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Allyl imine bridged ferrocene-rhodamine B multichannel response receptor molecule and synthesizing method and application thereof

A technology for bridging ferrocene and acceptor molecules with allyl imine, which is applied in the directions of chemical reaction of materials, material analysis by observing the influence on chemical indicators, chemical instruments and methods, etc. Solve the problems of limited application scope and single detection method, and achieve the effect of improving detection sensitivity, fast response, and increasing binding sites

Active Publication Date: 2017-12-29
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, people have successfully designed and synthesized many fluorescent probes for detecting trace amounts of heavy metal palladium ions ((1) Wang, M.; Yuan, Y.L.; Wang, H.M.; Qin, Z.H. Analyst. 2016, 141, 832-835.( 2) Chen, Y.; Zhang, M.M.; Han, Y.F.; Wei, J.RSC Adv.2016, 6, 8380-8383.), which is characterized by the design based on a single optical signal response mode, relatively single detection means, limited range of application

Method used

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  • Allyl imine bridged ferrocene-rhodamine B multichannel response receptor molecule and synthesizing method and application thereof
  • Allyl imine bridged ferrocene-rhodamine B multichannel response receptor molecule and synthesizing method and application thereof
  • Allyl imine bridged ferrocene-rhodamine B multichannel response receptor molecule and synthesizing method and application thereof

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preparation example Construction

[0029] In a preferred embodiment of the present invention, a method for synthesizing the above-mentioned allylimine bridged ferrocene-rhodamine B multichannel response receptor molecule is also provided, which method includes rhodamine B spironolactone hydrazide and acetylvinyl A step in which ferrocene is condensed to form the acceptor molecule.

[0030] Among them, rhodamine B spironolide hydrazide and acetylvinylferrocene 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); , C.; Wu, S.; Wang, D.H.Inorg.Chem.2008, 47, 7190-7201.) prepared by the method provided.

[0031] In a preferred embodiment of the present invention, the preparation of the Rhodamine B spironolide hydrazide: Weigh a certain amount of Rhodamine B, dissolve it with ethanol, add excess hydrazine hydrate (80...

Embodiment 1

[0060] Synthesis of receptor molecules

[0061] In a 25mL two-necked flask equipped with a stirring magnet and a spherical condenser, add rhodamine B spironolide hydrazide (0.228g, 0.5mmol), acetylvinyl ferrocene (0.127g, 0.5mmol), ethanol ( 4mL) and glacial acetic acid (0.01mL), the mixture was stirred and heated to react (80°C), tracked by thin layer chromatography, after the reaction was complete, extracted with ethyl acetate, and the organic phase was washed successively with saturated sodium bicarbonate and saturated brine, Dry over anhydrous magnesium sulfate, separate by column chromatography (ethyl acetate / petroleum ether=1:3, R f =0.5), to obtain 0.297g of orange powdery solid (acceptor molecule of the present invention), yield rate is 86%, m.p.225-226 ℃).IR (cm –1 ):v max 1687(C=O), 1611(C=N). 1 H NMR (300MHz, CDCl 3 ,TMS):δ7.96-7.93(m,1H),7.50-7.47(m,2H),7.17-7.15(m,1H),6.81(d,1H,J=16.3Hz),6.59(d,2H ,J=8.7Hz),6.48(d,1H,J=16.4Hz),6.41(s,2H),6.32(d,2H,J=8.8Hz),4...

Embodiment 2

[0063] Recognition effect of acceptor molecules on various tested ions in the ultraviolet-visible spectrum detection embodiment 1

[0064] Prepare 5×10 in a 10mL volumetric flask -4 Receptor molecule standard solution of M, prepare 1×10 in a 10mL volumetric flask -3 Different ion aqueous solutions of M to be tested; respectively pipette 100 μL 5×10 in the colorimetric tube -4 M receptor molecule standard solution and 50 μL of the above-mentioned ion aqueous solution to be tested, with H 2 After the volume of O / THF (9:1, v:v) was adjusted to 5 mL, the UV-Vis absorption intensity was measured respectively.

[0065] The result is as figure 1 , indicating that only the addition of Pd 2+ ions, the UV-visible absorption of the acceptor molecule changes significantly, and a new strong absorption peak appears at 562nm, indicating that the acceptor molecule can be highly selective with Pd 2+ ion binding.

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Abstract

The invention discloses an allyl imine bridged ferrocene-rhodamine B multichannel response receptor molecule and application thereof in the efficient detection of Pd<2+> ions in a water phase and living cells. The allyl imine bridged ferrocene-rhodamine B multichannel response receptor molecule has the advantages that an electric signal response group ferrocene and an optical signal response group rhodamine B are connected through an allyl imine bridge to form the receptor molecule, binding sites are increased, the receptor molecule has multichannel response functions such as electrochemistry, ultraviolet, fluorescence and color comparison, the Pd<2+> ions in the water phase and living cells can be selectively, efficiently and fast detected by methods such as cyclic voltammetry, an raviolet visible light method and a fluorescence spectrum method, lowest detection limit is 8.46*10<-9>M, and the receptor molecule is promising in application prospect.

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 an allyl imine bridged ferrocene-rhodamine B multiple response receptor molecule. Background technique [0002] In the field of organic synthetic chemistry research, palladium and its complexes, as an important class of catalysts, are widely used in the synthesis of drugs, materials and related organic reactions to improve the preparation efficiency ((1) Iwasawa, T.; Tokunaga, M. ; Obora, Y.; Tsuji, Y.J.Am.Chem.Soc.2004,126,6554-6555.(2) Lafrance,M.; ) Tietze, L.F.; Ila, H.; Bell, H.P.Chem.Rev.2004,104,3453-3516.), however, palladium has excellent affinity with various heteroatoms, especially with certain heterocyclic drugs Combination of increased its residues in final products such as drugs ((1) Huang, J.P.; Chen, X.X.; Gu, S.X.; Zhao, L.; Chen, W.X.; Chen, F.E.Org. Process Res. Dev.2010, 14, 939-941...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C09K11/06G01N21/31G01N21/64G01N21/78G01N27/26
CPCC07F17/02C09K11/06C09K2211/187G01N21/31G01N21/6428G01N21/6456G01N21/78G01N27/26G01N2021/6439G01N2021/6443
Inventor 郭佃顺黄丹丹郭玉双孟凡德郭璇
Owner SHANDONG NORMAL UNIV
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