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A preparation method of rare earth nanowires modified by tetraphenylethylene derivatives that can be used for the detection of organic carboxylic acids

A technology of tetraphenylethylene and organic carboxylic acid, applied in the field of nano-luminescent materials, can solve the problems of expensive instruments and high cost, and achieve the effects of simple preparation method, strong practicability and high detection efficiency

Active Publication Date: 2020-05-12
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Tetraphenylethylene fluorescent probes are widely used in the field of molecular detection, such as: volatile solvents, toxic gases, metal ions and biomolecules, but the detection of organic carboxylic acids is rarely studied, and the detection method of organic carboxylic acids is usually High-performance liquid chromatography, gas chromatography and ion chromatography, etc., these methods are relatively expensive, and the equipment is expensive, so the preparation of low-cost and efficient fluorescent probes needs to be studied urgently

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  • A preparation method of rare earth nanowires modified by tetraphenylethylene derivatives that can be used for the detection of organic carboxylic acids
  • A preparation method of rare earth nanowires modified by tetraphenylethylene derivatives that can be used for the detection of organic carboxylic acids
  • A preparation method of rare earth nanowires modified by tetraphenylethylene derivatives that can be used for the detection of organic carboxylic acids

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preparation example Construction

[0036] The preparation method of the rare earth nanowires modified by tetraphenylethylene derivatives and the detection method of organic carboxylic acids are mainly characterized in that the following steps are followed in sequence:

[0037] (1) Synthesis of tetraphenylethylene derivatives: Dissolve 12mmoL diphenylmethane in dry 20mL tetrahydrofuran, add 10mmoL n-butyllithium, stir for 1 hour at 0°C under nitrogen protection, then add 9mmoL 4-methyldiphenyl Benzophenone, the temperature was raised to normal temperature, reacted at normal temperature for 6 hours, added 10wt% aluminum chloride solution to stop the reaction, extracted the organic layer with dichloromethane, added saturated saline solution to wash, dried over anhydrous magnesium sulfate, added 80mL Benzoic acid and 1.8mmoL p-toluenesulfonic acid, heated the mixture under reflux for 4 hours in a Dean Stark apparatus, collected the product of the toluene layer, added 10wt% sodium bicarbonate to wash, dried over anhy...

Embodiment 1

[0045] 1. Synthesis of Tetraphenylethylene Derivatives

[0046] (1) In dry 20mL tetrahydrofuran, add 12mmoL diphenylmethane, 10mmoL n-butyllithium and 9mmoL 4-methylbenzophenone, and stir at 0°C for 1 hour under nitrogen protection;

[0047] (2) then raise the temperature, and react at normal temperature for 6 hours;

[0048] (3) adding 10wt% aluminum chloride solution to stop the reaction;

[0049] (4) Extract the organic layer with dichloromethane, add saturated saline solution to wash, and dry over anhydrous magnesium sulfate;

[0050] (5) Add 80 mL of benzoic acid and 1.8 mmoL p-toluenesulfonic acid, heat the mixture to reflux for 4 hours in a Dean Stark apparatus, collect the product of the toluene layer, add 10 wt% sodium bicarbonate for washing, and dry over anhydrous magnesium sulfate;

[0051] (6) rotary steaming, recrystallization in dichloromethane and methanol to obtain white powder 1-(4-methylphenyl)-1,2,2-triphenylethylene;

[0052] (7) Take 5mmoL 1-(4-methylp...

Embodiment 2

[0070] 1. Synthesis of Tetraphenylethylene Derivatives

[0071] (1) In dry 20mL tetrahydrofuran, add 12mmoL diphenylmethane, 10mmoL n-butyllithium and 9mmoL 4-methylbenzophenone, and stir at 0°C for 1 hour under nitrogen protection;

[0072] (2) then raise the temperature, and react at normal temperature for 6 hours;

[0073] (3) adding 10wt% aluminum chloride solution to stop the reaction;

[0074] (4) Extract the organic layer with dichloromethane, add saturated saline solution to wash, and dry over anhydrous magnesium sulfate;

[0075] (5) Add 80 mL of benzoic acid and 1.8 mmoL p-toluenesulfonic acid, heat the mixture to reflux for 4 hours in a Dean Stark apparatus, collect the product of the toluene layer, add 10 wt% sodium bicarbonate for washing, and dry over anhydrous magnesium sulfate;

[0076] (6) rotary steaming, recrystallization in dichloromethane and methanol to obtain white powder 1-(4-methylphenyl)-1,2,2-triphenylethylene;

[0077] (7) Take 5mmoL 1-(4-methylp...

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Abstract

The invention provides a method for preparing rare earth nanowires modified by tetraphenylethylene derivatives that can be used for the detection of organic carboxylic acids. The tetraphenylethylene derivatives with two carboxyl groups connected to the benzene ring at one end were prepared by organic synthesis, and then by modifying the rare earth nanowires coated with PSS, the carboxyl groups of the tetraphenylethylene derivatives were fixed on the surface of the nanowires through electrostatic interaction, so that the benzene The rotation in the ring molecule is limited to produce fluorescence. Different organic carboxylic acids have different acidity and carbon chain length. The tetraphenylethylene derivatives coated on the surface of the nanowire will be replaced by the relatively strong acidic carboxylic acid with a carbon chain length of less than ten. Instead, the intramolecular rotation of the benzene ring is no longer limited, and the fluorescence intensity decreases, while the relatively weak acidic carboxylic acid with a carbon chain length greater than ten is directly further loaded on the positively charged rare earth nanowires on the surface, thus showing different Based on the single-molecule characteristic emission of the former. The steps are simple, the operation is convenient and the practicability is strong.

Description

technical field [0001] The invention belongs to the field of fluorescent probe preparation, in particular to a nano-luminescent material modified by tetraphenylethylene derivatives responsive to organic carboxylic acids. Background technique [0002] Tetraphenylethylene derivatives modified by different kinds of functional groups have unique aggregation and luminescent properties, and are an important organic functional material. At present, restricting the intramolecular rotation of tetraphenylethylene derivatives by adding a poor solvent is a common method to obtain fluorescence enhancement, and fixing one end of tetraphenylethylene derivatives on stable inorganic nanoparticles is a way to enhance fluorescence intensity. new method. Tetraphenylethylene fluorescent probes are widely used in the field of molecular detection, such as: volatile solvents, toxic gases, metal ions and biomolecules, but the detection of organic carboxylic acids is rarely studied, and the detectio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C27/02C07C65/28C09K11/06G01N21/64
CPCC07C51/09C09K11/06C09K2211/1007G01N21/643C07C65/28
Inventor 王曦柏铭吴建斌马庆林
Owner SHANDONG UNIV