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Benzothiazole derivative and application thereof as fluorescent dye

A technology of benzothiazole and fluorescent dyes, applied in the directions of luminescent materials, azo dyes, organic dyes, etc., can solve problems such as the inability to meet the needs of analysis and detection, and achieve the effects of easier products, mild reaction conditions, and simple synthesis

Inactive Publication Date: 2021-03-19
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among most of the widely used organic fluorescent dyes, they have defects in photophysical and photochemical properties, which cannot meet the needs of current chemical biology research and complex system analysis and detection.

Method used

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  • Benzothiazole derivative and application thereof as fluorescent dye
  • Benzothiazole derivative and application thereof as fluorescent dye
  • Benzothiazole derivative and application thereof as fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Synthesis of Compound HBTA

[0051]It is weighing 4- (benzo [D] thiazole-2-yl) -3-hydroxybenzaldehyde (63.1 mg, 0.25 mmol), 9,10-phenanthin (63.1 mg, 0.30 mmol), ammonium acetate (95.3 mg, 1.24 mmol) was dissolved in 5 ml of acetic acid, reflux at 110 ° C, and the reaction TLC dot plate monitored to the feedstock reaction, poured into 20 ml of water, yellow solid precipitation, washed after filtration, and dried to give a yellow solid after drying. That is, the dye HBTA, 52.6 mg (yield 47%).

Embodiment 2

[0052] Example 2: Synthesis of Compound HBTB

[0053] 4- (benzoxyl [D] thiazole-2-yl) -3-hydroxybenzaldehyde (76.3 mg, 0.3 mmol), benzophenyl (108.8 mg, 0.52 mmol), ammonium acetate (123 mg, 1.6 mmol) Dissoluble in 5 ml of acetic acid, refluxed at 110 ° C, and the TLC dot plate monitored to the feedstock reaction. The reaction solution was poured into 20 mL of water, and yellow solid precipitated, washed after filtration, and dried, it gave a pale yellow solid, ie the dye HBTb, 82.8 mg (yield 62%).

Embodiment 3

[0054] Example 3: Synthesis of Compound HBTC

[0055] Tighted 4- (benzo [D] thiazol-2-yl) -3-hydroxybenzaldehyde (63.1 mg, 0.25 mmol), 1,10-Philippine-5,6-dilute (56.4 mg, 0.26 mmol ), Ammonium acetate (59.1 mg, 0.76 mmol) is dissolved in 5 ml of acetic acid, refluxed at 110 ° C, and the TLC point plate monitoring reaction is complete, pour the reaction liquid into 20 ml of water, orange solid precipitation, filtration After washing, then the orange solid was obtained, that is, the dye HBTC, 67.4 mg (yield 72%).

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Abstract

The invention discloses a benzothiazole derivative and application of the benzothiazole derivative as a fluorescent dye. Specifically, four organic fluorescent dyes with excited state intramolecular proton transfer mechanism respectively react with an aryl diketone derivative through 4-(benzo[d]thiazole-2-yl)-3-hydroxybenzaldehyde to synthesize a series of imidazole ring-containing compounds, theexcited state intramolecular proton transfer mechanism of 4-(benzo[d]thiazole-2-yl)-3-hydroxybenzaldehyde is reserved, and meanwhile a conjugated system of the fluorescent dye is added, the fluorescent dye is simple and convenient to prepare and low in cost, and the series of fluorescent dyes show relatively strong fluorescence, and also have a great application prospect in research on synthesis of a fluorescent probe.

Description

Technical field [0001] The present invention belongs to the field of fine chemical technology, and more particularly to the synthesis and spectral properties of benzothiazole fluorescent dyes containing a aryl imidazole ring structure, mainly including this type of benzothiazolic fluorescent dye containing aryl imidazole ring structure. Synthesis and fluorescent properties. Background technique [0002] The organic fluorescent dye and its derivative have achieved many breakthrough progress in materials, biological, medical, etc., which gradually became a key research direction in dye chemistry. An organic fluorescent dye is a class of important fluorescent dyes with a variable structure. However, from essentially, its structure typically comprises a female core that can emit fluorescence and a helper group capable of altering fluorescence wavelength and enhancing fluorescence. With the rapid development of analytical chemistry, biological science, life science, medicine and other...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/10C07D471/14C07D417/14C09K11/06C09B57/00G01N21/64
CPCC07D417/10C07D417/14C07D471/14C09B57/00C09K11/06C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1074G01N21/6402
Inventor 郑开波王丽红郑海峡余威
Owner CHINA THREE GORGES UNIV
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