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AIE (aggregation-induced emission) compound as well as preparation method and application thereof

A compound and chemical formula technology, applied in the field of organic compounds and their preparation, can solve the problems of cumbersome preparation process and difficult separation, and achieve the effects of simple preparation process, operation of reaction conditions and fast growth

Active Publication Date: 2019-01-04
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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  • AIE (aggregation-induced emission) compound as well as preparation method and application thereof
  • AIE (aggregation-induced emission) compound as well as preparation method and application thereof
  • AIE (aggregation-induced emission) compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1. Measure 40 milliliters of absolute ethanol, dissolve 2.4868 grams (10 mmol) of 3-bromo-5-nitrosalicylaldehyde, and in a round-bottomed flask, the solution is reddish-yellow; measure 61 μL (2 mmol) of hydrazine hydrate, Add dropwise to the above solution, stir, add a drop of 6mol / L sulfuric acid, heat and reflux for 2 hours, stop heating, wait for the reaction temperature to drop to room temperature, vacuum filter the reactant, water / ethanol mixed solvent (volume ratio 1:2) The precipitate was washed and filtered with suction to obtain a pale yellow solid, which was dried. The light yellow solid was dissolved in dimethyl sulfoxide (DMSO) solution, sealed and left standing, after several hours, orange needle-like crystals were precipitated. 1 HNMR (600MHz, DMSO-d 6 ) (ppm) 9.262 (s, 2H, -HC=N-), 8.658 (s, 2H, Ph-H), 8.551 (s, 2H, Ph-H). Electrospray mass spectrometry results (m / z), found: 486.87 (100%), calcd: [M-H] - 486.87. Collected by filtration in 6...

Embodiment 2

[0032] Example 2. Measure 40 milliliters of absolute ethanol, dissolve 2.9842 grams (12 mmol) of 3-bromo-5-nitrosalicylaldehyde, and in a round-bottomed flask, the solution is reddish-yellow; measure 61 μL (2 mmol) of hydrazine hydrate, Add dropwise to the above solution, stir, add a drop of 6mol / L sulfuric acid, heat and reflux for 2 hours, stop heating, wait for the reaction temperature to drop to room temperature, vacuum filter the reactant, water / ethanol mixed solvent (volume ratio 1:2) The precipitate was washed and filtered with suction to obtain a pale yellow solid, which was dried. The light yellow solid was dissolved in dimethyl sulfoxide (DMSO) solution, sealed and left standing, after several hours, orange needle-like crystals were precipitated. 1 HNMR (600MHz, DMSO-d 6 ) (ppm) 9.262 (s, 2H, -HC=N-), 8.658 (s, 2H, Ph-H), 8.551 (s, 2H, Ph-H). Electrospray mass spectrometry results (m / z), found: 486.87 (100%), calcd: [M-H] - 486.87. Collected by filtration, yield ...

Embodiment 3

[0033] Embodiment 3. Measure 40 milliliters of absolute ethanol, dissolve 2.9842 grams (12 mmol) of 3-bromo-5-nitrosalicylaldehyde, and in a round bottom flask, the solution is reddish-yellow; Measure hydrazine hydrate 76 μ L (2.5 mmol) , added dropwise in the above solution, stirred, added a drop of 6mol / L sulfuric acid, heated to reflux for 2 hours, then stopped heating, until the reaction temperature dropped to room temperature, vacuum filtered the reactant, water / ethanol mixed solvent (volume ratio 1:2 ) to wash the precipitate, filter with suction to obtain a pale yellow solid, and dry. The light yellow solid was dissolved in dimethyl sulfoxide (DMSO) solution, sealed and left standing, after several hours, orange needle-like crystals were precipitated. 1 H NMR (600MHz, DMSO-d 6 ) (ppm) 9.262 (s, 2H, -HC=N-), 8.658 (s, 2H, Ph-H), 8.551 (s, 2H, Ph-H). Electrospray mass spectrometry results (m / z), found: 486.87 (100%), calcd: [M-H] - 486.87. Collected by filtration in 3...

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Abstract

The invention relates to a compound with AIE (aggregation-induced emission) property and a preparation method of the compound. The chemical formula of the compound is C14H8Br2N4O6.2(C2H6OS), wherein C2H6OS is DMSO (dimethyl sulfoxide). The preparation method comprises the following steps: hydrazine hydrate is slowly added to anhydrous ethanol of 3-bromo-5-nitrosalicylaldehyde for mixing and stirring; hydrazine hydrate and 3-bromo-5-nitrosalicylaldehyde are in a molar ratio of 1: (4-6); during stirring, 1-5 drops of 6-mol / L sulfuric acid are added dropwise, and heating, reflux and stirring areperformed for 2 hours; suction filtration is performed after reaction, precipitant is washed with a water / ethanol mixed solvent, and a solid product (C14H8Br2N4O6) is obtained by suction filtration and dissolved in a DMSO solution, and the obtained crystal is the compound. The compound has strong AIE effect and has different responses to H<+> in different pH buffer solutions. The compound C14H8Br2N4O6.2(C2H6OS) can be used as a pH fluorescence probe.

Description

technical field [0001] The present invention relates to an organic luminescent material, in particular to an organic luminescent material which has aggregation-induced emission (AIE) effect and is sensitive to H in different pH buffer solutions. + Organic compounds with different responses and methods for their preparation. Background technique [0002] Luminescent materials characterized by aggregation-induced emission (AIE) have attracted great interest. In general, there are two effects of chromophore aggregation on the luminescent process, namely the aggregation-induced quenching (ACQ) phenomenon and the aggregation-induced emission (AIE) phenomenon. Generally, organic light-emitting materials show strong fluorescence in dilute solution, but show weak or even no fluorescence in the aggregated state, which is the ACQ phenomenon. Some compound molecules hardly emit light in solution, but the luminescence is enhanced in the state of aggregation. Since the luminescence enh...

Claims

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Application Information

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Patent Type & Authority Applications(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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