Synthesis method of novel high-pi conjugated molecule containing benzophosphopentadiene structure
By using benzofosazolecyclopentadiene and thiolete and combined with transition metal catalyst, the problem of synthesis of high π conjugated structure benzofosazolecyclopentadiene in the prior art is solved, and high-efficiency synthesis is achieved Optoelectronic materials with high carrier mobility and stability.
Patent Information
- Application Number
- CN202411510694.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-10-28
- Publication Date
- 2025-02-07
AI Technical Summary
In the prior art, there are fewer methods for synthesizing benzophosphoheteropentadiene compounds, and it is difficult to effectively build a high π conjugated structure, which limits its application in the field of organic photoelectric materials.
By using benzofosazocyclopentadiene compound and thiolide as reaction substrates, combining transition metal catalysts, the C-H bond of benzofosazocyclopentadiene was activated, and a high π-conjugated structure was constructed through cyclization reaction. .
Achieved the efficient synthesis of benzophosphazanocene cyclopentadiene compounds with high π conjugated structure, with rigid conjugation plane, improve carrier mobility and fluorescence efficiency, enhance the stability of the material, and have photoelectricity The potential of the material.
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Figure CN119390729A_ABST
Abstract
Description
Technical Field
[0001] The invention relates to the technical field of phosphorus heterocyclic compounds, and in particular to a method for synthesizing a novel high-π conjugated molecule containing a benzophospholene structure. Background Art
[0002] Phosphorus heterocyclic compounds are widely used in organic synthesis, medicine, and materials science. Among them, benzophosphorus heterocyclic compounds have become an indispensable member of organic conjugated heterocyclic systems due to their unique physical and photoelectric properties, and have great application potential in the field of organic photoelectric materials. At present, there are few known methods for synthesizing such compounds. Therefore, it is very important to develop novel and efficient methods to construct benzophosphorus heterocyclic derivatives.
[0003] The invention uses a benzophosphaolinyl cyclopentadiene compound and a sulfur ylide as reaction substrates, screens a suitable catalyst, catalytically activates the CH bond at the 2-position of the benzophosphaolinyl cyclopentadiene and further cyclizes the benzophosphaolinyl cyclopentadiene, and explores a simple and efficient method for synthesizing a benzophosphaolinyl cyclopentadiene with a high π conjugated structure. The reaction product has both a phosphaolinyl core and a condensed ring structure formed with two benzene rings, forming a four-ring large π conjugated structure, so that the structure has a rigid conjugated plane, can not only ensure high carrier mobility and high fluorescence efficiency, but also significantly improve the stability of the material, and has the potential to be applied to optoelectronic materials. Summary of the invention
[0004] In view of the shortcomings of the prior art, the object of the present invention is to provide a novel method for synthesizing a highly π-conjugated molecule containing a benzophosphole structure.
[0005] A novel method for synthesizing a novel high-π conjugated molecule containing a benzophosphole structure comprises the following steps:
[0006] S1: Synthesis of benzophosphazolyl cyclopentadiene compounds
[0007] Phenyl hypophosphite, 1,1-diphenylethylene and DMAP were added to the reaction tube under argon protection, followed by toluene solvent, and then Tf 2 O was added dropwise to the mixed system and the reaction was stirred at room temperature. Then 3 drops of H 2 O 2 , continue to stir the reaction at room temperature, extract with water and ethyl acetate respectively, combine the extracted organic phases, dry, filter, and remove the solvent by rotary evaporation to purify and obtain the benzophosphazolyl cyclopentadiene compound;
[0008] S2: Synthesis of Sulfur Ylide Compounds
[0009] Under nitrogen protection, add benzoyl chloride and trimethylsulfoxide iodide to a dry reaction bottle, then add DMSO and stir for 5 minutes, add potassium tert-butoxide, raise the temperature to 60°C, stir and react, extract the organic layer with ethyl acetate, wash once with water, then wash once with saturated brine, dry over anhydrous sodium sulfate, separate by column chromatography, and obtain a sulfur ylide compound;
[0010] S3: Synthesis of highly π-conjugated benzophosphorol cyclopentadiene compounds
[0011] Under argon protection, benzophosphoryl cyclopentadiene compound and sulfur ylide compound were added to the reaction bottle, and CH 3 CN was used as solvent, stirred at room temperature, and then CuSO 4 and MeCN as catalysts, heating, stirring and reacting, and after the reaction is complete, the reaction solution is cooled to room temperature, separated and purified by column chromatography, and eluted with an eluent to obtain a high-π-conjugated benzophosphaquinone cyclopentadiene compound.
[0012] Furthermore, step S1 of synthesizing a benzophosphazolyl cyclopentadiene compound comprises the following steps:
[0013] S1.1: 0.02 parts by volume of phenylphosphite, 0.070 parts by volume of 1,1-diphenylethylene and 0.064 parts by volume of DMAP were added to the reaction tube under argon protection, followed by 2 parts by volume of toluene solvent, and then 0.080 parts by volume of Tf 2 O was added dropwise to the mixed system and stirred at room temperature for 6 h;
[0014] S1.2: Monitor the reaction progress by TLC analysis. After the reaction is completed, add 3 drops of H 2 O 2 , continue stirring the reaction at room temperature for 15 min;
[0015] S1.3: Extract with water and ethyl acetate three times respectively, combine the organic phases after extraction, and pass through anhydrous MgSO 4 Dry, filter, and remove the solvent by rotary evaporation;
[0016] S1.4: Finally, the benzophosphaolinyl cyclopentadiene compound is purified by silica gel column chromatography.
[0017] Further, step S2 synthesizes the sulfur ylide compound, comprising the following steps:
[0018] S2.1: Under nitrogen protection, add 0.073 parts by volume of benzoyl chloride and 0.077 parts by volume of trimethylsulfoxide iodide to a dry reaction bottle, add 3 parts by volume of DMSO and stir for 5 minutes, add 0.11 parts by volume of potassium tert-butoxide, heat to 60°C, and stir to react for 1-3 hours;
[0019] S2.2: The reaction was monitored by thin layer chromatography (TLC). After the reaction was complete, the reaction solution was cooled to room temperature and extracted with ethyl acetate three times. The organic layer was washed with water once and then with saturated brine once, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain the sulfur ylide compound.
[0020] Furthermore, step S3 of synthesizing a high π-conjugated benzophosphazolyl cyclopentadiene compound comprises the following steps:
[0021] S3.1: Under argon protection, add the benzophosphoryl cyclopentadiene compound and the sulfur ylide compound in a molar mass ratio of 1:2 into the reaction flask, and add CH 3 CN was used as solvent and stirred at room temperature for 20-40 min;
[0022] S3.2: Add 3-5% CuSO to the total mass of the system 4 and MeCN as a catalyst, heated to 80° C., stirred for 18-24 hours, and detected by thin layer chromatography (TLC). After the reaction is complete, the reaction solution is cooled to room temperature, separated and purified by column chromatography, and eluted with an eluent to obtain a high-π-conjugated benzophosphaquinone cyclopentadiene compound.
[0023] Furthermore, methyl, ethyl, halogen, phenyl, and methoxy groups may be introduced into the benzophosphazolylcyclopentadiene compound and the sulfur ylide compound.
[0024] Furthermore, in step S1.2, H 2 O 2 The concentration is 30wt%.
[0025] Furthermore, in step S1.4, the volume ratio of petroleum aldehyde:ethyl acetate in the silica gel column chromatography is (5-20):1.
[0026] Furthermore, in step S2.2, the volume ratio of n-hexane to ethyl acetate in column chromatography is (8-10):1.
[0027] Furthermore, in step S3.2, the volume ratio of n-hexane to ethyl acetate in the column chromatography method is (6-8):1.
[0028] Furthermore, the eluent in step S3.2 is prepared by mixing petroleum ether and ethyl acetate in a volume ratio of 1:1.
[0029] Compared with the prior art, the present invention has at least the following beneficial effects:
[0030] 1. The present invention develops a new method for constructing a tetracyclic large π conjugated structure compound by activating the C2-position CH bond of benzophosphole catalyzed by transition metals. The method has mild reaction conditions and simple operation, and it not only solves the previous problems of low universality and poor regioselectivity; but also because of its rigid conjugated plane, it not only ensures high carrier mobility and high fluorescence efficiency, but also improves the stability of the material and the subsequent various modified electrical properties. It can not only ensure high carrier mobility and high fluorescence efficiency, but also significantly improve the stability of the material, and has the potential to be applied to optoelectronic materials.
[0031] 2. The novel high-π-conjugated benzophospholinocyclopentadiene molecular compounds synthesized by the present invention are all brand-new organic heterocyclic functional molecules, providing a brand-new chemical substance basis and expanding the diversity of novel benzophospholinocyclopentadiene. BRIEF DESCRIPTION OF THE DRAWINGS
[0032] The accompanying drawings, which are incorporated herein and constitute a part of the specification, illustrate embodiments of the present disclosure and, together with the description, further serve to explain the principles of the present disclosure and to enable those skilled in the relevant art to make and use the present disclosure.
[0033] Figure 1 The present invention is a flowchart of a novel method for synthesizing a highly π-conjugated molecule containing a benzophospholene structure used in an embodiment of the present invention. DETAILED DESCRIPTION
[0034] The following is a detailed description of a novel method for synthesizing a high π-conjugated molecule containing a benzophosphopentene structure provided by the present invention in conjunction with the accompanying drawings and specific embodiments. At the same time, it is explained here that in order to make the embodiments more detailed, the following embodiments are the best and preferred embodiments, and those skilled in the art may also adopt other alternatives to implement some known technologies; and the accompanying drawings are only for a more specific description of the embodiments, and are not intended to specifically limit the present invention.
[0035] Embodiment 1:
[0036] A novel method for synthesizing highly π-conjugated molecules containing benzophospholene structures, such as Figure 1 As shown, the following steps are included:
[0037] S1: Synthesis of benzophosphazolyl cyclopentadiene compounds
[0038] S1.1: 0.02 parts by volume of phenylphosphite, 0.07 parts by volume of 1,1-diphenylethylene and 0.064 parts by volume of DMAP were added to the reaction tube under argon protection, followed by 2 parts by volume of toluene solvent, and then 0.08 parts by volume of Tf 2 O was added dropwise to the mixed system and stirred at room temperature for 6 h;
[0039] S1.2: Monitor the reaction progress by TLC analysis. After the reaction is completed, add 3 drops of 30 wt% H 2 O 2 , continue stirring the reaction at room temperature for 15 min;
[0040] S1.3: Extract with water and ethyl acetate three times respectively, combine the organic phases after extraction, and pass through anhydrous MgSO 4 Dry, filter, and remove the solvent by rotary evaporation;
[0041] S1.4: Finally, the benzophosphorol cyclopentadiene compound is purified by silica gel column chromatography, and the volume ratio of petroleum aldehyde:ethyl acetate in silica gel column chromatography is 20:1.
[0042] The reaction route of this step is:
[0043]
[0044] S2: Synthesis of Sulfur Ylide Compounds
[0045] S2.1: Under nitrogen protection, add 0.073 parts by volume of benzoyl chloride and 0.077 parts by volume of trimethylsulfoxide iodide to a dry reaction bottle, add 3 parts by volume of DMSO and stir for 5 minutes, add 0.11 parts by volume of potassium tert-butoxide, heat to 60°C, and stir for 3 hours;
[0046] S2.2: The reaction was detected by thin layer chromatography (TLC). After the reaction was complete, the reaction solution was cooled to room temperature and extracted with ethyl acetate three times. The organic layer was washed with water once and then with saturated brine once, dried over anhydrous sodium sulfate, and separated by column chromatography. The volume ratio of n-hexane to ethyl acetate in column chromatography was 10:1 to obtain a sulfur ylide compound.
[0047] The reaction route of this step is:
[0048]
[0049] S3: Synthesis of highly π-conjugated benzophosphorol cyclopentadiene compounds
[0050] S3.1: Under argon protection, add the benzophosphoryl cyclopentadiene compound and the sulfur ylide compound in a molar mass ratio of 1:2 into the reaction flask, and add CH 3 CN was used as solvent and stirred at room temperature for 40 min;
[0051] S3.2: Add 5% CuSO to the total mass of the system 4and MeCN as catalyst, heated to 80°C, stirred for 24 hours, and detected by thin layer chromatography (TLC). After the reaction is complete, the reaction solution is cooled to room temperature and separated and purified by column chromatography. The volume ratio of n-hexane to ethyl acetate in column chromatography is 8:1, and the eluent is eluted. The eluent is a mixture of petroleum ether and ethyl acetate in a volume ratio of 1:1 to obtain a high π-conjugated benzophosphorocyclopentadiene compound.
[0052] The reaction route of this step is:
[0053]
[0054] Methyl, ethyl, halogen, phenyl, and methoxy groups can be introduced into benzophosphorylcyclopentadiene compounds and sulfur ylide compounds. The reaction route is as follows:
[0055]
[0056] Embodiment 2:
[0057] A novel method for synthesizing highly π-conjugated molecules containing benzophospholene structures, such as Figure 1 As shown, the following steps are included:
[0058] S1: Synthesis of benzophosphazolyl cyclopentadiene compounds
[0059] S1.1: 0.02 parts by volume of phenylphosphite, 0.07 parts by volume of 1,1-diphenylethylene and 0.064 parts by volume of DMAP were added to the reaction tube under argon protection, followed by 2 parts by volume of toluene solvent, and then 0.08 parts by volume of Tf 2 O was added dropwise to the mixed system and stirred at room temperature for 6 h;
[0060] S1.2: Monitor the reaction progress by TLC analysis. After the reaction is completed, add 3 drops of 30 wt% H 2 O 2 , continue stirring the reaction at room temperature for 15 min;
[0061] S1.3: Extract with water and ethyl acetate three times respectively, combine the organic phases after extraction, and pass through anhydrous MgSO 4 Dry, filter, and remove the solvent by rotary evaporation;
[0062] S1.4: Finally, the benzophosphorol cyclopentadiene compound is purified by silica gel column chromatography, and the volume ratio of petroleum aldehyde:ethyl acetate in silica gel column chromatography is 5:1.
[0063] S2: Synthesis of Sulfur Ylide Compounds
[0064] S2.1: Under nitrogen protection, add 0.073 parts by volume of benzoyl chloride and 0.077 parts by volume of trimethylsulfoxide iodide to a dry reaction bottle, add 3 parts by volume of DMSO and stir for 5 minutes, add 0.11 parts by volume of potassium tert-butoxide, heat to 60°C, and stir for 1 hour;
[0065] S2.2: The reaction was detected by thin layer chromatography (TLC). After the reaction was complete, the reaction solution was cooled to room temperature and extracted with ethyl acetate three times. The organic layer was washed with water once and then with saturated brine once, dried over anhydrous sodium sulfate, and separated by column chromatography. The volume ratio of n-hexane to ethyl acetate in column chromatography was 8:1 to obtain a sulfur ylide compound.
[0066] S3: Synthesis of highly π-conjugated benzophosphorol cyclopentadiene compounds
[0067] S3.1: Under argon protection, add the benzophosphoryl cyclopentadiene compound and the sulfur ylide compound in a molar mass ratio of 1:2 into the reaction flask, and add CH 3 CN was used as solvent and stirred at room temperature for 20 min;
[0068] S3.2: Add 5% CuSO to the total mass of the system 4 and MeCN as catalyst, heated to 80°C, stirred for 18 hours, and detected by thin layer chromatography (TLC). After the reaction is complete, the reaction solution is cooled to room temperature and separated and purified by column chromatography. The volume ratio of n-hexane to ethyl acetate in column chromatography is 6:1, and eluted with an eluent, which is a mixture of petroleum ether and ethyl acetate in a volume ratio of 1:1, to obtain a high π-conjugated benzophosphorocyclopentadiene compound.
[0069] Embodiment 3:
[0070] A novel method for synthesizing highly π-conjugated molecules containing benzophospholene structures, such as Figure 1 As shown, the following steps are included:
[0071] S1: Synthesis of benzophosphazolyl cyclopentadiene compounds
[0072] S1.1: 0.02 parts by volume of phenylphosphite, 0.07 parts by volume of 1,1-diphenylethylene and 0.064 parts by volume of DMAP were added to the reaction tube under argon protection, followed by 2 parts by volume of toluene solvent, and then 0.08 parts by volume of Tf 2 O was added dropwise to the mixed system and stirred at room temperature for 6 h;
[0073] S1.2: Monitor the reaction progress by TLC analysis. After the reaction is completed, add 3 drops of 30 wt% H 2 O 2 , continue stirring the reaction at room temperature for 15 min;
[0074] S1.3: Extract with water and ethyl acetate three times respectively, combine the organic phases after extraction, and pass through anhydrous MgSO 4 Dry, filter, and remove the solvent by rotary evaporation;
[0075] S1.4: Finally, the benzophosphorol cyclopentadiene compound is purified by silica gel column chromatography, and the volume ratio of petroleum aldehyde:ethyl acetate in silica gel column chromatography is 20:1.
[0076] S2: Synthesis of Sulfur Ylide Compounds
[0077] S2.1: Under nitrogen protection, add 0.073 parts by volume of benzoyl chloride and 0.077 parts by volume of trimethylsulfoxide iodide to a dry reaction bottle, add 3 parts by volume of DMSO and stir for 5 minutes, add 0.11 parts by volume of potassium tert-butoxide, heat to 60°C, and stir for 3 hours;
[0078] S2.2: The reaction was detected by thin layer chromatography (TLC). After the reaction was complete, the reaction solution was cooled to room temperature and extracted with ethyl acetate three times. The organic layer was washed with water once and then with saturated brine once, dried over anhydrous sodium sulfate, and separated by column chromatography. The volume ratio of n-hexane to ethyl acetate in column chromatography was 10:1 to obtain a sulfur ylide compound.
[0079] S3: Synthesis of highly π-conjugated benzophosphorol cyclopentadiene compounds
[0080] S3.1: Under argon protection, add the benzophosphoryl cyclopentadiene compound and the sulfur ylide compound in a molar mass ratio of 1:2 into the reaction flask, and add CH 3 CN was used as solvent and stirred at room temperature for 40 min;
[0081] S3.2: Add 3% CuSO to the total mass of the system 4 and MeCN as catalyst, heated to 80°C, stirred for 24 hours, and detected by thin layer chromatography (TLC). After the reaction is complete, the reaction solution is cooled to room temperature and separated and purified by column chromatography. The volume ratio of n-hexane to ethyl acetate in column chromatography is 8:1, and the eluent is eluted. The eluent is a mixture of petroleum ether and ethyl acetate in a volume ratio of 1:1 to obtain a high π-conjugated benzophosphorocyclopentadiene compound.
[0082] The yields of the high-π-conjugated benzophosphaolinyl cyclopentadiene compounds of Examples 1-3 were calculated, as shown in Table 1.
[0083] Table 1
[0084] Yield (%) Example 1 87 Example 2 85 Example 3 81
[0085] It can be seen that the solution ratio and the amount of catalyst in the column chromatography will affect the high-π-conjugated benzophosphazolylcyclopentadiene compound. The catalyst addition amount of Example 1 with the highest yield is 5% of the total mass of the system.
[0086] The above embodiments are merely illustrative of the principles and effects of the present invention, and are not intended to limit the present invention. Anyone familiar with the art may modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all modifications or alterations made by a person of ordinary skill in the art without departing from the spirit and technical concept disclosed by the present invention shall still be covered by the claims of the present invention.
Claims
1. A method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure, characterized in that: The steps include: S1: Synthesis of benzophosphazolyl cyclopentadiene compounds Phenyl hypophosphorous acid, 1,1-diphenylethylene and DMAP are added to a reaction tube under argon protection, and then a toluene solvent is added, and then Tf2O is added dropwise to the mixed system, and the mixture is stirred and reacted at room temperature, and then 3 drops of H2O2 are added dropwise to the reaction system, and the mixture is stirred and reacted at room temperature, and the mixture is extracted with water and ethyl acetate respectively, and the organic phases after the extraction are combined, dried, filtered, and the solvent is removed by rotary evaporation, and the benzophosphazolyl cyclopentadiene compound is purified; S2: Synthesis of Sulfur Ylide Compounds Under nitrogen protection, add benzoyl chloride and trimethylsulfoxide iodide to a dry reaction bottle, then add DMSO and stir for 5 minutes, add potassium tert-butoxide, raise the temperature to 60°C, stir and react, extract the organic layer with ethyl acetate, wash once with water, then wash once with saturated brine, dry over anhydrous sodium sulfate, separate by column chromatography, and obtain a sulfur ylide compound; S3: Synthesis of highly π-conjugated benzophosphorol cyclopentadiene compounds Under the protection of argon, a benzophosphaolinol cyclopentadiene compound and a sulfur ylide compound are added to a reaction bottle, and CH3CN is added as a solvent, and stirred at room temperature. CuSO4 and MeCN are then added as catalysts, heated, and stirred to react. After the reaction is complete, the reaction solution is cooled to room temperature, separated and purified by column chromatography, and eluted with an eluent to obtain a high-π-conjugated structure benzophosphaolinol cyclopentadiene compound.
2. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 1, characterized in that: Step S1 synthesizes a benzophosphazolyl cyclopentadiene compound, comprising the following steps: S1.1: 0.02 parts by volume of phenylphosphite, 0.070 parts by volume of 1,1-diphenylethylene and 0.064 parts by volume of DMAP were added to a reaction tube under argon protection, followed by adding 2 parts by volume of toluene solvent, and then 0.080 parts by volume of Tf2O was added dropwise to the mixed system, and stirred at room temperature for 6 hours; S1.2: Monitor the progress of the reaction by TLC analysis. After the reaction is completed, add 3 drops of H2O2 to the reaction system and continue stirring the reaction at room temperature for 15 minutes; S1.3: Extract with water and ethyl acetate three times respectively, combine the organic phases after extraction, dry over anhydrous MgSO4, filter, and remove the solvent by rotary evaporation; S1.4: Finally, the benzophosphaolinol cyclopentadiene compound is purified by silica gel column chromatography.
3. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 2, characterized in that: Step S2 synthesizes the sulfur ylide compound, comprising the following steps: S2.1: Under nitrogen protection, add 0.073 parts by volume of benzoyl chloride and 0.077 parts by volume of trimethylsulfoxide iodide to a dry reaction bottle, add 3 parts by volume of DMSO and stir for 5 minutes, add 0.11 parts by volume of potassium tert-butoxide, heat to 60°C, and stir to react for 1-3 hours; S2.2: The reaction was monitored by thin layer chromatography (TLC). After the reaction was complete, the reaction solution was cooled to room temperature and extracted with ethyl acetate three times. The organic layer was washed with water once and then with saturated brine once, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain the sulfur ylide compound.
4. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 3, characterized in that: S3 synthesizes a high π-conjugated benzophosphazolyl cyclopentadiene compound, comprising the following steps: S3.1: under argon protection, add the benzophosphoryl cyclopentadiene compound and the sulfur ylide compound in a molar mass ratio of 1:2 into a reaction bottle, add CH3CN as a solvent, and stir at room temperature for 20-40 minutes; S3.2: Add 3-5% CuSO4 and MeCN as catalysts to the total mass of the system, heat to 80°C, stir and react for 18-24 hours, and detect the reaction by thin layer chromatography (TLC). After the reaction is complete, the reaction solution is cooled to room temperature, separated and purified by column chromatography, and eluted with an eluent to obtain a high-π-conjugated benzophosphazolyl cyclopentadiene compound.
5. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 4, characterized in that: Methyl, ethyl, halogen, phenyl, and methoxy groups can be introduced into the benzophospholocyclopentadiene compounds and the sulfur ylide compounds.
6. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 5, characterized in that: The H2O2 concentration in step S1.2 is 30wt%.
7. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 6, characterized in that: The volume ratio of petroleum aldehyde to ethyl acetate in the silica gel column chromatography in step S1.4 is (5-20):
1.
8. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 7, characterized in that: In step S2.2, the volume ratio of n-hexane to ethyl acetate in column chromatography is (8-10):
1.
9. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 8, characterized in that: The volume ratio of n-hexane to ethyl acetate in the column chromatography in step S3.2 is (6-8):
1.
10. The method for synthesizing a novel high π-conjugated molecule containing a benzophosphole structure according to claim 9, characterized in that: The eluent in step S3.2 is prepared by mixing petroleum ether and ethyl acetate in a volume ratio of 1:1.