed and synthesized by using the hybridization dye has good selectivity on copper ions; the primary application value of the dye is shown.

Description

[0001] 【Technical field】 [0002] The invention relates to the preparation of fluorescent dyes in photoelectric devices and optical sensing imaging detection technologies, in particular to a preparation method and application of fluorescent dyes based on a carbazole-rhodamine hybrid structure. [0003] 【Background technique】 [0004] In recent years, fluorescence analysis technology has gradually become an important method in modern analysis technology. Because of its high sensitivity and selectivity, it has become an important method in the identification, detection and monitoring of some important substances in biology, environment and medicine. The main application direction. Although some conventional detection methods such as high-resolution liquid chromatography, mass spectrometry, atomic absorption spectroscopy, inductively coupled plasma atomic emission spectroscopy, and electrochemical sensing have been used for the analysis of related substances, these detection metho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/20C09K11/06C09B57/00G01N21/64
CPCC07D491/20C09B57/00C09K11/06C09K2211/1029C09K2211/1088G01N21/643
Inventor 曾宪顺肖志刚刘畅何松
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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