CN109293563B - Carbazole derivative and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a carbazole derivative and a preparation method and application thereof, wherein the carbazole derivative is prepared by taking methylbenzene, 2, 5-dibromo terephthaloyl chloride and carbazole as raw materials and sequentially carrying out Friedel-crafts acylation reaction and C-N coupling reaction. The carbazole derivative takes a benzene ring as a core, and benzophenone and carbazole as two arms, and belongs to a cross-shaped D-A structural molecule. The fluorescent probe can be used for detecting trace water and realizing quantitative detection of water content as a fluorescent sensing probe, has the detection limit of 85ppm by optimizing a fluorescence intensity signal, and has the characteristic of quick detection.
Description
Technical Field
The invention relates to a heterocyclic compound, in particular to a carbazole derivative and a preparation method and application thereof.
Background
The method has extremely important application in the fields of industrial production, scientific research, national defense industry and the like for analyzing and accurately monitoring the water content. The characterization of water content in products such as medicine, chemical industry, food, materials and the like is an important index, and the water content in organic solvents is often required to be measured. Therefore, it is important to study a method for detecting a trace amount of water.
At present, there are many methods for analyzing and detecting the water content, such as karl fischer coulometry, electrolysis, chromatography, etc. However, these methods have the disadvantages of expensive detection, limited application range, and strict testing requirements.
The fluorescence spectroscopy has the characteristics of convenience, rapidness, high sensitivity, selectivity and the like, and is widely applied to water content measurement at present. The ratio-type fluorescent probe can judge the water content through the positions of the fluorescence intensity and the wavelength, so that the ratio-type fluorescent probe molecules can obtain a quick and sensitive detection result, the sensitivity of the detection method is further improved, the dynamic response range is wider, and the ratio-type fluorescent probe has a good application prospect in the fields of medicines, chemical engineering, foods, materials and the like.
Disclosure of Invention
The invention aims to provide a carbazole derivative, a preparation method and application thereof, the carbazole derivative solves the problems of high cost, limited application range, strict test requirement and the like of the existing water content detection method, the existence of water is rapidly detected, the water content in a solvent can be quantitatively analyzed through a fluorescence intensity value, and the detection limit reaches 85 ppm.
In order to achieve the above object, the present invention provides a carbazole derivative having a structure represented by formula (I):
the invention also provides a preparation method of the carbazole derivative, and the synthesis method of the carbazole derivative comprises the following steps:
(1) toluene and 2, 5-dibromo-p-phthaloyl chloride react in an organic solvent under the catalysis of Lewis acid to generate a 2, 5-dibromo-p-phthaloyl toluene intermediate;
(2) dissolving the 2, 5-dibromo-p-phthaloyl toluene intermediate and carbazole in an organic solvent, and then performing a C-N coupling reaction (Buchwald-hartwig coupling reaction) under the action of a palladium catalyst and an alkaline substance to obtain the carbazole derivative.
Wherein, the organic solvent is an inert solvent.
Preferably, in step (1), the lewis acid comprises: anhydrous aluminum chloride; the inert solvent comprises: dichloromethane; the reaction is carried out at normal temperature.
Preferably, in the step (1), 2, 5-dibromoterephthalic acid is heated and refluxed in thionyl chloride, and after the reaction is finished, the excessive thionyl chloride is removed to obtain the 2, 5-dibromoterephthaloyl chloride; and dissolving the toluene and the Lewis acid in the organic solvent, and dropwise adding the solution into the 2, 5-dibromo-p-phthaloyl chloride for reaction at room temperature.
Preferably, in step (1), the ratio of the amounts of the substances of 2, 5-dibromoterephthalic acid, toluene and Lewis acid is 1: 2.2-3.5: 2.0 to 3.
Preferably, in step (2), the palladium catalyst comprises: pd2(dba)3And 2-dicyclohexylphosphonium-2 ',6' -diisopropoxy-1, 1' -biphenyl; the alkaline substance comprises: potassium phosphate.
Preferably, in the step (2), the ratio of the amounts of the 2, 5-dibromoterephthaloyl toluene, carbazole, palladium catalyst and potassium phosphate is 1: 3-10: 0.1-0.5: 1.6-2.5: 8 to 16.
Preferably, in step (2), the organic solvent comprises: toluene; the reaction is carried out under heating reflux conditions.
The invention also provides application of the carbazole derivative, and the carbazole derivative is used as a fluorescent sensing probe for detecting water content.
The carbazole derivative and the preparation method and the application thereof solve the problems of high cost, limited application range, strict test requirement and the like of the existing water content detection method, and have the following advantages:
the carbazole derivative is a cross donor-acceptor type (D-A type) ratio type fluorescent molecule, can be used for a fluorescent sensing probe, and forms a donor-acceptor system of push-pull electrons by taking carbazole part as electron donor carbazole and methyl as donor units (D) and taking electron-deficient carbonyl as acceptor units (A). In the presence of a trace amount of water, the fluorescence intensity of the fluorescent molecule (carbazole derivative) gradually decreases as the water content increases due to its sensitivity to water. The fluorescence intensity signal is processed, so that the quantitative detection of the fluorescence test on the water content is realized, the detection limit can reach 85ppm, and the detection is rapid.
Drawings
FIG. 1 is a graph showing fluorescence spectra of water content from 0 to 1% at an excitation wavelength of 390 nm.
FIG. 2 is a graph of the detection limit for water content from 0 to 1%.
Detailed Description
The embodiments of the present invention will be described in detail with reference to examples, which are only a part of the embodiments of the present invention, but not all of the embodiments. Therefore, the realization process of solving the technical problems and achieving the technical effects by applying the technical means can be fully understood and implemented. 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.
The invention discloses a preparation method of a carbazole derivative, which can be used for detecting trace water and comprises the following steps:
the method comprises the following steps: synthesis of intermediate 2, 5-dibromo-p-phthaloyl toluene:
the synthetic route is as follows:
thionyl chloride (SOCl) to which 2, 5-dibromoterephthalic acid was added2) Heating and refluxing the mixture in the liquid for 10 hours, and removing excessive thionyl chloride in vacuum to obtain the 2, 5-dibromo-p-phthaloyl chloride. Then methylene dichloride containing toluene and catalyst anhydrous aluminum trichloride is added dropwise into the 2, 5-dibromo-p-phthaloyl chloride. The mass ratio of the 2, 5-dibromoterephthalic acid, the toluene and the Lewis acid is 1: 2.2-3.5: 2.0 to 3. After the reaction is finished, cooling to room temperature, extracting the reaction liquid by using dichloromethane, washing an organic phase obtained by extraction by using saturated saline solution, drying by using anhydrous magnesium sulfate, filtering, carrying out rotary evaporation and sample mixing on the obtained liquid, carrying out silica gel column chromatography separation on the obtained concentrate, collecting eluent containing the target compound by using petroleum ether/dichloromethane as an eluent, evaporating the solvent, and drying to obtain an intermediate product.
Step two: target product carbazole derivative
Weighing the prepared 2, 5-dibromo-p-benzenedicarboxyl toluene Intermediate (IV), carbazole and Pd2(dba)3Ruphos (2-dicyclohexyl-phosphorus-2 ',6' -diisopropoxy-1, 1' -biphenyl), K3PO4Dissolved in 25mL of toluene and reacted under reflux under an inert gas atmosphere. Wherein the mass ratio of the 2, 5-dibromo-p-phthaloyl toluene, carbazole, palladium catalyst and potassium phosphate is 1: 3-10: 0.1-0.5: 1.6-2.5: 8 to 16. The reflux reaction temperature is 105 ℃ and 130 ℃, and the reaction time is 15-30 hours. After the reaction was completed, extraction was carried out three times with chloroform solution, washing was carried out with saturated sodium chloride solution, and the aqueous phases were combined and extracted with chloroform. The organic phases were finally combined and dried over anhydrous magnesium sulfate. Filtering, concentrating the filtrate under reduced pressure, subjecting the residue to thin layer chromatography with silica gel column, eluting with petroleum ether/dichloromethane, and evaporating the solvent under reduced pressure to obtain carbazole derivative as shown in formula (I).
EXAMPLE 1 preparation of 2, 5-dibromo-p-benzenedicarboxy-lene intermediate
2, 5-Dibromoterephthalic acid (3.25g,10mmol) was added to 40mL of thionyl chloride (SOCl)2) Heating and refluxing for 10 hours, and removing excessive thionyl chloride in vacuum to obtain 2, 5-dibromo-p-phthaloyl chloride.
Methylene chloride containing toluene (3.45g,25mmol) and anhydrous aluminum trichloride (2.67g,20mmol) as a catalyst was added dropwise to 2, 5-dibromoterephthaloyl chloride and reacted at room temperature for 8 hours.
After the reaction is finished, cooling the reaction liquid to room temperature, extracting the reaction liquid by using dichloromethane, washing an organic phase obtained by extraction by using saturated saline solution, drying by using anhydrous magnesium sulfate, filtering, carrying out rotary evaporation and sample mixing on the obtained liquid, carrying out silica gel column chromatography separation on the obtained concentrate, and carrying out separation by using a petroleum ether/dichloromethane volume ratio of 6: 1 as eluent, collecting the eluent containing the target compound, evaporating the solvent, and drying to obtain 3.35g of 2, 5-dibromo-p-phthaloyl toluene intermediate shown in formula (IV), wherein the yield is 71%.
Structural formula is determined, and the substance structure is characterized as follows:1H NMR(400MHz,CDCl3)：δ7.76(d,J＝8.3Hz,4H),7.58(s,2H),7.32(d,J＝8.0Hz,8H),2.37(s,6H).MS(Maidl-Tof-MS):472.17。
EXAMPLE 2 preparation of 2, 5-dibromo-p-benzenedicarboxy-lene intermediate
2, 5-Dibromoterephthalic acid (3.90g,12mmol) was added to 40mL of thionyl chloride (SOCl)2) Heating and refluxing for 10 hours, and removing excessive thionyl chloride in vacuum to obtain 2, 5-dibromo-p-phthaloyl chloride.
Methylene chloride containing toluene (4.97g,36mmol) and anhydrous aluminum trichloride (4.01g,30mmol) as a catalyst was added dropwise to the above 2, 5-dibromoterephthaloyl chloride and reacted at room temperature for 8 hours.
After the reaction is finished, cooling the reaction liquid to room temperature, extracting the reaction liquid by using dichloromethane, washing an organic phase obtained by extraction by using saturated saline solution, drying by using anhydrous magnesium sulfate, filtering, carrying out rotary evaporation and sample mixing on the obtained liquid, carrying out silica gel column chromatography separation on the obtained concentrate, and carrying out separation by using a petroleum ether/dichloromethane volume ratio of 6: 1 as eluent, collecting the eluent containing the target compound, evaporating the solvent, and drying to obtain 3.50g of 2, 5-dibromo-p-phthaloyl toluene intermediate shown in formula (IV), wherein the yield is 62%.
The material structural characterization was the same as in example 1.
EXAMPLE 3 preparation of 2, 5-dibromo-p-benzenedicarboxyl toluene intermediate
2, 5-Dibromoterephthalic acid (4.88g,15mmol) was added to 50mL of thionyl chloride (SOCl)2) Heating and refluxing for 10 hours, and removing excessive thionyl chloride in vacuum to obtain 2, 5-dibromo-p-phthaloyl chloride.
Methylene chloride containing toluene (7.25g,55mmol) and anhydrous aluminum trichloride (6.01g,45mmol) as a catalyst was added dropwise to the above 2, 5-dibromoterephthaloyl chloride and reacted at room temperature for 8 hours.
After the reaction is finished, cooling the reaction liquid to room temperature, extracting the reaction liquid by using dichloromethane, washing an organic phase obtained by extraction by using saturated saline solution, drying by using anhydrous magnesium sulfate, filtering, carrying out rotary evaporation and sample mixing on the obtained liquid, carrying out silica gel column chromatography separation on the obtained concentrate, and carrying out separation by using a petroleum ether/dichloromethane volume ratio of 6: 1 as eluent, collecting the eluent containing the target compound, evaporating the solvent, and drying to obtain 5.60g of the intermediate 2, 5-dibromo-p-phthaloyl toluene shown in the formula (IV), wherein the yield is 79%.
The material structural characterization was the same as in example 1.
Example 4 preparation of carbazole derivative
The 2, 5-dibromoterephthaloyltoluylene Intermediate (IV) prepared above (0.94g, 2mmol), carbazole (0.84g, 6mmol), Pd were weighed2(dba)3(0.18g，0.2mmol)、Ruphos(0.75g，1.6mmol)、K3PO4(1.70g, 8.0mmol) was dissolved in 25mL of toluene and heated at 110 ℃ for 22h under an inert gas atmosphere.
After the reaction was completed, extraction was carried out three times with chloroform solution, washing was carried out with saturated sodium chloride solution, and the aqueous phases were combined and extracted with chloroform. The organic phases were finally combined and dried over anhydrous magnesium sulfate. Filtering, concentrating the filtrate under reduced pressure, subjecting the residue to thin layer chromatography with silica gel column chromatography, eluting with mixed solution of petroleum ether/dichloromethane at volume ratio of 10/1, and evaporating the solvent under reduced pressure to obtain carbazole derivative (I) 0.72g as yellow solid with yield of 56%.
Structural formula is determined, and the substance structure is characterized as follows:1H NMR(400MHz,CDCl3)：δ8.10(s,2H),7.88(d,J＝7.6Hz,4H),7.45-7.42(m,8H),7.22(t,J＝7.6Hz,4H),7.13(d,J＝8.4Hz,4H),6.63(d,J＝7.6Hz,4H),2.10(s,6H)；MS(Maidl-Tof-MS):644.467。
example 5 preparation of carbazole derivative
The 2, 5-dibromoterephthaloyltoluylene Intermediate (IV) (1.18g,2.5mmol) prepared above, carbazole (1.11g, 8mmol), Pd were weighed2(dba)3(0.73g，0.8mmol)、Ruphos(2.33g，5mmol)、K3PO4(2.55g, 12mmol) was dissolved in 25mL of toluene. Heating to 110 ℃ under an inert gas atmosphere for reaction for 22 h.
After the reaction was completed, extraction was carried out three times with chloroform solution, washing was carried out with saturated sodium chloride solution, and the aqueous phases were combined and extracted with chloroform. The organic phases were finally combined and dried over anhydrous magnesium sulfate. Filtering, concentrating the filtrate under reduced pressure, subjecting the residue to thin layer chromatography with silica gel column chromatography, eluting with mixed solution of petroleum ether/dichloromethane at volume ratio of 10/1, and evaporating the solvent under reduced pressure to obtain carbazole derivative (I) 0.74g as yellow solid with yield of 47%.
The material structural characterization was the same as in example 4.
Example 6 preparation of carbazole derivative
The 2, 5-dibromoterephthaloyl toluene Intermediate (IV) (1.42g, 3mmol) prepared above, carbazole (4.18g, 30mmol), Pd were weighed2(dba)3(1.37g，1.5mmol)、Ruphos(0.53g，7.5mmol)，K3PO4(10.19g, 48mmol) was dissolved in 30mL of toluene. Heating to 110 ℃ under an inert gas atmosphere for reaction for 22 h.
After the reaction was completed, extraction was carried out three times with chloroform solution, washing was carried out with saturated sodium chloride solution, and the aqueous phases were combined and extracted with chloroform. The organic phases were finally combined and dried over anhydrous magnesium sulfate. Filtering, concentrating the filtrate under reduced pressure, subjecting the residue to thin layer chromatography with silica gel column chromatography, eluting with mixed solution of petroleum ether/dichloromethane at volume ratio of 10/1, and evaporating the solvent under reduced pressure to obtain 1.23g of carbazole derivative shown in formula (I) as yellow solid with yield of 64%.
The material structural characterization was the same as in example 4.
Experimental example 7 test of fluorescence quenching
When the water content is 0 to 1 percent, the test shows that the fluorescence is quenched rapidly, and the method has good sensitivity to water. Further verifying the detection limit of trace water, 1mL of 1X 10 was removed-4Dropping the mol/L solution into a 10mL volumetric flask, dropping 9.00, 8.98, 8.96, 8.94, 8.92 and 8.90 tetrahydrofuran solutions into the volumetric flask respectively, and finally fixing the volume with distilled water to prepare 0, 0.2%, 0.4%, 0.6%, 0.8% and 1% equivalent of 1 × 10-5mixed solution of mol/L.
The prepared carbazole derivative solutions with different equivalent weights are excited at 390nm, and the fluorescence spectrum of the test solution with the water content of 0-1% is researched by a fluorescence spectrum test means. As shown in FIG. 1, which is a graph of the ultraviolet absorption spectrum of water content from 0 to 1% at an excitation wavelength of 390nm, it can be seen from FIG. 1 that the emission peak position does not significantly shift with increasing water content, but the fluorescence intensity gradually decreases slowly. As shown in FIG. 2, which is a data processing diagram of fluorescence test for water content from 0 to 1%, the test is found to be capable of detecting micro water content with high sensitivity and high speed, and has good proportional linear relation, and more importantly, the detection limit reaches 85 (ppm).
In conclusion, the carbazole derivative disclosed by the invention can be used for processing the fluorescence intensity signal to realize the quantitative detection of the water content by a fluorescence test, the detection limit can reach 85ppm, and the detection is rapid.
While the present invention has been described in detail with reference to the preferred embodiments, it should be understood that the above description should not be taken as limiting the invention. Various modifications and alterations to this invention will become apparent to those skilled in the art upon reading the foregoing description. Accordingly, the scope of the invention should be determined from the following claims.
Claims (8)
1. A carbazole derivative having a structure represented by formula (I):
2. a method for producing the carbazole derivative according to claim 1, wherein the synthesis method of the compound comprises:
(1) toluene and 2, 5-dibromo-p-phthaloyl chloride react in an organic solvent under the catalysis of Lewis acid to generate a 2, 5-dibromo-p-phthaloyl toluene intermediate;
(2) dissolving the 2, 5-dibromo-p-benzenedicarboxyl toluene intermediate and carbazole in an organic solvent, and then performing a C-N coupling reaction under the action of a palladium catalyst and an alkaline substance to obtain the carbazole derivative;
wherein, the organic solvent is an inert solvent;
the structural formula of the 2, 5-dibromo-p-phthaloyl toluene intermediate is shown as follows:
3. the preparation method of a carbazole derivative according to claim 2, characterized in that, in step (1), the lewis acid is: anhydrous aluminum chloride; the inert solvent is: dichloromethane; the reaction is carried out at normal temperature.
4. The preparation method of a carbazole derivative according to claim 2, characterized in that in the step (1), 2, 5-dibromoterephthalic acid is heated and refluxed in thionyl chloride, and after the reaction is finished, excess thionyl chloride is removed to obtain the 2, 5-dibromoterephthaloyl chloride; and dissolving the toluene and the Lewis acid in the organic solvent, and dropwise adding the solution into the 2, 5-dibromo-p-phthaloyl chloride for reaction at room temperature.
5. The preparation method of a carbazole derivative according to claim 4, characterized in that, in step (1), the mass ratio of the 2, 5-dibromoterephthalic acid, toluene, and the Lewis acid is 1: 2.2-3.5: 2.0 to 3.
6. The method for producing a carbazole derivative according to claim 2, wherein, in the step (2), the palladium catalyst is: pd2(dba)3And 2-dicyclohexylphosphonium-2 ',6' -diisopropoxy-1, 1' -biphenyl; the alkaline substance is as follows: potassium phosphate.
7. The preparation method of a carbazole derivative according to claim 2, characterized in that, in step (2), the organic solvent is: toluene; the reaction is carried out under heating reflux conditions.
8. Use of a carbazole derivative according to claim 1 as a fluorescence sensing probe for detecting water content.
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