Dinaphthosilole compound, synthesis method and application in fluorescence detection of nitro aromatic ring compound

Abstract

The invention discloses a dinaphthosilole compound and a preparation method thereof. The dinaphthosilole compound disclosed by the invention is good in chemical optical stability, simple in synthetic route and easy to control; raw materials required by synthesis are easy to obtain; meanwhile, the obtained organic silicon fluorescent light-emitting material dinaphtho-silole compound can be used for high-sensitivity visual fluorescence detection of nitro explosives-nitro aromatic ring compounds, especially 2, 4, 6-trinitrophenol. The catalyst used for synthesizing silole is sodium amide which is milder compared with the commonly used catalyst n-butyllithium, so that the reaction is more operable, and meanwhile, the post-treatment method of the final reaction product is simple and convenient. The yield of the silole synthesized by the preparation method disclosed by the invention is as high as 92%, and popularization and application of industrial production are facilitated. Based on the invention, the compound can be further used for manufacturing a chemical sensor for fluorescence detection, so that the compound can be used for rapidly and sensitively detecting an explosive, namely a nitro aromatic ring compound, more safely and conveniently.

Description

Technical Field

[0001] The present invention belongs to the field of new fluorescent materials, especially organic silicon luminescent materials and fluorescence detection technology. Specifically, the present invention relates to a dinaphthosilole compound, a synthesis method and application in fluorescence detection of nitroaromatic compounds. Background Art

[0002] Existing nitro explosives - nitroaromatic compounds mainly include p-nitrotoluene (4-NT), nitrotoluene (NB), 1,3-dinitrobenzene (1,3-DNB), 2,4,6-trinitrophenol (TNP), 2,4-dinitrotoluene (2,4-DNT), etc. In addition, these nitroaromatic compounds are also widely present in explosives, dyes, pesticides, and medicines. During the production process, they will pollute the air, water quality, and soil, and cause harm to human health and safety. Among them, 2,4,6-trinitrophenol (TNP) has a strong explosion power and is more toxic than other common nitroaromatic compounds. Therefore, high-speed and high-sensitivity detection of nitroaromatic compounds, especially 2,4,6-trinitrophenol, is of great significance in social security, environmental protection, scientific research, and many other aspects, and has attracted widespread attention. Conventional detection equipment includes complex instruments such as gas chromatography-mass spectrometry and nuclear magnetic resonance, which are widely used to detect aromatic nitro explosives. However, these devices have the disadvantages of high operator skill requirements, complex operation, and high cost. Chemical sensing based on fluorescence detection has been proven to be a method that can quickly and sensitively detect nitro aromatic compounds. Among them, the method based on luminescent materials to detect nitro aromatic compounds has attracted widespread attention from scientific researchers due to its many advantages such as simple operation, high sensitivity, short reaction time, recyclability, and ability to detect different types of nitro aromatic compounds.

[0003] Silole, also known as silole, is obtained by replacing the bridgehead carbon atom in the cyclopentadiene structure with a silicon atom. This replacement causes the outer σ* orbital of the silicon atom to form a σ*-π* conjugation with the π* orbital of cyclopentadiene, resulting in the lowest unoccupied orbital (LUMO) of the silole molecule having a significantly lower energy than other five-membered heterocyclic compounds such as furan, pyrrole and thiophene. Silole has attracted much attention due to its application potential in the field of optoelectronic materials, especially in the development of blue light-emitting materials. Blue light materials based on silole structure have been widely studied and applied. Article Tetrahedron Letters.2023,21:154489 In the preparation of silole compounds, dibromo-substituted compounds are reacted with dichlorodimethylsilane in the presence of a catalyst n-butyl lithium. However, due to the extremely unstable reaction conditions of n-butyl lithium, the reaction process is difficult to control, which is not conducive to the production and application of silole compounds. Summary of the invention

[0004] In view of the above, the purpose of the present invention is to provide a dinaphthosilole compound, namely 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole blue light emitting compound and its preparation method. The compound is an organic silicon-containing luminescent material, which has the visual fluorescence detection performance of sensitively detecting nitro explosives-nitroaromatic compounds, especially 2,4,6-trinitrophenol. Specifically, the technical solution adopted by the present invention is as follows:

[0005] In one aspect, the present invention provides a method for synthesizing the dinaphthosilole compound, comprising the following steps: (1) preparing 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl from 2,2'-dibromo-1,1'-binaphthyl;

[0006] (2) 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl is reacted with sodium amide and dichlorodimethylsilane at -40 to -100°C under nitrogen or argon protection to prepare a dinaphthosilole compound.

[0007] For the preparation of step (1), please refer to the article Tetrahedron Letters.2023,21:154489.

[0008] Preferably, the molar ratio of the 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl to sodium amide and dichlorodimethylsilane in step (2) is 1:1-3:1.2-2.2.

[0009] In the above-mentioned synthesis method, preferably, the method for preparing the dinaphthosilole compound in step (2) is: to an anhydrous toluene solution of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl at -40 to -60°C, a n-hexane solution of sodium amide is added dropwise, and the mixture is reacted at -40 to -60°C for 30 to 60 minutes; then the temperature is lowered to -60 to -90°C, dichlorodimethylsilane is slowly added, the temperature is raised to room temperature, the reaction is carried out for 3 to 12 hours, and the reaction is then processed after the reaction is completed.

[0010] In the above-mentioned synthesis method, preferably, the molar ratio of the 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl to sodium amide and dichlorodimethylsilane is 1:1.5-2.5:1.5-2.0.

[0011] In the above-mentioned synthesis method, preferably, a n-hexane solution of sodium amide is added dropwise to an anhydrous toluene solution of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl at -50°C, and the mixture is reacted at -50°C for 50 to 60 minutes; then the temperature is lowered to -70 to -80°C, dichlorodimethylsilane is slowly added, and the mixture is heated to room temperature for reaction for 3 to 6 hours.

[0012] In the above-mentioned synthesis method, preferably, the post-treatment is first treated with a saturated aqueous solution of sodium chloride, extracted with petroleum ether, dried with anhydrous magnesium sulfate, concentrated by rotary evaporation, purified by alumina chromatography column, and recrystallized.

[0013] The synthetic method described above, its synthetic route is roughly as follows:

[0014]

[0015] In the above synthesis route, the first three steps of the reaction can be referred to the articles Tetrahedron Letters.2023,21:154489 and Tetrahedron Letters.2009,50:2425–2429.

[0016] The dinaphthosilole compound obtained in the present invention is named 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole and has the following structural formula:

[0017]

[0018] On the other hand, the present invention also provides the use of the dinaphthosilole compound in the fluorescence detection of nitroaromatic ring compounds. Wherein, the nitroaromatic ring compound includes at least one of p-nitrotoluene (4-NT), nitrotoluene (NB), 1,3-dinitrobenzene (1,3-DNB), 2,4,6-trinitrophenol (TNP), and 2,4-dinitrotoluene (2,4-DNT). For the application, the nitroaromatic ring compound can be mixed with the dinaphthosilole compound to quench the blue color of the dinaphthosilole compound. Specifically, for example, the prepared blue light material dinaphthosilole compound (1 mg) is dispersed in 1 ml of N,N-dimethylformamide, different volumes of N,N-dimethylformamide solution containing 2,4,6-trinitrophenol (5 mmol per liter) are added thereto, and its fluorescence intensity is tested under excitation light of 350-400nm. As the amount of 2,4,6-trinitrophenol increases, the fluorescence intensity of the blue light material dinaphthosilole compound gradually decreases until it is completely quenched, thereby realizing visual fluorescence detection of nitro explosives-nitroaromatic compounds.

[0019] The dinaphthothiole compound of the present invention has good chemical optical stability, and its synthesis route is simple and easy to control; the raw materials required for the synthesis are easily available; at the same time, the obtained organosilicon fluorescent luminescent material dinaphthothiole compound can be used for highly sensitive visual fluorescence detection of nitro explosives-nitro aromatic ring compounds, especially 2,4,6-trinitrophenol. The catalyst used in the synthesis of silanthiole of the present invention is sodium amide, which is milder than the catalyst n-butyl lithium usually used, making the reaction more operable. At the same time, the post-treatment method of the final product of the reaction is simple. The yield of silanthiole synthesized by the preparation method of the present invention is as high as 92%, which is conducive to the popularization and application of industrial production. Based on the present invention, it can be further used to make a chemical sensor for fluorescence detection, so as to be more safe and convenient for rapid and sensitive detection of explosives-nitro aromatic ring compounds. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 Absorption and emission spectra of the compound 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole prepared in toluene in Example 1;

[0021] Figure 2 This is the hydrogen nuclear magnetic resonance spectrum of the compound 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole prepared in Example 1.

[0022] Figure 3 The single crystal diffraction pattern of the compound 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole prepared in Example 1.

[0023] Figure 4 Fluorescence quenching graphs showing the addition of different volumes of 2,4,6-trinitrophenol solution to the N,N-dimethylformamide suspension of the compound 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole prepared in Example 1. DETAILED DESCRIPTION

[0024] The following embodiments are further descriptions of the content of the present invention as an explanation of the technical content of the present invention, but the essential content of the present invention is not limited to the following embodiments. Ordinary technicians in this field can and should know that any simple changes or replacements based on the essential spirit of the present invention should fall within the scope of protection required by the present invention.

[0025] Example 1

[0026] (1) 2,2'-dibromo-1,1'-binaphthyl was used as a raw material. 2,2'-dibromo-1,1'-binaphthyl was prepared according to Tetrahedron Letters. 2023, 21: 154489 and Tetrahedron Letters. 2009, 50: 2425–2429. A 100 mL two-port reflux apparatus was added with a rotor and replaced with argon. Under the protection of argon, 1.33 g (2 mmol) of 2,2'-dibromo-1,1'-binaphthyl-3,3'-diiodoalkane, 15 mL of ethylene glycol dimethyl ether solvent, sodium carbonate solution (2 M, 2.2 mL, 4.4 mmol), 116 mg (5 mol%) of tetrakistriphenylphosphine palladium and 512 mg (4.2 mmol) of 2-methoxyphenylboronic acid in ethanol (1.8 mL) were added, and then refluxed for 24 hours. After 3 hours, the starting material disappeared after TLC plate detection, and the reaction was completed. The organic solvent was removed under reduced pressure, and the mixture was extracted with dichloromethane (3×30 mL). The organic phase was washed with saturated saline solution (2×50 mL) and dried over anhydrous sodium sulfate for several hours. The low-boiling organic solvent was removed by rotary evaporation, and the obtained mixture was purified by silica gel column chromatography using petroleum ether / dichloromethane (80:20) as eluent to obtain 1.124 g of white 2,2'-dibromo-3,3'-di(2-methoxybenzene)-1,1'-binaphthyl solid with a yield of 90.0%.

[0027] (2) Take a 100 mL cold hydrazine reaction tube and replace it with argon. Under argon protection, add 1248 mg (2.0 mmol) of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl in anhydrous toluene solution (20 mL). Cool the temperature to -50°C with liquid nitrogen, slowly add sodium amide (1.5 mL, 2.0 M, 3.0 mmol) in n-hexane solution, react at -50°C for 60 min, then cool the temperature to -80°C with liquid nitrogen, and slowly add dichlorodimethylsilane (412 mg, 3.2 mmol). anhydrous toluene solution (10 mL), slowly warmed to room temperature, stirred for 3 h, and detected by thin layer chromatography. When the raw material disappeared, the reaction was completed. A saturated aqueous solution of sodium chloride (30 mL) was added, extracted with petroleum ether (2×50 mL), dried over anhydrous magnesium sulfate, and concentrated under rotary evaporation. The crude product was purified by neutral alumina chromatography column using petroleum ether as eluent to obtain a transparent liquid. A small amount of seed crystals was added for recrystallization to obtain 7,7'-dimethyl-3,3'-di(2-methoxyphenyl)-1,1'-dinaphthosilole as a white solid 922.1 mg with a yield of 88.2%.

[0028] 1HNMR (400MHz, CDCl3) δ [ppm]: 8.08 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H) 7.82 (s, 2H), 7.55-7. 51(m,2H),7.42-7.34(m,4H),7.31-7.29(m,2H),7.03-6.95(m,4H),3.70(s,6H),-0.25(s,6H).

[0029] (3) Detection performance test of 2,4,6-trinitrophenol: The prepared blue light material (1 mg) was dispersed in 2 ml of N,N-dimethylformamide, and different volumes of N,N-dimethylformamide solution (5 mmol / L) containing 2,4,6-trinitrophenol were added thereto, and their fluorescence intensity was tested under 396 nm excitation light.

[0030] Example 2

[0031] (1) The preparation of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl was the same as in Example 1.

[0032] (2) Take a 100 mL cold hydrazine reaction tube and replace it with argon. Under argon protection, add 1248 mg (2.0 mmol) of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl in anhydrous toluene solution (20 mL). Cool the temperature to -50°C with liquid nitrogen, slowly add sodium amide (1.5 mL, 2.0 M, 3.0 mmol) in n-hexane solution, react at -50°C for 60 min, then cool the temperature to -80°C with liquid nitrogen, and slowly add dichlorodimethylsilane (515 mg, 4.0 mmol). anhydrous toluene solution (10 mL), slowly warmed to room temperature, stirred for 3 h, and detected by thin layer chromatography. When the raw material disappeared, the reaction was completed. A saturated aqueous solution of sodium chloride (30 mL) was added, extracted with petroleum ether (2×50 mL), dried over anhydrous magnesium sulfate, and concentrated under rotary evaporation. The crude product was purified by neutral alumina chromatography column using petroleum ether as eluent to obtain a transparent liquid. A small amount of seed crystals was added for recrystallization to obtain 7,7'-dimethyl-3,3'-di(2-methoxybenzene)-1,1'-dinaphthosilole as a white solid 930.4 mg, with a yield of 89.0%.

[0033] 1HNMR (400MHz, CDCl3) δ [ppm]: 8.08 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H) 7.82 (s, 2H), 7.55-7. 51(m,2H),7.42-7.34(m,4H),7.31-7.29(m,2H),7.03-6.95(m,4H),3.70(s,6H),-0.25(s,6H).

[0034] (3) Detection performance test of 2,4,6-trinitrophenol: The prepared blue light material (1 mg) was dispersed in 2 ml of N,N-dimethylformamide, and different volumes of N,N-dimethylformamide solution (5 mmol / L) containing 2,4,6-trinitrophenol were added thereto, and their fluorescence intensity was tested under 396 nm excitation light.

[0035] Example 3

[0036] (1) The preparation of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl was the same as in Example 1.

[0037] (2) Take a 100 mL cold hydrazine reaction tube and replace it with argon. Under argon protection, add 1248 mg (2.0 mmol) of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl in anhydrous toluene solution (20 mL). Cool the temperature to -50°C with liquid nitrogen, slowly add sodium amide (2.4 mL, 2.0 M, 4.8 mmol) in n-hexane solution, react at -50°C for 60 min, then cool the temperature to -80°C with liquid nitrogen, and slowly add dichlorodimethylsilane (412 mg, 3.2 mmol). anhydrous toluene solution (10 mL), slowly warmed to room temperature, stirred for 3 h, and detected by thin layer chromatography. When the raw material disappeared, the reaction was completed. A saturated aqueous solution of sodium chloride (30 mL) was added, extracted with petroleum ether (2×50 mL), dried over anhydrous magnesium sulfate, and concentrated under rotary evaporation. The crude product was purified by neutral alumina chromatography column using petroleum ether as eluent to obtain a transparent liquid. A small amount of seed crystals was added for recrystallization to obtain 7,7'-dimethyl-3,3'-di(2-methoxybenzene)-1,1'-dinaphthosilole as a white solid 956.6 mg, with a yield of 91.5%.

[0038] 1HNMR (400MHz, CDCl3) δ [ppm]: 8.08 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H) 7.82 (s, 2H), 7.55-7. 51(m,2H),7.42-7.34(m,4H),7.31-7.29(m,2H),7.03-6.95(m,4H),3.70(s,6H),-0.25(s,6H).

[0039] (3) Detection performance test of 2,4,6-trinitrophenol: The prepared blue light material (1 mg) was dispersed in 2 ml of N,N-dimethylformamide, and different volumes of N,N-dimethylformamide solution (5 mmol / L) containing 2,4,6-trinitrophenol were added thereto, and their fluorescence intensity was tested under 396 nm excitation light.

[0040] Example 4

[0041] (1) The preparation of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl was the same as in Example 1.

[0042] (2) Take a 100 mL cold hydrazine reaction tube and replace it with argon. Under argon protection, add 1248 mg (2.0 mmol) of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl in anhydrous toluene solution (20 mL). Cool the temperature to -50°C with liquid nitrogen, slowly add sodium amide (1.5 mL, 2.0 M, 3.0 mmol) in n-hexane solution, react at -50°C for 60 min, then cool the temperature to -80°C with liquid nitrogen, and slowly add dichlorodimethylsilane (412 mg, 3.2 mmol). anhydrous toluene solution (10 mL), slowly warmed to room temperature, stirred for 12 h, and detected by thin layer chromatography. When the starting material disappeared, the reaction was completed. A saturated aqueous solution of sodium chloride (30 mL) was added, and the mixture was extracted with petroleum ether (2×50 mL). The mixture was dried over anhydrous magnesium sulfate and concentrated under rotary evaporation. The crude product was purified by neutral alumina chromatography column using petroleum ether as eluent to obtain a transparent liquid. A small amount of seed crystals was added for recrystallization to obtain 7,7'-dimethyl-3,3'-di(2-methoxybenzene)-1,1'-dinaphthosilole as a white solid (966.0 mg) with a yield of 92.4%.

[0043] 1HNMR (400MHz, CDCl3) δ [ppm]: 8.08 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H) 7.82 (s, 2H), 7.55-7. 51(m,2H),7.42-7.34(m,4H),7.31-7.29(m,2H),7.03-6.95(m,4H),3.70(s,6H),-0.25(s,6H).

[0044] (3) Detection performance test of 2,4,6-trinitrophenol: The prepared blue light material (1 mg) was dispersed in 2 ml of N,N-dimethylformamide, and different volumes of N,N-dimethylformamide solution (5 mmol / L) containing 2,4,6-trinitrophenol were added thereto, and their fluorescence intensity was tested under 396 nm excitation light.

[0045] Example 5

[0046] (1) The preparation of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl was the same as in Example 1.

[0047] (2) Take a 100 mL cold hydrazine reaction tube and replace it with argon. Under argon protection, add 1248 mg (2.0 mmol) of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl in anhydrous toluene solution (20 mL). Cool the temperature to -50°C with liquid nitrogen, slowly add sodium amide (1.5 mL, 2.0 M, 3.0 mmol) in n-hexane solution, react at -50°C for 60 min, then cool the temperature to -70°C with liquid nitrogen, and slowly add dichlorodimethylsilane (412 mg, 3.2 mmol). anhydrous toluene solution (10 mL), slowly warmed to room temperature, stirred for 3 h, and detected by thin layer chromatography. When the raw material disappeared, the reaction was completed. A saturated aqueous solution of sodium chloride (30 mL) was added, extracted with petroleum ether (2×50 mL), dried over anhydrous magnesium sulfate, and concentrated under rotary evaporation. The crude product was purified by neutral alumina chromatography column using petroleum ether as eluent to obtain a transparent liquid. A small amount of seed crystals was added for recrystallization to obtain 837.4 mg of 7,7'-dimethyl-3,3'-di(2-methoxybenzene)-1,1'-dinaphthosilole as a white solid with a yield of 80.1%.

[0048] 1HNMR (400MHz, CDCl3) δ [ppm]: 8.08 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H) 7.82 (s, 2H), 7.55-7. 51(m,2H),7.42-7.34(m,4H),7.31-7.29(m,2H),7.03-6.95(m,4H),3.70(s,6H),-0.25(s,6H).

[0049] (3) Detection performance test of 2,4,6-trinitrophenol: The prepared blue light material (1 mg) was dispersed in 2 ml of N,N-dimethylformamide, and different volumes of N,N-dimethylformamide solution (5 mmol / L) containing 2,4,6-trinitrophenol were added thereto, and their fluorescence intensity was tested under 396 nm excitation light.

[0050] It should be noted that the above-mentioned technical contents of the present invention are only for explanation and clarification to enable those skilled in the art to understand the technical essence of the present invention, so the technical contents are not used to limit the substantial protection scope of the present invention. The substantial protection scope of the present invention shall be subject to the claims. Those skilled in the art should know that any modification, equivalent substitution and improvement based on the substantial spirit of the present invention shall be within the substantial protection scope of the present invention.

Claims

1. A method for synthesizing a dinaphthosilole compound, comprising the following steps: (1) Preparing 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl from 2,2'-dibromo-1,1'-binaphthyl; (2) 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl is reacted with sodium amide and dichlorodimethylsilane at -40 to -100°C under nitrogen or argon protection to prepare a dinaphthosilole compound.

2. The synthesis method according to claim 1, characterized in that In step (2), the molar ratio of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl to sodium amide and dichlorodimethylsilane is 1:1-3:1.2-2.

2.

3. The synthesis method according to claim 1 or 2, characterized in that: The method for preparing the dinaphthosilole compound in step (2) is as follows: a n-hexane solution of sodium amide is added dropwise to an anhydrous toluene solution of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl at -40 to -60°C, and the mixture is reacted at -40 to -60°C for 30 to 60 minutes; the mixture is then cooled to -60 to -90°C, dichlorodimethylsilane is slowly added, the mixture is heated to room temperature and reacted for 3 to 12 hours, and the mixture is disposed of after the reaction is completed.

4. The synthesis method according to claim 3, characterized in that The molar ratio of the 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl to sodium amide and dichlorodimethylsilane is 1:1.5-2.5:1.5-2.

0.

5. The synthesis method according to claim 3, characterized in that To a -50°C anhydrous toluene solution of 2,2'-dibromo-3,3'-di(2-methoxyphenyl)-1,1'-binaphthyl, add a n-hexane solution of sodium amide dropwise and react at -50°C for 50-60 min; then cool to -70--80°C, slowly add dichlorodimethylsilane, and heat to room temperature to react for 3-6 h.

6. The synthesis method according to claim 2, characterized in that The post-treatment is firstly treated with a saturated aqueous solution of sodium chloride, extracted with petroleum ether, dried with anhydrous magnesium sulfate, concentrated by rotary evaporation, purified by an alumina chromatography column, and recrystallized.

7. Use of the dinaphthosilole compound obtained by the synthesis method according to any one of claims 1 to 6 in the fluorescence detection of nitro aromatic compounds.

8. The use according to claim 7, characterized in that The nitro aromatic ring compound includes at least one of p-nitrotoluene, nitrotoluene, 1,3-dinitrobenzene, 2,4,6-trinitrophenol and 2,4-dinitrotoluene.

9. The use according to claim 8, characterized in that The method adopts the following steps: a nitro aromatic ring compound is mixed with a dinaphthosilole compound to quench the blue color of the dinaphthosilole compound.

10. The use according to claim 9, characterized in that The prepared dinaphthosilole compound was dispersed in N,N-dimethylformamide, and an N,N-dimethylformamide solution containing 2,4,6-trinitrophenol was added thereto, and the fluorescence intensity was tested under an excitation light of 396 nm.

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