A red-light nitrogen-thiadinonahelite and its synthesis method and application

Abstract

The invention relates to the technical field of a process for synthesizing helicene compounds, and in particular to a red-light nitrogen-thiabis-nonahelite and a synthesis method and application thereof. The invention comprises the following steps: using benzothiophene-2-boric acid as a raw material, adding 2-bromo-4-(tert-butyl)-1-iodobenzene, a catalyst and anhydrous potassium carbonate, and heating to obtain compound 2; using compound 2 as a raw material, adding n-butyl lithium for reaction, and then adding trimethyl borate to obtain compound 3; using compound 3 as a raw material, adding 1-bromo-3,6-diiodocarbazole, a catalyst and anhydrous potassium carbonate, and heating to obtain compound 4; using compound 4 as a raw material, adding an anhydrous ferric chloride solution dissolved in nitromethane to obtain compound 5; using compound 5 as a raw material, adding sodium tert-butoxide, a catalyst and a phosphine ligand, and heating to obtain compound 6, a red-light nitrogen-thiabis-nonahelite. The invention embeds an antiaromatic module into a helicene system, and finally obtains a nitrogen-thiabis-nonahelite compound with orange-red fluorescence emission.

Description

Technical Field

[0001] The present invention relates to the technical field of synthesis technology of helicene compounds, and in particular to a red-light nitrogen-thiadinonahelite helicene and a synthesis method and application thereof. Background Art

[0002] Chirality is a fundamental property of nature, referring to the property of an object being similar to, but not identical to, its mirror image. Chirality is ubiquitous in the material world, from small molecules to macromolecules. In the field of organic small molecules, chirality is primarily categorized as central chirality, helical chirality, planar chirality, and axial chirality.

[0003] Helicene and its derivatives are typical helical chiral compounds. They are unique polycyclic aromatic hydrocarbons with a non-planar helical backbone formed by ortho-fused benzene or other aromatic rings. Helicene compounds often exhibit unique chiral optical properties, and the π-conjugated system of helicene can be expanded by introducing other heteroatoms or luminescent groups into the backbone, making them ideal backbones for the design and synthesis of excellent circularly polarized luminescence properties. Helical nanographene structures have attracted great interest due to their unique kinetic behavior and thermodynamic properties, and have broad application prospects in 3D displays, optical switches, and chiral sensing.

[0004] Compared to monohelicene, dihelicenes offer greater synthetic novelty, providing design strategies for the synthesis of novel helicene topologies. Furthermore, the increased π-conjugation of dihelicenes favors a red-shift in fluorescence spectra and enhanced luminescence properties. Furthermore, studying the chiral luminescence properties of dihelicenes can provide insights into the nature of chirality. However, due to the difficulty in synthesizing dihelicene polycyclic aromatic hydrocarbons, high-performance circularly polarized luminescent dihelicene compounds are rare, especially reports of dihelicene compounds emitting long-wavelength red or near-infrared light. However, long-wavelength emitting chiral molecules have attracted widespread attention in liquid crystal materials, biomedicine, and photodetectors.

[0005] Antiaromatic π-conjugated systems have attracted widespread attention as core frameworks for organic optoelectronic materials. Embedding antiaromatic modules into π-conjugated systems often yields near-infrared photophysical properties and multiple redox behaviors. However, existing methods for synthesizing antiaromatic polycyclic aromatic hydrocarbons (PAHs) are difficult, and the resulting products exhibit poor performance. Summary of the Invention

[0006] In view of the deficiencies of the above-mentioned prior art, the purpose of the present invention is to provide a red-light nitrogen-thiabis-nonahelite and its synthesis method and application. The present invention embeds an antiaromatic module into the bihelicene system, and finally obtains a nitrogen-thiabis-nonahelite compound with orange-red fluorescence emission.

[0007] In order to solve the above technical problems, the present invention adopts the following technical solutions:

[0008] A method for synthesizing red-light nitrogen-thiadinonahelite comprises the following steps:

[0009] In a mixed solvent of an organic solvent and water, benzothiophene-2-boronic acid is used as the raw material. 2-bromo-4-(tert-butyl)-1-iodobenzene, a palladium catalyst, and anhydrous potassium carbonate are added thereto under a protective atmosphere. The reaction is heated, and the iodine in the 2-bromo-4-(tert-butyl)-1-iodobenzene undergoes oxidative addition with the palladium catalyst to generate organopalladium intermediate 1. Anhydrous potassium carbonate removes the halogen from organopalladium intermediate 1 and combines with it to form organopalladium intermediate 2. After combining with alkaline potassium carbonate, benzothiophene-2-boronic acid undergoes transmetallation with organopalladium intermediate 2, the boronic acid is removed, and the original group connected to the boronic acid combines with palladium. Finally, compound 2 is obtained through reduction elimination.

[0010] In an organic solvent, compound 2 is used as a raw material. Under a protective atmosphere, n-butyl lithium is added thereto to react, and then trimethyl borate is added. n-butyl lithium removes the halogen from compound 2. After the halogen is removed, the carbon here negatively attacks trimethyl borate, and compound 3 is obtained through subsequent acidification.

[0011] In a mixed solvent of an organic solvent and water, compound 3 is used as a raw material. Under a protective atmosphere, 1-bromo-3,6-diiodocarbazole, a palladium catalyst and anhydrous potassium carbonate are added thereto. The reaction is heated, and 1-bromo-3,6-diiodocarbazole and the palladium catalyst undergo oxidative addition to generate an organopalladium intermediate 3. Anhydrous potassium carbonate removes the halogen in the organopalladium intermediate 3 and combines with it to form an organopalladium intermediate 4. After compound 3 combines with alkaline potassium carbonate, it is transmetallated with the organopalladium intermediate 4, and the boronic acid in compound 3 is removed. The original group connected to the boronic acid combines with palladium, and finally compound 4 is obtained through reduction elimination.

[0012] In an organic solvent, compound 4 is used as a raw material, and an anhydrous ferric chloride solution dissolved in nitromethane is added thereto under a protective atmosphere to carry out an oxidative dehydrogenation cyclization reaction to obtain compound 5.

[0013] In an organic solvent, compound 5 is used as a raw material. Under a protective atmosphere, sodium tert-butoxide, a palladium catalyst and a phosphine ligand are added thereto. The reaction is heated. First, the halogenated hydrocarbon undergoes oxidative addition with the palladium catalyst. The NH bond in compound 5 further undergoes oxidative addition with the palladium catalyst. The base removes the H on the N. Finally, the final product, compound 6 red-light nitrogen-thiadinonahelite, is obtained by reduction elimination.

[0014] The synthetic route is:

[0015] .

[0016] The present invention embeds an antiaromatic module into a dispirene system, and the synthesized dispirene compound has strong stability and good luminescence performance, and the solid has strong orange-red light emission.

[0017] In a preferred embodiment of the present invention, the mass ratio of benzothiophene-2-boric acid to 2-bromo-4-(tert-butyl)-1-iodobenzene is 6.3:10, the mass ratio of the palladium catalyst to benzothiophene-2-boric acid is 0.414-0.6:6.3, and the mass ratio of anhydrous potassium carbonate to benzothiophene-2-boric acid is 10.2:6.3.

[0018] In a preferred embodiment of the present invention, when synthesizing compound 2, the heating reaction temperature is 80° C., and the heating reaction time is 12 h to 15 h.

[0019] In a preferred embodiment of the present invention, the usage ratio of compound 2 to n-butyl lithium and trimethyl borate is 11.5 g:16 mL:20 g to 30 g.

[0020] In a preferred embodiment of the present invention, when preparing compound 3, the reaction temperature is increased from -78°C to room temperature.

[0021] In a preferred embodiment of the present invention, the mass ratio of compound 3 to 1-bromo-3,6-diiodocarbazole is 5.24:4, the mass ratio of palladium catalyst to compound 3 is 0.426~0.6:5.24, the mass ratio of anhydrous sodium carbonate to compound 3 is 2.78:5.24, and the heating reaction temperature for preparing compound 4 is 100°C.

[0022] In a preferred embodiment of the present invention, the dosage ratio of compound 4 to anhydrous ferric chloride solution dissolved in nitromethane is 500 mg:10 mL, and the dosage ratio of nitromethane solution to anhydrous ferric chloride is 10 mL~1 g~1.5 g.

[0023] In a preferred embodiment of the present invention, the mass ratio of compound 5 to sodium tert-butoxide is 2:1, the mass ratio of palladium catalyst to compound 5 is 1:4, and the mass ratio of phosphine ligand to compound 5 is 8:25.

[0024] The second object of the present invention is to provide a red-light nitrogen-thiadinonahelite, the structural formula of which is:

[0025] .

[0026] The plane structure after rotation at different angles is as follows:

[0027] .

[0028] The third object of the present invention is to provide an application of the above-mentioned red-light emitting nitrogen-thiadinonahelite in organic photoelectric materials.

[0029] Compared with the prior art, the present invention has the following beneficial effects:

[0030] The present invention provides a method for synthesizing red-light nitrogen-thiabis-nonaspirene, which uses benzothiophene-2-boric acid as a raw material, adds 2-bromo-4-(tert-butyl)-1-iodobenzene, a catalyst and anhydrous potassium carbonate to the compound under a protective atmosphere, heats the compound, and generates a Suzuki-Miyaura catalytic coupling reaction to obtain compound 2. Then, using compound 2 as a raw material, n-butyl lithium is added to the compound under a protective atmosphere to react, and then trimethyl borate is added. The n-butyl lithium removes the halogen atom in compound 2, and then the carbon negative attacks the trimethyl borate to obtain compound 3 through acidification. Then, using compound 3 as a raw material, 1-bromo-3,6-diiodocarbazole, a catalyst and anhydrous potassium carbonate are added to the compound under a protective atmosphere. Potassium carbonate is heated to cause a Suzuki-Miyaura catalytic coupling reaction to obtain compound 4. Using compound 4 as a raw material, an anhydrous ferric chloride solution dissolved in nitromethane is added thereto under a protective atmosphere to carry out an oxidative dehydrogenation cyclization reaction to obtain compound 5. Finally, using compound 5 as a raw material, sodium tert-butoxide, a catalyst and a phosphine ligand are added thereto under a protective atmosphere, and heating is carried out to cause a Buchwald-Hartwig carbon-nitrogen metal catalytic coupling reaction to obtain compound 6, a red-light nitrogen-thiadinonahelite. The present invention embeds an antiaromatic module into the bishelioxene system, and the synthesized bishelioxene compound has strong stability, good luminescence performance, and the solid has strong orange-red light emission. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 This is the H NMR spectrum of compound 6 prepared in Example 1 of the present invention.

[0032] Figure 2 This is the mass spectrum of compound 6 prepared in Example 1 of the present invention.

[0033] Figure 3 These are the absorption and emission spectra of compound 6 prepared in Example 1 of the present invention in toluene and dichloromethane, as well as its solid-state emission spectrum. DETAILED DESCRIPTION

[0034] The following is a detailed description of the technical solutions in the embodiments of the present invention, using preferred embodiments and accompanying drawings in conjunction with the embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0035] It should be noted that all professional terms used in the present invention are only for the purpose of describing specific embodiments and are not intended to limit the scope of protection of the present invention. Unless otherwise specified, the various raw materials, reagents, instruments and equipment used in the following embodiments of the present invention can be purchased from the market or prepared by existing methods.

[0036] Example 1

[0037] A method for synthesizing red-light nitrogen-thiadinonahelite comprises the following steps:

[0038] The synthetic route is as follows:

[0039] .

[0040] (1) 6.3 g of compound 1, benzothiophene-2-boronic acid, 10 g of 2-bromo-4-(tert-butyl)-1-iodobenzene, 414 mg of Pd(PPh3)2Cl2 catalyst, and 10.2 g of anhydrous potassium carbonate were placed in a reaction flask. 160 mL of ethylene glycol dimethyl ether and 22 mL of water were added. The mixture was deoxygenated three times under nitrogen protection. The mixture was heated and stirred at 80 °C for 12 h. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The organic phases were combined and purified by column chromatography to obtain compound 2 with a yield of 40%.

[0041] (2) Weigh 11.5 g of compound 2 and place it in a reaction flask. Replace nitrogen three times, add anhydrous tetrahydrofuran from the purification system, and place the reaction flask in a -78 °C cryostat after replenishing nitrogen. Slowly add 16 mL of 2.5 M n-butyl lithium and stir at -78 °C for 1 hour. After 1 hour, slowly add 30 g of trimethyl borate. After the addition is completed, turn off the refrigeration and stir overnight to slowly return to room temperature. After the reaction is completed, add dilute hydrochloric acid to the reaction flask and extract with ethyl acetate. Combine the organic phases, dry them, and recrystallize them with n-hexane to obtain compound 3 with a yield of 84%.

[0042] (3) 5.24 g of compound 3, 4 g of 1-bromo-3,6-diiodocarbazole, 426 mg of Pd(PPh3)4 catalyst, and 2.78 g of anhydrous potassium carbonate were placed in a reaction flask, and a mixed solvent of toluene, ethanol, and water in a volume ratio of 40:20:20 was added. The mixture was frozen and deoxygenated three times under nitrogen protection, and the reaction was refluxed with heating and stirring overnight for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The organic phases were combined and purified by column chromatography to obtain compound 4 with a yield of 70%.

[0043] (4) Weigh 500 mg of compound 4 and place it in a reaction flask. Replace nitrogen three times and fill the reaction flask with nitrogen. Add anhydrous dichloromethane and cool the reaction flask to 0°C. Take another vial and add 1.1 g of anhydrous ferric chloride. Add nitromethane solution to the vial and allow the nitromethane solution to dissolve the ferric chloride solid by ultrasonication. Slowly add the ferric chloride-nitromethane solution dropwise to the reaction flask and stir at 0°C for one hour. After the reaction is completed, quench the reaction with saturated sodium bicarbonate aqueous solution and extract with dichloromethane solution. Combine the organic layers and purify by column chromatography to obtain compound 5 with a yield of 50%.

[0044] (5) 100 mg of compound 5, 50 mg of sodium tert-butoxide, 25 mg of Pd2dba3 catalyst, 32 mg of P( t The phosphine ligand (-Bu)3HBF4 was placed in a reaction flask, and anhydrous toluene was added. The mixture was deoxygenated three times under nitrogen and heated with stirring under reflux overnight for 15 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The combined organic phases were purified by column chromatography and recrystallized to obtain compound 6 in a 20% yield.

[0045] The H NMR spectrum data of compound 6 are: 1 H NMR (400 MHz, chloroform) δ 9.57 (s, 2H), 9.28 (d, J = 8 Hz, 2H), 9.03 (d, J = 8 Hz, 2H), 8.93 (d, J = 8 Hz, 4H), 7.93 (m, ,4H), 7.79-7.74 (m, 4H), 7.67 (d, J = 8 Hz, 4H), 6.80 – 6.73 (m, 4H), 6.53 (d,J = 8 Hz, 2H), 6.34 (d, J = 8 Hz, 2H), 5.86 – 5.79 (m, 4H), 1.56 (s, 36H).

[0046] Example 2

[0047] A method for synthesizing red-light nitrogen-thiadinonahelite comprises the following steps:

[0048] The synthetic route is as follows:

[0049] .

[0050] (1) 6.3 g of compound 1, benzothiophene-2-boronic acid, 10 g of 2-bromo-4-(tert-butyl)-1-iodobenzene, 500 mg of Pd(PPh3)2Cl2 catalyst, and 10.2 g of anhydrous potassium carbonate were placed in a reaction flask. 160 mL of ethylene glycol dimethyl ether and 22 mL of water were added. The mixture was deoxygenated three times under nitrogen protection. The mixture was heated and stirred at 80 °C for 13 h. After the reaction was completed, the temperature was cooled to room temperature, extracted with ethyl acetate, and the organic phases were combined and purified by column chromatography to obtain compound 2.

[0051] (2) Weigh 11.5 g of compound 2 and place it in a reaction flask. Replace nitrogen three times, add anhydrous tetrahydrofuran from the purification system, and place the reaction flask in a -78 °C cryostat after replenishing nitrogen. Slowly add 16 mL of 2.5 M n-butyl lithium and stir at -78 °C for 1 hour. After 1 hour, slowly add 20 g of trimethyl borate. After the addition is completed, turn off the refrigeration and stir overnight to slowly return to room temperature. After the reaction is completed, add dilute hydrochloric acid to the reaction flask and extract with ethyl acetate. Combine the organic phases, dry them, and recrystallize them with n-hexane to obtain compound 3.

[0052] (3) 5.24 g of compound 3, 4 g of 1-bromo-3,6-diiodocarbazole, 500 mg of Pd(PPh3)4 catalyst, and 2.78 g of anhydrous potassium carbonate were placed in a reaction flask, and a mixed solvent of toluene, ethanol, and water in a volume ratio of 40:20:20 was added. The mixture was frozen and deoxygenated three times under nitrogen protection, and the reaction was heated and stirred to reflux overnight for 12 h. After the reaction was completed, the temperature was cooled to room temperature, extracted with ethyl acetate, and the organic phases were combined and purified by column chromatography to obtain compound 4.

[0053] (4) Weigh 500 mg of compound 4 and place it in a reaction flask. Replace nitrogen three times and fill the flask with nitrogen. Add anhydrous dichloromethane and cool the flask to 0°C. Take another vial and add 1.0 g of anhydrous ferric chloride. Add nitromethane solution to the vial and allow the nitromethane solution to dissolve the ferric chloride solid by ultrasonication. Slowly add the ferric chloride-nitromethane solution dropwise to the reaction flask and stir at 0°C for one hour. After the reaction is complete, quench the reaction with saturated sodium bicarbonate aqueous solution and extract with dichloromethane solution. Combine the organic layers and purify by column chromatography to obtain compound 5.

[0054] (5) 100 mg of compound 5, 50 mg of sodium tert-butoxide, 25 mg of Pd2dba3 catalyst, 32 mg of P( t The phosphine ligand (-Bu)3HBF4 was placed in a reaction flask, and anhydrous toluene was added. The mixture was deoxygenated three times under nitrogen and heated with stirring under reflux overnight for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The organic phases were combined, purified by column chromatography, and recrystallized to obtain compound 6.

[0055] Example 3

[0056] A method for synthesizing red-light nitrogen-thiadinonahelite comprises the following steps:

[0057] The synthetic route is as follows:

[0058] .

[0059] (1) 6.3 g of compound 1, benzothiophene-2-boronic acid, 10 g of 2-bromo-4-(tert-butyl)-1-iodobenzene, 600 mg of Pd(PPh3)2Cl2 catalyst, and 10.2 g of anhydrous potassium carbonate were placed in a reaction flask. 160 mL of ethylene glycol dimethyl ether and 22 mL of water were added. The mixture was deoxygenated three times under nitrogen protection. The mixture was heated and stirred at 80 °C for 15 h. After the reaction was completed, the temperature was cooled to room temperature, extracted with ethyl acetate, and the organic phases were combined and purified by column chromatography to obtain compound 2.

[0060] (2) Weigh 11.5 g of compound 2 and place it in a reaction flask. Replace nitrogen three times, add anhydrous tetrahydrofuran from the purification system, and place the reaction flask in a -78 °C cryostat after replenishing nitrogen. Slowly add 16 mL of 2.5 M n-butyl lithium and stir at -78 °C for 1 hour. After 1 hour, slowly add 25 g of trimethyl borate and turn off the refrigeration after the addition. Stir overnight and slowly return to room temperature. After the reaction is completed, add dilute hydrochloric acid to the reaction flask and extract with ethyl acetate. Combine the organic phases, dry them, and recrystallize them with n-hexane to obtain compound 3.

[0061] (3) 5.24 g of compound 3, 4 g of 1-bromo-3,6-diiodocarbazole, 600 mg of Pd(PPh3)4 catalyst, and 2.78 g of anhydrous potassium carbonate were placed in a reaction flask, and a mixed solvent of toluene, ethanol, and water in a volume ratio of 40:20:20 was added. The mixture was frozen and deoxygenated three times under nitrogen protection, and the reaction was refluxed with heating and stirring overnight for 12 hours. After the reaction was completed, the temperature was cooled to room temperature, extracted with ethyl acetate, and the organic phases were combined and purified by column chromatography to obtain compound 4.

[0062] (4) Weigh 500 mg of compound 4 and place it in a reaction flask. Replace nitrogen three times and fill the flask with nitrogen. Add anhydrous dichloromethane and cool the flask to 0°C. Take another vial and add 1.5 g of anhydrous ferric chloride. Add nitromethane solution to the vial and allow the nitromethane solution to dissolve the ferric chloride solid by ultrasonication. Slowly add the ferric chloride-nitromethane solution dropwise to the reaction flask and stir at 0°C for one hour. After the reaction is complete, quench the reaction with saturated sodium bicarbonate aqueous solution and extract with dichloromethane solution. Combine the organic layers and purify by column chromatography to obtain compound 5.

[0063] (5) 100 mg of compound 5, 50 mg of sodium tert-butoxide, 25 mg of Pd2dba3 catalyst, 32 mg of P( t The phosphine ligand (-Bu)3HBF4 was placed in a reaction flask, and anhydrous toluene was added. The mixture was deoxygenated three times under nitrogen and heated with stirring under reflux overnight for 14 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The organic phases were combined, purified by column chromatography, and recrystallized to obtain compound 6.

[0064] The synthesis methods of Examples 2 and 3 are the same as those of Example 1, except that the amounts of certain raw materials and the reaction conditions are changed. The methods of Examples 2 and 3 can also be used to synthesize red-light-emitting nitrogen-thiadinonahylidene with strong orange-red light emission.

[0065] Result Analysis

[0066] Depend on Figure 1 It can be seen that according to the characteristic peaks and integration of NMR, the product can be confirmed to be the designed product red-light nitrogen-thiadinonahelite. Figure 2 The molecular weight of the mass spectrum peak is consistent with the molecular weight of the designed molecule, which once again verifies the correctness of the product. Figure 3 The maximum fluorescence emission peak is at 510 nm, with another at 560 nm, indicating green fluorescence in the liquid state. Its solid-state emission peaks are at 580 nm and 620 nm, indicating orange-red fluorescence in the solid state. This study embeds an antiaromatic module into a dihelicene system, ultimately yielding a nitrogen-thiadihelicene compound with orange-red fluorescence.

[0067] It should be noted that when the present invention relates to numerical ranges, it should be understood that both endpoints of each numerical range and any value between the two endpoints can be selected. Since the steps and methods used are the same as those in the embodiments, in order to avoid redundancy, the present invention describes the preferred embodiments. Although the preferred embodiments of the present invention have been described, those skilled in the art may make additional changes and modifications to these embodiments once they understand the basic inventive concepts. Therefore, the attached protection scope is intended to be interpreted as including the preferred embodiments and all changes and modifications that fall within the scope of the present invention.

[0068] Obviously, those skilled in the art may make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. Thus, if such changes and modifications fall within the scope of the present invention and its equivalents, the present invention is intended to include such changes and modifications.

Claims

1. A method for synthesizing red-light nitrogen-thiadinonahelite, characterized in that: The following steps are involved: In a mixed solvent of an organic solvent and water, benzothiophene-2-boronic acid is used as the raw material. Under a protective atmosphere, 2-bromo-4-(tert-butyl)-1-iodobenzene, a palladium catalyst, and anhydrous potassium carbonate are added thereto. The mixture is heated to cause a Suzuki-Miyaura catalytic coupling reaction to produce compound 2. In an organic solvent, compound 2 is used as a raw material. Under a protective atmosphere, n-butyl lithium is added thereto to react, and then trimethyl borate is added. n-butyl lithium removes the halogen atom in compound 2, and then the carbon negative attacks the trimethyl borate, and compound 3 is obtained by acidification. In a mixed solvent of an organic solvent and water, compound 3 is used as a raw material. 1-bromo-3,6-diiodocarbazole, a palladium catalyst, and anhydrous potassium carbonate are added thereto under a protective atmosphere, and the mixture is heated to cause a Suzuki-Miyaura catalytic coupling reaction to obtain compound 4. In an organic solvent, compound 4 is used as a raw material, and an anhydrous ferric chloride solution dissolved in nitromethane is added thereto under a protective atmosphere to carry out an oxidative dehydrogenation cyclization reaction to obtain compound 5; In an organic solvent, compound 5 is used as a raw material. Under a protective atmosphere, sodium tert-butoxide, a palladium catalyst, and a phosphine ligand are added thereto. The mixture is heated to cause a Buchwald-Hartwig carbon-nitrogen metal-catalyzed coupling reaction to obtain compound 6, a red-light nitrogen-thiadinonahelite. The synthetic route is: 。 2. The method for synthesizing the red-light nitrogen-thiadinonahylidene according to claim 1, wherein: The mass ratio of benzothiophene-2-boric acid to 2-bromo-4-(tert-butyl)-1-iodobenzene is 6.3:10, the mass ratio of palladium catalyst to benzothiophene-2-boric acid is 0.414~0.6:6.3, and the mass ratio of anhydrous potassium carbonate to benzothiophene-2-boric acid is 10.2:6.

3.

3. The method for synthesizing red-light nitrogen-thiadinonahylidene according to claim 1, characterized in that: When compound 2 was synthesized, the heating reaction temperature was 80°C and the heating reaction time was 12h~15h.

4. The method for synthesizing the red-light nitrogen-thiadinonahylidene according to claim 1, wherein: The usage ratio of compound 2 to n-butyl lithium and trimethyl borate is 11.5 g:16 mL:20 g~30 g.

5. The method for synthesizing red-light nitrogen-thiadinonahylidene according to claim 1, characterized in that: The reaction temperature for preparing compound 3 is from -78°C to room temperature.

6. The method for synthesizing red-light nitrogen-thiadinonahelite according to claim 1, characterized in that: The mass ratio of compound 3 to 1-bromo-3,6-diiodocarbazole is 5.24:4, the mass ratio of palladium catalyst to compound 3 is 0.426~0.6:5.24, the mass ratio of anhydrous sodium carbonate to compound 3 is 2.78:5.24, and the heating reaction temperature for preparing compound 4 is 100°C.

7. The method for synthesizing red-light nitrogen-thiadinonahylidene according to claim 1, characterized in that: The dosage ratio of compound 4 to anhydrous ferric chloride solution dissolved in nitromethane is 500 mg:10 mL, and the dosage ratio of nitromethane solution to anhydrous ferric chloride is 10 mL:1 g~1.5 g.

8. The method for synthesizing red-light nitrogen-thiadinonahelite according to claim 1, characterized in that: The mass ratio of compound 5 to sodium tert-butoxide is 2:1, the mass ratio of palladium catalyst to compound 5 is 1:4, and the mass ratio of phosphine ligand to compound 5 is 8:

25.

9. A red-light azathiabisnonahelite prepared by the preparation method according to any one of claims 1 to 8, characterized in that: The structural formula of the red-light nitrogen-thiadinonahelite is: 。 10. Use of the red-light-emitting nitrogen-thiadinonahelite according to claim 9 in organic photoelectric materials.

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