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Organic gelling compound of azo phenyl thiourea derivatives, preparation method thereof, organic gel and applications

A technology of azophenylthiourea and organogel, which is applied in the field of supramolecular chemistry, can solve the problems of cumbersome detection methods and processes, and achieve the effect of simple and fast detection methods

Inactive Publication Date: 2019-04-19
XINYANG NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the method of instrumental analysis is often used to detect the above-mentioned copper ions, iron ions, mercury ions, gaseous acids and organic amines, and the detection methods and processes are relatively cumbersome

Method used

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  • Organic gelling compound of azo phenyl thiourea derivatives, preparation method thereof, organic gel and applications
  • Organic gelling compound of azo phenyl thiourea derivatives, preparation method thereof, organic gel and applications
  • Organic gelling compound of azo phenyl thiourea derivatives, preparation method thereof, organic gel and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The organogel compound of the azophenylthiourea derivative in this example has the structure shown in formula I:

[0045]

[0046] The preparation route of the organogel compound of the azophenylthiourea derivative of this embodiment is as follows:

[0047]

[0048] Concrete preparation method comprises the following steps:

[0049] 1.0g (3.54mmol) 4-dimethylaminoazobenzene-4'-thioisocyanate, 2.54g (3.54mmol) N-(2-aminoethyl)-3,4,5-tri(dodecane Oxy)benzamide was mixed in 100ml of anhydrous tetrahydrofuran, and then refluxed at 90°C for 12h, then the tetrahydrofuran was distilled off under reduced pressure, and the remaining product was purified by a silica gel column, and the eluent was methanol / dichloromethane (1 / 1200, v / v), finally obtained yellow powder, which is the compound shown in formula I, yield 70.5%, 1 HNMR (600MHz, DMSO-d 6 ):9.70(s,1H),8.36(s,1H),7.92(s,1H),7.75(d,J=9.0Hz,2H),7.69(d,J=9.0Hz,2H),7.58(d ,J=9.0Hz,2H),7.15(s,2H),6.82(d,J=9.0Hz,2H),3.99...

Embodiment 2

[0053] The organogel compound of the azophenylthiourea derivative prepared in Example 1 (compound 1 for short) and the organic solvent were placed in a sealed vial, and heated to about the boiling point of the solvent (above 80° C.), so that the azophenylthiourea The organogel compounds of urea derivatives were dissolved and then cooled down to 25°C to observe their gel-forming ability in different solvents. The gels are all thermodynamically reversible, and become flowable sols after heating. The specific gel properties are shown in Table 1.

[0054] The gelation state of organogel compounds of table 1 azophenylthiourea derivatives in different solvents

[0055] Organic solvents

gel state

Organic solvents

gel state

DMF

S

1,4-dioxane

S

n-Hexane

G(1.9)

Acetonitrile

G(12.5)

Methanol

P

ethanol

G(25.0)

acetone

P

ethyl acetate

P

petroleum ether

G(1.8)

Toluene

S

Dimethyl ...

experiment example 1

[0061] The organogel compound (compound 1) of the azophenylthiourea derivative shown in formula I is to the detection research of metal ion, selects Ag respectively + ,Cd 2+ , Fe 2+ ,K + ,Mg 2+ ,Mn 2+ , Na + , Ni 2+ ,Pb 2+ ,Zn 2+ ,Hg 2+ ,Fe 3+ ,Cu 2+ conduct experiment.

[0062] To the acetonitrile solution of compound 1 (c=10 -4 M) Add different metal ions Ag + ,Cd 2+ ,Fe 3+ ,K + ,Mg 2+ ,Mn 2+ , Na + , Ni 2+ ,Pb 2+ ,Zn 2+ ,Hg 2+ , Fe 3+ ,Cu 2+ ,Such as Figure 5 As shown in a, adding Fe 3+ After the solution turns from yellow to wine red, add Hg 2+ After the solution turned from yellow to bright red, adding Cu 2+ Afterwards, the solution changed from yellow to ginger yellow, and after adding other metal ions, the color had no obvious change; as Figure 5 b shows Fe 3+ and Cu 2+ The acetonitrile solution is colorless, as a control to exclude Fe 3+ and Cu 2+ The influence of the color itself, by Figure 5 It can be seen that compound 1 has an e...

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Abstract

The invention belongs to the technical field of supramolecular chemistry, and specifically relates to an organic gelling compound of azo phenyl thiourea derivatives, a preparation method thereof, organic gel and applications. The organic gelling compound of azo phenyl thiourea derivatives has a structure represented by the formula I. The provided organic gelling compound of azo phenyl thiourea derivatives can form gel in an n-hexane, petroleum ether, dimethyl sulfoxide, acetonitrile or ethanol solvent. The provided organic gelling compound of azo phenyl thiourea derivatives can sensitively detect Hg<2+>, Cu<2+>, Fe<3+>, volatile acids, and organic amine. Moreover, the detection method is simple, no instrument is needed, and the detection on Hg<2+>, Cu<2+>, Fe<3+>, volatile acids, and organic amine can be realized through naked eyes.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry, and specifically relates to an organogel compound of azophenylthiourea derivatives, a preparation method, an organogel and applications. Background technique [0002] Copper is an essential trace element present in animals and humans. It is involved in a wide range of metabolic processes as a cofactor for some enzymes and proteins. However, high content of copper will cause serious harm to life and health, leading to biochemical disorders, physiological dysfunction and various pathological changes of internal organs. [0003] Mercury is the only metal that is liquid and easy to flow at room temperature. It is mainly used in scientific instruments, mercury boilers, mercury pumps and mercury gas lamps. It is also widely used in medicine. For a long time, mercury products can be seen everywhere in people's lives . Mercury in the environment can be enriched by animals and plants, a...

Claims

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Application Information

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IPC IPC(8): C07C335/20G01N21/31G01N21/78
CPCC07C335/20G01N21/31G01N21/78
Inventor 曹新华黒笑涵高爱萍邹国栋于永生
Owner XINYANG NORMAL UNIVERSITY
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