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Iron ion probe based on open-closed loop and synthesis method thereof

A synthesis method, a technology of iron ions, applied in chemical instruments and methods, fluorescence/phosphorescence, instruments, etc., to achieve the effect of strong fluorescence performance

Active Publication Date: 2022-06-28
HUANGSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The research on fluorescent probes based on rhodamine-based metal ions is a very popular and promising field, and fluorescence analysis technology has also been widely recognized and applied. How to synthesize iron ion probes with specific recognition functions and based on their There is still room for exploration and expansion in the detection and application of properties in the fields of biosensing, drug delivery and release, environmental monitoring, pure aqueous media, etc.

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  • Iron ion probe based on open-closed loop and synthesis method thereof
  • Iron ion probe based on open-closed loop and synthesis method thereof
  • Iron ion probe based on open-closed loop and synthesis method thereof

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Embodiment 1

[0032] A method for synthesizing an open-closed ring-based iron ion probe, comprising the following experimental steps:

[0033] The synthesis of N-aminoethyl-rhodamine 101 imide, the synthesis of 8-hydroxyjulonidine-9-carbaldehyde and the synthesis of probe M.

Embodiment 2

[0035] Structural characterization and determination of N-aminoethyl-rhodamine 101 imide, 8-hydroxyjulonidine-9-carbaldehyde and probe M:

[0036] The purified compounds N-aminoethyl-rhodamine 101 imide, 8-hydroxyjulonidine-9-formaldehyde and probe M were put into a clean and dry NMR tube, and the experimental bench under ventilation conditions Add an appropriate amount of deuterated chloroform to dissolve it, put it into a nuclear magnetic resonance apparatus to carry out the detection of hydrogen NMR and carbon spectra, and detect the skeleton structure of each compound according to the measurement results of the hydrogen nuclear magnetic resonance and carbon spectra;

[0037] The measurement results are as follows:

[0038] 1. Hydrogen spectrum of N-aminoethyl-rhodamine 101 imide: 1H NMR (400MHz, CDCl3, TMS) δ: 7.89 (m, 1H), 7.42 (m, 2H), 7.07 (m, 1H), 5.99(s, 2H), 3.15(dt, 6H), 3.08(dt, 4H), 2.89(t, 4H), 2.49(dq, 4H), 2.41(t, 2H), 2.04(m, 4H), 1.85 (m, 4H), 1.12 (s, 2H) ...

Embodiment 3

[0042] Determination methods and results of properties of compound M

[0043] Determination method: The purified product M was prepared into an acetonitrile solution of a certain concentration, and then 15 clean 5mL centrifuge tubes were prepared, and 250μL of the prepared probe M solution was added to each centrifuge tube using a pipette. Then take 2.7mL of acetonitrile aqueous solution [V(acetonitrile) / V(water)=4:1], add it into each centrifuge tube as diluent, and then take 50μL of prepared 3mmol / L metal ion solution and add 14 of them respectively. In the centrifuge tube, add 50 μL of deionized water to the remaining centrifuge tube as a blank reference, shake it up and let it stand for a period of time, put it into a small glass bottle, and observe the fluorescence performance under ultraviolet light with a wavelength of 365 nm. The change;

[0044] Measurement results: Different metal ion solutions have different color changes after reacting with probe M solution. When...

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Abstract

The invention provides an iron ion probe based on open-closed loop and a synthetic method thereof, and relates to the technical field of metal ion detection, the synthetic method comprises synthesis of N-aminoethyl-rhodamine 101 imide, synthesis of 8-hydroxyjulolidine-9-formaldehyde and synthesis of a probe M, the invention provides a complete method for synthesizing a compound M through a condensation reaction and a Vilsmeier-Haack reaction, namely a novel method for synthesizing the metal ion probe with a D-pi-A structure, in addition, the structure of the compound M is characterized by using a hydrogen spectrum and a carbon spectrum, and meanwhile, the optical performance of the probe M is preliminarily researched, so that the metal ion probe with the D-pi-A structure is obtained. Finally, the result shows that the probe has strong fluorescence performance on Fe < 3 + >, has good application prospects in the fields of medicine, environmental science and clinical biochemistry, and makes meaningful exploration for development of novel rhodamine fluorescent probes.

Description

technical field [0001] The invention relates to the technical field of metal ion detection, in particular to an open-closed loop-based iron ion probe and a synthesis method thereof. Background technique [0002] Fluorescence probes refer to a class of fluorescent organic small molecules with characteristic fluorescence performance in the ultraviolet-visible-near-infrared region, and their own fluorescence properties (excitation and emission wavelengths, intensity, lifetime, polarization, etc.) A class of fluorescent molecules that change sensitively with the change of the properties of the environment in which they are located, are widely used in molecular, ion detection and quantitative analysis in the field of analytical science. [0003] The research based on rhodamine-like metal ion fluorescent probes is a very hot and promising field, and the fluorescence analysis technology has also been widely recognized and applied. There is still some room for exploration and expan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06G01N21/6428C09K2211/1062C09K2211/1029Y02P20/55
Inventor 李长江江蓉史建俊黄良芳柯仲成亓昭鹏陈贺
Owner HUANGSHAN UNIV