A tetraphenylethylene Schiff base al3+ fluorescent probe and its preparation method and application

A technology of tetraphenylethylene and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of growth inhibition and hindering plant growth, and achieve low detection limit, high anti-interference ability, detection The effect of high sensitivity

Active Publication Date: 2022-03-01
南通敏言生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, excessive aluminum ion concentration in surface water will hinder the growth of plants and have a significant inhibitory effect on the growth of their roots and seeds.

Method used

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  • A tetraphenylethylene Schiff base al3+ fluorescent probe and its preparation method and application
  • A tetraphenylethylene Schiff base al3+ fluorescent probe and its preparation method and application
  • A tetraphenylethylene Schiff base al3+ fluorescent probe and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0068] Tetraphenylethylene Schiff base Al 3+ Preparation of fluorescent probe L:

[0069] (1) Synthesis of the first intermediate product: put 1g (2.87mmol) of 4-hydroxytetraphenylethylene and 0.40g (2.87mmol) of hexamethylenetetramine into a 100mL round bottom flask, add 8mL of acetic acid and Dissolve 8mL of trifluoroacetic acid, heat to 90°C, stir for 3 hours and then stop the reaction; cool down to 20°C, remove the solvent acetic acid and trifluoroacetic acid by rotary evaporation of the liquid under reduced pressure, mix in 4.0g of silica gel, use petroleum ether: ethyl acetate = The 50:1 eluent was separated by column chromatography to obtain a yellow solid (the first intermediate product 4-hydroxy-5-formyltetraphenylethylene), and the yield was 48.6%.

[0070] (2) Synthesis of the second intermediate product: 6.25g (50mmol) of niacin was put into a 250mL round-bottomed flask, dissolved in 150ml of methanol, and 11.90g (100mmol) of acetyl chloride was slowly added in an...

Embodiment 2

[0075] Tetraphenylethylene Schiff base Al 3+ Fluorescent Probe L on Al 3+ Selective detection of:

[0076] Configure the tetraphenylethylene Schiff base Al with a molar concentration of 1mmol / L 3+ Fluorescent probe dimethyl sulfoxide standard solution; and adding a metal ion solution with a molar concentration of 10mmol / L therein; after stirring evenly, detect the change in the fluorescence emission spectrum of the solution within 15s; wherein the metal ions include: Pb 2+ , Ni + , Na + , Mn 2+ , Li + , K + , Hg 2+ , Fe 3+ , Fe 2+ , Cu 2+ , Cr 3+ ,Co 2+ , Cd 2 + , Ca 2+ , Ba 2+ , Al 3+ , Ag + , Mg 2+ ;Such as Figure 4 As shown, the fluorescent probe has almost no emission peak at 423nm, when adding Al 3+ Finally, the fluorescent probe solution has a strong emission peak at 423nm, so the experimental results show that only adding Al 3+ , can cause the fluorescent probe solution to show obvious fluorescence enhancement at 423nm, the tetraphenylethylene Sch...

Embodiment 3

[0078] Tetraphenylethylene Schiff base Al 3+ Fluorescent Probe L on Al 3+ Fluorescence titration experiment:

[0079] Configure the tetraphenylethylene Schiff base Al with a molar concentration of 1mmol / L 3+ Fluorescent probe dimethyl sulfoxide standard solution 4.8ml; averagely divided into 24 equal parts, the equivalent of 0eq, 0.2eq, 0.4eq, ..., 4.6eq, 4.8eq of Al was added to the 1st to 24th aliquots respectively 3+ , after stirring evenly for 15s, detect the fluorescence emission spectrum of each sample, the results are as follows Figure 5 shown by Figure 5 As known, with Al 3+ As the concentration increases gradually, the fluorescence intensity of the probe solution at 423nm also increases gradually. When Al 3+ When the concentration reaches 4.8 times of the probe concentration, i.e. 4.8mmol / L, the fluorescence intensity is basically no longer enhanced, and the titration reaches saturation. Therefore, the experimental results show that the tetraphenylethylene fluo...

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Abstract

The invention belongs to the field of fluorescent molecular probes, and discloses a tetraphenylethylene Schiff base Al 3+ Fluorescent probe and its preparation method and application. The preparation method of the present invention comprises: dissolving 4-hydroxytetraphenylethylene and hexamethylenetetramine in a mixed solvent of acetic acid and trifluoroacetic acid and reacting to obtain the first intermediate product 4-hydroxyl-5-formyl tetraphenylethylene Dissolving nicotinic acid in methanol solvent, adding acetyl chloride dropwise, and reacting to obtain the second intermediate product nicotinic acid methyl ester; dissolving the second intermediate product in methanol solvent, adding hydrazine hydrate, and reacting to obtain the third intermediate product nicotinamide; The first intermediate product and the third intermediate product are dissolved in ethanol solvent, react, obtain tetraphenylethylene class Schiff base Al of the present invention 3+ fluorescent probe. Fluorescent probe of the present invention is paired with Al 3+ Has specific selectivity and can be used to recognize Al in vitro 3+ ; There is basically no change in the fluorescent signal when interacting with other common ions, with high sensitivity and low detection limit.

Description

technical field [0001] The invention belongs to the field of fluorescent molecular probes, in particular to a tetraphenylethylene Schiff base Al 3+ Fluorescent probes and their preparation methods and applications. Background technique [0002] al 3+ As the third most abundant metal element in the earth's crust, it is widely used in food packaging, pharmaceutical packaging and food additives. Excessive intake of aluminum ions will bring some hidden dangers to the human health system, such as senile dementia, Alzheimer's disease, Parkinson's disease and so on. In addition, the excessively high aluminum ion concentration in surface water will hinder the growth of plants, and have a significant inhibitory effect on the growth of their roots and seeds. Therefore, designing a fluorescent chemical sensor that can efficiently identify ions and molecules has attracted more and more attention. Such fluorescent chemical sensors have potential applications in biology, pharmacology,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/86C09K11/06G01N21/64
CPCC07D213/86C09K11/06G01N21/643C09K2211/1007C09K2211/1029
Inventor 朱金丽陆麟霞王敏敏王金孙同明王淼王纯
Owner 南通敏言生物医药科技有限公司
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