Synthesis method and performance of ethylene glycol protected pyrene
By reacting compound A with trifluoromethanesulfonic acid, a simplified route for synthesizing ethylene glycol-protected pyrene derivative B was achieved. This solved the problems of complex synthesis steps and low yields in the synthesis of polycyclic aromatic hydrocarbons, realizing a high-yield and simple synthesis method with optical properties and potential for widespread application.
Patent Information
- Application Number
- CN202411347010.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-09-26
- Publication Date
- 2025-10-31
AI Technical Summary
The existing synthesis of large polycyclic aromatic hydrocarbons involves complex steps, harsh reaction conditions, low yields, and high costs, which limits their large-scale synthesis and widespread application.
The ethylene glycol-protected pyrene derivative B was synthesized by reacting compound A with trifluoromethanesulfonic acid, followed by steps such as dissolution, stirring, washing, drying, and chromatography. This simplified the synthetic route and improved the yield.
The synthesis of ethylene glycol-protected pyrene derivatives, which is simple to operate and has a high yield, has been achieved. These derivatives possess unique optical properties and have good potential for widespread application.
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of organic light-emitting material synthesis and application technology, specifically relating to a method for synthesizing ethylene glycol-protected pyrene and its properties. Background Technology
[0002] In existing research in this field, researchers have designed various synthetic routes and established many methods for synthesizing polycyclic aromatic hydrocarbons (PAHs), resulting in PAHs with specific structures, such as linear, cyclic, and cage-like forms. For example, through stepwise cyclization reactions, PAHs with specific sizes and shapes can be synthesized, which is of great significance for studying the physicochemical properties and potential applications of PAHs.
[0003] The synthesis of large polycyclic aromatic hydrocarbons typically involves multiple cyclization reactions and subsequent modifications to obtain the target product. The synthetic steps are complex, the reaction conditions are demanding, and the conditions at each step are difficult to control, resulting in low yields and poor reproducibility. Furthermore, the need for highly efficient catalysts and high-purity reagents significantly increases the synthesis cost, limiting its large-scale synthesis and widespread application. Therefore, finding more convenient synthetic routes, reducing the number of reaction steps, and improving the efficiency of product separation and purification are crucial research objectives.
[0004] Based on the above analysis, this invention designs a synthetic route, specifically using compound A as a raw material and reacting it with trifluoromethanesulfonic acid to obtain compound B. This synthetic method features mild reaction conditions, a relatively simple operation process, and a high product yield. Furthermore, the target product possesses unique optical properties, therefore, this synthetic technology has significant potential for widespread application and promotion. Summary of the Invention
[0005] This invention, through analysis of existing technologies and products in the field, designs a reasonable synthetic route and provides a simple and practical method for synthesizing ethylene glycol-protected pyrene derivatives (B). This method has the advantages of simple synthetic process operation and high yield. This invention uses compound A as a raw material, which reacts with trifluoromethanesulfonic acid to obtain compound B. The reaction equation is as follows:
[0006] The specific operating steps are as follows: Synthesis of Compound B: A certain amount of Compound A was added to a double-necked flask. After purging with nitrogen three times, it was dissolved in a certain amount of ultra-dry dichloromethane solution under a nitrogen atmosphere. The mixture was stirred for a certain time until completely dissolved. A certain amount of trifluoromethanesulfonic acid was added, and the mixture was stirred at a certain temperature for a certain time. After the reaction was completed, a certain amount of hydrazine hydrate was added to the reaction solution, and the mixture was stirred for a certain time. The mixed solution was washed with a certain amount of saturated saline solution each time, for a total of 3 washes. The organic phase was separated and dried with anhydrous sodium sulfate for a certain time. The solution was filtered, and the solvent was recovered by vacuum distillation. The residue was separated by silica gel column chromatography using a mixed solvent of dichloromethane and n-hexane with a volume ratio of 1:1 as the eluent. The first band showing blue fluorescence under 365 nm ultraviolet light was collected, yielding a solution of Compound B. The solvent was recovered by vacuum distillation, and the solution was dried under vacuum to obtain a light green solid, which is Compound B. Attached Figure Description
[0007] Figure 1 This is the 1H NMR spectrum of compound B.
[0008] Figure 2 This is the carbon NMR spectrum of compound B.
[0009] Figure 3 This is the UV-Vis and fluorescence spectrum of compound B. Detailed Implementation
[0010] Example 1. Synthesis of Compound B
[0011] 22 mg (0.05 mmol) of compound A was added to a dried 25 mL double-necked flask. After purging with nitrogen three times, 10 mL of ultra-dry dichloromethane was added under a nitrogen atmosphere, and the mixture was stirred for 5 minutes to completely dissolve the solid. Then, 0.1 mL of trifluoromethanesulfonic acid was added, and the mixture was stirred at 25 °C for 0.5 h. After the reaction was complete, 0.5 mL of hydrazine hydrate was added and stirred for 5 minutes. The mixture was washed three times with an equal volume of saturated brine each time, and the organic phase was separated. The organic phase was dried with anhydrous sodium sulfate for 0.5 h, filtered, and the solvent was recovered by vacuum distillation of the filtrate to obtain a light brown solid, which was the crude product. The crude product was separated by silica gel column chromatography with a 200-300 mesh, using a 1:1 volume ratio of dichloromethane and n-hexane as the eluent. The first band, which showed blue fluorescence under 365 nm UV light, was collected, yielding a solution of compound B. The solvent was recovered by vacuum distillation, and the solution was dried under vacuum to obtain 12 mg of light green solid, which was compound B, with a yield of 75%.
[0012] The NMR spectrum of compound B was measured using a Bruker AVANCE NEO NMR spectrometer, the UV-Vis absorption spectrum was measured using a Shimadzu UV-3600i Plus spectrometer, and the fluorescence spectrum was measured using an F-4700 fluorescence spectrometer.
[0013] The proton NMR spectrum of compound B is attached. Figure 1 The specific data is as follows: 1 H NMR (600 MHz, CDCl3) δ 8.30 (d,J = 7.8 Hz, 4H), 7.98 (t,J = 7.8 Hz, 2H), 4.63 (s, 8H).
[0014] The carbon spectrum results for compound B are attached. Figure 2 The specific data is as follows: 13 C NMR (151 MHz, CDCl3) δ 134.45, 125.96, 125.53, 117.29, 116.68, 64.98.
[0015] The UV-Vis and fluorescence spectra of compound B are shown in the appendix. Figure 3 .
Claims
1. Claim 1: A method for synthesizing ethylene glycol-protected pyrene and its properties, characterized in that: The present invention synthesizes an ethylene glycol-protected pyrene compound, the structure of which is as follows:
2. Claim 2: A method for synthesizing ethylene glycol-protected pyrene and its properties, characterized in that: The molar ratio of the raw materials for synthesizing compound B is: compound A : TfOH = 1 :
22.
3. Claim 3: A method for synthesizing ethylene glycol-protected pyrene and its properties, characterized in that: The solvent for synthesizing compound B is dichloromethane, and the amount used is 200 ml dichloromethane / mmol compound A.
4. Claim 4: A method for synthesizing ethylene glycol-protected pyrene and its properties, characterized in that: The synthesis conditions for compound B were: a reaction temperature of 25℃ and a reaction time of 0.5h.
5. Claim 5: A method for synthesizing ethylene glycol-protected pyrene and its properties, characterized in that: Compound B exhibits blue fluorescence in solution under 365 nm ultraviolet light illumination. The ultraviolet absorption wavelength of compound B is 359 nm, and the fluorescence emission wavelength is 391 nm. Therefore, compound B is expected to be applied in the field of organic light-emitting materials.