CN110668957B - Fluorescent probe for quickly detecting phosgene with high sensitivity and synthesis method and application thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for quickly detecting phosgene with high sensitivity and a synthesis method and application thereof, wherein the probe compound is 3, 6-di (1,2, 2-triphenylethylene) benzene-1, 2-diamine, named as DATPE, the structural formula of the fluorescent probe is shown as formula (1), o-phenylenediamine is used as a phosgene reaction site, and di (triphenylethylene) is used as a fluorescent chromophore; the synthesis method is a ring opening reaction for reducing the benzothiadiazole unit into o-phenylenediamine. The DATPE probe can be cured and smeared on filter paper to prepare detection test paper, so that real-time and visual monitoring of phosgene in a gas phase is realized. The probe DATPE and the test strip thereof have the advantages of high sensitivity, good selectivity, portability and the like for the photo-gas detection, and the synthetic method has simple steps, mild reaction conditions and good development prospect.
Description
Technical Field
The invention belongs to the technical field of detection of virulent hazardous gases, and relates to a fluorescent probe, in particular to a fluorescent probe for quickly detecting phosgene with high sensitivity and a synthesis method and application thereof.
Background
Phosgene (COCl)2) Is a highly toxic gas with asphyxia, which can irritate eyes and skin when exposed to phosgene, and cause pulmonary edema, acute respiratory distress syndrome and death when inhaled. Meanwhile, phosgene is an important chemical basic raw material and is widely applied to industrial chemical processes to produce various organic intermediates, pesticides and medicines. Accidental leaks in industrial production or use in chemical terrorist attacks constitute a serious threat to the environment and public safety, among other things. Therefore, the development of a convenient, rapid and reliable method for detecting phosgene in real time is of great significance.
At present, various methods for detecting phosgene based on different mechanisms, such as gas chromatography-mass spectrometry, Raman spectroscopy, electrochemical sensors and the like, exist; generally, most of these methods require expensive special instruments or complicated operation methods. Compared with the colorimetric method or the fluorescence probe method, the method has the advantages of portability, simplicity in operation and the like, and is receiving wide attention.
Most of the reported fluorescent probes have slow response speed to phosgene, high detection limit and poor selectivity. Therefore, the design of a rapid, sensitive and highly selective fluorescent probe is of great significance for the detection of phosgene.
Disclosure of Invention
The invention aims to provide a fluorescent probe for quickly detecting phosgene with high sensitivity, good selectivity and high sensitivity, and can quickly detect phosgene.
The second purpose of the invention is to provide a method for synthesizing the fluorescent probe for quickly detecting phosgene with high sensitivity, which has simple steps.
The third purpose of the invention is to provide the application of the fluorescent probe for quickly detecting phosgene with high sensitivity.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a fluorescent probe for quickly detecting phosgene with high sensitivity is a compound 3, 6-bis (1,2, 2-triphenylethylene) benzene-1, 2-diamine which takes o-phenylenediamine as a phosgene reaction site and bis (triphenylethylene) as a fluorescent chromophore and is named as DATPE, and the chemical structural formula is shown as formula (1):
the invention also provides a synthesis method of the fluorescent probe for quickly detecting phosgene with high sensitivity, which adopts ring-opening reaction for reducing benzothiadiazole unit into o-phenylenediamine, and comprises the following steps: dissolving the compound shown in the formula (2) in a mixed solvent of tetrahydrofuran and ethanol, adding 3-10 times of equivalent of sodium borohydride and 0.1 time of equivalent of cobalt chloride hexahydrate, stirring and reacting at 80-90 ℃ for 3-5 hours, and monitoring the completion of the reaction through thin-layer chromatography; and extracting, washing, drying and concentrating the reaction mixture to obtain a reaction crude product, and finally separating and purifying by silica gel column chromatography to obtain the fluorescent probe compound DATPE.
The reaction equation is expressed as:
preferably, in the mixed solvent of tetrahydrofuran and ethanol, the volume ratio of tetrahydrofuran to ethanol is 1: 2-2: 1.
preferably, the eluent used in the silica gel column chromatography is a mixed solvent of dichloromethane and ethyl acetate with a volume ratio of 50: 1.
The invention also provides application of the fluorescent probe compound DATPE in phosgene detection.
And sequentially dissolving polystyrene and DATPE in dichloromethane to prepare a solution, soaking filter paper in the solution to enable the fluorescent probes to be uniformly adsorbed on the filter paper, taking out and naturally drying to prepare the DATPE test strip for detecting phosgene.
The prepared DATPE test strip has very weak blue light emission under 365nm ultraviolet light. When the test strip is in phosgene atmosphere, the test strip immediately shows very strong blue light emission, the response time is less than 1 second, and the phosgene can be monitored in real time. Particularly, under the condition of phosgene with the concentration of 0.1ppm, the fluorescence of the test strip is obviously enhanced and can be seen by naked eyes.
Compared with the prior art, the invention has the following beneficial effects:
1. the DATPE probe can perform fluorescence detection on phosgene in a liquid phase, and response is quick and sensitive; the portable test strip prepared by the DATPE can be used for carrying out real-time visual monitoring on phosgene in a gas phase, and has high selectivity and low detection limit (0.1 ppm).
2. The probe synthesis method disclosed by the invention is simple in steps, only adopts one-step reduction reaction, is mild in reaction conditions, and has a good development prospect.
Drawings
FIG. 1 shows the fluorescent probe DATPE of the present invention1H NMR chart.
FIG. 2 is a fluorescence spectrum of the fluorescent probe DATPE of the invention under different concentrations of phosgene (0-20 μ M).
FIG. 3 is a photograph showing the color change of fluorescent probe DATPE test strip exposed to phosgene gas (0-5ppm) at different concentrations under an ultraviolet lamp (365 nm).
FIG. 4 is a photograph showing the color change of fluorescent probe DATPE test strip of the present invention when exposed to other similar test substances (20ppm) under UV lamp (365 nm). Wherein # 0 is blank reference, # 1 is phosgene (5ppm), # 2 is oxalyl chloride, # 3 is diethyl chlorophosphate, # 4 is thionyl chloride, # 5 is sulfuryl chloride, # 6 is phosphorus oxychloride, # 7 is acetyl chloride, # 8 is p-toluenesulfonyl chloride, # 9 is benzenesulfonyl chloride, and # 10 is 4-nitrobenzoyl chloride.
Detailed Description
The invention is described in further detail below with reference to the figures and specific examples.
The synthetic route of DATPE is as follows:
example 1: synthesis of fluorescent Probe DATPE
A100 mL round-bottom flask was charged with a magnetic stirrer, and the compound of formula (2) (0.4g, 0.62mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1: 2, V/V). Sodium borohydride (0.07g, 1.85mmol) was added to the reaction flask followed by cobalt chloride hexahydrate (0.015g, 0.06mmol) with rapid stirring. The reaction was stirred at 90 ℃ for 3 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50mL × 2). The organic layer was collected and washed with water (100 mL. times.5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified by silica gel column chromatography (dichloromethane/ethyl acetate, 50/1, V/V) to give the fluorescent probe dape as a pale green solid (0.2g, 0.32 mmol). The yield was 52%.
Nuclear magnetic resonance hydrogen spectrum of the prepared fluorescent probe DATPE (fig. 1):1H NMR(400MHz，CDCl3)δ7.21-6.88(m，30H)，6.34(d，J＝18.7Hz，2H)，3.26(s，4H)
high-resolution mass spectrum of the prepared fluorescent probe DATPE: EI-MS m/z calcd for C46H36N2:616.2878，found:616.2874[M]+.
Example 2: synthesis of fluorescent Probe DATPE
A100 mL round-bottom flask was charged with a magnetic stirrer, and the compound of formula (2) (0.4g, 0.62mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (2: 1, V/V). Sodium borohydride (0.07g, 1.85mmol) was added to the reaction flask followed by cobalt chloride hexahydrate (0.015g, 0.06mmol) with rapid stirring. The reaction was stirred at 90 ℃ for 3 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50mL × 2). The organic layer was collected and washed with water (100 mL. times.5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified by silica gel column chromatography (dichloromethane/ethyl acetate, 50/1, V/V) to give the fluorescent probe dape as a pale green solid (0.2g, 0.32 mmol). The yield was 45%.
The light green solid product prepared in this example was proved to be fluorescent probe DATPE according to its hydrogen nuclear magnetic resonance spectrum and high resolution mass spectrum.
Example 3: synthesis of fluorescent Probe DATPE
A100 mL round-bottom flask was charged with a magnetic stirrer, and the compound of formula (2) (0.4g, 0.62mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1: 2, V/V). Sodium borohydride (0.07g, 1.85mmol) was added to the reaction flask followed by cobalt chloride hexahydrate (0.015g, 0.06mmol) with rapid stirring. The reaction was stirred at 90 ℃ for 5 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50mL × 2). The organic layer was collected and washed with water (100 mL. times.5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified by silica gel column chromatography (dichloromethane/ethyl acetate, 50/1, V/V) to give the fluorescent probe dape as a pale green solid (0.2g, 0.32 mmol). The yield was 50%.
The light green solid product prepared in this example was proved to be fluorescent probe DATPE according to its hydrogen nuclear magnetic resonance spectrum and high resolution mass spectrum.
Example 4: synthesis of fluorescent Probe DATPE
A100 mL round-bottom flask was charged with a magnetic stirrer, and the compound of formula (2) (0.4g, 0.62mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1: 2, V/V). Sodium borohydride (0.07g, 1.85mmol) was added to the reaction flask followed by cobalt chloride hexahydrate (0.015g, 0.06mmol) with rapid stirring. The reaction was stirred at 80 ℃ for 3 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50mL × 2). The organic layer was collected and washed with water (100 mL. times.5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified by silica gel column chromatography (dichloromethane/ethyl acetate, 50/1, V/V) to give the fluorescent probe dape as a pale green solid (0.2g, 0.32 mmol). The yield was 48%.
The light green solid product prepared in this example was proved to be fluorescent probe DATPE according to its hydrogen nuclear magnetic resonance spectrum and high resolution mass spectrum.
Example 5: synthesis of fluorescent Probe DATPE
A100 mL round-bottom flask was charged with a magnetic stirrer, and the compound of formula (2) (0.4g, 0.62mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1: 2, V/V). Sodium borohydride (0.07g, 1.85mmol) was added to the reaction flask followed by cobalt chloride hexahydrate (0.015g, 0.06mmol) with rapid stirring. The reaction was stirred at 80 ℃ for 5 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50mL × 2). The organic layer was collected and washed with water (100 mL. times.5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified by silica gel column chromatography (dichloromethane/ethyl acetate, 50/1, V/V) to give the fluorescent probe dape as a pale green solid (0.2g, 0.32 mmol). The yield was 46%.
The light green solid product prepared in this example was proved to be fluorescent probe DATPE according to its hydrogen nuclear magnetic resonance spectrum and high resolution mass spectrum.
Example 6: synthesis of fluorescent Probe DATPE
A100 mL round-bottom flask was charged with a magnetic stirrer, and the compound of formula (2) (0.4g, 0.62mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1: 2, V/V). Sodium borohydride (0.23g, 6.2mmol) was added to the reaction flask followed by cobalt chloride hexahydrate (0.015g, 0.06mmol) with rapid stirring. The reaction was stirred at 90 ℃ for 3 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50mL × 2). The organic layer was collected and washed with water (100 mL. times.5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified by column chromatography (dichloromethane/ethyl acetate, 50/1, V/V) to give the fluorescent probe dape as a pale green solid (0.2g, 0.32 mmol). The yield was 52%.
The light green solid product prepared in this example was proved to be fluorescent probe DATPE according to its hydrogen nuclear magnetic resonance spectrum and high resolution mass spectrum.
Example 7: fluorescence spectrum experiment for detecting phosgene by using fluorescent probe DATPE
12.3mg of DATPE, a fluorescent probe compound, was dissolved in 20ml of tetrahydrofuran, and 20. mu.L of triethylamine (0.1%) was added to prepare 1X 10-3A solution of mmol/ml DATPE in tetrahydrofuran (0.1% triethylamine);
59.35mg of triphosgene were then weighed out and dissolved in 2ml of tetrahydrofuran to obtain 1X 10-3A mmol/ml triphosgene solution;
finally, preparing a mixed solvent of 95% of water and 5% of tetrahydrofuran.
Transferring 40 mu L of triphosgene solution, adding the triphosgene solution into 2ml of DATPE tetrahydrofuran solution (0.1% triethylamine), slightly shaking for 30 seconds, taking out 20 mu L of the triphosgene solution, adding the mixture into 2ml of mixed solvent of water and tetrahydrofuran, and recording the fluorescence spectrum change of the DATPE before and after the reaction.
FIG. 2 is a graph of the fluorescence spectra of DATPE in tetrahydrofuran (0.1% triethylamine) without phosgene and with phosgene (20 μ M) for 30 seconds (excitation wavelength 360 nm); from fig. 2, it can be seen that the addition of phosgene rapidly increases the fluorescence intensity of the dape, and the above phenomenon shows that the fluorescence probe dape can respond to phosgene in liquid phase and can detect the response signal thereof through fluorescence spectrum.
Example 8: preparation of fluorescent probe DATPE test strip
2g of polystyrene was dissolved in 50ml of dichloromethane and dissolved by sonication at room temperature to give a colorless transparent solution. Then 2mg of compound DATPE was weighed out and dissolved in the solution. A piece of clean qualitative filter paper was dipped into it, immediately taken out, and naturally dried. And finally, shearing the test paper into a size of 5cm multiplied by 2.5cm to obtain the portable test paper strip for detecting phosgene.
Example 9: detection experiment of phosgene in gas phase by fluorescent probe DATPE test strip
The portable test strip of example 8 was suspended in a 20ml glass vial using a copper wire, and 10. mu.L of triphosgene (2X 10) was pipetted into glass vials numbered 2,3,4,5 (test strip No. 1 was blank) using a microsyringe at different concentrations-4M,1×10-3M,2×10-3M,1×10-2M) and 10. mu.L of triethylamine in dichloromethane (4X 10)-2M). The two were mixed by gentle shaking, and after 0.5 min the test strip was removed and the color change of the test strip was recorded.
The concentrations of phosgene gas in the five glass bottles were found to be 0ppm, 0.1ppm, 0.5ppm, 1ppm and 5ppm, respectively, as calculated from the chemical reaction formula. As shown in FIG. 3, under phosgene with a concentration of 0.1ppm, the fluorescence of the test strip is obviously enhanced and can be seen with naked eyes, which indicates that the detection limit of the DATPE test strip to the phosgene with the naked eyes reaches 0.1ppm, and indicates the fast response and the high sensitivity of the test strip.
Example 10: gas phase selective recognition experiment of fluorescent probe DATPE test strip
Respectively preparing dichloromethane solutions of oxalyl chloride, diethyl chlorophosphate, thionyl chloride, sulfuryl chloride, phosphorus oxychloride, acetyl chloride, p-toluenesulfonyl chloride, benzenesulfonyl chloride and 4-nitrobenzoyl chloride, wherein the concentrations of the dichloromethane solutions are 2 multiplied by 10-2And M. The portable test strip of example 8 was suspended in 20ml glass vials using copper wire, 10. mu.L of the above solution was transferred to each of glass vials 3,4,5, 6, 7, 8, 9, 10, 11 using a micropipette, and No. 1 glass vial containing no detection gas was used as a reference, and No. 2 glass vial was filled with 10. mu.L of triphosgene (1X 10) by the method of example 9-2M) and 10. mu.L of triethylamine in dichloromethane (4X 10)-2M). The test strip can be taken out after slight shaking for 0.5 minute, and the test is recordedThe color of the paper strip changes. FIG. 4 is a photograph showing the color change of test strips exposed to different gas environments (phosgene: 5ppm, other gases: 10 ppm; numbers 3-11 represent different gas environments: 3. oxalyl chloride, 4. diethyl chlorophosphate, 5. thionyl chloride, 6. sulfuryl chloride, 7. phosphorus oxychloride, 8. acetyl chloride, 9. p-toluenesulfonyl chloride, 10. benzenesulfonyl chloride, 11.4-nitrobenzoyl chloride) under UV lamp (365 nm). As shown in FIG. 4, only the test strip in phosgene gas environment changed from weak blue emission to very strong blue emission under UV lamp (365nm), which indicates that the test strip in example 8 can selectively detect phosgene in gas phase.
In conclusion, the fluorescent probe molecule DATPE is prepared by only one-step reduction reaction, has mild reaction conditions and simple operation, and has the characteristic of quickly detecting phosgene with high sensitivity. The portable test strip prepared by the DATPE can realize real-time monitoring of phosgene. The fluorescent probe DATPE and the test strip thereof have high selectivity, quick and sensitive response, simple analysis and good development prospect on phosgene detection.
Claims (7)
1. A fluorescent probe for quickly detecting phosgene with high sensitivity is characterized in that o-phenylenediamine is used as a phosgene reaction site, and di (tristyryl) is used as a compound 3, 6-di (1,2, 2-tristyryl) benzene-1, 2-diamine of a fluorescent chromophore, is named as DATPE, and has a chemical structural formula shown in a formula (1):
2. the method for synthesizing the fluorescent probe for quickly detecting phosgene with high sensitivity according to claim 1, which is characterized in that a ring opening reaction for reducing a benzothiadiazole unit into o-phenylenediamine is adopted, and the method comprises the following specific steps: dissolving the compound shown in the formula (2) in a mixed solvent of tetrahydrofuran and ethanol, adding 3-10 times of equivalent of sodium borohydride and 0.1 time of equivalent of cobalt chloride hexahydrate, stirring and reacting at 80-90 ℃ for 3-5 hours, and monitoring the completion of the reaction through thin-layer chromatography; and extracting, washing, drying and concentrating the reaction mixture to obtain a reaction crude product, and finally separating and purifying by silica gel column chromatography to obtain the fluorescent probe compound DATPE.
3. The method for synthesizing the fluorescent probe for rapidly detecting phosgene with high sensitivity as claimed in claim 2, wherein the volume ratio of tetrahydrofuran to ethanol in the mixed solvent of tetrahydrofuran and ethanol is 1: 2-2: 1.
4. the method for synthesizing the fluorescent probe for quickly detecting phosgene with high sensitivity as claimed in claim 2, wherein the eluent used in the silica gel column chromatography is a mixed solvent of dichloromethane and ethyl acetate with a volume ratio of 50: 1.
5. The use of the fluorescent probe for the rapid detection of phosgene with high sensitivity as claimed in claim 1 in the detection of phosgene.
6. The use of claim 5, wherein a test strip of DATPE for phosgene detection is prepared.
7. The use of claim 6, wherein the DATPE strip is prepared as follows: and sequentially dissolving polystyrene and DATPE in dichloromethane to prepare a solution, soaking filter paper in the solution to enable the fluorescent probe to be uniformly adsorbed on the filter paper, taking out and naturally drying.
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