CN113788779A - A series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, and preparation methods and applications thereof - Google Patents

A series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, and preparation methods and applications thereof Download PDF

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CN113788779A
CN113788779A CN202111212849.1A CN202111212849A CN113788779A CN 113788779 A CN113788779 A CN 113788779A CN 202111212849 A CN202111212849 A CN 202111212849A CN 113788779 A CN113788779 A CN 113788779A
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李旭萍
卢建军
张晨晨
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Taiyuan University of Technology
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Abstract

The invention relates to the technical field of organic luminescent materials, in particular to a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, and a preparation method and application thereof. The invention uses indole derivatives as electron donor (D) and diphenyl sulfone as electron acceptor (A) to form D-A or D-A-D type compounds; the series of compounds of the invention have the characteristics of twisted intramolecular charge transfer and aggregation induced luminescence, and are sensitive to the existence of water in an organic solvent; the concrete expression is as follows: within a certain range, with the increase of the water fraction, the maximum emission peak position of the water-soluble polymer shows regular red shift, and the intensity ratio of the water-soluble polymer also gradually rises and shows good linear relation; therefore, the series of compounds of the invention can be used as a novel fluorescence sensor for detecting the water content in the organic solvent in real time by using the intensity ratio and the wavelength.

Description

A series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, and preparation methods and applications thereof
Technical Field
The invention relates to the technical field of organic luminescent materials, in particular to a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, and a preparation method and application thereof.
Background
The organic fluorescent material has the advantages of simple structure, stable light emission and the like, and has wide application in the fields of fluorescent imaging, sensing, organic light emitting diodes and the like. However, common organic fluorescent materials are molecules which aggregate to cause quenching (ACQ), that is, although the organic fluorescent materials have excellent luminescence properties in a dilute solution state, the degree of pi-pi stacking in an aggregate state increases with the increase of concentration, which causes a phenomenon that luminescence intensity is sharply reduced and even fluorescence quenching occurs, and therefore, the development of the organic fluorescent materials in related fields is greatly limited. To reduce the effects of ACQ, researchers in down loyalty et al have proposed a series of luminescent molecules with Aggregation Induced Emission (AIE) and Aggregation Induced Enhanced Emission (AIEE) properties (Y Hong, et al chem. In recent years, due to the broad prospects for the development of AIE molecules, many researchers have focused on the design principles, the mechanism of light emission, and the relationship between structure and properties of AIE molecules. Until now, AIE molecules with superior performance have attracted the attention of a large number of researchers (Q Wang et al, j.mater.chem.b.,2016,4, 4033.).
Further, due to the characteristic of intramolecular charge conversion, in recent years, organic compounds composed of an electron donor (D) and an electron acceptor (a) have become popular materials in the field of photovoltaics (S Sasaki, et al, j. In a polar environment, a molecule having a twisted intramolecular charge transfer undergoes a rapid intramolecular charge transfer process between a donor and an acceptor, accompanied by a relaxed stacking mode in which, in addition to a charge transfer from low energy, a relaxation process from a high-energy local excited state is easily regulated by conditions such as a molecular substituent and polarity, and thus a molecule having a Twisted Intramolecular Charge Transfer (TICT) property is widely used in various fields of biochemistry. Therefore, more and more researchers are focusing on designing molecules with both AIE and TICT functions, so as to construct a fluorescent material with TICT-AIE synergistic effect, and the application of the fluorescent molecules in fluorescence imaging and organic light emitting diodes is greatly promoted due to strong emission in both dilute solution and aggregation state.
However, such molecules are not widely used for the detection of water content in organic solvents. Since water is the most common impurity in organic solvents, detection and quantification of water is critical in both chemical reactions and industrial applications. At present, some traditional technologies for detecting trace water exist, such as Karl Fischer titration, chromatography, electrochemical methods and the like (H Jung, chem.Soc.Rev.,2016,45, 1242), but generally, the methods have the defects of high cost, long time and the like, so that the operation requirement is greatly improved, and therefore, it is necessary to design organic fluorescent molecules with simple structures and obvious color development to replace the traditional detection method. In addition, most of the existing water sensors perform quantitative analysis on water only through the linear relation between the intensity and the water content, and certain errors may affect the measurement accuracy in actual operation.
The method combines the research backgrounds to develop a double-parameter three-dimensional detection sensor which is sensitive to trace water in the organic solvent and utilizes the change of the intensity ratio and the wavelength along with the water content, has important significance, can greatly improve the quantitative accuracy, and is suitable for quantitative detection of water in the organic solvent under the conditions of laboratory or industrial application and the like.
Disclosure of Invention
The invention aims to provide a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, a preparation method and application thereof, and overcomes the defects of the prior art, the D-A or D-A-D type compounds formed by taking indole derivatives as electron donors (D) and diphenyl sulfone as electron acceptors (A) are sensitive to the existence of water in an organic solvent due to the characteristics of twisted intramolecular charge transfer and aggregation induced luminescence, and can be used as a novel fluorescence water sensor for detecting the water content in the organic solvent in real time by using ratio intensity and emission wavelength. .
The technical scheme adopted by the invention for solving the technical problems is as follows:
a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives are donor-acceptor type compounds formed by taking indole derivatives as electron donors and diphenyl sulfone as electron acceptors, and the structural formula of the donor-acceptor type compounds is shown as a general formula I or a general formula II:
Figure BDA0003309476030000021
wherein: r is hydrogen, or halogen atom, or indole, or indoline
The donor-acceptor type compound based on the diphenyl sulfone and the indole derivative has the characteristics of charge transfer in a twisted molecule and aggregation-induced luminescence, and can be used as a sensor for detecting water in an organic solvent.
A series of methods for preparing receptor type compounds based on diphenyl sulfone and indole derivatives, comprising the steps of: adding indole, 4 '-difluorodiphenyl sulfone and potassium carbonate into a reaction vessel, wherein the molar mass ratio of the indole to the 4,4' -difluorodiphenyl sulfone to the potassium carbonate is 0.9-1.1 mmol: 1.8-2.2 mmol: 0.9-1.1mmol, injecting into 2-12ml N-methyl pyrrolidone under the protection of nitrogen, reacting for 0.5 hour at 100 ℃, pouring the reaction liquid into ice water, extracting for three times by using ethyl acetate, washing by using saturated saline solution, removing the solvent by rotary evaporation of an organic phase, and separating and purifying by column chromatography to obtain the product 4-fluoro-4 '-indolylsulfone, wherein the 4-fluoro-4' -indolylsulfone is the compound shown in the general formula I.
A series of methods for preparing receptor type compounds based on diphenyl sulfone and indole derivatives, comprising the steps of: adding indole, 4 '-difluoro diphenyl sulfone and potassium carbonate into a reaction container, wherein the mol mass ratio of the indole to the 4,4' -difluoro diphenyl sulfone to the potassium carbonate is 2-2.4 mmol: 0.9-1.1 mmol: 9-11mmol, injecting into 2-12ml N-methyl pyrrolidone under the protection of nitrogen, reacting for 4 hours at 160 ℃, naturally cooling to room temperature, pouring the reaction liquid into ice water under stirring, extracting with ethyl acetate for three times, washing with saturated saline solution, removing the solvent by rotary evaporation of an organic phase, and separating and purifying by column chromatography to obtain a product of bis (4-indolylphenyl) sulfone, wherein the product of bis (4-indolylphenyl) sulfone is a compound shown in a general formula I.
A series of methods for preparing receptor type compounds based on diphenyl sulfone and indole derivatives, comprising the steps of: adding indoline, 4 '-difluoro diphenyl sulfone and potassium carbonate into a reaction container, wherein the molar mass ratio of the indoline, the 4,4' -difluoro diphenyl sulfone and the potassium carbonate is 0.9-1.1 mmol: 2-2.4 mmol: 9-11mmol, injecting into 2-12ml N-methyl pyrrolidone under the protection of nitrogen, reacting for 2 hours at 160 ℃, adding the reaction liquid into cold water, extracting for three times by using ethyl acetate, washing by using saturated saline solution, removing the solvent by rotary evaporation of an organic phase, and separating and purifying by column chromatography to obtain the product 4-fluoro-4 '-indoline phenyl sulfone, wherein the 4-fluoro-4' -indoline phenyl sulfone is a compound shown in a general formula II.
A series of methods for preparing receptor type compounds based on diphenyl sulfone and indole derivatives, comprising the steps of: adding indoline, 4 '-difluorodiphenyl sulfone and sodium hydride into a reaction vessel, wherein the molar mass ratio of the indoline to the 4,4' -difluorodiphenyl sulfone to the sodium hydride is 4-4.8 mmol: 0.9-1.1 mmol: 4-4.8mmol, injecting into 2-12ml of N, N dimethyl formamide under the protection of nitrogen, reacting for 10 hours at 100 ℃, naturally cooling to room temperature, pouring the reaction liquid into ice water under stirring, extracting with ethyl acetate for three times, washing with saturated saline solution, performing rotary evaporation on an organic phase to remove a solvent, and performing column chromatography separation and purification to obtain a product, namely bis (4-indolylphenyl) sulfone, wherein the bis (4-indolinylphenyl) sulfone is a compound shown in a general formula II.
The synthetic routes of the four preparation methods are shown as the following formula:
Figure BDA0003309476030000041
the 4-fluoro-4 '-indolylsulfone is the compound C-1 in the reaction formula, the di (4-indolylbenzene) sulfone is the compound C-2, 4-fluoro-4' -indolinylphenylsulfone in the reaction formula is the compound C-3 in the reaction formula, and the di (4-indolinylbenze) sulfone is the compound C-4 in the reaction formula.
A series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives are applied to detection of water content in an organic solvent as a fluorescence sensor.
Preferably, a series of compounds of the donor-acceptor type based on diphenyl sulfone and indole derivatives are applied, the application method comprises the following steps:
(1) dissolving a compound of formula I or formula II in a mixed solution of water and tetrahydrofuran;
(2) and measuring the change of system luminescence caused by the change of the volume fraction of the water, thereby detecting the water content in the organic solvent.
The fluorescence spectrum shows regular changes along with the change of the water content.
A series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives synthesized by the invention are D-A or D-A-D type compounds formed by taking indole derivatives as electron donors (D) and diphenyl sulfone as electron acceptors (A); research shows that the series of compounds have the characteristics of twisted intramolecular charge transfer and aggregation-induced luminescence, and are sensitive to the presence of water in an organic solvent; the concrete expression is as follows: within a certain range, with the increase of the water fraction, the maximum emission peak position of the water-soluble polymer shows regular red shift, and the intensity ratio of the water-soluble polymer also gradually rises and shows good linear relation; therefore, the series of compounds can be used as a novel fluorescence sensor for detecting the water content in the organic solvent in real time by using the intensity ratio and the wavelength.
The invention has the beneficial effects that: compared with the prior art, the series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives, and the preparation method and the application thereof have the following advantages: the series of compounds provided by the invention have the characteristic of sensitivity to water, can detect the water content of the organic solvent according to the emission intensity and the emission displacement change, has the advantages of cheap and easily-obtained raw materials, simple synthesis and convenient detection, solves the technical problems of high detection cost and complex synthesis route in the prior art, and effectively improves the detection precision.
Drawings
FIG. 1 is a fluorescence emission spectrum of a compound 4-fluoro-4' -indoline phenylsulfone with a concentration of 5. mu. mol/L in tetrahydrofuran and water mixed solutions with different water volume contents in example 3 of the present invention;
FIG. 2 is a graph showing the relationship between the water volume fraction in the mixed solution of tetrahydrofuran and water, the emission wavelength and the ratio of fluorescence intensity of 4-fluoro-4' -indoline phenylsulfone, a compound of 5. mu. mol/L in example 3 of the present invention;
FIG. 3 is a fluorescence emission spectrum of the compound bis (4-indoline phenyl) sulfone of example 4 of the present invention at a concentration of 5. mu. mol/L in a mixed solution of tetrahydrofuran and water with different water volume contents;
FIG. 4 is a graph showing the relationship between the water volume fraction, the emission wavelength and the ratio of fluorescence intensity in a mixed solution of tetrahydrofuran and water, of bis (4-indolinylphenyl) sulfone compound of 5. mu. mol/L in example 4 of the present invention.
Detailed Description
Example 1
Adding indole (0.23g,2mmol), 4' -difluoro diphenyl sulfone (1.02g,4mmol) and potassium carbonate (0.28g,2mmol) into a 20mL round-bottom flask, injecting 5mL of N-methyl pyrrolidone under the protection of nitrogen, reacting at 100 ℃ for 0.5 hour, cooling to room temperature, pouring the reaction liquid into 20mL of ice water, extracting with ethyl acetate for three times, washing with saturated saline solution, carrying out rotary evaporation on the organic phase to obtain a light yellow solid, and separating and purifying by column chromatography, wherein the weight ratio of petroleum ether: ethyl acetate 10: 1(v/v) is used as eluent to obtain white solid 2-1, namely 4-fluoro-4' -indoxyl phenylsulfone, and the yield is 68 percent. 1H NMR (400MHz, DMSO-d6) δ (ppm) 8.19-8.09(m,4H),7.91-7.84(m,2H),7.76(d, J ═ 3.4Hz,1H),7.68(dd, J ═ 11.0,4.1Hz,2H),7.55-7.44(m,2H),7.21(dtd, J ═ 14.8,7.1,1.2Hz,2H),6.78(dd, J ═ 3.4,0.6Hz, 1H).
Example 2
Adding indole (0.52g,4.4mmol), 4' -difluoro diphenyl sulfone (0.508g,2mmol) and potassium carbonate (2.76g,20mmol) into a 20mL round-bottom flask, injecting 10mL of N-methyl pyrrolidone under the protection of nitrogen, reacting at 160 ℃ for 4 hours, naturally cooling to room temperature, pouring the reaction liquid into 50mL of ice water under stirring, extracting with ethyl acetate for three times, washing with saturated saline, removing the solvent by rotary evaporation of an organic phase to obtain a light yellow solid, and separating and purifying by column chromatography, wherein the weight ratio of petroleum ether: ethyl acetate 10: 1(v/v) is used as eluent to obtain white solid 2-2, namely, the di (4-indolylbenzene) sulfone, and the yield is 81 percent. 1H NMR (400MHz, DMSO-d6) δ (ppm) 8.22-8.14(m,4H),7.90-7.86(m,4H),7.75(d, J ═ 3.4Hz,2H),7.67(dd, J ═ 12.8,7.8Hz,4H),7.26-7.12(m,4H),6.76(d, J ═ 3.4Hz, 2H).
Example 3
Indoline (0.24g,2mmol), 4' -difluorodiphenyl sulfone (1.12g,4.4mmol) and potassium carbonate (2.76g,20mmol) are added into a 20mL round-bottom flask, 10mL of N-methylpyrrolidone is injected under the protection of nitrogen, the mixture reacts at 160 ℃ for 2 hours, the temperature is naturally reduced to room temperature, the reaction solution is poured into 50mL of ice water, extraction is carried out three times by ethyl acetate, washing is carried out by saturated saline solution, the organic phase is subjected to rotary evaporation to remove the solvent, a light yellow solid is obtained, and the light yellow solid is separated and purified by column chromatography, and petroleum ether: ethyl acetate 10: 1(v/v) is used as eluent to obtain off-white solid 2-3, namely 4-fluoro-4' -indoline phenyl sulfone with the yield of 69%. 1H NMR (400MHz, DMSO-d6) δ (ppm) 8.04-7.7(m,2H),7.90-7.83(m,2H),7.50-7.40(m,2H),7.40-7.34(m,2H),7.32(d, J ═ 8.0Hz,1H),7.28-7.20(m,1H),7.12(t, J ═ 7.7Hz,1H),6.86(td, J ═ 7.5,0.7Hz,1H),4.00(t, J ═ 8.4Hz,2H),3.21-3.02(m, 2H).
Example 4
Indoline (1.04g,8.8mmol), 4' -difluorodiphenyl sulfone (0.508g,2mmol) and sodium hydride (0.22g,8.8mmol) are added into a 20mL round-bottom flask, 10mL of anhydrous N, N-dimethylformamide is injected under the protection of nitrogen, the reaction is carried out for 10 hours at 100 ℃, the reaction solution is naturally reduced to room temperature, the reaction solution is poured into 50mL of ice water, extracted with ethyl acetate for three times, washed with saturated saline, and the organic phase is subjected to rotary evaporation to remove the solvent, so as to obtain a light yellow solid, and the light yellow solid is separated and purified by column chromatography, and then the weight ratio of petroleum ether: ethyl acetate 10: 1(v/v) is used as eluent to obtain 2-4 white solid, namely bis (4-indoline phenyl) sulfone, and the yield is 47%. 1H NMR (400MHz, DMSO-d6) δ (ppm) 7.91-7.66(m,4H),7.39-7.32(m,4H),7.30(d, J ═ 8.0Hz,2H),7.24(dd, J ═ 7.3,0.8Hz,2H),7.11(t, J ═ 7.8Hz,2H),6.85(td, J ═ 7.4,0.8Hz,2H),4.00(dd, J ═ 15.2,6.9Hz,4H),3.11(t, J ═ 8.4Hz, 4H).
Test example 1
The compound obtained in example 3 was prepared as a mixed solution of tetrahydrofuran and water in the proportions of 0%, 1%, 3%, 5% and 7% in this order, and the concentrations were all 5. mu. mol/L. 2mL of each solution was added to a 1cm × 1cm × 4cm cuvette and the fluorescence emission spectrum was measured, with λ ex ═ 345nm, and the results are shown in fig. 1.
As can be seen from FIG. 1, the fluorescence intensity gradually decreases and the emission wavelength gradually increases with increasing water content in the solution within a certain range.
Test example 2
The compound obtained in example 3 was prepared as a mixed solution of tetrahydrofuran and water in the proportions of 0%, 1%, 3%, 5% and 7% in this order, and the concentrations were all 5. mu. mol/L. 2mL of each solution was added to a 1 cm. times.1 cm. times.4 cm cuvette and the fluorescence emission spectrum, lambda. was measuredexThe emission wavelength was observed as a function of the water fraction at 345nm, and the result is shown by the broken line a in fig. 2.
As can be seen from FIG. 2, the emission wavelength and the water content in the solution show a good linear relationship in a certain range, R2＝0.9982。
Test example 3
The compound obtained in example 3 was prepared as a mixed solution of tetrahydrofuran and water in the proportions of 0%, 1%, 3%, 5% and 7% in this order, and the concentrations were all 5. mu. mol/L. 2mL of each solution was added to a 1 cm. times.1 cm. times.4 cm cuvette and the fluorescence emission spectrum, lambda. was measuredexThe emission intensity ratio was observed as a function of the water fraction at 345nm, and the result is shown by the broken line B in fig. 2.
As can be seen from attempt 2, within a certain range, the emission intensity ratio thereof exhibits a good linear relationship with the water content in the solution, R2＝0.9826。
Test example 4
The compound obtained in example 4 was prepared as a mixed solution of tetrahydrofuran and water in the proportions of 0%, 1%, 3%, 5% and 7% in this order, and the concentrations were all 5. mu. mol/L. 2mL of each solution was added to a 1 cm. times.1 cm. times.4 cm cuvette and the fluorescence emission spectrum, lambda. was measuredex350nm, the results are shown in figure 3.
As can be seen from fig. 3, the fluorescence intensity gradually decreases and the emission wavelength gradually increases with the increase of the water content in the solution within a certain range.
Test example 5
The compound obtained in example 4 was prepared as a mixed solution of tetrahydrofuran and water in the proportions of 0%, 1%, 3%, 5% and 7% in this order, and the concentrations were all 5. mu. mol/L. 2mL of each solution was added to a 1 cm. times.1 cm. times.4 cm cuvette and the fluorescence emission spectrum, lambda. was measuredexObserved at 350nmThe wavelength as a function of the water fraction is shown in FIG. 4 as a dashed line C.
As can be seen from FIG. 4, the emission wavelength and the water content in the solution show a good linear relationship in a certain range, R2＝0.9736。
Test example 6
The compound obtained in example 4 was prepared as a mixed solution of tetrahydrofuran and water in the proportions of 0%, 1%, 3%, 5% and 7% in this order, and the concentrations were all 5. mu. mol/L. 2mL of each solution was added to a 1 cm. times.1 cm. times.4 cm cuvette and the fluorescence emission spectrum, lambda. was measuredexThe emission intensity ratio was observed as a function of the water fraction at 350nm, and the result is shown by the dotted line D in fig. 4.
As can be seen from FIG. 4, the emission intensity ratio has a good linear relationship with the water content in the solution within a certain range, R2＝0.9889。
Similar results were obtained by testing the compounds obtained in examples 1 and 2 in test examples 3 to 6.
The above embodiments are only specific examples of the present invention, and the protection scope of the present invention includes but is not limited to the product forms and styles of the above embodiments, and any suitable changes or modifications made by those skilled in the art according to the claims of the present invention shall fall within the protection scope of the present invention.

Claims (7)

1. A series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives characterized by: the compound is a donor-acceptor type compound formed by taking indole derivatives as an electron donor and diphenyl sulfone as an electron acceptor, and the structural formula of the compound is shown as a general formula I or a general formula II:
Figure FDA0003309476020000011
wherein: r is hydrogen, or halogen atom, or indole, or indoline.
2. The process for the preparation of a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives as claimed in claim 1, characterized in that: the method comprises the following steps: adding indole, 4 '-difluorodiphenyl sulfone and potassium carbonate into a reaction vessel, wherein the molar mass ratio of the indole to the 4,4' -difluorodiphenyl sulfone to the potassium carbonate is 0.9-1.1 mmol: 1.8-2.2 mmol: 0.9-1.1mmol, injecting into 2-12ml N-methyl pyrrolidone under the protection of nitrogen, reacting for 0.5 hour at 100 ℃, cooling to room temperature, pouring the reaction liquid into ice water, extracting with ethyl acetate for three times, washing with saturated saline, removing the solvent by rotary evaporation of an organic phase, and separating and purifying by column chromatography to obtain the product 4-fluoro-4' -indolylsulfone which is a compound shown in the general formula I.
3. The process for the preparation of a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives as claimed in claim 1, characterized in that: the method comprises the following steps: adding indole, 4 '-difluoro diphenyl sulfone and potassium carbonate into a reaction container, wherein the mol mass ratio of the indole to the 4,4' -difluoro diphenyl sulfone to the potassium carbonate is 2-2.4 mmol: 0.9-1.1 mmol: 9-11mmol, injecting into 2-12ml N-methyl pyrrolidone under the protection of nitrogen, reacting for 4 hours at 160 ℃, naturally cooling to room temperature, pouring the reaction liquid into ice water under stirring, extracting with ethyl acetate for three times, washing with saturated saline solution, removing the solvent by rotary evaporation of an organic phase, and separating and purifying by column chromatography to obtain a product of bis (4-indolylphenyl) sulfone, wherein the product of bis (4-indolylphenyl) sulfone is a compound shown in a general formula I.
4. The process for the preparation of a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives as claimed in claim 1, characterized in that: the method comprises the following steps: adding indoline, 4 '-difluoro diphenyl sulfone and potassium carbonate into a reaction container, wherein the molar mass ratio of the indoline, the 4,4' -difluoro diphenyl sulfone and the potassium carbonate is 0.9-1.1 mmol: 2-2.4 mmol: 9-11mmol, injecting into 2-12ml N-methyl pyrrolidone under the protection of nitrogen, reacting for 2 hours at 160 ℃, adding the reaction liquid into cold water, extracting for three times by using ethyl acetate, washing by using saturated saline solution, removing the solvent by rotary evaporation of an organic phase, and separating and purifying by column chromatography to obtain the product 4-fluoro-4 '-indoline phenyl sulfone, wherein the 4-fluoro-4' -indoline phenyl sulfone is a compound shown in a general formula II.
5. The process for the preparation of a series of donor-acceptor type compounds based on diphenyl sulfone and indole derivatives as claimed in claim 1, characterized in that: the method comprises the following steps: adding indoline, 4 '-difluorodiphenyl sulfone and sodium hydride into a reaction vessel, wherein the molar mass ratio of the indoline to the 4,4' -difluorodiphenyl sulfone to the sodium hydride is 4-4.8 mmol: 0.9-1.1 mmol: 4-4.8mmol, injecting into 2-12ml of N, N dimethyl formamide under the protection of nitrogen, reacting for 10 hours at 100 ℃, naturally cooling to room temperature, pouring the reaction liquid into ice water under stirring, extracting with ethyl acetate for three times, washing with saturated saline solution, performing rotary evaporation on an organic phase to remove a solvent, and performing column chromatography separation and purification to obtain a product, namely bis (4-indolylphenyl) sulfone, wherein the bis (4-indolinylphenyl) sulfone is a compound shown in a general formula II.
6. The use according to claim 1 of a series of compounds of the donor-acceptor type based on diphenyl sulfone and indole derivatives, characterized in that: the fluorescent sensor is applied to detecting the water content of the organic solvent.
7. The use according to claim 6 of a series of compounds of the donor-acceptor type based on diphenyl sulfone and indole derivatives, characterized in that: the application method comprises the following steps:
(1) dissolving a compound of formula I or formula II in a mixed solution of water and tetrahydrofuran;
(2) and measuring the change of system luminescence caused by the change of the volume fraction of the water, thereby detecting the water content in the organic solvent.
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