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Water-soluble carboxyl-containing hydroxyl benzo coumarin sodium sulfonate and preparation method and application thereof

A technology of sodium coumarin sulfonate and benzocoumarin carboxylic acid, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc. Limitation and other issues, to achieve the effect of low production cost, easy operation and high utilization rate of raw materials

Active Publication Date: 2018-06-15
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor fat solubility and water solubility of natural coumarin compounds, it is not easy to penetrate biomembranes, and its application is greatly limited.

Method used

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  • Water-soluble carboxyl-containing hydroxyl benzo coumarin sodium sulfonate and preparation method and application thereof
  • Water-soluble carboxyl-containing hydroxyl benzo coumarin sodium sulfonate and preparation method and application thereof
  • Water-soluble carboxyl-containing hydroxyl benzo coumarin sodium sulfonate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of compounds a~d

[0038] Add 0.5 g of 7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid into a 25 mL reactor, and slowly add 2.0 mL of sulfuric acid with a mass concentration of 98%, dropwise After completion, react at 60°C for 2 hours. After the reaction is complete, cool it down, pour it into saturated NaCl aqueous solution, and precipitate a light yellow precipitate. After filtering the precipitate, salting out and purifying, the pure product of compound a is obtained.

[0039] In this example, the same mass of 7-hydroxy-3-methoxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid, 3,7-dihydroxy-6- Oxo-6H-benzo[c]chromene-8-carboxylic acid, 1,7-dihydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid were replaced by For 7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid in Example 1, other steps were the same as in Example 1 to obtain compounds b, c, and d sequentially.

[0040] Table 1 Substituents, chemical names and yields of compounds a~d

[0041] ...

Embodiment 2

[0054] In this example, the amount of sulfuric acid with a mass concentration of 98% was 3.0 mL. Other steps were the same as in Example 1 to obtain compounds a to d. The yields of each compound are shown in Table 3.

[0055] The productive rate of compound a~d when table 3 solid-liquid ratio is 1g:6mL

[0056] compound a

Embodiment 3

[0058] In this example, the amount of sulfuric acid with a mass concentration of 98% was 1.5 mL. Other steps were the same as in Example 1 to obtain compounds a to d. The yields of each compound are shown in Table 4.

[0059] The productive rate of compound a~d when table 4 solid-liquid ratio is 1g:3mL

[0060] compound a

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PUM

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Abstract

The invention discloses water-soluble carboxyl-containing hydroxyl benzo coumarin sodium sulfonate and a preparation method and application thereof. The structural formula of the compound is as shownin the specification. In the formula, R1 represents H, OCH3 or OH, and R2 represents H or OH. 3, 4-benzo coumarin carboxylic acids compound is taken as a raw material, and a sulfonation reaction is carried out under a mild condition, namely carboxyl-containing hydroxyl benzo coumarin sodium sulfonate is obtained; the compound has relatively high photoluminescence performance, relatively high fluorescence quantum yield and stoke displacement, and is a novel water-soluble photoluminescence material; and simultaneously, the compound has relatively high selectivity for Fe3+ and relatively high anti-interference, and can serve as a fluorescence detection probe for Fe3+ in a water solution.

Description

technical field [0001] The invention belongs to the technical field of synthesizing heterocyclic compounds, in particular to heterocyclic compounds containing six-membered rings without hydrogenation, having oxygen atoms as ring heteroatoms and fused with other rings. Background technique [0002] Coumarin is a structural compound based on benzopyrone, and its derivatives have various biological activities such as anti-tumor, anti-HIV virus, anti-depression, anti-acetylcholinesterase, and hypoglycemic in clinical practice. Wide application prospects. There are C=C, C=O double bonds and a special lactone structure in the molecular structure of the natural product coumarin, forming a larger π conjugated system (the π electron mobility is better, and the intramolecular charge is induced under the excitation of ultraviolet light Transfer, and redistribution of electron density) and relatively rigid planar structure, so that coumarin compounds have good optical properties. If i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/80C09K11/06G01N21/64
Inventor 张尊听史娟
Owner SHAANXI NORMAL UNIV
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