A tetrastyryl cationic fluorescent probe and its preparation method and application

Abstract

The invention discloses a tetrastyryl cationic fluorescent probe and its preparation method and application. The method comprises the following steps: preparing solid compound 1; preparing light yellow solid compound 2; preparing yellow solid compound 3; Dissolve in 20-25ml of ethanol, add 150-200uL of substituting agent with a pipette gun, the substituting agent is any one of salicylaldehyde, aromatic aldehyde and heterocyclic formaldehyde, under the protection of argon, raise the temperature to 80- Heat to reflux at 90°C for 4-5 hours. After the reaction, the reaction solution is filtered hot, the filtrate is recrystallized with ethanol, the crystals are washed three times with cold ethanol, and naturally dried in the shade to obtain a yellow solid compound. The application is the application of the tetrastyryl cation fluorescent probe of the present invention in cation recognition. The fluorescent probe of the invention has an aggregation-inducing effect, overcomes the disadvantages of the traditional aggregation-inducing quenching effect fluorescent probe, and expands its application range.

Description

technical field

[0001] The invention relates to the field of fluorescent probes, in particular to a tetrastyryl cationic fluorescent probe and its preparation method and application. Background technique

[0002] Copper plays important roles in biological, environmental and chemical systems. It is an essential trace element for plants and animals, including humans. In addition to zinc and iron, copper ranks third in the abundance of essential heavy metals in the human body. However, the disorder of copper ions seriously affects human health, which leads to a series of diseases such as Menke's syndrome, Wilson's disease, and Alzheimer's disease. Merlin's disease, Parkinson's disease, Huntington's disease, etc.

[0003] After years of exploration, a series of methods for detecting copper ions have been developed, including atomic absorption spectrometry, inductively coupled plasma mass spectrometry, inductively coupled plasma atomic emission spectrometry, voltammetry and ano...

Examples

Embodiment 1

[0044] The following is the structural formula of compound TS1:

[0045]

[0046] The following is the synthetic route of TS1:

[0047]

[0048] (1) Synthesis of compound 1

[0049] Step 1: Add 12mmol of diphenylmethane into a two-necked bottle, add 20ml of double-distilled tetrahydrofuran under the protection of argon to dissolve, add 4.0ml of 2.5M / cyclohexane n-butyllithium under stirring in an ice bath, and stir for 30min;

[0050] Step 2, after stirring, 4mmol of 4,4' Dimethylbenzophenone was dissolved in 10ml redistilled tetrahydrofuran, added dropwise to the reaction system, and stirred at room temperature for 6h;

[0051] Step 3, after the reaction is finished, quench by adding saturated ammonium chloride, extract three times with dichloromethane, combine the organic phases, wash once with saturated brine, dry the organic phases with anhydrous sodium sulfate, and distill off the organic solvent under reduced pressure to obtain light yellow Liquid, dissolve the...

Embodiment 2

[0064] The preparation method of TS1 comprises the following steps:

[0065] (1) Synthesis of compound 1

[0066] Step 1: Add 13 mmol of diphenylmethane into a two-necked bottle, add 20 ml of distilled tetrahydrofuran under the protection of argon to dissolve, add 3.2 ml of 2.6M / cyclohexane n-butyllithium under stirring in an ice bath, and stir for 22 minutes;

[0067] Step 2, after the stirring is completed, dissolve 5 mmol of 4,4'-dimethylbenzophenone in 12 ml of redistilled tetrahydrofuran, add it dropwise to the reaction system, and stir at room temperature for 7 hours;

[0068] Step 3, after the reaction is finished, quench by adding saturated ammonium chloride, extract three times with dichloromethane, combine the organic phases, wash once with saturated brine, dry the organic phases with anhydrous sodium sulfate, and distill off the organic solvent under reduced pressure to obtain light yellow Liquid, dissolve the light yellow liquid with toluene, add 17mmol p-toluenes...

Embodiment 3

[0079] The preparation method of TS1 comprises the following steps:

[0080] (1) Synthesis of compound 1

[0081] Step 1: Add 15 mmol of diphenylmethane into a two-necked bottle, add 20 ml of redistilled tetrahydrofuran under the protection of argon to dissolve, add 3.8 ml of 2.9M / cyclohexane n-butyllithium under stirring in an ice bath, and stir for 20 to 30 minutes;

[0082] Step 2, after stirring, dissolve 5.5 mmol of 4,4'-dimethylbenzophenone in 18 ml of redistilled tetrahydrofuran, add it dropwise to the reaction system, and stir at room temperature for 9 h:

[0083] Step 3, after the reaction is finished, quench by adding saturated ammonium chloride, extract three times with dichloromethane, combine the organic phases, wash once with saturated brine, dry the organic phases with anhydrous sodium sulfate, and distill off the organic solvent under reduced pressure to obtain light yellow Liquid, dissolve the light yellow liquid with toluene, add 17.5mmol p-toluenesulfonic a...

technical field

[0001] The invention relates to the field of fluorescent probes, in particular to a tetrastyryl cationic fluorescent probe and its preparation method and application. Background technique

[0002] Copper plays important roles in biological, environmental and chemical systems. It is an essential trace element for plants and animals, including humans. In addition to zinc and iron, copper ranks third in the abundance of essential heavy metals in the human body. However, the disorder of copper ions seriously affects human health, which leads to a series of diseases such as Menke's syndrome, Wilson's disease, and Alzheimer's disease. Merlin's disease, Parkinson's disease, Huntington's disease, etc.

[0003] After years of exploration, a series of methods for detecting copper ions have been developed, including atomic absorption spectrometry, inductively coupled plasma mass spectrometry, inductively coupled plasma atomic emission spectrometry, voltammetry and ano...

Examples

Embodiment 1

[0044] The following is the structural formula of compound TS1:

[0045]

[0046] The following is the synthetic route of TS1:

[0047]

[0048] (1) Synthesis of compound 1

[0049] Step 1: Add 12mmol of diphenylmethane into a two-necked bottle, add 20ml of double-distilled tetrahydrofuran under the protection of argon to dissolve, add 4.0ml of 2.5M / cyclohexane n-butyllithium under stirring in an ice bath, and stir for 30min;

[0050] Step 2, after stirring, 4mmol of 4,4' Dimethylbenzophenone was dissolved in 10ml redistilled tetrahydrofuran, added dropwise to the reaction system, and stirred at room temperature for 6h;

[0051] Step 3, after the reaction is finished, quench by adding saturated ammonium chloride, extract three times with dichloromethane, combine the organic phases, wash once with saturated brine, dry the organic phases with anhydrous sodium sulfate, and distill off the organic solvent under reduced pressure to obtain light yellow Liquid, dissolve the...

Embodiment 2

[0064] The preparation method of TS1 comprises the following steps:

[0065] (1) Synthesis of compound 1

[0066] Step 1: Add 13 mmol of diphenylmethane into a two-necked bottle, add 20 ml of distilled tetrahydrofuran under the protection of argon to dissolve, add 3.2 ml of 2.6M / cyclohexane n-butyllithium under stirring in an ice bath, and stir for 22 minutes;

[0067] Step 2, after the stirring is completed, dissolve 5 mmol of 4,4'-dimethylbenzophenone in 12 ml of redistilled tetrahydrofuran, add it dropwise to the reaction system, and stir at room temperature for 7 hours;

[0068] Step 3, after the reaction is finished, quench by adding saturated ammonium chloride, extract three times with dichloromethane, combine the organic phases, wash once with saturated brine, dry the organic phases with anhydrous sodium sulfate, and distill off the organic solvent under reduced pressure to obtain light yellow Liquid, dissolve the light yellow liquid with toluene, add 17mmol p-toluenes...

Embodiment 3

[0079] The preparation method of TS1 comprises the following steps:

[0080] (1) Synthesis of compound 1

[0081] Step 1: Add 15 mmol of diphenylmethane into a two-necked bottle, add 20 ml of redistilled tetrahydrofuran under the protection of argon to dissolve, add 3.8 ml of 2.9M / cyclohexane n-butyllithium under stirring in an ice bath, and stir for 20 to 30 minutes;

[0082] Step 2, after stirring, dissolve 5.5 mmol of 4,4'-dimethylbenzophenone in 18 ml of redistilled tetrahydrofuran, add it dropwise to the reaction system, and stir at room temperature for 9 h:

[0083] Step 3, after the reaction is finished, quench by adding saturated ammonium chloride, extract three times with dichloromethane, combine the organic phases, wash once with saturated brine, dry the organic phases with anhydrous sodium sulfate, and distill off the organic solvent under reduced pressure to obtain light yellow Liquid, dissolve the light yellow liquid with toluene, add 17.5mmol p-toluenesulfonic a...

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