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Formyl thiourea bridged ferrocene-rhodamine B spironolactam multi-channel response receptor molecule and synthesis method and application thereof

A formyl thiourea bridge, biferrocene technology, applied in the direction of chemical reaction of materials for analysis, material analysis by observing the influence on chemical indicators, chemical instruments and methods, etc., can solve the problem of selectivity differences. High, identification information can not produce electrochemical response and other problems, to achieve the effect of improving detection efficiency and ensuring effective output

Inactive Publication Date: 2019-11-12
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these receptor molecules are all based on reversible coordination reactions to achieve Hg 2+ The photoelectric multi-channel response detection of ions has the disadvantages of low selectivity and sometimes the identification information cannot produce electrochemical responses.

Method used

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  • Formyl thiourea bridged ferrocene-rhodamine B spironolactam multi-channel response receptor molecule and synthesis method and application thereof
  • Formyl thiourea bridged ferrocene-rhodamine B spironolactam multi-channel response receptor molecule and synthesis method and application thereof
  • Formyl thiourea bridged ferrocene-rhodamine B spironolactam multi-channel response receptor molecule and synthesis method and application thereof

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preparation example Construction

[0030] In a preferred embodiment of the present invention, there is also provided a method for preparing the above-mentioned reactive formylthiourea bridged ferrocene-rhodamine B spironolactam multichannel response receptor molecule, the method comprising rhodamine B spironolactam The step of performing an addition reaction with ferroceneformyl isothiocyanate to generate the acceptor molecule.

[0031] The structural formula of rhodamine B spironolide hydrazide is:

[0032]

[0033] The structural formula of ferroceneformyl isothiocyanate is:

[0034]

[0035] Among them, rhodamine B spironolide hydrazide and ferroceneformyl isothiocyanate are existing substances that can be prepared by those skilled in the art through conventional methods, and no special limitation is required here. For example, rhodamine B spironolide hydrazide can be prepared by the method in the patent (CN 106323893A); -281.) prepared by the method provided.

[0036] In a preferred embodiment of t...

Embodiment 1

[0063] Synthesis of receptor molecules

[0064] Equipped with stirring magnet, constant pressure dropping funnel, condenser tube and N 2 Ferrocenecarbonyl chloride (0.4970g, 2mmol) and anhydrous acetone (10mL) were added to a three-necked flask with a catheter, and then a solution of dry KSCN (0.2138g, 2.2mmol) in acetone (5mL) was added dropwise. After the dropwise addition, heat to reflux for 0.5 h, cool to room temperature, filter off the insoluble matter, evaporate the solvent under reduced pressure to obtain ferroceneformyl isothiocyanate, which is directly used in the next reaction.

[0065] Equipped with stirring magnet, constant pressure dropping funnel and N 2 Rhodamine B spironolide hydrazide (0.4566g, 1.0mmol) and DMF (5mL) were added to the three-necked flask of the catheter, and then ferroceneformyl isothiocyanate (0.4067g, 1.5mmol) in DMF (3mL) was added dropwise solution. Thin-layer chromatography tracking, after the reaction, the reaction solution was poured...

Embodiment 2

[0067] Recognition effect of acceptor molecules on various tested ions in the ultraviolet-visible spectrum detection embodiment 1

[0068] Prepare 5.0×10 in a 10mL volumetric flask -4 Receptor molecule standard solution of M, prepare 1.0×10 in 10mL volumetric flask -3 Different ionic aqueous solutions of M; respectively pipette 100 μL of 5.0×10 -4 The receptor molecule standard solution of M and 50 μL of the above-mentioned ion aqueous solution to be tested were mixed with H 2 O / THF (4:1, v:v) was adjusted to 5 mL, and its UV-visible absorption intensity was measured respectively.

[0069] The result is as figure 1 , indicating that only the addition of Hg 2+ Ions, the UV-visible absorption of acceptor molecules will change significantly, and there will be obvious enhancement at 569nm, and there is no obvious interference from other ions to be measured, so acceptor molecules can selectively recognize Hg 2+ ion.

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Abstract

The invention discloses a formyl thiourea bridged ferrocene-rhodamine B spironolactam multi-channel response receptor molecule and a synthesis method and application thereof. Combining ferrocene and rhodamine B spironolactam into a reactive photoactive acceptor molecule with formyl thiourea as a bridge structure, the specificity of Hg<2+> ions are used for promoting desulfurization and ring closing reaction to form a 1,3,4-oxadiazole heterocyclic ring, a rhodamine B spironolactone ring is simultaneously opened, the efficient and quick detection of selectivity of Hg<2+> ions in aqueous phases or cells based on electrochemistry, ultraviolet visibility, fluorescence spectroscopy and other technologies is realized, and broad application prospects are achieved.

Description

technical field [0001] The invention belongs to the field of photoelectric functional materials, and in particular relates to the design, synthesis method and application of a formylthiourea-bridged ferrocene-rhodamine B spironolactam multi-channel response receptor molecule. Background technique [0002] Mercury is a highly toxic element. Mercury and its compounds are one of the world's most concerned environmental pollutants. They are widely distributed in the environment and directly cause great pollution to soil, air and water ((1) Boening, D.W. Chemosphere 2000, 40, 1335-1351. (2) Hylander, L.D.; Goodsite, M.E. Sci. Total Environ. 2006, 368, 352-370.). In particular, the inorganic mercury compounds that flow into the water body can be further transformed into more toxic organic mercury compounds, which enter the human body through the food chain and accumulate, seriously damaging the nervous system, kidneys, liver and other organs, threatening human health ((1) Harris, ...

Claims

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Application Information

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IPC IPC(8): C07F17/02C09K11/06G01N21/31G01N21/64G01N21/78G01N27/48
CPCC07F17/02C09K11/06C09K2211/187G01N21/31G01N21/6428G01N21/78G01N27/48
Inventor 郭佃顺赵梅郭玉双苑琳姜鑫解慧敏
Owner SHANDONG NORMAL UNIV
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