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Amphiphilic dinaphthalene derivative containing double hydroxyls as well as preparation method and application of amphiphilic dinaphthalene derivative containing double hydroxyls in distinguishing chiral diaminocyclohexane gas

A technology of cyclohexanediamine and derivatives is applied in the field of supramolecular fluorescence sensing thin film materials, and achieves the effects of high yield, simple preparation method and mild reaction conditions

Active Publication Date: 2020-02-14
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is worth noting that so far, there have been few reports on the enantioselective sensing of chiral amine vapors, which also motivates us to apply fluorescent sensing systems to detect chiral organic compound vapors.

Method used

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  • Amphiphilic dinaphthalene derivative containing double hydroxyls as well as preparation method and application of amphiphilic dinaphthalene derivative containing double hydroxyls in distinguishing chiral diaminocyclohexane gas
  • Amphiphilic dinaphthalene derivative containing double hydroxyls as well as preparation method and application of amphiphilic dinaphthalene derivative containing double hydroxyls in distinguishing chiral diaminocyclohexane gas
  • Amphiphilic dinaphthalene derivative containing double hydroxyls as well as preparation method and application of amphiphilic dinaphthalene derivative containing double hydroxyls in distinguishing chiral diaminocyclohexane gas

Examples

Experimental program
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Effect test

Embodiment 1

[0039] 1. Preparation of the compound of formula I

[0040] Dissolve 1.51g (8.07mmol) 6-hydroxy-2-naphthylboronic acid and 1.17g (11.25mmol) 2,2-dimethyl-1,3-propanediol in 50mL purified dichloromethane at 35℃ The reaction was stirred for 4 hours. After the reaction was completed, the dichloromethane was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography with a mixed solvent of 1:1 volume ratio of ethyl acetate and petroleum ether as the mobile phase and silica gel as the stationary phase. After vacuum drying, 1.72 g of a white solid was obtained, namely the compound of formula I. The yield was 83.5% . The reaction equation is as follows:

[0041]

[0042] The hydrogen nuclear magnetic spectrum characterization results of the obtained compound of formula I are as follows: 1 H NMR(600MHz, CDCl 3 ,Me 4 Si)δ H : 8.28 (1H), 7.79 (2H), 7.65 (1H), 7.13 (1H), 7.08 (1H), 3.87 (4H),

[0043] 1.05 (6H).

[0044] 2. Preparation...

Embodiment 2

[0057] The application of the dihydroxy-containing amphiphilic binaphthyl derivative in the discrimination of chiral cyclohexanediamine gas in Example 1 is as follows:

[0058] Dissolve the dihydroxy-containing amphiphilic binaphthyl derivative in PEG 200 to prepare a 60μmol / L dihydroxy-containing amphiphilic binaphthyl derivative stock solution; store the dihydroxy-containing amphiphilic binaphthyl derivative The liquid is in contact with the gold substrate with hydrophilic and hydrophobic microdomains, and an ordered pattern with a droplet diameter of 50μm is formed in the hydrophilic mercaptoundecanoic acid monolayer area, and a microarray is prepared into a gas-liquid interface monolayer fluorescence transmission. Sense film (see figure 1 with figure 2 ).

[0059] Place the above-mentioned fluorescent sensing film in the air without chiral cyclohexanediamine, use FLS980 single photon counting time-resolved fluorescence spectrometer to measure the fluorescence emission spectrum...

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Abstract

The invention discloses an amphiphilic dinaphthalene derivative containing double hydroxyls as well as a preparation method and application of the amphiphilic dinaphthalene derivative containing double hydroxyls in distinguishing chiral diaminocyclohexane gas. A structural formula of the derivative is shown in the description, wherein n is an integer selected from 3-5, the amphiphilic dinaphthalene derivative containing double hydroxyls is an amphiphilic fluorescent molecule taking a dinaphthalene host molecule containing double hydroxyls as a hydrophobic head group and taking an ether oxygenchain as a hydrophilic tail, the preparation method of the amphiphilic dinaphthalene derivative containing double hydroxyls is simple, mild in reaction conditions and high in yield, the amphiphilic dinaphthalene derivative containing double hydroxyls has a self-assembly characteristic and can form a monomolecular-layer fluorescent sensing film on a PEG 200 gas-liquid interface by self-assembly, the fluorescent sensing film can be applied to chiral distinguishing and recognition of the diaminocyclohexane gas, rapid and efficient selective detection of (1S,2S)-diaminocyclohexane gas is realized,and the fluorescent sensing film can be recycled.

Description

Technical field [0001] The invention belongs to the technical field of supramolecular fluorescent sensing film materials, and specifically relates to a dihydroxy-containing amphiphilic binaphthyl derivative, as well as a preparation method and application of the derivative. Background technique [0002] Chirality is a ubiquitous phenomenon in nature. Most important biological macromolecules have chirality, and many important life processes involve specific interactions between chiral substances. In addition, most modern drugs and drugs under development are single enantiomers of chiral compounds, and they tend to have higher efficacy and lower toxicity than similar drugs. For example, (1R, 2R)-cyclohexanediamine is used as an important intermediate in the synthesis of oxaliplatin, and is often used as a common anti-cancer drug in oncology. In addition, most asymmetric synthesis involves the synthesis of chiral catalysts, and (1S,2S)-cyclohexanediamine can be used as a chiral sou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/26C07F5/02C07C41/30C07C43/30G01N21/64
CPCC07C43/23C07C41/26C07F5/025C07C41/30G01N21/6402G01N21/643C07B2200/07C07C43/30
Inventor 刘静何文慧花盼盼赵琪严军林
Owner SHAANXI NORMAL UNIV
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