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Chiral silver nanocluster and preparation and application thereof

A technology of silver nanoclusters and chirality, which is applied in the fields of silver organic compounds, color/spectral characteristic measurement, organic chemistry, etc. It can solve the problems of complex preparation process, high requirements for instruments, and difficult condition screening, etc., and achieve low raw material cost , Excellent optical performance and good repeatability

Active Publication Date: 2020-01-17
ANHUI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current chiral detection mainly includes direct circular dichroism spectroscopy and chiral high-performance liquid chromatography column separation. The former has higher requirements for instruments because the luminescence signals of chiral drugs are generally in the ultraviolet or deep ultraviolet region, and Disadvantages such as large errors (Chem.Soc.Rev.2013,42,5408-5424.); and the current commercialized chiral columns due to the complicated preparation process, high cost of use, and few types make chiral HPLC The chromatographic column separation method has defects such as difficult condition screening and poor separation effect.

Method used

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  • Chiral silver nanocluster and preparation and application thereof
  • Chiral silver nanocluster and preparation and application thereof
  • Chiral silver nanocluster and preparation and application thereof

Examples

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preparation example Construction

[0056] The preparation method of the chiral silver nanocluster of the present invention comprises the following steps:

[0057] Add 600mg of silver acetate and 50ml of methanol into a three-necked flask, stir until evenly dispersed, then add 0.4mL of p-tert-butylbenzylmercaptan, react for 30min until the solution is light yellow and turbid, then add 20mL of 1.5g of triacetoxy Sodium borohydride in methanol or tetrahydrofuran solution, react at room temperature for 20 hours; after the reaction, centrifuge first, pour off the supernatant, dissolve the precipitate with 50mL of dichloromethane and centrifuge, and then evaporate the supernatant of dichloromethane with a rotary evaporator The solvent was removed and dried, then dissolved with 50 mL of n-hexane, centrifuged, and the n-hexane supernatant was evaporated with a rotary evaporator to remove the solvent and dried to obtain a crude product; the crude product was recrystallized with dichloromethane: acetonitrile = 1:2 (v / v) t...

Embodiment 1

[0058] Example 1: Ag 40 Concentration detection of R-2-chloropropionic acid in dichloromethane solution

[0059] 1mL of Ag 40 Dichloromethane solution (concentration is 1.16x10 -7 mol / mL) and 1mL of R-2-chloropropionic acid in dichloromethane solution (concentration from 1.16x10 -7 mol / mL to 1.16x10 -6 mol / mL) was uniformly mixed and tested by a circular dichroism spectrometer. The result shows: the concentration of R-2-chloropropionic acid is 1.16x10 -7 mol / mL to 1.16x10 -6 In the range of mol / mL, there is a linear relationship between its circular dichroism spectrum signal and the concentration of R-2-chloropropionic acid, and the linear equation is y=-2.0423x 10 7 C+0.07009, linear correlation coefficient R 2 =0.99976, wherein y is the absorption value at 331 nm on the circular dichroism spectrum, the unit is mdeg, and C is the concentration of R-2-chloropropionic acid, the unit is mol / mL.

Embodiment 2

[0060] Example 2: Ag 40 Measurement of the e.e. value of R-2-chloropropionic acid in dichloromethane solution

[0061] 1mL of Ag 40 Dichloromethane solution (concentration is 1.16x10 -7 mol / mL) and 1mL of R-2-chloropropionic acid in dichloromethane solution (concentration of 1.16x10 -6 mol / mL, e.e. values ​​from 0% to 100%) were uniformly mixed and then tested by a circular dichroism spectrometer. The result shows: the e.e. value of R-2-chloropropionic acid ranges from 0% to 100%, and its circular dichroism spectrum signal is linearly related to the e.e. value of R-2-chloropropionic acid, and the linear equation is y=- 0.24382C+0.46794, linear correlation coefficient R 2 =0.99949, wherein y is the absorption value at 331 nm on the circular dichroism spectrum, the unit is mdeg, and C is the e.e. value of R-2-chloropropionic acid, the unit is %.

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Abstract

The invention discloses a chiral silver nanocluster and preparation and application thereof. The molecular formula of the chiral silver nanocluster is Ag40(TBBM)22(CH3COO)10 which is abbreviated as Ag40, wherein TBBM is p-tert-butyl benzyl mercaptan. The Ag40 nanocluster provided by the invention can realize sensitive, rapid and quantitative reaction with chiral carboxylic acid drugs (such as 2-chloropropionic acid, ibuprofen, naproxen, isoleucine and the like) so as to allow the chiral signals of the chiral carboxylic acid drugs to be transmitted to the Ag40 nanocluster, so the content and the chiral e.e. value of the chiral carboxylic acid drugs can be conveniently measured. According to the invention, reaction conditions are mild; operation is simple; and a substrate can be recycled andhas good universality.

Description

technical field [0001] The invention relates to a chiral detection agent, specifically a chiral silver nanocluster and its preparation and application for detecting the concentration and e.e. value of chiral carboxylic acid drugs. Background technique [0002] Drugs, especially chiral drugs with chiral configuration orientation, are ubiquitous in life sciences, disease treatment and other fields. The physical properties of chiral drugs are basically the same, but their chemical and biological properties often have certain differences. For example, S-ofloxacin can play an antibacterial and anti-inflammatory effect, while R-ofloxacin has no drug effect; S -Ketoprofen can treat rheumatism, and R-ketoprofen is used to prevent and treat periodontal disease; S-dopa is the drug of choice for the treatment of Parkinson's syndrome, but R-dopa can cause granulocyte leukopenia, endangering human s life. In order to avoid the influence caused by chiral enantiomers, chiral detection of...

Claims

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Application Information

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IPC IPC(8): C07F1/10G01N21/31
CPCC07F1/005G01N21/31C07B2200/07
Inventor 朱满洲独文俊汪恕欣康熙金山
Owner ANHUI UNIVERSITY
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