Preparation and Application of Tetraphenylpyrazine-Based Nitrile Vinyl Functionalized AIE Molecules

A technology of tetraphenylpyrazine and nitrile vinyl, which is applied in the preparation and application of AIE molecules, can solve the problems of easy photoisomerization and photooxidation, comprehension of complex AIE mechanism, poor chemical stability, etc., and achieve convenient Visual observation, fast response time, high sensitivity effect

Active Publication Date: 2021-11-16
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For silole derivatives, they are often difficult to synthesize and purify, and their chemical stability is poor; for tetraphenylethylene derivatives, the presence of double bonds makes them prone to photoisomerization and photooxidation, which complicates the process on the one hand. The understanding of the AIE mechanism, on the other hand, reduces the stability of these AIE molecules as materials

Method used

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  • Preparation and Application of Tetraphenylpyrazine-Based Nitrile Vinyl Functionalized AIE Molecules
  • Preparation and Application of Tetraphenylpyrazine-Based Nitrile Vinyl Functionalized AIE Molecules
  • Preparation and Application of Tetraphenylpyrazine-Based Nitrile Vinyl Functionalized AIE Molecules

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of monoaldehyde substituted tetraphenylpyrazine derivatives:

[0038]

[0039] Add 3g (6.5mmol) monobromosubstituted tetraphenylpyrazine (refer to J.Mater.Chem.C, 2016, 4, 2901 for the synthetic route), 1.17g (7.8mmol) p-formylphenylboronic acid in a 250mL round bottom flask and 372 mg (0.32 mmol) tetrakistriphenylphosphine palladium. After the system was evacuated and nitrogen exchanged three times, 100 mL of distilled tetrahydrofuran and 50 mL of 2M potassium carbonate aqueous solution were injected. The reaction system was stirred overnight at reflux. Subsequently, the system was returned to room temperature, extracted with dichloromethane and washed with water several times. The collected organic phase was distilled off under reduced pressure to remove the solvent. The crude product was purified by column chromatography with n-hexane / dichloromethane (volume ratio 1:1) to obtain 2.79 g (5.7 mmol) of a white solid with a yield of 88.2%. 1 H NMR (400MH...

Embodiment 2

[0043] Example 2 Time Response of Fluorescent Molecules to Hydrogen Sulfide

[0044] Fluorescent molecules were dissolved in dimethyl sulfoxide, and a stock solution with a concentration of 250 μM was prepared. Take 1mL of the mother liquor in a glass bottle, add 8mL of dimethyl sulfoxide, and then add 1mL of sodium hydrosulfide in PBS buffer (buffer concentration is 10mM, pH is 7.4), to ensure that the equivalent ratio of probe molecules to sodium hydrosulfide is 1 :10. Measure the fluorescence emission spectrum as a function of time with a fluorescence spectrometer. from figure 1 In (A) and (B), it can be seen that before adding sodium hydrosulfide solution, the probe emits orange light at 565nm; after adding sodium hydrogensulfide solution, as time goes on, the orange light gradually weakens, and the dark blue at 429nm The light was gradually increased, and the probe response was completed within 10 minutes.

Embodiment 3

[0045] Embodiment 3 Fluorescent molecules respond to the concentration of hydrogen sulfide

[0046] Fluorescent molecules were dissolved in dimethyl sulfoxide, and a stock solution with a concentration of 250 μM was prepared. Take 1mL of the mother liquor in a glass bottle, add 8mL of dimethyl sulfoxide, and then add 1mL of sodium hydrosulfide in PBS buffer (buffer concentration is 10mM, pH is 7.4), to ensure that the concentration of sodium hydrosulfide solution is in the range of 0-500μM Variety. Ten minutes after adding the sodium hydrosulfide solution, the fluorescence emission spectra were measured respectively. from figure 1 In (C) and (D), it can be seen that as the concentration of sodium hydrosulfide solution increases, the orange-yellow light emitted by the probe at 565nm gradually weakens, while the dark blue light at 429nm gradually increases, and the response ends at 250μM . Moreover, the ratio of the intensity of deep blue light at 429nm to the intensity of o...

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Abstract

The invention discloses an aggregation-induced emission (AIE) material of nitrile vinyl functionalized tetraphenylpyrazine. Due to the chemical activity of the nitrile vinyl group in the structure, it can be used as a proportional fluorescent probe for detecting hydrogen sulfide, and has high sensitivity and good selectivity, so it has good applications in biological detection and environmental safety assessment. prospect. In addition, the flexible configuration of the molecules allows them to adjust the molecular packing during aggregation, so powders with green and orange light can be obtained by recrystallization. Among them, the powder emitting orange light undergoes a blue shift (green light emission) under grinding, and the luminescence can be restored by annealing the powder, and this process is reversible. This blue-shifted mechanochromic behavior is different from previously reported luminescent red-shifted, luminescent off-on and on-off transition mechanochromic materials, which provides new ideas for designing smart materials and information storage materials.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, in particular to the preparation and application of tetraphenylpyrazine-based nitrile vinyl functionalized AIE molecules. Background technique [0002] Hydrogen sulfide is a poisonous, corrosive, flammable gas with the smell of rotten eggs. Hydrogen sulfide, which is comparable in toxicity to carbon monoxide, can bind to iron in mitochondrial cytochrome enzymes, preventing cellular respiration and causing apnea asphyxiation. Hydrogen sulfide is also an important endogenous gas transporter, present in high concentrations (10-600 μM) in the brain of cattle, rats, and humans, and has also been demonstrated in various physiological processes such as vasodilation, cellular Regulation of growth, antioxidant and inflammation. The abnormal presence of hydrogen sulfide in the body has also been linked to conditions such as Alzheimer's disease and diabetes. Due to the high selectiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/12C09K11/06C09K9/02G01N21/64
CPCC07D241/12C09K9/02C09K11/06C09K2211/1007C09K2211/1044G01N21/643
Inventor 唐本忠陈明
Owner THE HONG KONG UNIV OF SCI & TECH
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