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 open realize the detection of Hg 2+ Few reactive photoactive receptors for highly selective detection of ions
In particular, the rhodamine dyes commonly used to construct photoactive receptors, whose fluorescence emission wavelength is not in the near-infrared region (600-900nm), are easily affected by the background fluorescence interference of biological samples in practical applications, which limits the use of such receptors in biological Effects in tissue and in vivo imaging detection

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

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preparation example Construction

[0038] In a preferred embodiment of the present invention, there is also provided a method for preparing the above-mentioned reactive near-infrared photoelectrically active acceptor, the method comprising the addition reaction of silarhodamine spironolactone and ferroceneformyl isothiocyanate to generate The acceptor step.

[0039] The structural formula of silarhodamine spironolide hydrazide is:

[0040]

[0041] The structural formula of ferroceneformyl isothiocyanate is:

[0042]

[0043] Among them, silarhodamine spironolide hydrazide and ferroceneformyl isothiocyanate are existing substances that can be prepared by those skilled in the art through conventional methods, and there is no special limitation here. For example, silarhodamine spironolide hydrazide can be found in the 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.) method prepared; ferrocene formyl isothi...

Embodiment 1

[0066] synthesis of receptors

[0067] Equipped with stirring magnet, constant pressure dropping funnel and N 2 Add silarhodamine spironolide hydrazide (0.443g, 1.0mmol) and DMF (5mL) into the three-necked flask of the catheter, and then add ferroceneformyl isothiocyanate (1.356g, 5.0mmol) in DMF (3mL) dropwise. ) 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, filter off the desiccant, evaporate the filtrate to remove the solvent under reduced pressure, and the residue is separated by column chromatography (ethyl acetate / petroleum ether=1:3, R f =0.3), obtain orange solid powder (acceptor of the present invention) 0.594g, productive rate 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(m,1H),7.46-7.44(m,2H),6.98-6.8...

Embodiment 2

[0069] The recognition effect of receptors on various tested ions in the ultraviolet-visible spectrum detection embodiment 1

[0070] Prepare 5.0×10 in a 10mL volumetric flask -4 Receptor standard solution of M, respectively prepare 1.0×10 in 10mL volumetric flask -3 Different ion aqueous solutions of M to be tested; respectively pipette 100 μL of 5.0×10 -4 The acceptor standard solution of M 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 the ultraviolet-visible absorption intensities were measured respectively.

[0071] The result is as figure 1 , indicating that only the addition of Hg 2+ Ions, the UV-visible absorption of the acceptor changes significantly, and a new strong UV-visible absorption peak appears at 659nm, which is caused by the opening of the spiro ring in the structure of sila rhodamine, while the addition of other ions is not obvious change, so the receptor can recognize Hg wi...

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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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