Green synthesis method of 13-aryl-13H-indeno [1, 2-L] phenanthrene compound

Abstract

The invention discloses a green synthesis method of 13-aryl-13H-indeno [1, 2-L] phenanthrene compounds, which comprises the following steps: adding a raw material 2-((9H-fluorene-9-alkenylene) (aryl) methyl) benzaldehyde into a toluene solution, adding a raw material boron trifluoride diethyl etherate, introducing nitrogen, and heating and stirring to react; after the reaction is finished, extracting and washing with ethyl acetate, and drying and concentrating the obtained organic phase to obtain an intermediate product; and carrying out chromatographic separation on the intermediate product to obtain the target product 13-aryl-13H-indeno [1, 2-L] phenanthrene compound. The novel functionalized 13-aryl-13H-indeno [1, 2-L] phenanthrene compound is synthesized in a green, rapid and efficient manner by adopting a boron trifluoride diethyl etherate promotion strategy, and the method has the advantages that the operation is simple, the raw materials are cheap and easy to obtain, the reaction conditions are mild, the method is green, the product is easy to separate, the compatibility of functional groups is relatively good, and the like.

Description

TECHNICAL FIELD

[0001] The present application relates to a green synthesis method of 13-aryl-13H-indenophanes, and belongs to the technical field of compound synthesis. BACKGROUND

[0002] Indenophanes are a class of polycyclic aromatic hydrocarbons with specific structures. Their special physical and chemical properties and biological activities make them a research object of great interest. In recent years, indenophanes have not only been widely used as drug molecules for research and development, but also have great application potential in the field of organic electronic materials, especially in the field of organic semiconductors. For example, the bipolar small molecule light-emitting material (I) with a diphenylindenofluorene unit as the core has good electron and hole transport properties, can balance carrier injection and transport, and can improve the light-emitting efficiency of OLED. The new 5,6,11,12-tetraaryl[1,2-b]fluorene (II) has good light stability and can be used as an electron donor for vacuum deposition photovoltaic devices. At the same time, indenophanes also have a very wide application prospect in the treatment of cancer and antibacterial aspects. 7H-indole (2,3-j) phenanthridine-7,13(8H)-dione can target and inhibit JAK2 protein, thereby inhibiting the growth, migration or tumorigenic ability of pancreatic cancer cells (such as human pancreatic cancer cells HPAC). The research of indole-dihydrobenzo (c) phenanthridine hybrid molecules provides a lead compound for the development of new antibacterial and anticancer drugs, which exhibits anti-tuberculosis, anticancer and anti-drug resistant bacterial activity, providing a new direction for addressing antibiotic resistance and cancer treatment challenges. Based on the important role of indenophanes in medicinal chemistry and synthetic chemistry, it can be boldly predicted that indenophanes will have potentially important application value.

[0003] However, there are still difficulties in how to efficiently and selectively synthesize complex indenophane compounds, especially in introducing specific functional groups while constructing the indenophane skeleton. There are almost no reports in related patent documents, and the synthesis routes of the technical solutions searched in papers have problems of low yield and many side reactions. Therefore, it is of great significance to develop a green, simple and mild method for synthesizing indenophanes in the fields of medicinal chemistry, synthetic chemistry and material science. SUMMARY

[0004] In order to make up for the deficiencies in the prior art, the purpose of the present application is to provide a simple and green method for synthesizing 13-aryl-13H-indenophanes.

[0005] To achieve the above objectives, the technical means adopted in this invention is as follows: a green synthesis method for 13-aryl-13H-indeno[1,2-L]phenanthrene compounds, wherein the raw material 2-((9H-fluorene-9-methylene)(aryl)methyl)benzaldehyde is added to a toluene solution, followed by the addition of boron trifluoride diethyl ether, and then nitrogen gas is introduced, and the reaction is heated and stirred; after the reaction is completed, the mixture is extracted and washed with ethyl acetate, and the resulting organic phase is dried and concentrated to obtain an intermediate product; the intermediate product is separated by chromatography to obtain the target product 13-aryl-13H-indeno[1,2-L]phenanthrene compounds.

[0006] The reaction is carried out in toluene using 2-((9H-fluorene-9-imenyl)(aryl)methyl)benzaldehyde and boron trifluoride diethyl ether as raw materials. This reaction has the advantages of simple operation, short reaction time, green and mild conditions, easy product separation, and good functional group compatibility.

[0007] The specific steps are as follows: Step 1: Take 2-((9H-fluorene-9-imendenyl)(aryl)methyl)benzaldehyde, add it to a reaction vessel containing toluene solution, add boron trifluoride diethyl ether solution, and then purge with nitrogen gas; Step 2: Place the reaction vessel from Step 1 on a stirrer and stir the reaction for a certain period of time under heating conditions; Step 3: After the reaction is complete, pour the reaction mixture into a separatory funnel containing deionized water, extract and wash three times with ethyl acetate, and combine the organic phases. Step 4: Dry the organic phase obtained in Step 3 with magnesium sulfate, filter to remove magnesium sulfate, concentrate the organic phase using a rotary evaporator to obtain the residue; Step 5: The residue was separated by column chromatography to obtain the target product, 13-aryl-13H-indeno[1,2-L]phenanthrene compounds.

[0008] Furthermore, in step one, 2-((9H-fluorene-9-imenyl)(phenyl)methyl)benzaldehyde refers to: 2-((9H-fluorene-9-imenyl)(phenyl)methyl)benzaldehyde, 2-((9H-fluorene-9-imenyl)(p-tolyl)methyl)benzaldehyde, 2-((4-(tert-butyl)phenyl)(9H-fluorene-9-imenyl)methyl)benzaldehyde, 2-((9H-fluorene-9-imenyl)methyl)benzaldehyde, 2-(9H-fluorene-9-imenyl)methyl)benzaldehyde, 2-(9H-fluorene-9-imenyl)methyl)benzaldehyde, 2-(9H-fluorene-9-imenyl)methyl)benzaldehyde, 2-(9H-fluorene-9-tolyl ... One of the following: 2-((9H-fluorene-9-imendenyl)(phenyl)methyl)-6-fluorobenzaldehyde, 2-((9H-fluorene-9-imendenyl)(phenyl)methyl)-4-chlorobenzaldehyde, 2-((4-chlorobenzene)(9H-fluorene-imendenyl)methyl)benzaldehyde, 2-((9H-fluorene-9-imendenyl)(phenyl)methyl)-5-chlorobenzaldehyde, and 2-((9H-fluorene-9-imendenyl)(3-fluorophenyl)methyl)benzaldehyde.

[0009] Furthermore, in step one, the molar ratio of 2-((9H-fluorene-9-imendenyl)(aryl)methyl)benzaldehyde to boron trifluoride ether is 1:2.

[0010] Furthermore, in step two, the stirring reaction time is 12-24 hours, and the heating temperature is 90℃.

[0011] Furthermore, in step five, column chromatography separation refers to using silica gel as the adsorbent, and petroleum ether and ethyl acetate as the mobile phase, with a volume ratio of 50:1.

[0012] The beneficial effects of this invention are: 1. A green, simple, effective, and additive-free strategy was adopted to achieve the intramolecular cyclization reaction of 2-((9H-fluorene-9-imendenyl)(aryl)methyl)benzaldehyde catalyzed by boron trifluoride ether, yielding 13-aryl-13H-indeno[1,2-L]phenanthrene compounds; 2. Using 2-((9H-fluorene-9-imenyl)(aryl)methyl)benzaldehyde as the reaction raw material has the advantages of simple operation, short reaction time, green and mild conditions, easy product separation, and good functional group compatibility. It lays the foundation for the further application of indene-phenanthrene-functionalized compounds in the fields of pharmaceutical chemistry and materials science. Attached Figure Description

[0013] The present invention will now be described in detail with reference to the views and embodiments.

[0014] Figure 1 The chemical reaction equation of this invention; Figure 2 The proton spectrum of compound 2a in Example 1 of this invention; Figure 3 Carbon spectrum of compound 2a in Example 1 of this invention; Figure 4 The proton NMR spectrum of compound 2b in Example 2 of this invention; Figure 5 Carbon spectrum of compound 2b in Example 2 of this invention; Figure 6 The proton NMR spectrum of compound 2c in Example 3 of this invention; Figure 7 Carbon spectrum of compound 2c in Example 3 of this invention; Figure 8 The proton NMR spectrum of compound 2d in Example 4 of this invention; Figure 9 Carbon spectrum of compound 2d in Example 4 of this invention; Figure 10 The proton NMR spectrum of compound 2e in Example 5 of this invention; Figure 11Carbon spectrum of compound 2e in Example 5 of this invention; Figure 12 The proton NMR spectrum of compound 2f in Example 5 of this invention; Figure 13 Carbon spectrum of compound 2f in Example 5 of this invention; Figure 14 The proton NMR spectrum of compound 2g of Example 5 of this invention; Figure 15 Carbon spectrum of compound 2g from Example 5 of this invention; Figure 16 The proton NMR spectrum of compound 2h in Example 5 of this invention; Figure 17 Carbon spectrum of compound 2h in Example 5 of this invention; Figure 18 Yield comparison table of embodiments of the present invention; Figure 19 The background is the molecular formula of the materials in the existing technology. Detailed Implementation Example

[0015] like Figure 1 The green synthesis method shown is for 13-aryl-13H-indeno[1,2-L]phenanthrene compounds. (1) Accurately weigh 89.5 mg of 2-((9H-fluorene-9-enenyl)(phenyl)methyl)benzaldehyde (1a) and add it to a reaction tube containing toluene solution, then add 140 mg of boron trifluoride ether solution and purge with nitrogen gas; (2) Place the reaction tube from step (1) on a magnetic stirrer and stir the reaction at 90°C for 12 hours. (3) After the reaction is complete, pour the reaction mixture into a separatory funnel containing 10.0 mL of deionized water, extract and wash three times with 5.0 mL of ethyl acetate each time, and combine the organic phases; (4) The organic phase obtained in step (3) is dried with magnesium sulfate, filtered to remove magnesium sulfate, and the organic phase is concentrated by rotary evaporator to obtain the residue; (5) The residue was separated by column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate = 50:1) to give 65.8 mg of the target product, phenanthrene-functionalized compound (2a), which was a yellow solid with a yield of 76%. The crude target product was easily separated by column chromatography.

[0016] like Figure 2 , 3 As shown, compound 2a is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.92 (d, J = 7.8 Hz, 1H), 8.81 (d, J = 8.4Hz, 1H), 8.69 (d, J = 8.4 Hz, 1H), 8.38 (d, J = 7.8 Hz, 1H), 7.78–7.74 (m,2H), 7.72 (t, J = 7.8 Hz, 1H), 7.53 (t, J = 7.2 Hz, 1H), 7.43 (t, J = 7.2 Hz,1H), 7.40–7.36 (m, 2H), 7.25 (t, J = 7.2 Hz, 1H), 7.22–7.16 (m, 3H), 7.11 (d,J = 7.2Hz, 2H), 5.31 (s, 1H); 13C NMR (150 MHz, CDCl3) δ:149.95, 142.75,141.71, 141.56, 135.33, 131.39, 130.58, 129.09, 129.02, 128.97, 127.94,127.28, 127.02, 126.83, 126.79, 126.37, 126.34, 126.22, 125.72, 124.90,124.68, 123.65, 123.27, 122.91, 54.30; HRMS (ESI) m / z: [M+H]+ calcd forC27H19+ 343.1481, found 343.1478. Example

[0017] The difference from the preparation method in Example 1 is that the reaction raw material 1a was changed to 2-((9H-fluorene-9-eneyl)(p-tolyl)methyl)benzaldehyde (1b), while other conditions were the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded the target product 2b as a yellow solid (yield: 71%).

[0018] like Figure 4 , 5 As shown, compound 2b is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.94 (d, J = 7.8 Hz, 1H), 8.83 (d, J = 8.4Hz, 1H), 8.72 (d, J = 7.8 Hz, 1H), 8.40 (d, J =7.8 Hz, 1H), 7.81–7.78 (m,2H), 7.73 (t, J = 7.8 Hz, 1H), 7.55 (t, J = 7.8 Hz, 1H), 7.45–7.38 (m, 3H), 7.26 (t, J = 7.2 Hz, 1H), 7.02 (t, J = 8.4 Hz, 3H), 5.34 (s, 1H); 2.27 (s, 3H); 13C NMR (150 MHz, CDCl3) δ: 150.16, 142.89, 141.52, 138.57, 136.34,135.23, 131.37, 130.57, 129.72, 129.16, 129.00, 127.77, 127.20, 126.99,126.78, 126.37, 126.20, 126.17, 125.76, 124.83, 124.68, 123.64, 123.24,122.86, 53.95, 21.12; HRMS (ESI) m / z: [M+H]+ calcd for C28H21+ 357.1638, found 357.1635. Example

[0019] The difference from the preparation method in Example 1 is that the reaction raw material 1a was changed to 2-((4-(tert-butyl)phenyl)(9H-fluorene-9-imendenyl)methyl)benzaldehyde (1c), while other conditions were the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded the target product 2c (yield: 67%) as a yellow solid.

[0020] like Figure 6 , 7 As shown, compound 2c is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.93 (d, J = 8.4 Hz, 1H), 8.81 (d, J = 8.4Hz, 1H), 8.70 (d, J = 8.4 Hz, 1H), 8.38 (d, J = 7.8 Hz, 1H), 7.80–7.76 (m,2H), 7.72 (d, J = 7.2 Hz, 1H), 7.54 (d, J = 7.8 Hz, 1H), 7.44–7.38 (m, 3H), 7.25 (d, J = 7.2 Hz, 1H), 7.21 (d, J = 7.8 Hz, 2H), 7.02 (d, J = 7.8 Hz, 2H),5.31 (s, 1H), 1.34(s, 9H); 13C NMR (150 MHz, CDCl3) δ: 150.09, 149.40, 142.89, 141.48, 138.28, 135.16, 131.31, 130.51, 129.15, 128.97, 127.38, 127.12, 126.92, 126.70, 126.22, 12 6.12, 126.09, 125.86, 125.83, 124.88, 124.62, 123.59, 123.16, 122.78, 53.79, 34.37, 31.31; HRMS (ESI) m / z: [M+H]+ calcd for C31H27+ 399.2107, found399.2103. Example

[0021] The preparation method differed from that in Example 1 in that the reactant 1a was changed to 2-((9H-fluorene-9-enenyl)(phenyl)methyl)-6-fluorobenzaldehyde (1d), while other conditions remained the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded the target product (2d) as a yellow solid, with a yield of 72%.

[0022] like Figure 8 , 9 As shown, compound 2d is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 9.22 (t, J = 9.6 Hz, 1H), 8.80 (d, J = 7.8Hz, 1H), 8.70 (d, J = 8.4 Hz, 1H), 7.78–7.71 (m, 3H), 7.55 (t, J = 8.4 Hz,1H), 7.39 (t, J = 7.8 Hz, 1H), 7.24–7.10 (m, 8H), 5.39 (s, 1H); 13C NMR (150MHz, CDCl3) δ: 156.19 (d, J = 247.3 Hz), 152.71, 152.68, 142.58, 141.47,135.46, 135.44, 131.26 (d, J = 59.8 Hz), 129.09, 128.61, 128.23 (d, J = 8.3Hz), 127.87, 127.82, 127.80, 127.62, 127.56, 127.47, 127.00, 126.91, 126.72,126.52, 126.40, 125.81, 123.19, 123.15, 120.98, 120.96, 115.44 (d, J = 27.1Hz), 54.88; HRMS (ESI) m / z: [MH]- calcd for C27H16F- :359.1242, found359.1243. Example

[0023] The difference from the preparation method in Example 1 is that the reactant 1a was changed to 2-((9H-fluorene-9-imendenyl)(phenyl)methyl)-4-chlorobenzaldehyde (1e), while other conditions were the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded the target product 2e as a yellow solid (yield: 68%).

[0024] like Figure 10 , 11 As shown, compound 2e is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.82 (t, J = 7.2 Hz, 2H), 8.73 (d, J = 8.4Hz, 1H), 8.28 (d, J = 8.4 Hz, 1H), 7.80–7.71 (m, 3H), 7.60 (t, J = 7.2 Hz,2H), 7.42–7.39 (m, 2H), 7.32 (s, 1H), 7.25–7.20 (m, 3H), 7.10 (d, J = 6.6 Hz,1H), 5.29 (s, 1H); 13C NMR (150 MHz, CDCl3) δ: 151.60, 142.73, 140.80,140.06, 134.42, 132.19, 131.40, 130.66, 129.18, 128.84, 128.57, 127.87,127.45, 127.14, 126.90, 126.48, 126.42, 125.67, 125.22, 124.41, 123.72,123.62, 123.29, 54.12; HRMS (ESI) m / z: [MH]- calcd for C27H16Cl- 375.0946, found 375.0945. Example

[0025] The difference from the preparation method in Example 1 is that the reaction raw material 1a was changed to 2-((4-chlorobenzene)(9H-fluorene-9-eneyl)methyl)benzaldehyde (1f), while other conditions were the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded the target product 2f as a yellow solid (yield: 74%).

[0026] like Figure 12 , 13 As shown, compound 2f is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.82 (d, J = 7.8 Hz, 1H), 8.72 (d, J = 7.8Hz, 1H), 8.62 (d, J = 7.8 Hz, 1H), 8.3 (d, J = 7.8 Hz, 1H), 7.71 (d, J = 7.2Hz, 1H), 7.66 (d, J = 7.2 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 7.49 (t, J = 7.2Hz, 1H), 7.39 (t, J = 7.2 Hz, 1H), 7.35 (t, J = 7.2 Hz, 1H), 7.26 (d, J = 7.2Hz, 1H), 7.21 (t, J = 7.2 Hz, 1H), 7.14 (d, J = 8.4Hz, 2H), 6.96 (d, J = 8.4Hz, 2H), 5.08 (s, 1H); 13C NMR (150 MHz, CDCl3) δ: 149.31, 142.07, 141.40,140.24, 135.27, 132.42, 131.28, 130.48, 129.15, 129.11, 128.73, 128.70,127.36, 126.96, 126.73, 126.34, 126.24, 125.40, 124.66, 124.55, 123.54,123.24, 122.92, 53.31; HRMS (ESI) m / z: [MH]- calcd for C27H16Cl- 375.0946, found 375.0945. Example

[0027] The difference from the preparation method in Example 1 is that the reactant 1a was changed to 2-((9H-fluorene-9-enenyl)(phenyl)methyl)-5-chlorobenzaldehyde (1g), while other conditions were the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded 2g of the target product as a yellow solid (yield: 79%).

[0028] like Figure 14 , 15 As shown, compound 2g is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.74 (d, J = 8.4 Hz, 1H), 8.68 (d, J = 7.8Hz, 1H), 8.63 (d, J = 8.4 Hz, 1H), 8.22 (s, 1H), 7.75 (t, J = 7.2 Hz, 1H),7.70 (t, J = 7.2 Hz, 1H), 7.64 (d, J = 7.2 Hz, 1H), 7.53 (t, J = 7.2 Hz, 1H),7.37 (t, J = 7.2 Hz, 1H), 7.20–7.16 (m, 5H), 7.00 (d, J = 6.0 Hz, 2H), 5.02(s, 1H); 13C NMR (150 MHz, CDCl3) δ: 148.03, 143.59, 143.01, 140.99, 134.05,133.02, 131.22, 130.69, 129.03, 128.65, 128.41, 127.73, HRMS (ESI) m / z: [MH]- calcd for C27H16Cl- 375.0946, found 375.0947. Example

[0029] The difference from the preparation method in Example 1 is that the reaction raw material 1a was changed to 2-((9H-fluorene-9-phenylene)(3-fluorophenyl)methyl)benzaldehyde (1h), while other conditions were the same as in Example 1. Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (50:1)) yielded the target product as a yellow solid for 2h (yield: 74%).

[0030] like Figure 16 , 17 As shown, compound 2h is characterized as follows: 1H NMR (600 MHz, CDCl3) δ: 8.92 (d, J = 7.8 Hz, 1H), 8.82 (d, J = 8.4Hz, 1H), 8.71 (d, J = 8.4 Hz, 1H), 8.39 (d, J = 7.8 Hz, 1H), 7.78 (t, J = 6.6Hz, 1H), 7.75–7.71 (m, 2H), 7.56 (t, J = 7.2Hz, 1H), 7.45 (t, J = 7.2 Hz, 1H), 7.42 (t, J = 7.2 Hz, 1H), 7.37 (d, J = 7.8 Hz, 1H), 7.27 (t, J = 7.2 Hz,1H), 7.2 13C NMR (150 MHz, CDCl3) δ:163.14 (d, J = 244.8 Hz), 149.17, 144.27, 144.23, 141.77 (d, J = 75.8 Hz), 135.43, 131.40 130.58, 130.48, 130.42, 128.84, 128.81, 127.49, 127.04, 126.63(d, J = 63.8 Hz), 126.34, 125.47, 124.76, 124.65, 123.63, 123.31, 122.99,114.64 (d, J = 21.6 Hz), 113.81 (d, J = 21.2 Hz), 53.77; HRMS (ESI) m / z: [MH]- calcd for C27H16F- 359.1242, found 359.1243. The above examples are only some of the examples we have listed, used to verify the applicability of the method to different reaction substrates. The method can react 2-((9H-fluorene-9-enyl)(aryl)methyl)benzaldehyde containing different substituents with boron trifluoride diethyl ether to obtain 13-aryl-13H-indeno[1,2-L]phenanthrene compounds containing different functional groups.

[0031] The yield comparison table of the examples is as follows: Figure 18As shown, the yield of the target product varies due to the influence of different substituents.

[0032] It is easy to see from the above embodiments that the present invention has the following advantages: 1. A green synthesis of 13-aryl-13H-indeno[1,2-L]phenanthrene compounds was achieved.

[0033] 2. A simple, efficient, and green method was used to prepare 13-aryl-13H-indeno[1,2-L]phenanthrene compounds containing different substituents (methyl, tert-butyl, fluorine, chlorine). Toluene was used as the reaction solvent, and no other additives were required. Novel functionalized 13-aryl-13H-indeno[1,2-L]phenanthrene compounds were obtained. These compounds were confirmed by NMR and high-resolution mass spectrometry.

[0034] 3. The raw materials of this invention are readily available and inexpensive, the reaction time is short, the conditions are green and mild, the products are easy to separate, and the preparation process and technology are simple and easy to operate.

[0035] 4. The 13-aryl-13H-indeno[1,2-L]phenanthrene-functionalized compounds prepared in this invention provide a source of raw materials for screening active drug molecules and lay the foundation for further transformation in drugs and materials.

[0036] The embodiments disclosed in this invention are only for explaining the working process of this invention and are not intended to limit the technology of this invention. Any modifications made by those skilled in the art without inventiveness to this invention are within the protection scope of this application.

Claims

1. A green synthesis of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds, characterized by: The raw material 2-((9H-fluorene-9-alkenylene)(aryl)methyl) benzaldehyde is added into a toluene solution, and then the raw material boron trifluoride ether is added, and then nitrogen is flushed, and the reaction is stirred and heated; after the reaction is completed, the obtained organic phase is dried and concentrated to obtain an intermediate product; The intermediate product is separated by chromatography to obtain the target product 13-aryl-13H-indeno[1,2-L]phenanthrene compound.

2. A green synthesis process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 1, wherein, The steps are as follows: Step one, the 2-((9H-fluorene-9-alkenylene)(aryl)methyl) benzaldehyde is added into a toluene solution, and then the raw material boron trifluoride ether is added, and then nitrogen is flushed; Step two, the reaction container in step one is placed on a stirrer, and the reaction is stirred under heating for a period of time; Step three, after the reaction is completed, the reaction mixture is poured into a separatory funnel containing deionized water, and the organic phase is extracted and washed with ethyl acetate three times; Step four, the organic phase obtained in step three is dried with magnesium sulfate, and the magnesium sulfate is removed by suction filtration, and the organic phase is concentrated by a rotary evaporator to obtain a residue; Step five, the residue is separated by column chromatography to obtain the target product 13-aryl-13H-indeno[1,2-L]phenanthrene compound.

3. A green synthesis process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 2, wherein it comprises of: In step one, the mass ratio of 2-((9H-fluorene-9-alkenylene)(aryl)methyl) benzaldehyde to boron trifluoride ether is 1:

2.

4. A green synthetic process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 2, wherein: In step two, the stirring reaction time is 12-24 hours.

5. A green synthetic process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 2, wherein: In step five, the column chromatography separation refers to silica gel and mobile phase.

6. A green synthetic process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 2, wherein it comprises of: In step one, the 2-((9H-fluorene-9-alkenylene)(aryl)methyl) benzaldehyde refers to one of 2-((9H-fluorene-9-alkenylene)(phenyl)methyl) benzaldehyde, 2-((9H-fluorene-9-alkenylene)(p-tolyl)methyl) benzaldehyde, 2-((4-(tert-butyl)phenyl)(9H-fluorene-9-alkenylene)methyl) benzaldehyde, 2-((9H-fluorene-9-alkenylene)(3-fluorophenyl)methyl) benzaldehyde, 2-((9H-fluorene-9-alkenylene)(phenyl)methyl)-4-chlorobenzaldehyde, 2-((4-chlorophenyl)(9H-fluorene-9-alkenylene)methyl) benzaldehyde, 2-((9H-fluorene-9-alkenylene)(phenyl)methyl)-5-chlorobenzaldehyde, and 2-((9H-fluorene-9-alkenylene)(3-fluorophenyl)methyl) benzaldehyde.

7. A green synthetic process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 2, wherein it comprises of: In step five, the functionalized 13-aryl-13H-indeno[1,2-L]phenanthrene compound refers to one of 13-phenyl-13H-indeno[1,2-L]phenanthrene, 13-(p-tolyl)-13H-indeno[1,2-L]phenanthrene, 13-(4-(tert-butyl)phenyl)-13H-indeno[1,2-L]phenanthrene, 13-(3-fluorophenyl)-13H-indeno[1,2-L]phenanthrene, 11-chloro-13-phenyl-13H-indeno[1,2-L]phenanthrene, 13-(4-chlorophenyl)-13H-indeno[1,2-L]phenanthrene, 10-chloro-13-phenyl-13H-indeno[1,2-L]phenanthrene, and 13-(3-fluorophenyl)-13H-indeno[1,2-L]phenanthrene.

8. A green synthetic process of 13-aryl-13H-indeno[1,2-L]phenanthrene class of compounds as claimed in claim 5 wherein: The mobile phase is constituted by petroleum ether and ethyl acetate in a volume ratio of 50:

1. The mobile phase is constituted by petroleum ether and ethyl acetate in a volume ratio of 50:

1. The mobile phase is constituted by petroleum ether and eth

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