Preparation method and application of fluorescent carbon quantum dots

A technology of carbon quantum dots and fluorescence, which is applied in the field of preparation of fluorescent carbon quantum dots, can solve the problems of fluorescent carbon quantum dots limitations and inability to produce large quantities, and achieve the effect of promoting photoreaction and avoiding residues

Active Publication Date: 2022-05-10
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in general, fluorescent carbon quantum dots are still limited by the synthesis method and cannot be produced in large quantities. Fi...

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  • Preparation method and application of fluorescent carbon quantum dots
  • Preparation method and application of fluorescent carbon quantum dots
  • Preparation method and application of fluorescent carbon quantum dots

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preparation example Construction

[0039] Preparation of blue carbon quantum dots: Weigh 1.0g of citric acid and 1.2g of thiourea, then add 15mL of water into a sealed tube, and react at 140°C for 10h. After the reaction, cool to room temperature, and concentrate under reduced pressure to remove the solvent. The residue was purified by silica gel flash chromatography, concentrated and dried to obtain 1.8 g of light yellow solid powder.

[0040] Preparation of green carbon quantum dots: Weigh 1.5g of citric acid and 1.0g of urea, then add 15mL of formamide into a sealed tube, and react at 150°C for 12h. After the reaction, cool to room temperature, and concentrate under reduced pressure to remove the solvent. The product was purified by silica gel flash chromatography, concentrated and dried to obtain 1.2 g of yellow solid powder.

[0041] Preparation of yellow carbon quantum dots: Weigh 1.1g of p-phenylenediamine and 1.6g of urea, then add 15mL of dimethyl sulfoxide into a sealed tube, react at 160°C for 8h, af...

Embodiment 1

[0044]

[0045] Sequentially weigh p-methoxybenzenediazonium tetrafluoroborate 1a (0.3mmol), diboronic acid pinacol ester 2a (0.4mmol), B-CDots (10mg) into the photoreaction tube, under 0.3Mpa nitrogen atmosphere Add 5 mL of acetonitrile, and react at room temperature for 20 h under the light of 460 nm LEDs (10 W). After the reaction, extract with ethyl acetate and water, collect the organic phase, dry over anhydrous sodium sulfate, filter, remove volatile components under reduced pressure, and then use silica gel column chromatography to separate (eluent is petroleum ether (60-90°C) ) / ethyl acetate, v / v=20:1), the target product 3a was obtained as a colorless oil (59.7 mg, yield 85%). The target product was confirmed by NMR spectroscopy.

Embodiment 2

[0047]

[0048] Sequentially weigh benzenediazonium p-bromotetrafluoroborate 1b (0.3mmol), pinacol diborate 2a (0.45mmol), and B-CDots (15mg) into the photoreaction tube, and add them under an argon atmosphere of 0.3Mpa. 5 mL of toluene was reacted at room temperature for 18 h under the light of 495 nm LEDs (10 W). After the reaction, extract with ethyl acetate and water, collect the organic phase, dry over anhydrous sodium sulfate, filter, remove volatile components under reduced pressure, and then use silica gel column chromatography to separate (eluent is petroleum ether (60-90°C) ) / ethyl acetate, v / v=50:1), the target product 3b was obtained as a white solid (63.7 mg, yield 75%). The target product was confirmed by NMR spectroscopy.

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Abstract

The invention discloses a synthesis method of fluorescent carbon quantum dots and a method for catalyzing boronation and arylation reactions of small organic molecules by taking the carbon quantum dots as a novel photocatalyst. According to the invention, organic acid and organic amine which are cheap and easy to obtain are used as carbon sources or heteroatom precursors to react in an organic solvent or water, and separation and purification are carried out in a silica gel column chromatography manner, so that the full-wave-band carbon quantum dots are prepared. The synthesized carbon quantum dots have the advantages of cheap and easily available raw materials, simple and efficient reaction method, high yield and convenient post-treatment, and are suitable for large-scale production. The prepared carbon quantum dots have the advantages of photoluminescence characteristic, good water solubility, low toxicity, easiness in functionalization, environmental friendliness, good biocompatibility and the like, can catalyze boronation reaction and arylation reaction of small organic molecules, and have a certain application prospect.

Description

technical field [0001] The invention relates to a preparation method and application of fluorescent carbon quantum dots, in particular to the application as a photocatalyst to catalyze the borylation reaction and arylation reaction of small organic molecules. Background technique [0002] Aryl borates are widely used in the fields of organic synthesis, catalysis, materials science, drug development and analytical chemistry, so the synthesis of aryl borates has received extensive attention. People have been looking for green and effective synthetic methods to obtain aryl borate esters from simple and easy-to-obtain raw materials, which are environmentally friendly. Recently, visible light catalysis has brought new prospects for the construction of aryl boronic esters with its unique single-electron transfer properties. [0003] Arylated heteroaromatics are widely used in materials science due to their optical and electronic properties, and can also be used in biomedicine as ...

Claims

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Application Information

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IPC IPC(8): C09K11/65B82Y20/00B82Y40/00C01B32/15B01J21/18C07F5/02C07D307/38C07D307/42C07D207/333
CPCC09K11/65B82Y20/00B82Y40/00C01B32/15B01J21/18B01J35/004C07F5/025C07D307/38C07D307/42C07D207/333
Inventor 黄菲何天同姜莉雅谢皓东于杨乔纳森贝尔
Owner NANJING UNIV OF TECH
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