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CN-121974914-A - Halogen-containing solvent identification response organic fluorescent material and preparation method thereof

CN121974914ACN 121974914 ACN121974914 ACN 121974914ACN-121974914-A

Abstract

The invention provides a halogen-containing solvent identification response organic fluorescent material and a preparation method thereof. The structure of the fluorescent material is formed by condensing two carbazole molecules to form a rigid conjugated plane, so that the fluorescent material has a large conjugated degree, and the absorption position of the fluorescent material is expanded to a visible light region. The organic fluorescent material is an organic fluorescent sensor for photoexcitation and macroscopic recognition response, can be used for specific recognition of halogenated solvents, and has good application prospect.

Inventors

  • ZHAO YAN
  • CHEN YOUYANG
  • ZHOU YIKAI
  • DENG SHUQI
  • XIAO WANGCHUAN

Assignees

  • 三明学院

Dates

Publication Date
20260505
Application Date
20251212

Claims (6)

  1. 1. The halogen-containing solvent identification response organic fluorescent material is characterized by being DIP, and the structural formula of the organic fluorescent material is as follows: 。
  2. 2. the method for preparing an organic fluorescent material for halogen-containing solvent recognition response according to claim 1, comprising the steps of: (1) Adding 3, 6-di-tert-butylcarbazole into dichloromethane, fully stirring and dissolving, slowly dropwise adding a dichloromethane solution of N-bromosuccinimide under a dark condition, reacting for 6 hours at room temperature in a dark condition, cooling to room temperature, concentrating the product, washing with saturated saline water, drying with anhydrous magnesium sulfate, separating a concentrated organic layer, and separating by silica gel column chromatography to obtain the product Cz-Br; (2) Dissolving Cz-Br in acetone, adding KMnO 4 , heating a reaction system to 60 ℃, carrying out reflux reaction in a nitrogen atmosphere for 6 hours, cooling to room temperature, distilling under reduced pressure to remove acetone, dissolving a product in chloroform, filtering, separating and washing filter residues, washing the obtained solution with saturated sodium thiosulfate solution and saline solution in sequence, drying with anhydrous magnesium sulfate, separating and concentrating an organic layer, and separating by silica gel column chromatography to obtain a product DC Z -2Br; (3) The preparation of the DIP comprises the steps of sequentially adding DCz-2Br, palladium chloride, 2-dicyclohexylphosphine-2 ',6' -dimethoxy biphenyl and tetrabutylammonium bromide into a reaction container, filling nitrogen and deoxidizing, injecting toluene and K 2 CO 3 solution, reacting for 24 hours at 100 ℃ in nitrogen atmosphere, cooling to room temperature, sequentially washing a product by saturated saline water, extracting by ethyl acetate, drying by anhydrous magnesium sulfate, separating and concentrating an organic layer, and separating by silica gel column chromatography to obtain the product DIP.
  3. 3. The method according to claim 2, wherein the eluent of the silica gel column chromatography in the step (1) is petroleum ether, dichloromethane=30:1, in volume ratio.
  4. 4. The method according to claim 2, wherein the eluent for silica gel column chromatography in the step (2) is petroleum ether, dichloromethane=50:1, in volume ratio.
  5. 5. The method according to claim 2, wherein the eluent for silica gel column chromatography in the step (3) is petroleum ether, dichloromethane=60:1, in volume ratio.
  6. 6. Use of the organic fluorescent material of claim 1 in a halogen-containing solvent recognition response.

Description

Halogen-containing solvent identification response organic fluorescent material and preparation method thereof Technical Field The invention belongs to the field of fluorescent materials, and particularly relates to an organic fluorescent material with a halogen-containing solvent identification response and a preparation method thereof. Background Halogenated solvents, especially chlorinated solvents, are widely used in industrial and scientific fields. However, the widespread use of these chemicals poses many environmental problems and poses a threat to the health of the human body upon prolonged exposure. Halogenated solvents require finer treatments during waste treatment to minimize environmental pollution. Thus, organic solvent waste is classified into two separate categories, halogenated and non-halogenated, when disposed of. To date, detecting and distinguishing halogenated solvents from other solvents remains a very interesting but challenging area. Sensors are an important way to detect contaminants and monitor environmental conditions. Traditionally, methods for detecting organic solvents have mostly relied on analytical techniques (such as gas chromatography, high performance liquid chromatography and mass spectrometry) that require specially trained personnel and consume a great deal of time and money. The sensors based on color changes are of practical interest for ease of operation, especially when these changes can be easily identified by the naked eye. The development of new sensors and chemical detection methods is of increasing interest. Oyama et al (tetrahedron 69 (2013) 1755e 1760) designed several pyridine dyes of the D-pi-a type that have a greater red shift in halogenated solvents than in non-halogenated solvents. Ripp et al (biotechnol 39 (2012) 45-53.) have utilized the advantages of bioluminescent genes to create a biosensor for self-directed detection of CH 2Cl2. Murai et al (RSC adv. 7 (2017) 18132-18135) also synthesized several pyridine-5-aminothiazoles, which were used to detect halogenated solvents, particularly CH 2Cl2. Xu et al (chem. Commun. 52 (2016) 2095-2098) prepared a naphthalimide-based fluorescent sensor molecule that was effective in distinguishing halogenated solvents from non-halogenated solvents. Although these promising chemical sensors have been reported, relatively little research has been done on simple, low cost and macroscopic sensors. The invention provides an organic fluorescent sensor for light excitation and naked eye identification response and a high-yield preparation method thereof. Disclosure of Invention The invention aims to provide a halogen-containing solvent identification response organic fluorescent material and a preparation method thereof. In order to achieve the above purpose, the invention adopts the following technical scheme: a halogen-containing solvent identification response organic fluorescent material, designated DIP, having the formula: 。 the preparation method of the halogen-containing solvent identification response organic fluorescent material comprises the following steps: (1) Adding 3, 6-di-tert-butylcarbazole into dichloromethane, fully stirring and dissolving, slowly dropwise adding a dichloromethane solution of N-bromosuccinimide under a dark condition, reacting for 6 hours at room temperature in a dark condition, cooling to room temperature, concentrating the product, washing with saturated saline water, drying with anhydrous magnesium sulfate, separating a concentrated organic layer, and separating by silica gel column chromatography to obtain the product Cz-Br; (2) Dissolving Cz-Br in acetone, adding KMnO 4, heating a reaction system to 60 ℃, carrying out reflux reaction in a nitrogen atmosphere for 6 hours, cooling to room temperature, distilling under reduced pressure to remove acetone, dissolving a product in chloroform, filtering, separating and washing filter residues, washing the obtained solution with saturated sodium thiosulfate solution and saline solution in sequence, drying with anhydrous magnesium sulfate, separating and concentrating an organic layer, and separating by silica gel column chromatography to obtain a product DC Z -2Br; (3) The preparation of the DIP comprises the steps of sequentially adding DCz-2Br, palladium chloride, 2-dicyclohexylphosphine-2 ',6' -dimethoxy biphenyl and tetrabutylammonium bromide into a reaction container, filling nitrogen and deoxidizing, injecting toluene and K 2CO3 solution, reacting for 24 hours at 100 ℃ in nitrogen atmosphere, cooling to room temperature, sequentially washing a product by saturated saline water, extracting by ethyl acetate, drying by anhydrous magnesium sulfate, separating and concentrating an organic layer, and separating by silica gel column chromatography to obtain the product DIP. Further, the eluent of the silica gel column chromatography in the step (1) is petroleum ether, dichloromethane=30:1, and the volume ratio is the petroleum ether. Furth