CN111454212B - Aromatic compound containing tetraphenyl ethylene structure and preparation method and application thereof - Google Patents
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- 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"
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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
- 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
Abstract
The invention provides an aromatic compound containing a tetraphenyl ethylene structure, a preparation method and application thereof, belonging to the technical field of fluorescence sensing; and reacting the arylborate intermediate with halogenated tetraphenyl ethylene through SUZUKI. The aromatic compound containing the tetraphenyl ethylene structure provided by the invention has a larger conjugated structure, a wide charge delocalization range and a unique three-dimensional configuration, and is favorable for obtaining a good aggregation structure, so that the aromatic compound containing the tetraphenyl ethylene structure has a good application prospect in the fields of sensing technology and detection function, and has strong practicability and 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 tetraphenyl ethylene structure, and in addition, the invention also relates to a preparation method and application of the aromatic compound containing the tetraphenyl ethylene structure.
Background
The nitroaromatic explosives have more adverse effects on safety, environment and health, so the nitroaromatic explosives are required to be detected in the fields of anti-terrorism, nonmetallic mine detection, environment quality monitoring and the like.
Currently, explosives detection techniques can be broadly divided into two categories, body detection techniques and microscale detection techniques, respectively. The body detection technology is to detect the whole appearance of the explosive, and the method has the defects of large volume, high price, low detection sensitivity and the like of detection equipment. Compared with the volume detection technology, the micro-trace detection technology is used for detecting the volatile vapor of the explosive or the surface of any person/object contacted with the explosive, and the method has the advantages of high reliability, excellent performance, multifunctional integration, mass production of detection equipment and the like. Therefore, in recent years, the micro-trace amount detection technology has become a hotspot in the field of explosive detection research.
The prior art (CN 107782707A) discloses application of the tribenzothiazolyl benzene in fluorescence detection of nitroaromatic explosives, and describes that the tribenzothiazolyl benzene is applied to detection of the nitroaromatic explosives comprising 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, and has obvious quenching of fluorescence of the tribenzothiazolyl benzene, and has good fluorescence detection effect on typical nitroaromatic explosives, but the tribenzothiazolyl benzene has relatively complex preparation cost and expensive raw materials, and is unfavorable for popularization and application.
Disclosure of Invention
Based on the background problems, the invention aims to provide an aromatic compound containing a tetraphenyl ethylene structure, a preparation method and application thereof, wherein the preparation process of the aromatic compound containing the tetraphenyl ethylene structure is simple, the raw material cost is low, and the aromatic compound has an obvious fluorescence detection effect.
In order to achieve the above object, on one hand, the technical solution provided by the embodiment of the present invention is:
the structural general formula of the aromatic compound containing the tetraphenyl ethylene structure is shown as formula I, wherein the R group is a nitrogenous acene aromatic structure.
In one embodiment, the aromatic compound has a structural formula as shown in formula II:
in order to achieve the above object, in another aspect, the embodiment of the present invention further provides a method for preparing an aromatic compound having a tetraphenyl ethylene structure, comprising the steps of:
with halogenated aromatic ringsReacting with borate under anhydrous and anaerobic condition to obtain arylborate intermediate +.>
The aryl borate intermediate is reacted with halogenated tetraphenyl ethylene through SUZUKI to obtain the aromatic compound containing the tetraphenyl ethylene structure.
In one embodiment, the halogenated aromatic ring is obtained by reacting halogenated benzaldehyde, phenanthrenequinone, aniline and ammonium acetate in a weak acid solution, wherein the reaction temperature is controlled to be 120-140 ℃ and the reaction time is controlled to be 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-butyllithium is used as a catalyst for the reaction of the halogenated aromatic ring and the borate, and the molar ratio of the halogenated aromatic ring to the n-butyllithium to 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 tetraphenyl ethylene with the arylboronic acid ester intermediate is 75-85 ℃ and the reaction time is 12-24 hours.
Preferably, the molar ratio of halogenated tetraphenyl ethylene to arylboronic acid ester intermediate is 1:0.87-1.4.
The invention also provides application of the aromatic compound containing the tetraphenyl ethylene structure in fluorescence detection of explosives, wherein the aromatic compound containing the tetraphenyl ethylene structure is prepared into a solution and then placed in an explosive environment, and fluorescence quenching characteristics are observed.
Compared with the prior art, the invention has the following effects:
1. the aromatic compound containing the tetraphenyl ethylene structure provided by the invention has a larger conjugated structure, a wide charge delocalization range and a unique three-dimensional configuration, and is favorable for obtaining a good aggregation structure, so that the aromatic compound containing the tetraphenyl ethylene structure has a good application prospect in the fields of sensing technology and detection function, and has strong practicability and strong popularization and application values.
2. The aromatic compound containing the tetraphenyl ethylene 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 having a tetraphenyl ethylene structure prepared in example 1 of the present invention;
FIG. 2 is a graph of fluorescence quenching of PA solutions of different concentrations against aromatic compounds containing the tetraphenyl ethylene structure prepared in example 1.
Detailed Description
The aromatic compound containing the tetraphenyl ethylene structure has a larger conjugated structure, a wide charge delocalization range and a unique three-dimensional configuration, is favorable for obtaining a good aggregation structure, thereby having good application prospect in the fields of sensing technology and detection function, strong practicability and stronger popularization and application value.
The n-butyllithium described in the present invention was reacted in the form of an n-hexane solution of n-butyllithium at a concentration of 2.4M/L, and the present invention will be described in detail by way of specific examples.
Example 1
The preparation method of the aromatic compound containing the tetraphenyl ethylene structure comprises the following steps:
(1) Preparation of bromoaromatic rings
60mL of acetic acid was added to a 250mL two-necked flask, and 4-bromobenzaldehyde (2.50 g,13.50 mmol), 9, 10-phenanthrenequinone (2.80 g,13.50 mmol), aniline (6.30 mL,67.50 mmol) and ammonium acetate (4.20 g,54.50 mmol) were added to the two-necked flask, respectively, and the two-necked flask was evacuated, purged with nitrogen and heated to 120℃for 2 hours.
After the reaction is finished, the reaction solution is cooled to room temperature, a large amount of solids are separated out, the filtration is carried out, the filter residue is leached with glacial acetic acid for three times, and 5.5g of white solid is obtained after drying, and the yield is 90.6%. The chemical reaction equation is as follows:
1 HNMR(500MHz,DMSO,δ)：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
Dried bromoaromatic ring (5.00 g,11.10 mmol) is dissolved in 150ml of redistilled Tetrahydrofuran (THF), vacuum pumping and nitrogen protection are carried out, the reaction solution is cooled to-78 ℃, n-butyllithium n-BuLi (2.40M, 5.30 mL) is slowly added under the nitrogen protection, isopropanol pinacol borate (2.70 g,14.50 mmol) is quickly added after the reaction is carried out for 2h at low temperature, and the reaction time is slowly increased to room temperature overnight after 4h.
After the reaction, 100mL of water was added to quench the reaction, extraction was performed with ethyl acetate, extraction was performed twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with EA: pe=1:3 to give 2.50g of a white solid with a yield of 45.2%. The chemical reaction equation is as follows:
1 H NMR(500MHz,DMSO,δ)：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 tetraphenyl ethylene structure
Arylborate intermediate (1.39 g,2.80 mmol), 4-bromophenyl-1, 2-tetraphenyl ethylene (1.00 g,2.43 mmol), K was taken 2 CO 3 (0.69g,5.00mmol)、Pd(PPh 3 ) 4 (28.07 mg,0.02 mmol), toluene (17.50 mL), and water (3.00 mL) were added to a 100mL two-necked flask, and the flask was evacuated, nitrogen was replaced 5 times, and the reaction was heated to 85℃and reacted for 24 hours.
After the reaction, water was added to quench the mixture, extraction was performed with ethyl acetate, extraction was performed 2 times with methylene chloride, the organic phase was combined and dried over anhydrous magnesium sulfate, and 1.21g of a white solid was obtained after filtration, concentration and column passing, and the yield was 62.15%. The reaction equation is as follows:
1 HNMR(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)。
13 CNMR(500MHz,CDCl 3 )：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 tetraphenyl ethylene structure prepared above was subjected to matrix assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF-MS) and the results are shown in table 1:
TABLE 1 MALDI-TOF-MS detection results
The above analysis means confirmed that the aromatic compound having a tetraphenyl ethylene structure represented by the structural formula I could be produced by the method of example 1.
Example 2
The preparation method of the aromatic compound containing the tetraphenyl ethylene structure comprises the following steps:
(1) Preparation of bromoaromatic rings
60mL of acetic acid was added to a 250mL two-necked flask, and 4-bromobenzaldehyde (2.50 g,13.50 mmol), 9, 10-phenanthrenequinone (2.32 g,11.20 mmol), aniline (5.13 mL,55.08 mmol) and ammonium acetate (2.52 g,32.67 mmol) were added to the two-necked flask, respectively, and the two-necked flask was evacuated, purged with nitrogen and heated to 140℃for 3 hours. And cooling the reaction liquid to room temperature after the reaction is finished, precipitating a large amount of solids, filtering, leaching the filter residue with glacial acetic acid for three times, and drying to obtain white solids.
(2) Preparation of arylboronic acid ester intermediates
Dried bromoaromatic ring (5.00 g,11.10 mmol) is taken and dissolved in 150ml of redistilled Tetrahydrofuran (THF), vacuum pumping and nitrogen protection are carried out, the reaction solution is cooled to-60 ℃, n-butyllithium n-BuLi (2.40M, 6.47 mL) is slowly added under the nitrogen protection, isopropanol pinacol borate (1.90 g,10.21 mmol) is quickly added after the reaction is carried out for 2h at low temperature, and the reaction is carried out for 4h and then the reaction temperature is slowly increased to room temperature overnight.
After the reaction was completed, 100mL of water was added to quench, extraction was performed with ethyl acetate, extraction was performed twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with EA: pe=1:3 ratio to obtain a white solid.
(3) Aromatic compound containing tetraphenyl ethylene structure
Taking arylboronic acid ester intermediate (1.05 g,2.11 mmol), 4-bromophenyl-1, 2-tetraphenyl ethylene (1.00 g,2.43 mmol), K 2 CO 3 (0.69g,5.00mmol)、Pd(PPh 3 ) 4 (28.07 mg,0.02 mmol), toluene (17.50 mL), water (3.00 mL)Into a two-necked flask of 100ml, the flask was evacuated, nitrogen was replaced 5 times, and the reaction was heated to 75℃for 12 hours.
After the reaction, adding water for quenching, extracting with ethyl acetate, extracting the water phase with dichloromethane for 2 times, combining the organic phases, drying with anhydrous magnesium sulfate, filtering, concentrating, and passing through a column to obtain a white solid.
Example 3
The preparation method of the aromatic compound containing the tetraphenyl ethylene structure comprises the following steps:
(1) Preparation of bromoaromatic rings
60mL of acetic acid was added to a 250mL two-necked flask, and 4-bromobenzaldehyde (2.50 g,13.50 mmol), 9, 10-phenanthrenequinone (3.36 g,16.20 mmol), aniline (5.66 mL,60.75 mmol) and ammonium acetate (3.12 g,40.5 mmol) were added to the two-necked flask, respectively, and the two-necked flask was evacuated, purged with nitrogen and heated to 130℃for 4 hours. And cooling the reaction liquid to room temperature after the reaction is finished, precipitating a large amount of solids, filtering, leaching the filter residue with glacial acetic acid for three times, and drying to obtain white solids.
(2) Preparation of arylboronic acid ester intermediates
Dried bromoaromatic ring (5.00 g,11.10 mmol) is dissolved in 150ml of redistilled Tetrahydrofuran (THF), vacuum pumping and nitrogen protection are carried out, the reaction solution is cooled to-50 ℃, n-butyllithium n-BuLi (2.40M, 3.75 mL) is slowly added under the nitrogen protection, isopropanol pinacol borate (2.48 g,13.32 mmol) is quickly added after the reaction is carried out for 2h at low temperature, and the reaction time is slowly increased to room temperature overnight after 4h.
After the reaction was completed, 100mL of water was added to quench, extraction was performed with ethyl acetate, extraction was performed twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with EA: pe=1:3 ratio to obtain a white solid.
(3) Aromatic compound containing tetraphenyl ethylene structure
Arylborate intermediate (1.69 g,3.40 mmol), 4-bromophenyl-1, 2-tetraphenyl ethylene (1.00 g,2.43 mmol), K was taken 2 CO 3 (0.69g,5.00mmol)、Pd(PPh 3 ) 4 (28.07 mg,0.02 mmol), toluene (17.50 mL), water (3.00 mL) were added to a 100mL two-necked flaskVacuum pumping, nitrogen replacement for 5 times, reaction heating to 70 ℃ and reaction for 15h.
After the reaction, adding water for quenching, extracting with ethyl acetate, extracting the water phase with dichloromethane for 2 times, combining the organic phases, drying with anhydrous magnesium sulfate, filtering, concentrating, and passing through a column to obtain a white solid.
Example 4
The preparation method of the aromatic compound containing the tetraphenyl ethylene structure comprises the following steps:
(1) Preparation of chloro aromatic ring
60ml of acetic acid was added to 250ml of two-necked flask, and chlorobenzaldehyde (1.89 g,13.50 mmol), 9, 10-phenanthrenequinone (2.80 g,13.50 mmol), aniline (6.30 ml,67.50 mmol) and ammonium acetate (4.20 g,54.50 mmol) were added to the two-necked flask, respectively, and the two-necked flask was evacuated, purged with nitrogen and heated to 120℃for 2 hours.
After the reaction is finished, the reaction solution is cooled to room temperature, a large amount of solids are separated out, the solid is filtered, filter residues are leached with glacial acetic acid for three times, and 5.2g of white solid is obtained after drying, and the yield is 85.7%. The chemical reaction equation is as follows:
1 HNMR(500MHz,DMSO,δ)：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
Dried chloro aromatic ring (4.90 g,11.10 mmol) is dissolved in 150ml of redistilled Tetrahydrofuran (THF), vacuum pumping and nitrogen protection are carried out, the reaction solution is cooled to-78 ℃, n-butyllithium n-BuLi (2.40M, 5.30 mL) is slowly added under the nitrogen protection, isopropanol pinacol borate (2.70 g,14.50 mmol) is quickly added after the reaction is carried out for 2 hours at low temperature, and the reaction is slowly heated to room temperature overnight after the reaction is carried out for 4 hours.
After the reaction was completed, 100mL of water was added to quench, extraction was performed with ethyl acetate, extraction was performed twice with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and passed through a column with EA: pe=1:3 ratio to obtain a white solid.
(3) Aromatic compound containing tetraphenyl ethylene structure
Arylborate intermediate (1.39 g,2.80 mmol), 4-chlorophenyl-1, 2-tetraphenyl ethylene (0.98 g,2.43 mmol), K was taken 2 CO 3 (0.69g,5.00mmol)、Pd(PPh 3 ) 4 (28.07 mg,0.02 mmol), toluene (17.50 mL), and water (3.00 mL) were added to a 100mL two-necked flask, and the flask was evacuated, nitrogen was replaced 5 times, and the reaction was heated to 85℃and reacted for 24 hours.
After the reaction, adding water for quenching, extracting with ethyl acetate, extracting the water phase with dichloromethane for 2 times, combining the organic phases, drying with anhydrous magnesium sulfate, filtering, concentrating, and passing through a column to obtain a white solid.
Example 5
The aromatic compound having a tetraphenyl ethylene structure prepared in example 1 was dissolved in methylene chloride to prepare a compound having a concentration of 1.0X10 -4 The fluorescence spectrum obtained by measuring the mol/l methylene dichloride solution is shown in figure 1, the model of a fluorescence spectrometer is PE-LS555, and the aromatic compound containing the tetraphenyl ethylene structure can be seen as a fluorescent compound.
The solvent is not limited to methylene chloride, and may be dissolved in chloroform in other embodiments as long as the aromatic compound having a tetraphenyl ethylene structure can be effectively dissolved.
Example 6
The aromatic compound having a tetraphenyl ethylene structure prepared in example 1 was formulated to have a concentration of 1.0X10 -4 The results of fluorescence quenching of the molar methylene chloride solutions with different concentration gradients of 2,4, 6-trinitrophenol in methylene chloride solutions are shown in FIG. 2.
The results show that the 2,4, 6-trinitrophenol (PA) solutions with different concentrations have obvious quenching effect on aromatic compounds containing a tetraphenyl ethylene structure, and the initial emission quenching rate can reach 86 percent.
It should be noted that modifications and improvements can be made by those skilled in the art without departing from the inventive concept, and these are all within the scope of the present invention.
Claims (1)
1. The application of the aromatic compound containing the tetraphenyl ethylene structure in the fluorescence detection of the explosive is characterized in that the structural formula of the aromatic compound containing the tetraphenyl ethylene structure is as follows:
。
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| 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 |
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| 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 |
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