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A kind of AIE compound and its preparation method and application

A compound and chemical formula technology, applied in the field of organic compounds and their preparation, can solve problems such as difficult separation and cumbersome preparation process

Active Publication Date: 2021-05-14
JINZHONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the currently reported AIE molecules are based on derivatives such as polyphenylsilole and tetraphenylpyrazine. The preparation process of these compounds is cumbersome and difficult to separate.
Can selectively detect H + Ionic salicylaldehyde Schiff base compounds with AIE effect have not been reported yet

Method used

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  • A kind of AIE compound and its preparation method and application
  • A kind of AIE compound and its preparation method and application
  • A kind of AIE compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]Example 1. EtOAc EtOAc (EtOAc) EtOAc (EtOAc) EtOAc (EtOAc) EtOAc (EtOAc) EtOAc (EtOAc) EtOAc (EtOAc) The solution is red and yellow in the round bottom flask, and the solution is red-yellow; 2 mmol, Add it to the above solution, stirred, stirred with 6 mol / L sulfuric acid, heated and refluxed for 2 hours, stop heating, and the temperature is lowered to room temperature, vacuum filtration reactants, water / ethanol mixed solvent (volume ratio 1: 2) The precipitate was washed, filtered to give a light yellow solid, dried. The pale yellow solid was dissolved in the dimethyl sulfoxide (DMSO) solution, and the seal was sealed, and the orange needle crystal was precipitated after several hours.1HNMR (600MHz, DMSO-D6(PPM) 9.262 (S, 2H, -HC = N -), 8.658 (S, 2H, pH-H), 8.551 (S, 2H, pH-H). Electronic spray mass spectrometry (m / z), Found: 486.87 (100%), CALCD: [M-H]-486.87. Filter collection, yield is 68%.

[0023]The structure of the compound:

[0024]Crystal structure assay with Bruker...

Embodiment 2

[0032]Example 2. Quantity was removed from 40 ml of anhydrous ethanol, dissolved 3-bromo-5-nitrogen hydrarsedehyde 2.9842 g (12 mmol), in the round bottom flask, and the solution was red and yellow; 61 μl of hydrazine (2 mmol), Add it to the above solution, stirred, stirred with 6 mol / L sulfuric acid, heated and refluxed for 2 hours, stop heating, and the temperature is lowered to room temperature, vacuum filtration reactants, water / ethanol mixed solvent (volume ratio 1: 2) The precipitate was washed, filtered to give a light yellow solid, dried. The pale yellow solid was dissolved in the dimethyl sulfoxide (DMSO) solution, and the seal was sealed, and the orange needle crystal was precipitated after several hours.1HNMR (600MHz, DMSO-D6(PPM) 9.262 (S, 2H, -HC = N -), 8.658 (S, 2H, pH-H), 8.551 (S, 2H, pH-H). Electronic spray mass spectrometry (m / z), Found: 486.87 (100%), CALCD: [M-H]-486.87. Filter collection, yield is 50%.

Embodiment 3

[0033]Example 3. Substated 40 ml of anhydrous ethanol, dissolved 3-bromo-5-nitrogen hydrarse aldehyde 2.9842 g (12 mmol), in the round bottom flask, the solution was red and yellow; the amount of hydrazine was 76 μL (2.5 mmol) The above solution was added dropwise, stirred, stirred, add 6 mol / L sulfuric acid, and the heating was refluxed after 2 hours, stop heating, and the temperature was lowered to room temperature, vacuum filtration reactants, mixed with water / ethanol (volume ratio 1: 2) ) Wash the precipitate, remove filtration, to obtain a light yellow solid, dried. The pale yellow solid was dissolved in the dimethyl sulfoxide (DMSO) solution, and the seal was sealed, and the orange needle crystal was precipitated after several hours.1H NMR (600MHz, DMSO-D6(PPM) 9.262 (S, 2H, -HC = N -), 8.658 (S, 2H, pH-H), 8.551 (S, 2H, pH-H). Electronic spray mass spectrometry (m / z), Found: 486.87 (100%), CALCD: [M-H]-486.87. Filter collection, yield is 30%.

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Abstract

The present invention relates to compounds having AIE properties and processes for their preparation. The compound chemical formula is: C 14 h 8 Br 2 N 4 o 6 2(C 2 h 6 OS), where C 2 h 6 OS is dimethyl sulfoxide (DMSO). Slowly add hydrazine hydrate in the absolute ethanol of 3-bromo-5-nitrosalicylaldehyde, mix and stir; the molar ratio of hydrazine hydrate and 3-bromo-5-nitrosalicylaldehyde is 1:(4~6) ; During the stirring process, 1~5 drops of 6mol / L sulfuric acid were added dropwise, heated and refluxed and stirred for 2 hours; Suction filtration and water / ethanol mixed solvent washing precipitate after the completion of the reaction, suction filtration obtained solid product (C 14 h 8 Br 2 N 4 o 6 ), the solid product was dissolved in dimethyl sulfoxide (DMSO) solution, and the obtained crystal was the compound. The compound has a strong AIE effect and has a strong effect on H in different pH buffer solutions + have different responses, compound C 14 h 8 Br 2 N 4 o 6 2(C 2 h 6 OS) can be used as a pH fluorescent probe.

Description

Technical field[0001]The present invention relates to an organic light-emitting material, and more particularly to a aggregated inducing light-emitting (aie) effect and in different pH buffer solutions+Organic compounds with different responses and their preparation methods.Background technique[0002]The luminescent materials characterized by aggregation induced luminescence (AIE) have caused great interest in people. Typically, the chromophore aggregation has two effects on the light-emitting process, ie, the polymerization caused by quenching (ACQ) phenomenon and aggregation induced luminescence (AIE). In general, the organic luminescent material exhibits strong fluorescence in the dilute solution, but in the aggregation state, it exhibits weak fluorescence or even fluorescence, which is the ACQ phenomenon. Some compound molecules, almost no shining in the solution, but luminescence in the aggregated state, since this luminescence enhancement is caused by the compound molecule aggr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/02C07C251/24C09K11/06G01N21/64
CPCC07B2200/13C07C251/24C09K11/06C09K2211/1007G01N21/643
Inventor 马玲白杨路敏何婧
Owner JINZHONG UNIV
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