Reactive near-infrared photoactive receptor and synthesis method and application thereof

A near-infrared light and synthesis method technology, applied in chemical instruments and methods, luminescent materials, fluorescence/phosphorescence, etc., can solve problems such as limiting effects, achieve low autofluorescence interference, strong tolerance, and improve selectivity and sensitivity Effect

Pending Publication Date: 2020-11-13
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, based on the excellent photophysical properties of rhodamine dyes and the excellent electrochemical response function of ferrocene, most of the photoactive receptors designed and synthesized by changing the bridging structure are based on the reversible coordination reaction to make rhodamine Realization of Hg from Closed to Opened Spiral Ring 2+ The multi-mode detection of ions, and based on the irreversible chemical reaction to make the rhodamine spiro ring from close to o

Method used

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  • Reactive near-infrared photoactive receptor and synthesis method and application thereof
  • Reactive near-infrared photoactive receptor and synthesis method and application thereof
  • Reactive near-infrared photoactive receptor and synthesis method and application thereof

Examples

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Example Embodiment

[0038] In a preferred embodiment of the present invention, there is also provided a preparation method of the above reactive near-infrared photoelectric active acceptor, the method comprising the addition reaction of silarhodamine spirolactam and ferrocene formyl isothiocyanate to generate the receptor step.

[0039] The structural formula of silarhodamine spirolactone is:

[0040]

[0041] The structural formula of ferrocene formyl isothiocyanate is:

[0042]

[0043] Among them, silarhodamine spirolactam hydrazide and ferrocene formyl isothiocyanate are existing substances that can be prepared by those skilled in the art by conventional methods, and no special limitation is required here. For example, silarhodamine spirolactone can be obtained from literature (Mao, G.-J.; Liang, Z.-Z.; Bi, J.; Zhang, H.; Meng, H.-M.; Su, L.; Gong, Y.-J.; Feng, S.; Zhang, G. Anal. Chim. Acta 2019, 1048, 143-153.) prepared by the method; ferrocene formyl isothiocyanate can be prepared ...

Example Embodiment

[0065] Example 1

[0066] synthesis of receptors

[0067] Equipped with a stirring magnet, constant pressure dropping funnel and N 2 To the three-necked flask of the catheter, add silarhodamine spironolactazide (0.443g, 1.0mmol) and DMF (5mL), and then dropwise add ferrocene formyl isothiocyanate (1.356g, 5.0mmol) in DMF (3mL) ) solution. Thin-layer chromatography tracking, after the reaction, the reaction solution was poured into water, extracted with dichloromethane, the extract was washed with saturated brine, anhydrous MgSO 4 Dry, remove the desiccant by filtration, evaporate the filtrate to remove the solvent under reduced pressure, and separate the residue by column chromatography (ethyl acetate / petroleum ether=1:3, R f = 0.3) to obtain an orange solid powder (acceptor according to the present invention) 0.594g, the yield is 83.3%, m.p.182-183 ℃.IR (cm –1 ):v max 3333(N-H), 1711, 1655(C=O), 1349(C=S). 1 HNMR (300MHz, CDCl 3 ,TMS):δ11.42(s,1H),8.41(s,1H),8.02-8.00...

Example Embodiment

[0068] Example 2

[0069] Ultraviolet-visible spectroscopy detects the recognition effect of receptors on various ions to be tested in Example 1

[0070] Make up 5.0 x 10 in a 10mL volumetric flask -4 M's receptor standard solution, prepare 1.0 × 10 in a 10 mL volumetric flask -3 M aqueous solutions of different ions to be tested; pipette 100 μL 5.0×10 into the colorimetric tube -4 The M acceptor standard solution and 50 μL of the above-mentioned ion aqueous solution to be tested were adjusted to 5 mL with 0.5% acetone-water solution, and their ultraviolet-visible absorption intensity was measured respectively.

[0071] The result is as figure 1 , indicating that only the addition of Hg 2+ The UV-visible absorption of the ion and the acceptor changed significantly, and a new strong UV-visible absorption peak appeared at 659 nm, which was caused by the opening of the spiro ring in the structure of silarhodamine, while the addition of other ions did not significantly change...

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Abstract

The invention discloses a reactive near-infrared photoactive receptor as well as a synthesis method and application thereof. The chemical structural formula is shown in the specification. An acyl thiourea bridge is accurately designed to combine silicon-rhodamine spirolactam and ferrocene into the reactive near-infrared photoactive receptor for the first time; 1,3,4-oxadiazole is generated througha specific desulfurization cyclization reaction of Hg<2+> ions to open the silicon-rhodamine spirolactam ring, selective efficient multi-mode detection of Hg<2+> ions in a water phase based on ultraviolet visible spectrum, fluorescence spectrum, colorimetric or electrochemical analysis and other technologies is achieved, and the lowest detection lower limit is 8.4*10<-9> M. The receptor providedby the invention is good in chemical and biological stability, has near-infrared color developing capability and fluorescence response characteristics, is wide in pH detection range (pH is 3.9-9.9), is particularly suitable for living cell fluorescence imaging, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the field of photoelectric functional materials, and in particular relates to a reactive near-infrared photoelectric active receptor and its synthesis method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Mercury is a heavy metal element with strong physiological toxicity, which can cause serious ecological environment pollution and human diseases. With the rapid development of modern industry, mercury enters the ecological environment in various forms. Based on its unique persistence, easy migration and high bioaccumulation, it directly causes serious pollution to soil, air and water sources. In lakes and...

Claims

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Application Information

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IPC IPC(8): C07F17/00C07F7/08C09K11/06G01N21/64G01N27/48
CPCC07F17/02C07F7/0832C07F7/0816C09K11/06G01N21/6402G01N27/48C09K2211/104C09K2211/187
Inventor 郭佃顺赵梅郭玉双邵清浩傅国栋牛涵
Owner SHANDONG NORMAL UNIV
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