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Preparation of a Chiral Fluorescent Carbon Dot Applicable to Enantioselective Recognition

An enantioselective, fluorescent carbon dot technology, applied in nanotechnology for materials and surface science, fluorescence/phosphorescence, luminescent materials, etc. Fluorescent probe preparation and other issues

Active Publication Date: 2022-03-22
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, we noticed that during the synthesis process, chiral amine compounds are easy to lose the chiral center, which limits the preparation of chiral fluorescent probes

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The preparation of a kind of chiral carbon dot material comprises the following steps:

[0022] (1) Preparation of pyridine-modified fluorescent carbon dots: Weigh 0.210 g of citric acid and 0.324 g of 3-aminomethylpyridine with a molar ratio of 1:3, and stir at 500 rpm -1 , after hydrolysis at 155 °C for 8 h, concentrated by distillation under reduced pressure, and purified the crude product by silica gel column chromatography (dichloromethane:methanol = 95:5) to obtain 0.464 g of pyridine-modified fluorescent carbon dots;

[0023] (2) Preparation of bromine-containing chiral molecules: Add 0.675 g of 2-bromoethyl isocyanate and 0.258 g of left-handed single-configuration 1,2-diaminocyclohexane in 50 mL of dichloroethane under ice bath , magnetic stirring at 500 rpm -1 , after reacting for 4 h, concentrated by distillation under reduced pressure to obtain 0.898 g bromine-containing chiral molecules;

[0024] (3) Preparation of chiral fluorescent carbon dots material:...

Embodiment 2

[0026] Efficient recognition of tryptophan enantiomers by chiral carbon dot materials:

[0027] Weigh 20 mg of the chiral fluorescent carbon dot material prepared in step c and dissolve it in 150 mL of ultrapure water. At the same time, prepare 1.0 mM tryptophan aqueous solution and copper chloride aqueous solution with different configurations, and measure 1 mL of the prepared solution respectively. Chiral fluorescent carbon dot solution, mixed with 1mL copper chloride solution and 1mL L-tryptophan or D-tryptophan solution, scanned at 430 nm excitation wavelength to obtain the corresponding fluorescence emission peak (scanning interval is 440-700 nm ), the calculated fluorescence difference value is 1.8.

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Abstract

The invention belongs to the field of nanometer material preparation and molecular recognition, in particular to the preparation of a chiral fluorescent carbon point applicable to enantioselective recognition. The invention mainly aims at the shortcoming that the precursor chiral amine compound is easy to lose the chiral center during the preparation process of the fluorescent carbon dot, and provides a simple and cheap preparation method of the chiral fluorescent carbon dot. It mainly includes the following steps: (1) preparation of pyridine-modified fluorescent carbon dots; (2) preparation of bromine-containing chiral molecules; (3) reaction of fluorescent luminescent materials prepared in steps 1 and 2 with chiral selectors to obtain chiral Fluorescent carbon dot material; (4) The fluorescent carbon dot material obtained in step 3 realizes efficient recognition of tryptophan enantiomers. The beneficial effects of the invention are: the preparation method is simple, the prepared chiral carbon dot material has high quantum yield and strong sensitivity to the solution, and has good enantiomeric discrimination ability for the tryptophan enantiomer.

Description

technical field [0001] The invention relates to the preparation of a chiral fluorescent carbon point applicable to selective recognition of enantiomers, and belongs to the fields of nanometer material preparation and molecular recognition. Background technique [0002] At present, the construction of intelligent fluorescent recognition molecules for enantioselective recognition has received extensive attention. Selective fluorescence quenching or fluorescence enhancement is an effective means to identify different configurational isomers. Compared with identification technologies such as high performance liquid chromatography, gas chromatography, nuclear magnetic resonance, mass spectrometry, and electrochemical analysis, fluorescence chiral recognition technology has the advantages of low cost, fast speed, and high sensitivity. So far, a series of organic chiral fluorescent molecules with different structures have been reported. For example, a research group has reported ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/02C09K11/65B82Y20/00B82Y30/00G01N21/64
CPCC09K11/025C09K11/65B82Y20/00B82Y30/00G01N21/643G01N2021/6439
Inventor 吴大同潘菲高丽陶永新孔泳
Owner CHANGZHOU UNIV