CN109232627B - Fluorescent compound with sensing function on gas-phase acetone and peroxide explosive and preparation method and application of fluorescent sensing film - Google Patents
Fluorescent compound with sensing function on gas-phase acetone and peroxide explosive and preparation method and application of fluorescent sensing film Download PDFInfo
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- CN109232627B CN109232627B CN201811315218.0A CN201811315218A CN109232627B CN 109232627 B CN109232627 B CN 109232627B CN 201811315218 A CN201811315218 A CN 201811315218A CN 109232627 B CN109232627 B CN 109232627B
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- dichloromethane
- column chromatography
- acetone
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives and a preparation method and application of a fluorescent sensing film, wherein a molecular channel formed after a non-planar structure is accumulated on a molecular level is utilized, and the capillary condensation phenomenon and the solvation effect are utilized, so that the sensitive, high-selectivity, high-resilience and stability identification and detection of acetone vapor and peroxide explosive vapor at room temperature are realized, the problem of high working temperature in detection in the conventional method is basically solved, and a new thought is provided for the design of the fluorescent sensing film with excellent performance. The preparation method is simple and convenient to operate, the reaction conditions are mild, the prepared fluorescent compound is good in photochemical and thermodynamic stability, the obtained fluorescent sensing film is high in sensitivity, good in selectivity and long in service life, and the fluorescent sensing film is an excellent fluorescent sensing film, and the sensitive detection of acetone vapor and peroxide explosives can be realized by combining the film with a commercial fluorescent instrument.
Description
Technical Field
The invention belongs to the technical field of small-molecule fluorescent sensing film materials, relates to a fluorescent compound, and a preparation method and application of a fluorescent sensing film based on the fluorescent compound, and particularly relates to a fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives, and a preparation method and application of the fluorescent sensing film.
Background
In recent years, acetone has become an important material for organic synthesis due to its effective chemical properties and low cost, and is widely used in industrial production, laboratories, and the pharmaceutical industry. Acetone is a colorless, volatile and flammable gas, is easily changed into acetone vapor when being exposed in the air, can cause harm to human health after being contacted for a long time, can possibly cause irritation to eyes and throats and symptoms such as nausea, headache, vomiting and the like if being light, can damage the central nervous system of human beings if being heavy, and can even cause irreparable damage to the liver, kidney and pancreas of human bodies; meanwhile, acetone is one of the main components of unconventional emission pollutants in automobile exhaust and is considered as a potential dangerous carcinogen and an important pollutant; in addition, acetone is a product of animal body substance metabolism, the concentration of the acetone can reflect the organism condition of an organism, and the acetone can be used for the early-stage rapid nondestructive detection of lung cancer, diabetes and other diseases; more importantly, acetone is one of the most important raw materials for synthesizing peroxide explosives with large-scale lethality, which are often used for terrorist attacks, and the disaster of the human beings caused by the peroxide explosives can be reduced by detecting acetone gas. Therefore, from the perspective of environmental protection and human health and reducing terrorist crimes, the development of a low-cost, real-time, rapid, convenient, accurate and reliable acetone analysis and detection method is undoubtedly of great significance for early rapid and non-invasive detection of crime prevention, environmental protection and diseases.
Based on the importance of acetone, various detection techniques or methods have been developed so far. Techniques or methods such as gas chromatography-mass spectrometry, ion mobility spectrometry, surface enhanced raman, nuclear magnetic resonance, resistive sensors, etc. have been reported successfully. However, these methods often have the disadvantages of complicated operation, high cost, insufficient sensitivity, poor selectivity, portability and the like, and are difficult to popularize and use. For example, although the resistance sensor studied most fiery currently shows higher detection sensitivity to acetone, the main disadvantages are that it needs to be performed at a higher working temperature (200-. Therefore, the development of a detection technology for acetone gas with high sensitivity, high selectivity, repeatability, response and recovery speed at room temperature has important practical value and is a necessary trend for the development of acetone sensors. Fluorescence sensing is known as a new generation of micro-trace detection technology internationally recognized following ion mobility spectrometry. However, according to literature research, acetone detection technology based on fluorescence sensing means is rarely reported. In addition, the existing fluorescence detection technology still has the defects of low sensitivity, poor anti-interference capability, difficult gas phase detection and the like, and the nature of the technology is that the performance of the sensing material is not good, so that the development of the fluorescent material with excellent sensing performance is extremely important.
Perylene bisimide derivatives are widely concerned by people in the fields of photoelectric functional materials, fluorescence sensing, catalytic synthesis and the like due to excellent photoelectric properties, photochemical stability and thermal stability. However, due to the strong intermolecular interaction of perylene bisimide, the materials derived from perylene bisimide have the defects of low luminous efficiency, strong intermolecular aggregation, poor solubility and the like. The prepared fluorescent sensing film has the outstanding defects of poor permeability and the like, and is not beneficial to the diffusion of molecules of an object to be detected in the film, so that the sensing performance is poor.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives, and a preparation method and application of a fluorescent sensing film.
In order to achieve the purpose, the invention adopts the following technical scheme to realize the purpose:
the invention discloses a fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives, which has the following structural formula:
wherein n is 1-20.
The invention also discloses a preparation method of the fluorescent compound with the sensing function on the gas-phase acetone and the peroxide explosives, which comprises the following steps:
1) preparation of Compound 1
Sequentially adding perylene anhydride, alkylamine, zinc acetate dihydrate, imidazole and water into a reaction kettle, reacting for 24-30 hours at 190-200 ℃, naturally cooling reaction liquid to room temperature, then pouring the reaction liquid into water until complete precipitation, performing suction filtration, leaching with water and methanol, drying, and performing column chromatography separation to obtain a compound 1;
2) preparation of Compound 2
Dissolving the compound 1 in dichloromethane, adding liquid bromine into a reaction system, then refluxing and stirring for reaction for 5-8 hours, performing rotary evaporation on the reaction liquid to remove the solvent, and performing column chromatographic separation to obtain a compound 2;
3) preparation of Compound 3
Under the protection of argon, placing a compound 2, triisopropylethynylsilicon, tris (dibenzylideneacetone) dipalladium and tris (o-methylphenyl) phosphorus in a Schlenk tube, adding anhydrous toluene and anhydrous diisopropylamine into the Schlenk tube, reacting the reaction system at 65-80 ℃ for 18-24 hours, then removing the solvent by rotary evaporation, and performing column chromatography separation to obtain a compound 3;
4) preparation of Compound 4
Dissolving the compound 3 in anhydrous tetrahydrofuran, stirring at room temperature to fully dissolve the compound, then dropwise adding a tetrahydrofuran solution of tetrabutylammonium fluoride, continuously reacting for 3-5 hours at room temperature in a dark place, then adding water into a reaction system, filtering, drying, and performing column chromatography separation on the obtained dried substance to obtain a compound 4;
wherein the structural formula of the compound 4 is as follows:
wherein n in the structural formula is 1-20;
5) preparation of Compound 5
Dissolving 8-hydroxyquinoline, 4-iodophenylboronic acid and potassium phosphate in a solvent, reacting for 20-24 hours at 100-110 ℃, then removing the solvent by rotary evaporation, and performing column chromatography to obtain a yellow-green solid, namely a compound 5;
wherein the structural formula of the compound 5 is as follows:
6) preparation of the target product
Under the protection of argon, placing a compound 4, a compound 5, tris (dibenzylideneacetone) dipalladium and tris (o-methylphenyl) phosphorus in a Schlenk tube, adding anhydrous toluene and anhydrous triethylamine, reacting a reaction system at 65-80 ℃ for 18-24 hours, then removing the solvent by rotary evaporation, and performing column chromatography separation to obtain the target product, namely the fluorescent compound with the sensing function on gas phase acetone and peroxide explosives.
Preferably, the ratio of the used reactants in each step is as follows:
in the step 1), the molar ratio of perylene anhydride, alkylamine, zinc acetate dihydrate, imidazole and water is 1: (0.5-0.6): (0.19-0.25): (25-35): (45-55);
in the step 2), the molar ratio of the compound 1 to the liquid bromine to the dichloromethane is 1: (2.2-3): (1700 to 1800);
in the step 3), the molar ratio of the compound 2, triisopropylethynylsilicon, tris (dibenzylideneacetone) dipalladium, tris (o-methylphenyl) phosphorus, anhydrous toluene and anhydrous diisopropylamine is 1: (1.1-1.5): (1.1-1.2): (0.65-0.75): (90-100): (14-18);
in the step 4), the molar ratio of the compound 3, tetrabutylammonium fluoride and anhydrous tetrahydrofuran is 1: (3-4): (160-175);
in the step 5), the molar ratio of 8-hydroxyquinoline to 4-iodophenylboronic acid to potassium phosphate is 1: (8.5-9.5): (2.8-3.2);
in the step 6), the molar ratio of the compound 5, the compound 4, the tris (dibenzylideneacetone) dipalladium, the tris (o-methylphenyl) phosphorus, the anhydrous toluene and the anhydrous triethylamine is 1: (2.1-2.5): (0.1-0.15): (0.65-0.75): (20-25): (3.6-5).
Preferably, the column chromatography eluent of each step is selected as follows:
in the step 1), the column chromatography separation takes dichloromethane as eluent;
in the step 2), the column chromatography takes dichloromethane as eluent;
in the step 3), the column chromatography separation is performed by taking a dichloromethane-n-hexane system as an eluent, wherein the volume ratio of dichloromethane to n-hexane is 1: 1;
in the step 4), the column chromatography separation is performed by taking a dichloromethane-n-hexane system as an eluent, wherein the volume ratio of dichloromethane to n-hexane is 2: 1;
in the step 6), the column chromatography separation is performed by taking a dichloromethane-n-hexane system as an eluent, wherein the volume ratio of dichloromethane to n-hexane is 2: 1.
Preferably, in step 5), the solvent is 1, 4-dioxane, toluene or N, N-dimethylformamide.
The invention also discloses a method for preparing the fluorescent sensing film by adopting the fluorescent compound with the sensing function on the gas-phase acetone and the peroxide explosives, which comprises the following steps:
1) adding trichloromethane solvent into the fluorescent compound with sensing function on gas-phase acetone and peroxide explosive to prepare the fluorescent compound with the concentration of 1 × 10-4～1×10-3Standing and sealing the mol/L stock solution for later use;
2) uniformly coating the fluorescent compound assembly structure prepared in the step 1) on a substrate, standing at room temperature for 1-2 hours, drying in a vacuum drying oven at 40-60 ℃ under 3000Pa for 12-24 hours, taking out, sealing and storing to prepare the fluorescent sensing film.
Preferably, in step 2), the substrate is a silica gel plate substrate, a filter paper substrate, a glass substrate or a polymer oil substrate; the coating volume is 0.05-0.2 mu L/cm2。
The invention also discloses the fluorescent sensing film prepared by the method.
The invention also discloses application of the fluorescent sensing film in detecting acetone gas and/or peroxide explosive gas.
Preferably, the peroxide explosive gas is triacetoneperoxide and/or diproprione diperoxide.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a fluorescent compound with sensing function on gas-phase acetone and peroxide explosives, which is a designed perylene bisimide derivative modified four-coordination organic boron quinoline fluorescent compound, wherein in the molecular structure of the compound, boron atoms adopt classical sp3The hybridization mode enables the whole molecule to show a typical regular tetrahedron configuration with strong rigidity and a special space structure, can effectively inhibit strong intermolecular interaction of perylene bisimide, reduces the compact intermolecular accumulation, greatly increases the solubility, enhances the performance of the derived luminescent material, and lays a foundation for the construction of the fluorescent sensing film.
The invention also discloses a synthesis method of the fluorescent compound with the sensing function on the gas-phase acetone and the peroxide explosive, namely the perylene bisimide modified four-coordinate boron quinoline derivative.
The invention also discloses a preparation method of the fluorescent sensing film based on the fluorescent compound with the sensing function on the gas-phase acetone and the peroxide explosive, namely the perylene bisimide modified tetra-coordinate boron quinoline derivative.
The invention coats the assembled solution of the fluorescent compound on the surface of the silica gel matrix by dropping through a simple solution self-assembly technology to prepare the loose and porous fluorescent sensing film with excellent photochemical and thermodynamic stability. The fluorescent compound has a special non-planar structure, so that the prepared sensing film has large specific surface area and porosity, is rich in molecular channels, and can ensure that molecules of an object to be detected can be well diffused in the film; in addition, the formed pore channel has great help for improving the sensing selectivity and sensitivity. The research on the sensing performance shows that the fluorescent sensing film has high sensitivity and high selectivity response to acetone gas at room temperature, the response and recovery time is fast, the sensing process is completely reversible, the interference of common interferents is eliminated by utilizing factors of capillary condensation phenomenon and solvation effect caused by a non-planar structure, and the practicability is high. The film can be used together with a commercial fluorescent instrument to realize the sensitive detection of acetone gas. In addition, through the sensor film device, a special acetone gas detector can be developed. Finally, the response of the sensing film to the peroxide explosives TATP and DADP is tested, and the sensing film shows excellent sensing performance.
Drawings
FIG. 1 is a high resolution mass spectrum of a target fluorescent compound prepared according to the present invention;
FIG. 2 is a nuclear magnetic hydrogen spectrum of a target fluorescent compound prepared by the present invention;
FIG. 3 is a nuclear magnetic carbon spectrum of a target fluorescent compound prepared according to the present invention;
FIG. 4 is a nuclear magnetic boron spectrum of a target fluorescent compound prepared according to the present invention;
FIG. 5 is a diagram of the excitation emission spectrum of the fluorescence sensing film according to the present invention;
FIG. 6 is a diagram illustrating the monitoring of photochemical stability of a fluorescence sensing thin film according to the present invention;
FIG. 7 is a monitoring chart of the thermodynamic stability of the fluorescence sensing film prepared by the present invention;
FIG. 8 is a gas-phase fluorescence sensing response diagram of the fluorescence sensing film prepared by the present invention to acetone and common interferents;
FIG. 9 is a graph showing the sensitivity of the fluorescence sensing film prepared according to the present invention to acetone gas;
FIG. 10 is a graph showing the acetone gas recovery test of the fluorescence sensing film according to the present invention;
FIG. 11 is a graph showing the long-term stability of the response of the fluorescence sensing film prepared according to the present invention to acetone gas.
FIG. 12 is a graph showing the detection of the peroxide explosive gas triacetoneperoxide (a) and dipropone peroxide (b) by the fluorescence sensing film prepared by the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Furthermore, the terms "comprises," "comprising," and "having," and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed, but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
The invention is described in further detail below with reference to the accompanying drawings:
example 1
Preparation of the target fluorescent Compound (in this example, n ═ 7, isooctylamine was used as a starting material)
Synthesis of Compound 1
Sequentially adding 16.5g of perylene anhydride, 3.8mL of isooctylamine, 2.0g of zinc acetate dihydrate, 85g of imidazole and 36mL of water into a 200mL reaction kettle, heating the reaction system to 190 ℃, reacting for 24 hours under stirring, naturally cooling the reaction liquid to room temperature, then pouring the reaction liquid into a large amount of water, precipitating a large amount of precipitate, carrying out suction filtration, leaching with water and methanol, drying, and carrying out column chromatography separation by using dichloromethane as eluent to obtain a deep red compound 1;
the reaction equation is as follows:
② Synthesis of Compound 2
Weighing 0.636g of the compound 1 in a 250mL single-mouth bottle, adding 165mL of dichloromethane, stirring and dissolving, adding 0.19mL of liquid bromine into a reaction system by using an injector, heating to 45 ℃, refluxing, stirring and reacting for 5 hours, then performing rotary evaporation on the reaction liquid to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain an orange-red compound 2;
the reaction equation is as follows:
③ Synthesis of Compound 3
Under the protection of argon, 511mg of compound 2, 91.5mg of tris (dibenzylideneacetone) dipalladium and 236 mg of tris (o-methylphenyl) phosphorus are weighed into a 35mL Schlenk tube, 10mL of anhydrous toluene and 2mL of anhydrous diisopropylamine are added, 0.25mL of triisopropylethynylsilicon is added by a syringe, the reaction system is stirred and reacted for 18 hours at 65 ℃, and is naturally cooled to room temperature, and then the solvent is removed by rotary evaporation, and dichloromethane: separating the eluent by column chromatography with a normal hexane-1: 1 system to obtain a deep red compound 3;
the reaction equation is as follows:
synthesis of Compound 4
Weighing 150mg of compound 3 in a 10mL single-neck flask, adding 4mL of anhydrous tetrahydrofuran, stirring at room temperature for 5 minutes to fully dissolve the compound, adding 0.732mL of a 1mol/L tetrahydrofuran solution of tetrabutylammonium fluoride, keeping the reaction at room temperature in the dark for 3 hours, adding an appropriate amount of water, filtering, drying, and reacting the obtained dried product with dichloromethane: separating by column chromatography with a normal hexane-2: 1 system as an eluent to obtain a deep red compound 4;
the reaction equation is as follows:
fifthly, synthesizing a compound 5
Weighing 0.1452g of 8-hydroxyquinoline, 2.2316g of 4-iodophenylboronic acid and 0.6368g of potassium phosphate in a 100mL single-neck bottle, adding 50mL of anhydrous 1, 4-dioxane, raising the temperature of a reaction system to 100 ℃, stirring for reacting for 20 hours, then performing rotary evaporation to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain a yellow-green solid, namely a compound 5;
the reaction equation is as follows:
synthesis of target fluorescent compound
36mg of compound 4, 20mg of compound 5, 3.37mg of tris (dibenzylideneacetone) dipalladium and 6.9mg of tris (o-methylphenyl) phosphorus are weighed out in a 15mL Schlenk tube under argon atmosphere, 2.5mL of anhydrous toluene and 0.5mL of anhydrous triethylamine are added thereto, the reaction system is reacted at 65 ℃ for 18 hours, then the solvent is removed by rotary evaporation, and dichloromethane: performing column chromatography separation by using an n-hexane-2: 1 system as an eluent to obtain a target fluorescent compound, namely the fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives;
the reaction equation is as follows:
the results of the structural characterization data of the target fluorescent compound prepared by the present invention are shown in fig. 1-4.
Example 2
Preparation of the fluorescent Compound of interest (n ═ 3 in the present example)
Synthesis of Compound 1
Sequentially adding 16.5g of perylene anhydride, 2.3mL of butylamine, 2.0g of zinc acetate dihydrate, 85g of imidazole and 36mL of water into a 200mL reaction kettle, heating a reaction system to 190 ℃, reacting for 24 hours under stirring, naturally cooling reaction liquid to room temperature, then pouring the reaction liquid into a large amount of water, precipitating a large amount of precipitate, carrying out suction filtration, leaching with water and methanol, drying, and carrying out column chromatography separation by using dichloromethane as an eluent to obtain a crimson compound 1;
the reaction equation is as follows:
② Synthesis of Compound 2
Weighing 0.554g of compound 1 in a 250mL single-mouth bottle, adding 165mL of dichloromethane, stirring and dissolving, adding 0.19mL of liquid bromine into a reaction system by using an injector, heating to 45 ℃, refluxing and stirring for reaction for 5 hours, then performing rotary evaporation on the reaction liquid to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain an orange-red compound 2;
the reaction equation is as follows:
③ Synthesis of Compound 3
Under the protection of argon, 455mg of compound 2, 91.5mg of tris (dibenzylideneacetone) dipalladium and 236 mg of tris (o-methylphenyl) phosphorus are weighed into a 35mL Schlenk tube, 10mL of anhydrous toluene and 2mL of anhydrous diisopropylamine are added, 0.25mL of triisopropylethynylsilicon is added by a syringe, the reaction system is stirred and reacted for 18 hours at 65 ℃, and is naturally cooled to room temperature, and then the solvent is removed by rotary evaporation, and dichloromethane: separating the eluent by column chromatography with a normal hexane-1: 1 system to obtain a deep red compound 3;
the reaction equation is as follows:
synthesis of Compound 4
Weighing 136mg of compound 3 in a 10mL single-neck flask, adding 4mL of anhydrous tetrahydrofuran, stirring at room temperature for 5 minutes to fully dissolve the compound, adding 0.732mL of a 1mol/L tetrahydrofuran solution of tetrabutylammonium fluoride, keeping the reaction at room temperature in the dark for 3 hours, adding an appropriate amount of water, filtering, drying, and reacting the obtained dried product with dichloromethane: separating by column chromatography with a normal hexane-2: 1 system as an eluent to obtain a deep red compound 4;
the reaction equation is as follows:
fifthly, synthesizing a compound 5
Weighing 0.1452g of 8-hydroxyquinoline, 2.2316g of 4-iodophenylboronic acid and 0.6368g of potassium phosphate in a 100mL single-neck bottle, adding 50mL of anhydrous 1, 4-dioxane, raising the temperature of a reaction system to 100 ℃, stirring for reacting for 20 hours, then performing rotary evaporation to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain a yellow-green solid, namely a compound 5;
the reaction equation is as follows:
synthesis of compound 6
32mg of compound 4, 20mg of compound 5, 3.37mg of tris (dibenzylideneacetone) dipalladium and 6.9mg of tris (o-methylphenyl) phosphorus are weighed out in a 15mL Schlenk tube under argon atmosphere, 2.5mL of anhydrous toluene and 0.5mL of anhydrous triethylamine are added thereto, the reaction system is reacted at 65 ℃ for 18 hours, then the solvent is removed by rotary evaporation, and dichloromethane: performing column chromatography separation by using an n-hexane-2: 1 system as an eluent to obtain a target fluorescent compound, namely the fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives;
the reaction equation is as follows:
example 3
Preparation of the fluorescent Compound of interest (in this example n ═ 5)
Synthesis of Compound 1
Sequentially adding 16.5g of perylene anhydride, 3.1mL of hexylamine, 2.0g of zinc acetate dihydrate, 85g of imidazole and 36mL of water into a 200mL reaction kettle, heating the reaction system to 190 ℃, reacting for 24 hours under stirring, naturally cooling the reaction liquid to room temperature, then pouring the reaction liquid into a large amount of water, precipitating a large amount of precipitate, carrying out suction filtration, leaching with water and methanol, drying, and carrying out column chromatography separation by using dichloromethane as an eluent to obtain a crimson compound 1;
the reaction equation is as follows:
② Synthesis of Compound 2
Weighing 0.594g of the compound 1 into a 250mL single-mouth bottle, adding 165mL of dichloromethane, stirring and dissolving, adding 0.19mL of liquid bromine into a reaction system by using an injector, heating to 45 ℃, refluxing and stirring for reaction for 5 hours, then performing rotary evaporation on the reaction liquid to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain an orange-red compound 2; the reaction equation is as follows:
③ Synthesis of Compound 3
In a 35mL schlenk tube, 484mg of compound 2, 91.5mg of tris (dibenzylideneacetone) dipalladium and 236 mg of tris (o-methylphenyl) phosphorus were weighed under the protection of argon, 10mL of anhydrous toluene and 2mL of anhydrous diisopropylamine were added thereto, 0.25mL of triisopropylethynylsilicon was added by a syringe, the reaction system was stirred at 65 ℃ for 18 hours, cooled naturally to room temperature, and then the solvent was removed by rotary evaporation, and the mixture was stirred with dichloromethane: separating the eluent by column chromatography with a normal hexane-1: 1 system to obtain a deep red compound 3;
the reaction equation is as follows:
synthesis of Compound 4
Weighing 142mg of compound 3 into a 10mL single-neck flask, adding 4mL of anhydrous tetrahydrofuran, stirring at room temperature for 5 minutes to fully dissolve the compound, adding 0.732mL of 1mol/L tetrahydrofuran solution of tetrabutylammonium fluoride, keeping the reaction at room temperature in the dark for 3 hours, adding an appropriate amount of water, filtering, drying, and reacting the obtained dried product with dichloromethane: separating by column chromatography with a normal hexane-2: 1 system as an eluent to obtain a deep red compound 4;
the reaction equation is as follows:
fifthly, synthesizing a compound 5
Weighing 0.1452g of 8-hydroxyquinoline, 2.2316g of 4-iodophenylboronic acid and 0.6368g of potassium phosphate in a 100mL single-neck bottle, adding 50mL of anhydrous 1, 4-dioxane, raising the temperature of a reaction system to 100 ℃, stirring for reacting for 20 hours, then performing rotary evaporation to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain a yellow-green solid, namely a compound 5;
the reaction equation is as follows:
synthesis of target fluorescent compound
34mg of compound 4, 20mg of compound 5, 3.37mg of tris (dibenzylideneacetone) dipalladium and 6.9mg of tris (o-methylphenyl) phosphorus are weighed out in a 15mL Schlenk tube under argon atmosphere, 2.5mL of anhydrous toluene and 0.5mL of anhydrous triethylamine are added thereto, the reaction system is reacted at 65 ℃ for 18 hours, then the solvent is removed by rotary evaporation, and dichloromethane: performing column chromatography separation by using an n-hexane-2: 1 system as an eluent to obtain a target fluorescent compound, namely the fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives;
the reaction equation is as follows:
example 4
Preparation of the fluorescent Compound of interest (in this example n ═ 15)
Synthesis of Compound 1
Sequentially adding 16.5g of perylene anhydride, 6.8mL of hexadecylamine, 2.0g of zinc acetate dihydrate, 85g of imidazole and 36mL of water into a 200mL reaction kettle, heating the reaction system to 190 ℃, reacting for 24 hours under stirring, naturally cooling the reaction liquid to room temperature, then pouring the reaction liquid into a large amount of water, separating out a large amount of precipitates, carrying out suction filtration, leaching with water and methanol, drying, and carrying out column chromatography separation by using dichloromethane as eluent to obtain a crimson compound 1;
the reaction equation is as follows:
② Synthesis of Compound 2
Weighing 0.801g of compound 1 in a 250mL single-mouth bottle, adding 165mL of dichloromethane, stirring for dissolving, adding 0.19mL of liquid bromine into a reaction system by using an injector, heating to 45 ℃, refluxing and stirring for reaction for 5 hours, then performing rotary evaporation on the reaction liquid to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain an orange-red compound 2;
the reaction equation is as follows:
③ Synthesis of Compound 3
Weighing 624mg of compound 2, 91.5mg of tris (dibenzylideneacetone) dipalladium and 236 mg of tris (o-methylphenyl) phosphorus in a 35mL Schlenk tube under the protection of argon, adding 10mL of anhydrous toluene and 2mL of anhydrous diisopropylamine, adding 0.25mL of triisopropylethynylsilicon by using a syringe, stirring the reaction system at 65 ℃ for 18 hours, naturally cooling to room temperature, and then removing the solvent by rotary evaporation to obtain a mixture of dichloromethane: separating the eluent by column chromatography with a normal hexane-1: 1 system to obtain a deep red compound 3;
the reaction equation is as follows:
synthesis of Compound 4
177mg of compound 3 was weighed into a 10mL single-neck flask, 4mL of anhydrous tetrahydrofuran was added, and the mixture was stirred at room temperature for 5 minutes to be sufficiently dissolved, 0.732mL of a 1mol/L tetrahydrofuran solution of tetrabutylammonium fluoride was further added, the reaction was continued at room temperature in the dark for 3 hours, an appropriate amount of water was added thereto, filtration and drying were performed, and the resulting dried product was purified with dichloromethane: separating by column chromatography with a normal hexane-2: 1 system as an eluent to obtain a deep red compound 4;
the reaction equation is as follows:
fifthly, synthesizing a compound 5
Weighing 0.1452g of 8-hydroxyquinoline, 2.2316g of 4-iodophenylboronic acid and 0.6368g of potassium phosphate in a 100mL single-neck bottle, adding 50mL of anhydrous 1, 4-dioxane, raising the temperature of a reaction system to 100 ℃, stirring for reacting for 20 hours, then performing rotary evaporation to remove the solvent, and performing column chromatography separation by using dichloromethane as an eluent to obtain a yellow-green solid, namely a compound 5;
the reaction equation is as follows:
synthesis of compound 6
45mg of compound 4, 20mg of compound 5, 3.37mg of tris (dibenzylideneacetone) dipalladium and 6.9mg of tris (o-methylphenyl) phosphorus are weighed out under argon in a 15mL schlenk tube, 2.5mL of anhydrous toluene and 0.5mL of anhydrous triethylamine are added thereto, the reaction system is reacted at 65 ℃ for 18 hours, then the solvent is removed by rotary evaporation, and dichloromethane: performing column chromatography separation by using an n-hexane-2: 1 system as an eluent to obtain a target fluorescent compound, namely the fluorescent compound with a sensing function on gas-phase acetone and peroxide explosives;
the reaction equation is as follows:
example 5
In the synthetic compound 5 of the step (5) of preparing the perylene imide modified four-coordinate boron quinoline fluorescent compound in the embodiments 1 to 4, the 1, 4-dioxane used is replaced by the same volume of toluene, other steps in the embodiment are the same as those in the corresponding embodiments, and the compound 5 is prepared, and other steps are the same as those in the embodiments 1 to 4.
Example 6
In the synthetic compound 5 of the step (5) of preparing the perylene imide modified four-coordinate boron quinoline fluorescent compound in the embodiments 1 to 4, the 1, 4-dioxane used is replaced by the same volume of N, N-dimethylformamide, other steps in the embodiment are the same as those in the corresponding embodiments, and the compound 5 is prepared, and other steps are the same as those in the embodiments 1 to 4.
The method for preparing the fluorescent sensing film by adopting the target fluorescent compound prepared by the embodiment, namely the fluorescent compound with the sensing function on the gas-phase acetone and the peroxide explosive comprises the following steps:
1) preparing the target fluorescent compound with chloroform as solvent at a concentration of 1 × 10-4～1×10-3Standing the stock solution in mol/L to obtain an assembly structure of the fluorescent compound, and storing in a sealed manner for later use;
2) the stock solution is evenly coated on a clean silica gel plate substrate, and the coating volume is 0.05-0.2 mu L/cm2Standing at room temperature for 1 hour, vacuum drying in a vacuum drying oven at 50 ℃ under 3000Pa for 12 hours, taking out, sealing and storing to prepare the fluorescent sensing film.
In order to verify the effect of the present invention, a large number of laboratory research experiments were performed on the fluorescent sensing film based on the perylene bisimide four-coordinate boron quinoline fluorescent compound synthesized in example 1, and various experimental conditions were as follows:
1. basic fluorescence behavior characterization
The prepared fluorescence sensing film adopts an Edinburgh apparatus FLS 920 single photon counting fluorescence spectrometer to perform characterization of an excitation emission spectrum, and the result is shown in figure 5. As can be seen from FIG. 5, the maximum excitation wavelength of the fluorescence sensing film is 400nm and 500nm, and the maximum emission wavelength is 500nm and 590nm, which provides the light source and detection wavelength information for the construction of the fluorescence sensor. Specifically, we chose 400nm as the excitation light source and detected the fluorescence intensity at 590 nm.
2. Photochemical and thermodynamic stability test of fluorescent film
Photobleaching is a very important phenomenon that limits the practical application of fluorescent thin film sensors, and therefore, research on photochemical and thermodynamic stability of the thin film is very necessary before the thin film is used for fluorescence detection. The results of the relevant tests are shown in fig. 6 and 7. The test result shows that the fluorescence intensity of the prepared film is basically not changed after the film is irradiated by continuous 28-hour light, which shows that the prepared film has excellent photochemical stability; and the fluorescence color and intensity of the sensor are basically unchanged after being exposed in the air for more than six months, so that the sensor has better thermodynamic stability, and the results are all benefited from the non-planar structure of the four-coordination boron compound, thereby laying a solid foundation for the research of sensing behaviors.
3. Detection test of acetone and peroxide explosive vapor by fluorescent film
And (3) measuring the actual sample of the fluorescent sensing film by adopting a fluorescent sensing detection platform. Wherein, the sample to be analyzed is acetone vapor and peroxide explosive vapor, and the interferent is selected from common organic solvents (tetrahydrofuran, benzene, toluene, dichloromethane, trichloromethane, dioxane, n-pentane, n-hexane, n-heptane and methanol), hydrogen peroxide, common explosives (TNT, DNT, HMX, RDX and picric acid), water and aqueous washing products (shampoo, hair conditioner, hand cream, perfume and the like), cream, dirty clothes, fruits (apple, pear and banana) and air.
The operation process is as follows:
1) packaging a small amount of different samples to be analyzed in a 4L brown glass bottle, and standing overnight at room temperature for later use;
2) placing the fluorescence sensing film in a detection instrument, and respectively testing 28 analytes at room temperature;
3) and (3) testing the analyte, adopting a microsyringe for sample injection, using a 100mL glass injector to absorb the gas analyte with a certain volume from the bottle opening in the step 1), placing the glass injector at an instrument air exhaust opening, wherein the sample injection time is about 1-3 seconds, the sample injection speed is 1mL/s, and repeating the test after recovering.
4) The objects to be measured with different concentrations are obtained by diluting response times with air.
The test results are shown in FIGS. 8-11.
From the test result of fig. 8, it can be seen that the response of the film to acetone is fluorescence quenching type, common organic solvents show a certain degree of fluorescence sensitization, and water, common explosives, toiletries and fruits have no influence on the fluorescence intensity of the film, so that the film shows excellent sensing selectivity to acetone vapor, and a foundation is laid for the practical application of the film.
FIG. 9 is a graph showing the sensitivity of the fluorescence sensing film to acetone vapor. From the test results we can see that the fluorescence intensity of the film is significantly quenched as the acetone vapor concentration increases. At an acetone vapor concentration of 50ppm, there is still a large degree of fluorescence quenching, and thus it can also be said that the sensing sensitivity is below 50 ppm.
FIG. 10 is a test chart of acetone vapor response recoverability and sensing speed of the fluorescent sensing film. As can be seen, after 60 consecutive measurements, it still showed the same response curve as the first measurement, and thus showed excellent recovery; meanwhile, the response speed is lower than 1s, the recovery speed is lower than 10s, and the sensing process is completely reversible, so that the method completely has the possibility of realizing practical application.
FIG. 11 is a graph showing the measurement of the long-term response of the fluorescence sensing film to acetone vapor. After acetone vapor is tested for 30 consecutive days (every two days), the sensing performance of the acetone vapor is basically not changed, which shows that the acetone vapor shows excellent stability and lays a solid foundation for the practical application of the acetone vapor.
FIG. 12 is a graph showing the measurement of the response of the fluorescence sensing film to peroxidized explosives (TATP and DADP). As can be seen from the figure, the fluorescence intensity of the film is obviously reduced along with the increase of the amount of the peroxide explosive, so that the detection of the substances can be realized, and the practical application of the substances is possible.
In conclusion, the invention introduces the four-coordination organic boron derivative with a non-planar structure into the design of the fluorescence sensing, utilizes the molecular channel formed after the non-planar structure is accumulated on the molecular level, and utilizes the phenomenon of capillary condensation and the solvation effect to realize the sensitive, high-selectivity, recoverability and stability identification and detection of acetone vapor and peroxide explosive vapor at room temperature, basically solves the problem of high working temperature in detection in the prior method, and provides a new idea for the design of a fluorescence sensing film with excellent performance.
On the basis, a new strategy for sensing substance which is difficult to detect, namely peroxidized explosive (TATP/DADP) is provided, namely, the creative application of the gas-phase sensing of the peroxidized explosive is realized by sensing the acetone which is a decomposition product of the substance at room temperature. The method basically solves the problem of high working temperature in detection in the prior method, and provides a new idea for the design of the fluorescent sensing film with excellent performance.
The preparation method is simple and convenient to operate, the reaction conditions are mild, the prepared fluorescent compound is good in photochemical and thermodynamic stability, the obtained fluorescent sensing film is high in sensitivity, good in selectivity and long in service life, and the fluorescent sensing film is an excellent fluorescent sensing film, and the sensitive detection of acetone vapor and peroxide explosives can be realized by combining the film with a commercial fluorescent instrument. In addition, through the sensor film device, the special detector for acetone gas and peroxide explosive gas can be developed.
The above-mentioned contents are only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and any modification made on the basis of the technical idea of the present invention falls within the protection scope of the claims of the present invention.
Claims (9)
1. A fluorescent compound with sensing function for gas-phase acetone and peroxide explosives is characterized in that the structural formula of the fluorescent compound is as follows:
wherein n is 1-20.
2. The method for preparing a fluorescent compound having a sensing function for vapor phase acetone and peroxide explosives according to claim 1, comprising the steps of:
1) preparation of Compound 1
Sequentially adding perylene anhydride, alkylamine, zinc acetate dihydrate, imidazole and water into a reaction kettle, reacting for 24-30 hours at 190-200 ℃, naturally cooling reaction liquid to room temperature, then pouring the reaction liquid into water until complete precipitation, performing suction filtration, leaching with water and methanol, drying, and performing column chromatography separation to obtain a compound 1;
2) preparation of Compound 2
Dissolving the compound 1 in dichloromethane, adding liquid bromine into a reaction system, then refluxing and stirring for reaction for 5-8 hours, performing rotary evaporation on the reaction liquid to remove the solvent, and performing column chromatographic separation to obtain a compound 2;
3) preparation of Compound 3
Under the protection of argon, placing a compound 2, triisopropylethynylsilicon, tris (dibenzylideneacetone) dipalladium and tris (o-methylphenyl) phosphine in a Schlenk tube, adding anhydrous toluene and anhydrous diisopropylamine into the Schlenk tube, reacting the reaction system at 65-80 ℃ for 18-24 hours, then removing the solvent by rotary evaporation, and performing column chromatography separation to obtain a compound 3;
4) preparation of Compound 4
Dissolving the compound 3 in anhydrous tetrahydrofuran, stirring at room temperature to fully dissolve the compound, then dropwise adding a tetrahydrofuran solution of tetrabutylammonium fluoride, continuously reacting for 3-5 hours at room temperature in a dark place, then adding water into a reaction system, filtering, drying, and performing column chromatography separation on the obtained dried substance to obtain a compound 4;
wherein the structural formula of the compound 4 is as follows:
wherein n in the structural formula is 1-20;
5) preparation of Compound 5
Dissolving 8-hydroxyquinoline, 4-iodophenylboronic acid and potassium phosphate in a solvent, reacting for 20-24 hours at 100-110 ℃, then removing the solvent by rotary evaporation, and performing column chromatography to obtain a yellow-green solid, namely a compound 5;
wherein the structural formula of the compound 5 is as follows:
6) preparation of the target product
Under the protection of argon, placing a compound 4, a compound 5, tris (dibenzylideneacetone) dipalladium and tris (o-methylphenyl) phosphine in a Schlenk tube, adding anhydrous toluene and anhydrous triethylamine, reacting a reaction system at 65-80 ℃ for 18-24 hours, then removing the solvent by rotary evaporation, and performing column chromatography separation to obtain the target product, namely the fluorescent compound with the sensing function on gas phase acetone and peroxide explosives.
3. The method for preparing a fluorescent compound with sensing function on vapor-phase acetone and peroxide explosives according to claim 2, wherein the dosage ratio of reactants in each step is as follows:
in the step 1), the molar ratio of perylene anhydride, alkylamine, zinc acetate dihydrate, imidazole and water is 1: (0.5-0.6): (0.19-0.25): (25-35): (45-55);
in the step 2), the molar ratio of the compound 1 to the liquid bromine to the dichloromethane is 1: (2.2-3): (1700 to 1800);
in the step 3), the molar ratio of the compound 2, triisopropylethynylsilicon, tris (dibenzylideneacetone) dipalladium, tris (o-methylphenyl) phosphine, anhydrous toluene and anhydrous diisopropylamine is 1: (1.1-1.5): (1.1-1.2): (0.65-0.75): (90-100): (14-18);
in the step 4), the molar ratio of the compound 3, tetrabutylammonium fluoride and anhydrous tetrahydrofuran is 1: (3-4): (160-175);
in the step 5), the molar ratio of 8-hydroxyquinoline to 4-iodophenylboronic acid to potassium phosphate is 1: (8.5-9.5): (2.8-3.2);
in the step 6), the molar ratio of the compound 5, the compound 4, the tris (dibenzylideneacetone) dipalladium, the tris (o-methylphenyl) phosphine, the anhydrous toluene and the anhydrous triethylamine is 1: (2.1-2.5): (0.1-0.15): (0.65-0.75): (20-25): (3.6-5).
4. The method for preparing a fluorescent compound having sensing function for gaseous acetone and peroxide explosives according to claim 2, wherein the eluent for column chromatography in each step is selected as follows:
in the step 1), the column chromatography separation takes dichloromethane as eluent;
in the step 2), the column chromatography takes dichloromethane as eluent;
in the step 3), the column chromatography separation is performed by taking a dichloromethane-n-hexane system as an eluent, wherein the volume ratio of dichloromethane to n-hexane is 1: 1;
in the step 4), the column chromatography separation is performed by taking a dichloromethane-n-hexane system as an eluent, wherein the volume ratio of dichloromethane to n-hexane is 2: 1;
in the step 6), the column chromatography separation is performed by taking a dichloromethane-n-hexane system as an eluent, wherein the volume ratio of dichloromethane to n-hexane is 2: 1.
5. The method for preparing a fluorescent compound having a sensing function on vapor-phase acetone and peroxide explosives according to claim 2, wherein in the step 5), the solvent is 1, 4-dioxane, toluene or N, N-dimethylformamide.
6. The method for preparing the fluorescent sensing film by using the fluorescent compound with the sensing function on the gas-phase acetone and the peroxide explosives, which is characterized by comprising the following steps of:
1) adding trichloromethane solvent into the fluorescent compound with sensing function on gas-phase acetone and peroxide explosive to prepare the fluorescent compound with the concentration of 1 × 10-4～1×10-3Standing and sealing the mol/L stock solution for later use;
2) uniformly coating the fluorescent compound assembly structure prepared in the step 1) on a substrate, standing at room temperature for 1-2 hours, drying in a vacuum drying oven at 40-60 ℃ under 3000Pa for 12-24 hours, taking out, sealing and storing to prepare the fluorescent sensing film.
7. The method for preparing a fluorescence sensing film according to claim 6, wherein in step 2), the substrate is a silica gel plate substrate, a filter paper substrate, a glass substrate or a polymer oil substrate; the coating volume was 0.05～0.2μL/cm2。
8. A fluorescence sensing film produced by the method of claim 6 or 7.
9. The use of the fluorescence sensing film of claim 8 for detecting acetone gas and/or peroxyexplosive gas, wherein the peroxyexplosive gas is triacetoneperoxide and/or diproprione diperoxide.
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| CN107698614A (en) * | 2017-08-29 | 2018-02-16 | 陕西师范大学 | A kind of carborane diimide derivative and synthetic method and the sensor array based on it and preparation method and application |
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| CN107698614A (en) * | 2017-08-29 | 2018-02-16 | 陕西师范大学 | A kind of carborane diimide derivative and synthetic method and the sensor array based on it and preparation method and application |
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