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Chiral Tetrastyryltetramines for Enantiomeric Identification and Purity Analysis of Chiral Carboxylic Acids

A technology of chiral carboxylic acid and chiral amine, which is applied in the field of chemical analysis, can solve the problem of low accuracy of enantiomer purity analysis of chiral carboxylic acid, achieve high sensitivity, high accuracy, and improve the effect of accuracy

Inactive Publication Date: 2020-07-10
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The invention solves the technical problem of low accuracy of enantiomer purity analysis, especially chiral carboxylic acid in the existing fluorescence analysis technology

Method used

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  • Chiral Tetrastyryltetramines for Enantiomeric Identification and Purity Analysis of Chiral Carboxylic Acids
  • Chiral Tetrastyryltetramines for Enantiomeric Identification and Purity Analysis of Chiral Carboxylic Acids
  • Chiral Tetrastyryltetramines for Enantiomeric Identification and Purity Analysis of Chiral Carboxylic Acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Chiral fluorescence analysis reagent I (in general formula I, R 1 = cyclohexyl; R 2 = methyl) synthesis:

[0041]

[0042]

[0043]Add the compound of formula II (0.05g-2g), anhydrous potassium carbonate (0.01g-5.0g), S-1-cyclohexylethylamine (0.06-6.0g) and tetrahydrofuran (1mL-100mL) into a round bottom flask , heated and stirred at 70-100°C for 4h-20h, evaporated to remove the solvent, and the remaining solid was purified by column chromatography (aluminum oxide, eluent: methanol / dichloromethane) to obtain the compound described in formula I , the yield is greater than 60%.

[0044] Formula I compound in CDCl 3 middle 1 H-NMR spectrum see figure 1 , 13 C-NMR spectrum see figure 2 , HRMS spectrum see image 3 .

Embodiment 2

[0046] The compound prepared in Example 1 (in general formula I, R 1 = cyclohexyl; R 2 =methyl; S-configuration) was dissolved in acetone to make 1.0×10 -3 M's solution. In three 5mL glass bottles, add 0.04mL of the prepared solution above; then add 0.04mL of acetone, 0.04mL of 2.0×10 -3 M's D-p-toluoyl tartrate in acetone and 0.04mL 2.0×10 -3 M L-p-toluoyl tartrate acetone solution, after shaking well, add 3.92 ml of cyclohexane respectively. After mixing evenly, test the fluorescence spectrum of the solution in the three bottles and take a photo of the fluorescence under a 365nm portable ultraviolet lamp. It can be seen under ultraviolet light that the solution without p-toluoyl tartaric acid is yellow fluorescence, the solution with D-p-toluoyl tartaric acid is blue fluorescence, and the solution with L-p-toluoyl tartaric acid is green fluorescence. For spectrograms and fluorescence photos, see Figure 4 , Figure 4 Middle bold body 6 is the compound of formula I, an...

Embodiment 3

[0048] The compound prepared in Example 1 (in general formula I, R 1 = cyclohexyl; R 2 =methyl; S-configuration) was dissolved in acetone to make 1.0×10 -3 M's solution. In three 5mL glass bottles, add 0.04mL of the prepared solution above; then add 0.04mL of acetone, 0.04mL4.0×10 -3 M herbicide R-2,4-D acetone solution and 0.04mL 4.0×10 - 3 M's herbicide S-2,4-D acetone solution, shake well, add 3.92 ml of cyclohexane respectively. After mixing evenly, test the fluorescence spectrum of the solution in the three bottles and take a photo of the fluorescence under a 365nm portable ultraviolet lamp. It can be seen under ultraviolet light that the solution without 2,4-D is yellow fluorescence, the solution with R-2,4-D is green fluorescence, and the solution with S-2,4-D is very light yellow fluorescence. For spectrograms and fluorescence photos, see Figure 5 , Figure 5 The middle bold body 6 is the compound of formula I, and the bold body 18 is the herbicide 2,4-D.

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Abstract

The invention relates to a chiral tetrastyryltetramine for identification and purity analysis of chiral carboxylic acid enantiomers, and belongs to the technical field of chemical analysis. The chiraltetrastyryltetramine compound has an aggregation induced luminescence (AIE) effect. A preparation method of the chiral tetrastyryltetramine is characterized in that the chiral tetrastyryltetramine isobtained by reacting 3-(tetrachloromethylene)-4-(tetra-p-bromophenyl)tetrastyrene with optically pure chiral amine, and the optically pure chiral amine is optically pure chiral 1-cyclohexylethylamine, 1-cyclohexylpropylamine or 1-cyclopentylethylamine preferably. The prepared chiral tetrastyryltetramine can react with two enantiomers of a series of chiral carboxylic acids to respectively emit fluorescence with different colors, so the chiral tetrastyryltetramine can be used to distinguish the two enantiomers of chiral carboxylic acids; and the wavelength of the fluorescence varies linearly with the percent (ee) of the purity of the enantiomers or the purity of the enantiomers, so the chiral tetrastyryltetramine can be used for high-accuracy and high-sensitivity analysis of the purity of the chiral carboxylic acid enantiomers by the change of the fluorescence wavelength of the chiral tetrastyrene.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis, and more specifically relates to a chiral tetraphenylethylenetetramine with aggregation-induced emission (AIE) performance and the application of preparation, enantiomer recognition and purity analysis. Background technique [0002] The enantiomeric purity or enantiomeric purity (ee) analysis of chiral molecular enantiomers using chiral fluorescent reagents is simple, sensitive, and fast. It has important potential applications in quantitative analysis and has attracted extensive research and attention. However, in all ee analysis methods using fluorescent reagents, the analysis is based on the change of fluorescence intensity with the ee value (Chem.Rew.2014, 114, 4918-4959; Chem.Rew.20004, 104, 1687-1716; J. Am. Chem. Soc. 2019, 141, 175-181). Since fluorescence intensity is particularly sensitive to environmental changes, EE analysis based on fluorescence intensity tends to be inac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/29C07C209/68C09K11/06G01N21/64
CPCC07B2200/07C07C211/29C09K11/06C09K2211/1007G01N21/6402
Inventor 郑炎松胡明
Owner HUAZHONG UNIV OF SCI & TECH
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