Fluorescent sensing film as well as preparation method and application thereof

Abstract

The invention discloses a fluorescent sensing film as well as a preparation method and application thereof, and belongs to the technical field of small-molecule fluorescent sensing film materials. Thefluorescent sensing film is prepared by crosslinking trimesoyl amide and an o-carborane derivative, has no matrix effect and uniform and defect-free surface, has large specific surface area and porosity, and can ensure that molecules of an object to be detected can be well diffused in the film. The preparation method disclosed by the invention is simple and convenient to operate and mild in reaction condition, the prepared fluorescent compound is high in photochemical and thermodynamic stability, and the obtained fluorescent sensing film is high in sensitivity, high in selectivity, long in service life and controllable and uniform in thickness and is an excellent fluorescent sensing film. The fluorescent sensing film has good response to methanol and ethanol, but the strength of methanolis higher than that of ethanol, the recovery time is shorter than that of ethanol, and a new method is provided for methanol detection.

Description

technical field

[0001] The invention belongs to the technical field of small molecule fluorescent sensing thin film materials, and in particular relates to a fluorescent sensing thin film and its preparation method and application.

[0002] technical background

[0003] As an important chemical raw material, methanol is very common in daily production and life. However, methanol is absorbed by the human body through the skin and respiratory tract, stimulates the human nervous system, has an anesthetic effect, and can induce cerebral edema; methanol is selective to the retina and optic nerve, which can cause optic atrophy and severe blindness. Methanol is a colorless, transparent, and highly volatile substance. Methanol and ethanol cannot be accurately distinguished only by the naked eye. Therefore, the development of reliable, highly sensitive, and fast-response gas-phase methanol detection materials and methods is essential for methanol, The detection of alcohol and the det...

Examples

preparation example Construction

[0065] The present invention also discloses a synthesis method of the above-mentioned trimesisamide and o-carborane derivatives, comprising the following steps:

[0066] 1) Preparation of compound 1

[0067] Add 1,3,5-benzenetricarboxylic acid chloride, methyl p-aminobenzoate, triethylamine and tetrahydrofuran into the flask, and under the protection of an inert atmosphere, stir at room temperature for 9 to 12 hours. After the reaction is completed, filter to remove the precipitate. The solvent was concentrated under reduced pressure, and then methanol was added, and a white precipitate appeared immediately, the solution was filtered with suction, and the filter cake was washed with water and methanol several times, and the obtained product was dried to obtain compound 1;

[0068] Wherein, the structural formula of the compound 1 is:

[0069] 2) Preparation of Compound 2 (Trimellitic Tricarboxamides)

[0070] Add compound 1, methanol, and hydrazine hydrate into the flask i...

Embodiment 1

[0095] 1.1 Preparation of target compounds of trimesamide and o-carborane derivatives

[0096] 1) Synthesis of compound 1

[0097] Add 0.26g of 1,3,5-benzenetricarboxylic acid chloride, 0.76g of methyl p-aminobenzoate, 1ml of triethylamine and 30mL of tetrahydrofuran into the flask in sequence, and react under reflux at 20°C for 10 hours under a nitrogen atmosphere. After the reaction is completed, , the reaction solution was concentrated under reduced pressure, and 100 mL of methanol was added to the concentrated solution, and a white precipitate appeared immediately, the solution was filtered with suction, and the filter cake was washed with water and methanol several times, and the obtained substance was vacuum-dried to obtain a white compound 1;

[0098] Its reaction equation is as follows:

[0099]

[0100] 2) Synthesis of compound 2 (trimellitic tricarboxamides)

[0101]Add 0.2g of compound 1, 5mL of hydrazine hydrate, and 20mL of methanol into a 100mL two-necked ro...

Embodiment 2

[0116] 2.1 Preparation of target compounds of trimesamide and o-carborane derivatives

[0117] 1) Synthesis of compound 1

[0118] Add 0.26g of 1,3,5-benzenetricarboxylic acid chloride, 1.06g of methyl p-aminobenzoate, 2ml of triethylamine and 35mL of tetrahydrofuran into the flask in sequence, and react under reflux at 25°C for 11 hours under a nitrogen atmosphere. After the reaction is completed, , the reaction solution was concentrated under reduced pressure, and 100 mL of methanol was added to the concentrated solution, and a white precipitate appeared immediately, the solution was filtered with suction, and the filter cake was washed with water and methanol several times, and the obtained substance was vacuum-dried to obtain a white compound 1;

[0119] 2) Synthesis of compound 2 (trimellitic tricarboxamides)

[0120] Add 0.2g of compound 1, 8mL of hydrazine hydrate, and 30mL of methanol into a 100mL two-necked round-bottomed flask in sequence, and stir under reflux at 7...

technical field

[0001] The invention belongs to the technical field of small molecule fluorescent sensing thin film materials, and in particular relates to a fluorescent sensing thin film and its preparation method and application.

[0002] technical background

[0003] As an important chemical raw material, methanol is very common in daily production and life. However, methanol is absorbed by the human body through the skin and respiratory tract, stimulates the human nervous system, has an anesthetic effect, and can induce cerebral edema; methanol is selective to the retina and optic nerve, which can cause optic atrophy and severe blindness. Methanol is a colorless, transparent, and highly volatile substance. Methanol and ethanol cannot be accurately distinguished only by the naked eye. Therefore, the development of reliable, highly sensitive, and fast-response gas-phase methanol detection materials and methods is essential for methanol, The detection of alcohol and the det...

Examples

preparation example Construction

[0065] The present invention also discloses a synthesis method of the above-mentioned trimesisamide and o-carborane derivatives, comprising the following steps:

[0066] 1) Preparation of compound 1

[0067] Add 1,3,5-benzenetricarboxylic acid chloride, methyl p-aminobenzoate, triethylamine and tetrahydrofuran into the flask, and under the protection of an inert atmosphere, stir at room temperature for 9 to 12 hours. After the reaction is completed, filter to remove the precipitate. The solvent was concentrated under reduced pressure, and then methanol was added, and a white precipitate appeared immediately, the solution was filtered with suction, and the filter cake was washed with water and methanol several times, and the obtained product was dried to obtain compound 1;

[0068] Wherein, the structural formula of the compound 1 is:

[0069] 2) Preparation of Compound 2 (Trimellitic Tricarboxamides)

[0070] Add compound 1, methanol, and hydrazine hydrate into the flask i...

Embodiment 1

[0095] 1.1 Preparation of target compounds of trimesamide and o-carborane derivatives

[0096] 1) Synthesis of compound 1

[0097] Add 0.26g of 1,3,5-benzenetricarboxylic acid chloride, 0.76g of methyl p-aminobenzoate, 1ml of triethylamine and 30mL of tetrahydrofuran into the flask in sequence, and react under reflux at 20°C for 10 hours under a nitrogen atmosphere. After the reaction is completed, , the reaction solution was concentrated under reduced pressure, and 100 mL of methanol was added to the concentrated solution, and a white precipitate appeared immediately, the solution was filtered with suction, and the filter cake was washed with water and methanol several times, and the obtained substance was vacuum-dried to obtain a white compound 1;

[0098] Its reaction equation is as follows:

[0099]

[0100] 2) Synthesis of compound 2 (trimellitic tricarboxamides)

[0101]Add 0.2g of compound 1, 5mL of hydrazine hydrate, and 20mL of methanol into a 100mL two-necked ro...

Embodiment 2

[0116] 2.1 Preparation of target compounds of trimesamide and o-carborane derivatives

[0117] 1) Synthesis of compound 1

[0118] Add 0.26g of 1,3,5-benzenetricarboxylic acid chloride, 1.06g of methyl p-aminobenzoate, 2ml of triethylamine and 35mL of tetrahydrofuran into the flask in sequence, and react under reflux at 25°C for 11 hours under a nitrogen atmosphere. After the reaction is completed, , the reaction solution was concentrated under reduced pressure, and 100 mL of methanol was added to the concentrated solution, and a white precipitate appeared immediately, the solution was filtered with suction, and the filter cake was washed with water and methanol several times, and the obtained substance was vacuum-dried to obtain a white compound 1;

[0119] 2) Synthesis of compound 2 (trimellitic tricarboxamides)

[0120] Add 0.2g of compound 1, 8mL of hydrazine hydrate, and 30mL of methanol into a 100mL two-necked round-bottomed flask in sequence, and stir under reflux at 7...

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