CN111454212A - Aromatic compound containing tetraphenylethylene structure and preparation method and application thereof - Google Patents
Aromatic compound containing tetraphenylethylene structure and preparation method and application thereof Download PDFInfo
- Publication number
- CN111454212A CN111454212A CN202010317878.3A CN202010317878A CN111454212A CN 111454212 A CN111454212 A CN 111454212A CN 202010317878 A CN202010317878 A CN 202010317878A CN 111454212 A CN111454212 A CN 111454212A
- Authority
- CN
- China
- Prior art keywords
- aromatic compound
- tetraphenylethylene
- compound containing
- halogenated
- acid ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- G—PHYSICS
- G01—MEASURING; TESTING
- 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"
- G01N2021/6432—Quenching
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an aromatic compound containing a tetraphenylethylene structure and a preparation method and application thereof, belonging to the technical field of fluorescence sensing, wherein the aromatic compound containing tetraphenylethylene is prepared by reacting a halogenated aromatic ring with boric acid ester under anhydrous and oxygen-free conditions to obtain an aryl boric acid ester intermediate; and then the arylboronic acid ester intermediate and halogenated tetraphenylethylene are subjected to SUZUKI reaction to obtain the compound. The aromatic compound containing the tetraphenylethylene structure provided by the invention has a larger conjugated structure and a wide charge delocalized range, and the unique three-dimensional configuration of the aromatic compound is favorable for obtaining a good aggregation structure, so that the aromatic compound has a good application prospect in the fields of sensing technology and detection function, is strong in practicability and has strong popularization and application values.
Description
Technical Field
The invention belongs to the technical field of fluorescence sensing, and particularly relates to an aromatic compound containing a tetraphenylethylene structure.
Background
The nitro aromatic explosives have more adverse effects on safety, environment and health, so the detection of the nitro aromatic explosives is urgently needed in the fields of anti-terrorism, nonmetal land mine detection, environmental quality monitoring and the like.
Currently, explosive detection techniques can be broadly divided into two categories, namely, volume detection techniques and micro-trace detection techniques. The body detection technology is used for detecting the whole appearance of the explosive, and the method has the defects of large volume of detection equipment, high price, low detection sensitivity and the like. Compared with a body detection technology, the micro-trace detection technology is used for detecting steam volatilized by explosives or any human/object surface contacted with the explosives, and the method has the advantages of high reliability, excellent performance, multifunctional integration, capability of realizing mass production of detection equipment and the like. Therefore, in recent years, the micro-trace detection technology has become a hot spot in the field of explosive detection research.
The prior art (CN107782707A) discloses an application of triphenylthiazolyl benzene in fluorescence detection of nitroaromatic explosives, and describes that triphenylthiazolyl benzene is applied to detection of nitroaromatic explosives including 2,4, 6-trinitrotoluene, 2,4, 6-trinitrophenol, 2, 4-dinitrophenol, 3, 5-dinitrosalicylic acid, 4-nitrophenol, 2, 4-dinitrotoluene, 4-nitrotoluene, 4-nitrobenzaldehyde, nitrobenzene or 4-nitrobenzoic acid, wherein the fluorescence of triphenylthiazolyl benzene can be obviously quenched, and the triphenylthiazolyl benzene has a good fluorescence detection effect on typical nitroaromatic explosives, but the preparation cost of the triphenylthiazolyl benzene is complex and the raw materials are expensive, and is not beneficial to popularization and use.
Disclosure of Invention
Based on the background problems, the invention aims to provide the aromatic compound containing the tetraphenylethylene structure, and the preparation method and the application thereof.
In order to achieve the above object, in one aspect, the embodiment of the present invention provides a technical solution:
the structural general formula of the aromatic compound containing the tetraphenylethylene structure is shown as a formula I, wherein an R group is a nitrogen-containing acene aromatic structure.
In one embodiment, the aromatic compound has the formula II:
in order to achieve the above objects, in another aspect, the embodiments of the present invention further provide a method for preparing an aromatic compound containing a tetraphenylethylene structure, including the steps of:
by halogenating aromatic rings
Reacting with boric acid ester under anhydrous and oxygen-free conditions to obtain arylboronic acid ester intermediate
And (3) reacting the arylborate intermediate with halogenated tetraphenylethylene through SUZUKI to obtain the aromatic compound containing the tetraphenylethylene structure.
In one embodiment, the halogenated aromatic ring is obtained by reacting halogenated benzaldehyde, phenanthrenequinone, aniline and ammonium acetate in a weak acid solution, the reaction temperature is controlled to be 120-140 ℃, and the reaction time is 2-4 hours.
Preferably, the reaction molar ratio of the halogenated benzaldehyde to the phenanthrenequinone to the aniline to the ammonium acetate is 1: 0.83-1.2: 4.08-5: 2.42-4.04.
In one embodiment, n-butyl lithium is used as a catalyst for reacting a halogenated aromatic ring with a borate, and the reaction molar ratio of the halogenated aromatic ring, the n-butyl lithium and the borate is 1: 0.81-1.4: 0.92-1.31.
Preferably, the reaction temperature of the halogenated aromatic ring and the borate is-50 to-78 ℃.
In one embodiment, the reaction temperature of the halogenated tetraphenylethylene and the arylborate intermediate is 75-85 ℃, and the reaction time is 12-24 hours.
Preferably, the reaction molar ratio of the halogenated tetraphenylethylene to the arylboronic acid ester intermediate is 1: 0.87-1.4.
The invention also provides application of the aromatic compound containing the tetraphenylethylene structure in fluorescence detection of explosives, wherein the aromatic compound containing the tetraphenylethylene structure is prepared into a solution and then placed in an explosive environment to observe fluorescence quenching characteristics.
Compared with the prior art, the invention has the following effects:
1. the aromatic compound containing the tetraphenylethylene structure provided by the invention has a larger conjugated structure and a wide charge delocalized range, and the unique three-dimensional configuration of the aromatic compound is favorable for obtaining a good aggregation structure, so that the aromatic compound has a good application prospect in the fields of sensing technology and detection function, is strong in practicability and has strong popularization and application values.
2. The aromatic compound containing the tetraphenylethylene structure has the advantages of simple preparation process and low raw material cost, and is beneficial to popularization and use.
Drawings
FIG. 1 is a fluorescence spectrum of an aromatic compound containing a tetraphenylethylene structure prepared in example 1 of the present invention;
FIG. 2 is a graph showing the fluorescence quenching curves of various concentrations of PA solutions on the aromatic compound containing the tetraphenylethylene structure prepared in example 1.
Detailed Description
The aromatic compound containing the tetraphenylethylene structure has a larger conjugated structure, wide charge delocalization range and unique three-dimensional configuration, and is favorable for obtaining a good aggregation structure, so that the aromatic compound containing the tetraphenylethylene structure has a good application prospect in the fields of sensing technology and detection function, is strong in practicability and has strong popularization and application values.
It should be noted that n-butyllithium in the present invention is reacted in the form of n-hexane solution of n-butyllithium at a concentration of 2.4M/L, and the present invention will be described in detail by specific examples.
Example 1
The preparation method of the aromatic compound containing the tetraphenylethylene structure comprises the following steps:
(1) preparation of brominated aromatic rings
60m L acetic acid was put into a 250m L two-neck flask, and 4-bromobenzaldehyde (2.50g, 13.50mmol), 9, 10-phenanthrenequinone (2.80g, 13.50mmol), aniline (6.30m L, 67.50mmol) and ammonium acetate (4.20g, 54.50mmol) were put into the two-neck flask, respectively, followed by vacuum, nitrogen-blanketing, heating to 120 ℃ and reaction for 2 hours.
And after the reaction is finished, cooling the reaction solution to room temperature, separating out a large amount of solids, filtering, leaching the filter residue with glacial acetic acid for three times, and drying to obtain 5.5g of white solids with the yield of 90.6%. The chemical reaction equation is as follows:
1HNMR(500MHz,DMSO,)：8.95(d,J＝8.36Hz,1H)，8.90(d,J＝8.38Hz,1H)，8.70(d,J＝7.95Hz,1H)，7.80(t,J＝7.16Hz,7.72Hz,1H)，7.76-7.69(m,6H)，7.59(t,J＝8.56Hz,8.72Hz,3H)，7.53(d,J＝8.61S3 Hz,2H)，7.37(t,J＝7.36Hz,7.97Hz,1H)，7.10(d,J＝8.34Hz,1H)。
(2) preparation of arylboronic acid ester intermediates
Dissolving the dried brominated aromatic ring (5.00g,11.10mmol) in 150ml of redistilled Tetrahydrofuran (THF) solution, vacuumizing, introducing nitrogen for protection, cooling the reaction solution to-78 ℃, slowly adding n-butyllithium n-Bu L i (2.40M,5.30M L) under the protection of nitrogen, reacting at low temperature for 2h, quickly adding isopropanol pinacol borate (2.70g,14.50mmol), reacting for 4h, and slowly heating to room temperature overnight.
After the reaction is finished, water is added for quenching by 100m L, the mixture is extracted by ethyl acetate, an aqueous phase is extracted by dichloromethane twice, organic phases are combined, anhydrous magnesium sulfate is dried, the mixture is filtered and concentrated, and the mixture is subjected to column chromatography by using EA: PE (poly ethylene) 1:3 to obtain 2.50g of white solid with the yield of 45.2 percent, wherein the chemical reaction equation is as follows:
1H NMR(500MHz,DMSO,)：8.95(d,J＝8.58Hz,1H)，8.90(d,J＝8.46Hz,1H，8.71(d,J＝8.02Hz,1H)，7.80(t,J＝7.14Hz,7.78Hz,1H)，7.71(m,6H)，7.64(d,J＝8.18Hz,2H)，7.60-7.56(m,3H)，7.37(t,J＝7.44Hz,7.90Hz,1H)，7.12(d,J＝8.31Hz,1H)，1.30(s,J＝8.34Hz,12H)。
(3) aromatic compound containing tetraphenylethylene structure
An arylboronic acid ester intermediate (1.39g,2.80mmol), 4-bromophenyl-1, 1,2, 2-tetraphenylethylene (1.00g,2.43mmol), and K were taken2CO3(0.69g,5.00mmol)、Pd(PPh3)4(28.07mg,0.02mmol), toluene (17.50m L), and water (3.00m L) were charged in a 100ml two-necked flask, vacuum-pumped, and nitrogen was replaced by 5 times, and the reaction was heated to 85 ℃ for 24 hours.
After the reaction, water was added to quench, and extraction was performed with ethyl acetate, the aqueous phase was extracted with dichloromethane 2 times, the organic phase was combined and dried over anhydrous magnesium sulfate, and filtration, concentration and column chromatography gave 1.21g of a white solid with a yield of 62.15%. The reaction equation is as follows:
1HNMR(500MHz,DMSO)：d＝8.95(d,J＝8.43Hz,1H)，8.90(d,J＝8.58Hz,1H)，8.72(d,J＝6.73Hz,1H)，7.81–7.69(m,7H)，7.64(s,4H)，7.59(t,J＝8.18Hz,8.3Hz,1H)，7.53(d,J＝8.41Hz,2H)，7.37(t,J＝8.12Hz,7.22Hz,1H)，7.19–7.09(m,10H)，7.06–6.99ppm(m,8H)。
13CNMR(500MHz,CDCl3)：d＝131.87,131.42,131.34,127.72,126.13,123.12,120.91,77.28,77.03,76.78ppm。
FTIR(KBr)n～＝3117,3039,2975,2878,2004,1929,1854,1778,1710,1583,1447,1392,1305,1219,1054,989,852,746,677,620,567,471,399cm-1。
the aromatic compound containing the tetraphenylethylene structure prepared above was subjected to matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MA L DI-TOF-MS), and the results are shown in Table 1:
TABLE 1 MA L DI-TOF-MS test results
The above analysis means all confirmed that the aromatic compound containing a tetraphenylethylene structure having a structural formula I can be prepared by the method of example 1.
Example 2
The preparation method of the aromatic compound containing the tetraphenylethylene structure comprises the following steps:
(1) preparation of brominated aromatic rings
Adding acetic acid of 60m L into a two-neck bottle of 250m L, respectively adding 4-bromobenzaldehyde (2.50g, 13.50mmol), 9, 10-phenanthrenequinone (2.32g, 11.20mmol), aniline (5.13m L, 55.08mmol) and ammonium acetate (2.52g, 32.67mmol) into the two-neck bottle, vacuumizing, filling nitrogen gas for protection, heating to 140 ℃, reacting for 3h, cooling the reaction liquid to room temperature after the reaction is finished, separating out a large amount of solid, filtering, leaching filter residues with glacial acetic acid for three times, and drying to obtain a white solid.
(2) Preparation of arylboronic acid ester intermediates
Dissolving the dried brominated aromatic ring (5.00g,11.10mmol) in 150ml of redistilled Tetrahydrofuran (THF) solution, vacuumizing, introducing nitrogen for protection, cooling the reaction solution to-60 ℃, slowly adding n-butyllithium n-Bu L i (2.40M,6.47M L) under the protection of nitrogen, reacting at low temperature for 2h, quickly adding isopropanol pinacol borate (1.90g,10.21mmol), reacting for 4h, and slowly heating to room temperature overnight.
After the reaction, the mixture was quenched with 100m of water L, extracted with ethyl acetate, the aqueous phase was extracted twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with a ratio of EA to PE of 1:3 to give a white solid.
(3) Aromatic compound containing tetraphenylethylene structure
An arylboronic acid ester intermediate (1.05g,2.11mmol), 4-bromophenyl-1, 1,2, 2-tetraphenylethylene (1.00g,2.43mmol), and K were taken2CO3(0.69g,5.00mmol)、Pd(PPh3)4(28.07mg,0.02mmol), toluene (17.50m L), and water (3.00m L) were charged in a 100ml two-necked flask, vacuum-pumped, and nitrogen was replaced by 5 times, and the reaction was heated to 75 ℃ for 12 hours.
After the reaction is finished, water is added for quenching, ethyl acetate is used for extraction, the water phase is extracted for 2 times by dichloromethane, the organic phase is combined and dried by anhydrous magnesium sulfate, and white solid is obtained after filtration, concentration and column chromatography.
Example 3
The preparation method of the aromatic compound containing the tetraphenylethylene structure comprises the following steps:
(1) preparation of brominated aromatic rings
Adding acetic acid of 60m L into a two-neck bottle of 250m L, respectively adding 4-bromobenzaldehyde (2.50g, 13.50mmol), 9, 10-phenanthrenequinone (3.36g, 16.20mmol), aniline (5.66m L, 60.75mmol) and ammonium acetate (3.12g, 40.5mmol) into the two-neck bottle, vacuumizing, filling nitrogen for protection, heating to 130 ℃, reacting for 4h, cooling the reaction liquid to room temperature after the reaction is finished, separating out a large amount of solid, filtering, leaching filter residues with glacial acetic acid for three times, and drying to obtain a white solid.
(2) Preparation of arylboronic acid ester intermediates
Dissolving the dried brominated aromatic ring (5.00g,11.10mmol) in 150ml of redistilled Tetrahydrofuran (THF) solution, vacuumizing, introducing nitrogen for protection, cooling the reaction solution to-50 ℃, slowly adding n-butyllithium n-Bu L i (2.40M,3.75M L) under the protection of nitrogen, reacting at low temperature for 2h, quickly adding isopropanol pinacol borate (2.48g,13.32mmol), reacting for 4h, and slowly heating to room temperature overnight.
After the reaction, the mixture was quenched with 100m of water L, extracted with ethyl acetate, the aqueous phase was extracted twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with a ratio of EA to PE of 1:3 to give a white solid.
(3) Aromatic compound containing tetraphenylethylene structure
An arylboronic acid ester intermediate (1.69g,3.40mmol), 4-bromophenyl-1, 1,2, 2-tetraphenylethylene (1.00g,2.43mmol), and K were taken2CO3(0.69g,5.00mmol)、Pd(PPh3)4(28.07mg,0.02mmol), toluene (17.50m L), and water (3.00m L) were charged in a 100ml two-necked flask, vacuum-pumped, and nitrogen was replaced by 5 times, and the reaction was heated to 70 ℃ for 15 hours.
After the reaction is finished, water is added for quenching, ethyl acetate is used for extraction, the water phase is extracted for 2 times by dichloromethane, the organic phase is combined and dried by anhydrous magnesium sulfate, and white solid is obtained after filtration, concentration and column chromatography.
Example 4
The preparation method of the aromatic compound containing the tetraphenylethylene structure comprises the following steps:
(1) preparation of chlorinated aromatic rings
60ml of acetic acid is added into a 250ml two-mouth bottle, chlorobenzaldehyde (1.89g, 13.50mmol), 9, 10-phenanthrenequinone (2.80g, 13.50mmol), aniline (6.30ml, 67.50mmol) and ammonium acetate (4.20g, 54.50mmol) are respectively added into the two-mouth bottle, vacuum pumping is carried out, nitrogen protection is carried out, heating is carried out to 120 ℃, and reaction is carried out for 2 hours.
And after the reaction is finished, cooling the reaction solution to room temperature, separating out a large amount of solids, filtering, leaching filter residues with glacial acetic acid for three times, and drying to obtain 5.2g of white solids with the yield of 85.7%. The chemical reaction equation is as follows:
1HNMR(500MHz,DMSO,)：8.91(d,J＝8.36Hz,1H)，8.87(d,J＝8.38Hz,1H)，8.55(d,J＝7.95Hz,1H)，7.69(t,J＝7.16Hz,7.72Hz,1H)，7.56-7.39(m,6H)，7.35(t,J＝8.56Hz,8.72Hz,3H)，7.23(d,J＝8.61S3 Hz,2H)，7.17(t,J＝7.36Hz,7.97Hz,1H)，7.06(d,J＝8.34Hz,1H)
(2) preparation of arylboronic acid ester intermediates
Dissolving the dried chloroaromatic ring (4.90g,11.10mmol) in 150ml of redistilled Tetrahydrofuran (THF) solution, vacuumizing, introducing nitrogen for protection, cooling the reaction solution to-78 ℃, slowly adding n-butyllithium n-Bu L i (2.40M,5.30M L) under the protection of nitrogen, reacting at low temperature for 2h, quickly adding isopropanol pinacol borate (2.70g,14.50mmol), reacting for 4h, and slowly heating to room temperature overnight.
After the reaction, the mixture was quenched with 100m of water L, extracted with ethyl acetate, the aqueous phase was extracted twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with a ratio of EA to PE of 1:3 to give a white solid.
(3) Aromatic compound containing tetraphenylethylene structure
An arylboronic acid ester intermediate (1.39g,2.80mmol), 4-chlorophenyl-1, 1,2, 2-tetraphenylethylene (0.98g,2.43mmol), and K were taken2CO3(0.69g,5.00mmol)、Pd(PPh3)4(28.07mg,0.02mmol), toluene (17.50m L), and water (3.00m L) were charged in a 100ml two-necked flask, vacuum-pumped, and nitrogen was replaced by 5 times, and the reaction was heated to 85 ℃ for 24 hours.
After the reaction is finished, water is added for quenching, ethyl acetate is used for extraction, the water phase is extracted for 2 times by dichloromethane, the organic phase is combined and dried by anhydrous magnesium sulfate, and white solid is obtained after filtration, concentration and column chromatography.
Example 5
The aromatic compound containing a tetraphenylethylene structure prepared in example 1 was dissolved in methylene chloride to prepare a solution having a concentration of 1.0 × 10-4The fluorescence spectrum obtained by measuring the dichloromethane solution of mol/l is shown in figure 1, the model of a fluorescence spectrometer is PE-L S555, and the aromatic compound containing the tetraphenylethylene structure is a fluorescent compound.
The solvent is not limited to dichloromethane, and may be dissolved in chloroform in other embodiments as long as the aromatic compound having a tetraphenylethylene structure can be effectively dissolved.
Example 6
The aromatic compound containing a tetraphenylethylene structure prepared in example 1 was formulated to a concentration of 1.0 × 10-4The results of the fluorescence quenching of the dichloromethane solution with different concentration gradients of 2,4, 6-trinitrophenol in dichloromethane are shown in FIG. 2.
The result shows that 2,4, 6-trinitrophenol (PA) solutions with different concentrations have obvious quenching effect on aromatic compounds containing tetraphenylethylene structures, and the initial emission quenching rate can reach 86%.
It should be noted that, for those skilled in the art, various changes and modifications can be made without departing from the inventive concept of the present invention, and these changes and modifications belong to the protection scope of the present invention.
Claims (10)
1. The aromatic compound containing the tetraphenylethylene structure is characterized by having a structural general formula shown as a formula I:
wherein, the R group is an acene aromatic structure containing nitrogen.
2. The aromatic compound containing the tetraphenylethylene structure of claim 1, wherein the aromatic compound has a structural formula shown in formula II:
3. a process for the preparation of the aromatic compound containing a tetraphenylethylene structure of claim 2, comprising the steps of:
by halogenating aromatic rings
Reacting with boric acid ester under anhydrous and oxygen-free conditions to obtain arylboronic acid ester intermediate
And (3) reacting the arylborate intermediate with halogenated tetraphenylethylene through SUZUKI to obtain the aromatic compound containing the tetraphenylethylene structure.
4. The method for preparing the aromatic compound containing the tetraphenylethylene structure of claim 3, wherein the halogenated aromatic ring is obtained by reacting halogenated benzaldehyde, phenanthrenequinone, aniline, and ammonium acetate in a weak acid solution, the reaction temperature is controlled to be 120-140 ℃, and the reaction time is 2-4 hours.
5. The method for preparing the aromatic compound containing the tetraphenylethylene structure according to claim 4, wherein the reaction molar ratio of the halogenated benzaldehyde, the phenanthrenequinone, the aniline and the ammonium acetate is 1: 0.83-1.2: 4.08-5: 2.42-4.04.
6. The method for producing an aromatic compound having a tetraphenylethylene structure according to claim 3, characterized in that n-butyllithium is used as a catalyst for the reaction of the halogenated aromatic ring with the boric acid ester, and the reaction molar ratio of the halogenated aromatic ring, n-butyllithium and the boric acid ester is 1:0.81 to 1.4:0.92 to 1.31.
7. The method for producing the aromatic compound containing a tetraphenylethylene structure of claim 6, wherein the reaction temperature of the halogenated aromatic ring and the borate is-50 to-78 ℃.
8. The method for preparing the aromatic compound containing the tetraphenylethylene structure according to claim 3, wherein the reaction temperature of the halogenated tetraphenylethylene with the arylboronic acid ester intermediate is 75-85 ℃ and the reaction time is 12-24 hours.
9. The method for preparing the aromatic compound containing the tetraphenylethylene structure according to claim 8, wherein the reaction molar ratio of the halogenated tetraphenylethylene to the arylboronic acid ester intermediate is 1: 0.87-1.4.
10. Use of the aromatic compound containing a tetraphenylethylene structure of claim 1 or 2 in the fluorescence detection of explosives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010317878.3A CN111454212B (en) | 2020-04-21 | 2020-04-21 | Aromatic compound containing tetraphenyl ethylene structure and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010317878.3A CN111454212B (en) | 2020-04-21 | 2020-04-21 | Aromatic compound containing tetraphenyl ethylene structure and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111454212A true CN111454212A (en) | 2020-07-28 |
| CN111454212B CN111454212B (en) | 2023-08-29 |
Family
ID=71675559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010317878.3A Active CN111454212B (en) | 2020-04-21 | 2020-04-21 | Aromatic compound containing tetraphenyl ethylene structure and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111454212B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024591A (en) * | 2021-03-17 | 2021-06-25 | 浙江师范大学 | Aggregation-induced emission molecular compound, preparation method and application |
| CN113563278A (en) * | 2021-07-29 | 2021-10-29 | 南京信息工程大学 | Preparation method and application of tetraphenylethylene functionalized bithiazole derivative and iridium complex thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804318A (en) * | 2014-02-14 | 2014-05-21 | 中山大学 | Benzothiazole derivative containing triphenylethylene or tetraphenylethylene structure and having aggregation-induced emission property and preparation method and application thereof |
| CN108865117A (en) * | 2018-07-23 | 2018-11-23 | 吉林大学 | Aggregation-induced emission organic fluorescence small molecule material and its application in DNT and TNT gas fluorescence detection |
-
2020
- 2020-04-21 CN CN202010317878.3A patent/CN111454212B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804318A (en) * | 2014-02-14 | 2014-05-21 | 中山大学 | Benzothiazole derivative containing triphenylethylene or tetraphenylethylene structure and having aggregation-induced emission property and preparation method and application thereof |
| CN108865117A (en) * | 2018-07-23 | 2018-11-23 | 吉林大学 | Aggregation-induced emission organic fluorescence small molecule material and its application in DNT and TNT gas fluorescence detection |
Non-Patent Citations (6)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024591A (en) * | 2021-03-17 | 2021-06-25 | 浙江师范大学 | Aggregation-induced emission molecular compound, preparation method and application |
| CN113563278A (en) * | 2021-07-29 | 2021-10-29 | 南京信息工程大学 | Preparation method and application of tetraphenylethylene functionalized bithiazole derivative and iridium complex thereof |
| CN113563278B (en) * | 2021-07-29 | 2023-10-03 | 南京信息工程大学 | Preparation method and application of tetraphenyl ethylene functionalized dithiazole derivative and iridium complex thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111454212B (en) | 2023-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109400900B (en) | Supermolecule gel assembled based on column [5] arene main-object and application thereof in detection and adsorption of iron ions | |
| CN110372469B (en) | Hydrogenated cyclo [12] arene compound and preparation method thereof | |
| CN111454212A (en) | Aromatic compound containing tetraphenylethylene structure and preparation method and application thereof | |
| CN113149915B (en) | Method for synthesizing clonazepam compound | |
| CN112062756A (en) | Mannhouse donor-acceptor adduct of furan and 3-pyridine ethylamine activated by Merlox acid and synthetic method thereof | |
| CN114106029B (en) | Organic molecule containing boron-nitrogen coordination bond and preparation method thereof | |
| CN108774102B (en) | Fluorescent porous aromatic skeleton material and preparation method and application thereof | |
| CN108997299B (en) | Efficient long-life organic room-temperature phosphorescent material and preparation method thereof | |
| CN106432316B (en) | Indolizine and iso-indoles or benzindole piperazine and isoindole derivatives and its synthetic method | |
| CN112480130A (en) | Macrocyclic extended porphyrin compounds and methods of making the same | |
| CN105294540A (en) | Novel Schiff base compound taking triphenylamine as center and preparation of novel Schiff base compound | |
| CN106188152A (en) | A kind of near-infrared metal complex and preparation thereof and application | |
| CN112010854B (en) | Trnano-ger's alkali derivative, preparation method thereof and test method for mechanical-induced fluorescence enhancement characteristics | |
| CN110105272A (en) | A kind of amide acetals class compound and the preparation method and application thereof | |
| CN112939751B (en) | Fluoren aromatic hydrocarbon macrocycle, preparation method thereof and application thereof in construction of functional conjugated band-shaped compound | |
| CN112778272B (en) | 2, 2' -biazaaryl ring bidentate ligand and preparation method and application thereof | |
| CN110105160B (en) | Preparation method based on triphenylene alkyne type precursor and polycyclic aromatic hydrocarbon derivative thereof | |
| CN114573826B (en) | Two-dimensional metal organic framework based on isocyano coordination, preparation method and application | |
| CN105038293B (en) | Indoles [3,2 b] pyrylium dyes and its preparation method and application | |
| CN103130797A (en) | Triphenylamine line type materials modified by electron drawing group and preparation method and purpose thereof | |
| CN111154075B (en) | Fluoroquinoxaline-thiophene copolymer and preparation method thereof | |
| CN114805796B (en) | Two-dimensional strong fluorescence polyaniline material with metal ion detection performance and preparation method thereof | |
| CN109851567B (en) | Pyrazine compound and application thereof | |
| CN116514875A (en) | Triptycene-like platinum complex and preparation method thereof | |
| CN102344369A (en) | High oriented luminescent polyacetylene monomer with side chains containing fluorene group and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |