Xanthene dye, and preparation method and application thereof

A technology of condensation reaction and reaction temperature, which is applied in the field of xanthene dyes and its preparation and application, can solve the problems of ratio probe molecules, difficulties in large-scale promotion and use, cumbersome steps, etc., and achieve suppression of side reactions and good fluorescence The effect of labeling ability and simple operation of the experiment

Inactive Publication Date: 2014-09-10
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the resonance energy transfer system has strict requirements on the selection of donors, acceptors and linking arms, for example, the emission spectrum of the donor molecule and the absorption spectrum of the acceptor molecule must have a significant overlap, and the distance between the two must meet certain conditions, etc. , so it is difficult to construct a suitable ratio probe molecule
In addition, the synthesis of such probe molecules is often complicated and the yield is low, so it is difficult to promote the use on a large scale.

Method used

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  • Xanthene dye, and preparation method and application thereof
  • Xanthene dye, and preparation method and application thereof
  • Xanthene dye, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Preparation of compound (I)

[0037] (1) In a dry 50 mL round bottom flask, add 0.446 g (3.16 mmol) 2,4-dihydroxybenzaldehyde, 0.33 mL (3.12 mmol) o-aminothiophenol, 10 mL anhydrous DMF, and reflux for 2 h , after the reaction is complete, cool it to room temperature, then slowly drop it into 200 mL of cold water, precipitate out, filter, recrystallize with methanol, and dry to get 2-(2′,4′-dihydroxyphenyl)benzene And thiazole.

[0038] (2) In a dry 50 mL round bottom flask, add 0.991 g (6.00 mmol) of 3-diethylaminophenol, 1.066 g (7.20 mmol) of phthalic anhydride, and 15 ml of toluene. The reaction temperature was controlled at 80°C for 10 h, raised to 90°C for 5 h, then raised to 100°C for 2 h, and finally raised to 110°C for 1 h. After the reaction is complete, cool down, filter to obtain the crude product, then wash the crude product with n-butanol, recrystallize once, and dry to obtain 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid.

[0039] (3) In ...

Embodiment 2

[0043] Example 2 Preparation of compound (I)

[0044] Similar to Example 1, except that concentrated sulfuric acid was used as the reaction medium in step (3), and the yield was 27.6%.

Embodiment 3

[0045] Example 3 Preparation of compound (I)

[0046] Similar to Example 1, except that the reaction temperature in step (3) was 150°C, and the yield was 31.7%.

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Abstract

The invention discloses a compound represented by a structural formula (1) which is described in the specification. The compound is prepared by subjecting 2-(2',4'-dihydroxyphenyl)benzothiazole and 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid to a condensation reaction, wherein a condensation reaction medium is methanesulfonic acid and reaction temperature is 80 to 105 DEG C. The compound provided by the invention has high fluorescence quantum yield, long emission wavelength and good fluorescence labeling capability and is a xanthene hybrid with dual fluorescence emission performance, so the compound can be used as a ratio-dependent optical probe.

Description

technical field [0001] The present invention relates to a kind of xanthene dye and its preparation method and as Cu 2+ Application of ratiometric fluorescent probes. Background technique [0002] Fluorescence analysis has the characteristics of high detection sensitivity, good selectivity, low cost, easy operation, and wide application, and has gradually been widely used in recent years. Because xanthene dyes have the advantages of large molar absorptivity coefficient, high fluorescence quantum yield, and long emission wavelength, analysts have developed various optical probe molecules based on them. Among such probe molecules, the sensing system based on the ring-opening reaction of xanthene spiroamide has attracted extensive interest of analysts. Xanthene spiroamide compounds themselves are colorless and non-fluorescent. When such molecules undergo recognition reactions (such as coordination, hydrolysis, and group reactions, etc.), it often leads to the ring-opening reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D491/107C09B57/00C09K11/06G01N21/64
CPCC07D417/04C07D491/107C09B57/00C09K11/06C09K2211/1007C09K2211/1037C09K2211/1088G01N21/64
Inventor 文慧杨小峰
Owner NORTHWEST UNIV
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