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Dibenzothiophene derivative, preparation method and application thereof

A technology for dibenzothiophene and derivatives, which is applied in the field of dibenzothiophene derivatives and their preparation, can solve problems such as difficult formation of linear relationship and great influence on fluorescence intensity, etc., and achieves easy popularization and large-scale production, and simple preparation method , the effect of a wide linear range

Active Publication Date: 2017-08-11
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescence intensity is greatly affected by the environment (solvent, temperature, pH, etc.), and it is not easy to form a linear relationship

Method used

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  • Dibenzothiophene derivative, preparation method and application thereof
  • Dibenzothiophene derivative, preparation method and application thereof
  • Dibenzothiophene derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of 2-cyano-3-{2-[5-(4-dibenzo[b,d]thienyl)]thienyl}methyl acrylate

[0024] Weigh 2-[5-(4-dibenzo[b,d]thienyl)]thiophene aldehyde (2.94g, 10.0mmol) and dissolve it in a round bottom flask containing 100mL toluene, then add methyl cyanoacetate (1.09g, 11.0mmol) and catalyst hexahydropiperidine (0.04g, 0.5mmol), the mass ratio of thiophene aldehyde, methyl cyanoacetate and hexahydropiperidine is 20:22:1. Stir and heat to 110° C., and continue the reaction for 6 hours. After the reaction, 1 / 2 of the organic solvent in the reaction system was distilled off, and a yellow solid was precipitated, and the crude product was obtained by filtration, and recrystallized using chloroform / petroleum ether=1:1 (volume ratio), to obtain 3.15 g of a yellow solid, namely Methyl 2-cyano-3-{2-[5-(4-dibenzo[b,d]thienyl)]thienyl}acrylate in 84% yield.

[0025] 1 H NMR (400MHz, CDCl 3 ):δ8.35(s,1H,CH=C),8.21-8.18(m,2H,dibenzothiophene),7.91-7.88(m,1H,dibenzothiophene)...

Embodiment 2

[0026] Embodiment 2: application embodiment, with above-mentioned dibenzothiophene derivative as detection probe

[0027] Step 1: Drawing of working curve. The above 2-cyano-3-{2-[5-(4-dibenzo[b,d]thienyl)]thienyl}methyl acrylate was dissolved in anhydrous tetrahydrofuran to prepare 10 -4 mol / L solution (mother liquor), its ultraviolet-visible absorption spectrum in tetrahydrofuran solution is as figure 2 shown. Prepare 10.00mL of tetrahydrofuran aqueous solutions with different concentration gradients (the water content is 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%), and use a pipette to add 0.25mL of the above mother liquor, shake, shake well, test the fluorescence titration spectrum in tetrahydrofuran-water solution as image 3 shown. With the increase of water content, the fluorescence emission intensity increases linearly (excitation wavelength 400nm), showing aggregation-induced luminescence characteristics; meanwhile, the maximum emission wavelength of fluorescence also...

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PUM

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Abstract

The invention discloses a dibenzothiophene derivative, a preparation method and application thereof. Particularly, the dibenzothiophene derivative refers to 2-cyano-3-{2-[5-(4-dibenzo [b, d] thienyl)] thienyl} methyl acrylate. The derivative is prepared by adding 2-[5-(4-dibenzo [b, d] thienyl)] thiophene aldehyde, methyl cyanoacetate, hexahydropiperidine, and anhydrous toluene in a reaction container; stirring the components for 5-7 hours at 105-115 DEG C, wherein mass ratio of 2-[5-(4-dibenzo [b, d] thienyl)] thiophene aldehyde to methyl cyanoacetate to hexahydropiperidine is (19-21): (21-23): 1; after finishing reaction, concentrating and filtering the organic solvent in the reaction system; taking out a filter cake; recrystallizing the filter cake by mixed solvent of chloroform and petroleum ether. The 2-cyano-3-{2-[5-(4-dibenzo [b, d] thienyl)] thienyl} methyl acrylate can be used as a fluorescence detection probe, and the probe is used for detecting water content of tetrahydrofuran solution by using the fluorescence-emission wavelength as an index; the linear scale is wide, and the accuracy is high.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a dibenzothiophene derivative and a preparation method and application thereof. Background technique [0002] Tetrahydrofuran is a very important organic chemical raw material and solvent. It can be miscible with water in any proportion, so tetrahydrofuran produced and used in industry often contains different amounts of water. In addition, some unscrupulous enterprises secretly discharge tetrahydrofuran in industrial wastewater, seriously polluting the environment. Therefore, the proportion content detection of water and tetrahydrofuran is particularly important. The current methods for testing the water content in THF include the Karl Fischer reagent method, the density bottle method, the hydrometer method and the distillation method, etc., but the applicable range is often narrow or the time-consuming is too long. Due to its low cost, simple operation, real-time m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76G01N21/64
CPCC07D333/76G01N21/643
Inventor 陶涛甘逸涛于江华汪舒蓉赵煚珖宋克贤
Owner NANJING UNIV OF INFORMATION SCI & TECH