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Omega-vinylsulphonyl disulfide compound as well as preparation method and application thereof

A sulfur compound and vinyl sulfone technology, which is applied in the fields of ω-vinylsulfone-based disulfide compound, its preparation and application, and achieves the effects of simple and easy method, broad-spectrum reaction and convenient application

Active Publication Date: 2015-01-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still no compound and method that can directly prepare the surface containing vinylsulfone groups and realize the immobilization of biological / chemical molecules

Method used

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  • Omega-vinylsulphonyl disulfide compound as well as preparation method and application thereof
  • Omega-vinylsulphonyl disulfide compound as well as preparation method and application thereof
  • Omega-vinylsulphonyl disulfide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0027] The invention provides an ω-vinylsulfone-based disulfide compound, its preparation method and application. The ω-vinylsulfone-based disulfide compound of the present invention has the structure of general formula I:

[0028]

[0029] In the general formula I, n is an integer of 4-18; n is preferably an integer of 8-12; more preferably an integer of 9-11.

[0030] The preparation method of the ω-vinylsulfone group disulfide compound provided by the present invention comprises the following steps:

[0031] (1) the compound of formula II and triphenylphosphine molar ratio 1:1.2~1.4 were refluxed in carbon tetrachloride 4 hours and prepared the compound of formula III;

[0032]

[0033] Among them, m=n-1;

[0034] (2) the compound of formula III, azobisisobutyronitrile (AIBN) and mercaptoethanol in a molar ratio of 1:0.55:1.5~4 were reacted for 3 hours under the conditions of 70~90°C in petroleum ether to prepare the compound of formula IV;

[0035]

[0036] (3)...

Embodiment 1

[0057] The preparation (n=10) of compound i comprises the following steps:

[0058] (1) Compound ii and triphenylphosphine were refluxed in carbon tetrachloride for 4 hours at a molar ratio of 1:1.2 to prepare compound iii, 94.6%. 1 H NMR (400MHz, CDCl 3 ):δ5.80(m,1H,CH=CH 2 ),4.97(dd,2H,J 1 =16.8,J 2 =10.0, CH=CH 2 ), 3.53(t, 2H, J=6.8, ClCH 2 ),2.03(m,2H,CH 2 CH=CH 2 ),1.77(m,2H,ClCH 2 CH 2 ),1.28~1.44(m,12H, others CH 2 ). 13 C NMR (100MHz, CDCl 3 ): δ139.2 (CH=CH 2 ), 114.1 (CH=CH 2 ), 45.2 (ClCH 2 ), 33.8 (CH 2 =CHCH 2 ), 32.7 (ClCH 2 CH 2 ), 26.9 (ClCH 2 CH 2 CH 2 ),28.9~29.4(other CH 2 ).MS(EI + ):m / z[M] + 188.13.

[0059]

[0060] (2) Compound iii was reacted with azobisisobutyronitrile (AIBN) and mercaptoethanol at a molar ratio of 1:0.55:1.5 in petroleum ether at 84°C for 3 hours to prepare compound iv with a yield of 88.2%. 1 H NMR (400MHz, CDCl 3 ,): δ3.72(t,2H,J=6.0,CH 2 OH), 3.53(t, 2H, J=6.8, ClCH 2 ),2.73(t,2H,J=6.0,SCH 2 CH 2 ...

Embodiment 2

[0069] Preparation and Characterization of Self-Assembled Films

[0070] (1) Prepare a self-assembled film using the compound i prepared in Example 1 as a self-assembled material:

[0071] a. Preparing the mother liquor: using dichloromethane and ethanol as a solvent in a volume ratio of 1:1, fully dissolving compound i, and preparing a self-assembly mother liquor with a concentration of 1 mmol;

[0072] b. Soak the gold chip in the self-assembly mother solution prepared in step a, and let it stand at 25±2°C for 24 hours;

[0073] c. The resulting self-assembled membrane was rinsed with ethanol and stored in the dark.

[0074] (2) The XPS characterization results of the self-assembled membrane prepared in step (1) are as follows

[0075]

[0076] 1Binding Energy=84.2eV

[0077] 2 Binding Energy = 162.0eV

[0078] 3 Binding Energy = 168.4eV

[0079] 4Binding Energy=285.0eV

[0080] 5 Binding Energy = 286.2eV

[0081] 6Binding Energy=531.8eV

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Abstract

The invention discloses an omega-vinylsulphonyl disulfide compound as well as a preparation method and an application thereof. The compound has a structure with a structural formula I described in the specification, wherein n is an integer of 4-18. The compound can form a highly-ordered self-assembled film on the surfaces of noble metals such as gold and silver, wherein a vinylsulphonyl group on the surface of the self-assembled film can respectively react with biological / chemical molecules that contain sulfydryl, amino and hydroxyl under a certain condition for molecular coupling, biological active material preparation, biochemical sensor chip modification, and the like. The self-assembled film prepared by the compound has the advantages of hydrolysis resistance, alkali resistance, and response spectrum resistance, and the like.

Description

technical field [0001] The present invention relates to a class of ω-vinylsulfone-based disulfide compounds, a preparation method and application thereof. Background technique [0002] In modern biomedical technology, biochemical sensors, as the basis of biotechnology automation, have become a powerful tool, which has attracted widespread attention. Among them, label-free biochemical sensing technology has promoted the wider application of sensors in the biomedical field due to its advantages of no labeling, small sample demand, sample recyclability, and good repeatability. [0003] As one of the cores of biochemical sensors, the biochemical recognition system occupies an important position in biochemical sensors. The biochemical recognition system usually involves the specific binding of the measured biological / chemical molecules to the surface of the chip to realize the change of physical signals such as light and electricity, so as to achieve the specific quantitative de...

Claims

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Application Information

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IPC IPC(8): C07C323/65C07C319/22C07K17/10C07K17/02
Inventor 程昉王汉奇李明洋曲景平彭伟
Owner DALIAN UNIV OF TECH
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