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Preparation and application of fluorescent molecular probe for detecting hypochlorite ions

A fluorescent molecular probe and hypochlorite technology, applied in the field of chemical fluorescent materials, can solve problems such as interference in the interaction process between sensors and hypochlorous acid, and achieve the effects of low physiological toxicity, good effect and low detection limit

Active Publication Date: 2017-05-31
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the chemical sensor identification of hypochlorous acid at this stage, the interaction process between the sensor and hypochlorous acid will be interfered by various factors.

Method used

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  • Preparation and application of fluorescent molecular probe for detecting hypochlorite ions
  • Preparation and application of fluorescent molecular probe for detecting hypochlorite ions
  • Preparation and application of fluorescent molecular probe for detecting hypochlorite ions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Synthesis of intermediate compound 1 (8-phenyl-1,3,5,7-tetramethyl-fluoroborondipyrrole)

[0046]

[0047] Add 80 mL of dry dichloromethane and 0.58 mL of benzoyl chloride into a 250 mL round bottom flask, slowly add 1.1 mL of 2,4-dimethylpyrrole and 5 drops of trifluoroacetic acid (TFA ), after the addition, the solution was mixed evenly, and stirred at room temperature in the dark for 10 h. Afterwards, the sample solution was taken out, and 10 mL of triethylamine was added dropwise to the reaction in an ice bath, stirred for 15 min, and 10 mL of boron trifluoride diethyl ether (BF 3 ·Et 2 O), after the reaction, the ice bath was removed, and the reaction was continued at room temperature for 2 h. After the reaction was over, the product was washed with 100 mL saturated NaHCO 3 The solution was quenched, washed with distilled water (3×50 mL) and then extracted with dichloromethane (3×50 mL), the organic phases were combined, and anhydrous MgSO was adde...

Embodiment 2

[0049] Embodiment 2: Synthesis of fluorescent probes based on BODIPY dyes

[0050] (1) Synthesis of compound 2.

[0051] Add 9.0 mL (117 mmol) of N,N-dimethylformamide (DMF) into a 250 mL round bottom flask, add 9.0 mL (117.0 mmol) of phosphorus oxychloride under the condition of ice-water bath and nitrogen protection, stir After 10 min, the ice bath was removed, returned to room temperature, and stirred for another 30 min. Then, 316 mg (1 mmol) of Compound 1 synthesized in Example 1 weighed in advance was added to 60 mL of dichloroethane (ClCH 2 CH 2 Cl), dissolved and injected into the above reaction flask, and continued to react at 45°C for 3h. Then cooled to room temperature, slowly transferred to saturated NaHCO in an ice-water bath 3 solution, add an appropriate amount of NaHCO 3 solution until the solution is weakly alkaline, and continue stirring at room temperature for 1 h. After the reaction was finished, extract with dichloromethane (3×50 mL), combine the orga...

Embodiment 3

[0054] Example 3: Synthesis of fluorescent probes based on BODIPY dyes

[0055] (2) Synthesis of compound 2.

[0056] Add 15.0 mL (195 mmol) of N,N-dimethylformamide (DMF) into a 250 mL round bottom flask, add 15.0 mL (160.0 mmol) of phosphorus oxychloride under the condition of ice-water bath and nitrogen protection, and stir for 10 min Afterwards, the ice bath was removed, returned to room temperature, and stirred for another 30 min. Then, 316 mg (1 mmol) of compound 1 synthesized in Example 1 weighed in advance was added to 80 mL of dichloroethane (ClCH 2 CH 2 Cl), dissolved and injected into the above reaction flask, and continued to react at 55°C for 5h. Then cooled to room temperature, slowly transferred to saturated NaHCO in an ice-water bath 3 solution, add an appropriate amount of NaHCO 3 solution until the solution is weakly alkaline, and continue stirring at room temperature for 1 h. After the reaction was finished, extract with dichloromethane (3×50 mL), comb...

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Abstract

The invention relates to preparation and an application of a fluorescent molecular probe for detecting hypochlorite ions, and belongs to the technical field of chemical fluorescent materials. The probe is a BODIPY derivative with the molecular formula of C26H23BF2N6O4. Firstly, an intermediate compound 2 is synthesized. Secondly, a certain quantity of 2,4-dinitrophenylhydrazine is added mixed with the intermediate compound, a certain quantity of ethanol and ethyl acetate mixed solvents are added and dissolved, and stirring reaction is performed at room temperature after acetic acid serving as a catalyst is dropped in. A crude product is recrystallized by ethanol and then purified by column chromatography to finally obtain a purple pure probe. The probe is used for detecting the hypochlorite ions under various conditions, ClO-fluorescent enhanced recognition is realized by the synthesized novel fluorescent probe, the probe is remarkable and good in effect, high in sensitivity and low in measuring detection limit, and hypochlorite can be effectively recognized even under interference of some other ions.

Description

technical field [0001] The invention relates to the preparation and application of a fluorescent molecular probe for detecting hypochlorite ions, and belongs to the technical field of chemical fluorescent materials. Background technique [0002] As we all know, boron fluoride-complexed dipyrromethenes (Boradiazaindacenes, 4, 4-Difluoro-4-bora-3a, 4a-diaza-s-indacene, referred to as BODIPY) fluorescent matrix due to its incomparable physical and chemical characteristics, in the fluorescence detection Acupuncture has attracted the attention of many researchers. BODIPY has the following advantages: 1. The molar extinction coefficient value is relatively large; 2. The ultraviolet absorption peak and fluorescence emission peak are narrow and sharp; 3. The fluorescence quantum yield is high; 4. The matrix has good tolerance to polarity and pH, and Not easily disturbed in physiological environment. The fluorescence quantum yield of some modified compounds is close to 1.0; the sig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1096G01N21/6428G01N21/6486
Inventor 顾磊韩娟王赟李媛媛李程王蕾倪良
Owner JIANGSU UNIV
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