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On-off type fluorescent probe as well as preparation method and application thereof

An on-off, fluorescent probe technology that can be used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to solve problems such as limited specificity and sensitivity

Active Publication Date: 2022-03-15
NORTHEAST AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Using this principle to modify rhodamine can be used to detect metal cations, small gas molecules and inorganic anions. However, its detection ability is affected by other ions in the detection environment, and its specificity and sensitivity are limited.

Method used

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  • On-off type fluorescent probe as well as preparation method and application thereof
  • On-off type fluorescent probe as well as preparation method and application thereof
  • On-off type fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] The molecular structure of the "on-off" fluorescent probe prepared in this example is Its preparation example is as follows:

[0067] (1) Synthesis of compound shown in formula V

[0068] Add 2.77g (10.0mmol) of 4-bromo-1,8-naphthalic anhydride into 25mL of ethylene glycol monomethyl ether solvent, and stir at room temperature until dissolved. Add 0.96mL (11.0mmol) morpholine into the reaction system, set the temperature of the oil bath to 125°C, stir and reflux for 6h, and monitor the progress of the reaction by TLC. After the reaction was completed, the reaction was cooled at room temperature, and an orange-yellow needle-shaped solid was precipitated. After complete precipitation, it was filtered and dried to obtain a crude product. The crude product was recrystallized with ethanol to obtain a yellow needle-shaped solid that is the compound shown in the formula V. The yield is 85%;

[0069] (2) Synthesis of compound shown in formula IV

[0070] Add 2.28g (8.0mmol...

Embodiment 2

[0081] The molecular structure of the "on-off" fluorescent probe prepared in this example is Its preparation example is as follows:

[0082] Referring to Example 1, the compound shown in formula V and the compound shown in formula IV were obtained successively;

[0083] Dissolve 2.24g (5.0mmol) of the compound shown in Formula IV and 0.68g (5.0mmol) of benzohydrazide in 10mL of dry N,N-dimethylformamide, and use the coupling agent 1-ethyl-3- (3-dimethylaminopropyl)carbodiimide (EDC, 1 eq), N,N-diisopropylethylamine (DIEA, 2 eq), hydroxybenzotriazole (HOBt, 1.2 eq). After reflux reaction at 155°C for 11 hours, add water to quench the reaction, add water to the reaction mixture to precipitate, filter, and dry to obtain a crude product, and then recrystallize the crude product with ethanol to obtain a dark yellow solid, which is the pure product of the compound represented by formula III. Yield 76%, melting point >250°C.

[0084] The results of the structural characterization...

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Abstract

The invention discloses an on-off type fluorescent probe as well as a preparation method and application thereof. The on-off type fluorescent probe specifically has a molecular structure as shown in a formula I. In the formula I, R is independently selected from one of furyl, furanalkyl, furanhydroxyl, phenyl or alkylphenyl; preferably, R is independently selected from at least one of furyl, furanalkyl, phenyl or alkylphenyl, and alkyl is an alkyl group with no more than 3 carbon atoms. The fluorescent probe can specifically recognize F <->, CN <-> and Co < 2 + >, is extremely low in detection limit, and has potential application value in monitoring anions, cations and the like in polluted water.

Description

technical field [0001] This application relates to the technical field of "on-off" type fluorescent probes, in particular to "on-off" type fluorescent probes for detecting anions and cations, its preparation method and application. Background technique [0002] At present, there are many kinds of methods for detecting anions and cations, which are mainly divided into three categories according to their principles: chromatography detection method, biochemical detection method and fluorescence detection method. Among them, compared with chromatography and biochemical methods, fluorescence detection method has the characteristics of low cost, easy operation, fast signal response and signal visualization. Anions and cations can be analyzed by extinguishing or changing the fluorescence spectrum. [0003] Rhodamine and its derivatives are a kind of good fluorescent groups, which belong to the basic dyes of xanthenes. Due to the presence of oxygen bridges between benzene rings, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D405/12C09K11/06G01N21/64
CPCC07D221/14C07D405/12C09K11/06G01N21/643C09K2211/1029C09K2211/1033C09K2211/1088G01N2021/6432
Inventor 叶非付颖杨柳刘豫龙刘艳
Owner NORTHEAST AGRICULTURAL UNIVERSITY