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Chromenonaphthyridine-Troger's base Fe<3+> fluorescent probe, and preparation method and application thereof

A naphthyridine and fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve many problems, achieve high yield, mild reaction conditions, and good prospects for large-scale application Effect

Active Publication Date: 2020-11-10
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of fluorescent probes have been designed and synthesized to identify Fe in the natural environment 3+ , but endogenous Fe in cells 3+ There are not many reports on the detection, imaging, and tracing of base(TB) is the Fe of the skeleton 3+ fluorescent probe

Method used

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  • Chromenonaphthyridine-Troger's base Fe&lt;3+&gt; fluorescent probe, and preparation method and application thereof
  • Chromenonaphthyridine-Troger's base Fe&lt;3+&gt; fluorescent probe, and preparation method and application thereof
  • Chromenonaphthyridine-Troger's base Fe&lt;3+&gt; fluorescent probe, and preparation method and application thereof

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Embodiment

[0028] 1. Chromophthalazine- Synthesis of base derivatives:

[0029]

[0030] (1) Synthesis of Intermediate 2:

[0031] Add 4-bromoaniline (50.0mmol) and paraformaldehyde (100.0mmol) into a 200.0mL round-bottomed flask in sequence, place it in a low-temperature tank and adjust the temperature to -15°C, and slowly add trifluoroacetic acid ( 100.0mL, about 30min dropwise) after reaction at room temperature for 7 days. After the reaction was complete (TLC tracking), the mixture was poured into ice water, adjusted to pH 9-10 with ammonia water, cooled to room temperature, extracted with dichloromethane (50.0 mL×3), and spin-dried to obtain a crude product. Add acetone, heat until the crude product is completely dissolved, recrystallize at room temperature, filter with suction, and wash with acetone to obtain intermediate 2 (12.28 g, 65%).

[0032] (2) Synthesis of Intermediate 3:

[0033] Add Intermediate 2 (5.0mmol) into a 100.0mL round-bottomed flask. After pumping and e...

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Abstract

The invention provides a chromenonaphthyridine-Troger's base Fe<3+> fluorescent probe which has a structural formula as shown in the specification. The chromenonaphthyridine-Troger's base Fe<3+> fluorescent probe is prepared from p-bromoaniline, paraformaldehyde, malononitrile, substituted o-hydroxyacetophenone and the like through a multi-step reaction. A synthesis process of the probe has the advantages of mild reaction conditions, short reaction time and high yield. The chromenonaphthyridine-Troger's base Fe<3+> fluorescent probe emits blue fluorescence in a solution and green fluorescencein a solid state; fluorescence brightness is high; a part of compounds have specific recognition capability on Fe<3+>, and are low in detection limit, quick in response and good in stability; and a part of the compounds have a good inhibition effect on bacillus subtilis.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a class of chromene diazepine- base class Fe 3+ High-brightness fluorescent probe and its preparation method and application. Background technique [0002] As an essential trace element for the human body, iron is an essential component of hemoglobin and myoglobin, and participates in the transport and exchange of oxygen and carbon dioxide. But excess iron can cause harm to the human body. Therefore, it is of great significance to establish a fast and efficient detection method. At present, the methods for detecting iron ions mainly include atomic absorption spectrometry and high performance liquid chromatography. However, some methods are cumbersome, costly, and require large instruments and professionals to operate. Fluorescence spectroscopy has the advantages of fast response, low cost, and high sensitivity, and is widely used in the identification of iron ions. The rat...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06G01N21/64A61P31/10A61P31/04
CPCC07D519/00C09K11/06A61P31/10A61P31/04G01N21/6428C09K2211/1044C09K2211/1048
Inventor 宛瑜陈雯苑睿周生亮吴翚
Owner XUZHOU NORMAL UNIVERSITY
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