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Tetraphenyl ethylene-diaminomaleonitrile derivative and preparation method and application thereof

A technology of diaminomaleonitrile and tetraphenylethylene, which is applied in the field of tetraphenylethylene-diaminomaleonitrile derivatives and its preparation, can solve the problems of long response time of mercury ions, low detection sensitivity, and poor water solubility, and achieve The preparation method is simple and easy, the effect of high luminous intensity and mild conditions

Inactive Publication Date: 2017-08-18
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] Although the existing fluorescent probes for detecting mercury ions can detect trace amounts of mercury, there are still many defects, such as poor water solubility, and the presence of other competing metal ions interferes with the determination of mercury ions, resulting in the detection of mercury ions. Has technical flaws such as long response time and low detection sensitivity

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  • Tetraphenyl ethylene-diaminomaleonitrile derivative and preparation method and application thereof
  • Tetraphenyl ethylene-diaminomaleonitrile derivative and preparation method and application thereof
  • Tetraphenyl ethylene-diaminomaleonitrile derivative and preparation method and application thereof

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preparation example Construction

[0043]The invention provides a kind of preparation method of tetraphenylethylene-diaminomaleonitrile derivative, comprising the following steps:

[0044] A) under the action of a catalyst, after reacting triphenylbromoethylene, 4-formylphenylboronic acid, potassium carbonate and the first solvent, a reaction intermediate is obtained;

[0045] B) reacting the reaction intermediate obtained in the above steps, diaminomaleonitrile and the second solvent again to obtain tetraphenylethylene-diaminomaleonitrile derivatives.

[0046] In the present invention, under the action of a catalyst, triphenylbromoethylene, 4-formylphenylboronic acid, potassium carbonate and a first solvent are reacted to obtain a reaction intermediate.

[0047] The present invention has no special restrictions on the selection of the 4-formylphenylboronic acid, and the conventional 4-formylphenylboronic acid well-known to those skilled in the art can be selected. Those skilled in the art can select according ...

Embodiment 1

[0074]Dissolve 6mmol of triphenylbromoethylene and 8mmol of 4-formylphenylboronic acid in 50ml of methanol and 50ml of toluene and mix, add 3.5g of calcium carbonate and 0.05g of bis(triphenylphosphine)palladium dichloride, in a nitrogen atmosphere , heated and stirred at 75°C, condensed and refluxed for 16 hours, and cooled to room temperature. Purified by column chromatography, the eluent was n-hexane / dichloromethane, and a yellow-green solid was isolated, which was the first product I (reaction intermediate).

[0075] 2 mmol of the first product I and 2 mmol of diaminomaleonitrile were dissolved in 35 ml of ethanol, heated and stirred at 80° C., condensed and refluxed for 23 hours, and cooled to room temperature. Purified by column chromatography, the eluent was n-hexane / dichloromethane, and a yellow solid was obtained, which was the ligand HL (tetraphenylethylene-diaminomaleonitrile derivative).

[0076] The ligand HL prepared in Example 1 of the present invention was cha...

Embodiment 2

[0080] 6.6mmol of triphenylbromoethylene and 8.9mmol of 4-formylphenylboronic acid were dissolved in 50ml of methanol and 50ml of toluene and mixed, adding 3.5g of calcium carbonate and 0.05g of two (triphenylphosphine) palladium dichloride, in Under nitrogen atmosphere, heat and stir at 75°C, condense and reflux for 16 hours, and cool to room temperature. Purified by column chromatography, the eluent was n-hexane / dichloromethane, and a yellow-green solid was isolated, which was the first product I.

[0081] Dissolve 2mmol of the first product I and 2mmol of diaminomaleonitrile in 20ml of ethanol, heat and stir at 90°C, reflux for 20 hours, and cool to room temperature. Purified by column chromatography, the eluent was petroleum ether / ethyl acetate, and a yellow solid was obtained, which was the ligand HL.

[0082] The ligand HL prepared in Example 1 of the present invention was characterized and tested.

[0083] Ligand HL was characterized and identified as C 31 h 22 N 4...

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Abstract

The invention provides a tetraphenyl ethylene-diaminomaleonitrile derivative which has a structure in a formula (I) and provides a novel compound, namely the tetraphenyl ethylene-diaminomaleonitrile derivative. The tetraphenyl ethylene-diaminomaleonitrile derivative has the structure as shown in the formula (I), and the molecular formula is C31H22N4. The tetraphenyl ethylene-diaminomaleonitrile derivative has a typical AIE effect, is high in luminous intensity in water, sensitive in response to Hg<2+>, good in selectivity and high in specificity, is almost not disturbed by hetero-metal ions, and is an ideal sensing molecule for quickly detecting Hg<2+> in water. Furthermore, the preparation method is simple, feasible, mild in condition and suitable for industrialized application. The formula is as shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of metal ion fluorescent probe compounds, and relates to a tetraphenylethylene-diaminomaleonitrile derivative and its preparation method and application, in particular to a tetraphenylethylene-diaminomaleonitrile derivative capable of detecting mercury ions in an aqueous solution. Aminomaleonitrile derivatives and methods for their preparation. Background technique [0002] Mercury is a chemical element and one of the well-known highly toxic metals. It ranks 80th in the periodic table of elements, commonly known as mercury, and its element symbol is Hg. It is located in the sixth period and group IIB of the chemical element periodic table. Metal in liquid state. Mercury is a silver-white shiny heavy liquid with stable chemical properties, insoluble in acid and alkali, and can evaporate at room temperature. Mercury vapor and mercury compounds are highly toxic (chronic). [0003] Mercury has a long history o...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/61C09K11/06G01N21/64
CPCC07C45/68C07C253/30C09K11/06C09K2211/1007G01N21/6428G01N2021/6432C07C255/61C07C47/548
Inventor 霍延平王凯李宗植潘成强陆天华
Owner GUANGDONG UNIV OF TECH
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