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Novel pH-responsive fluorescent molecular probe and preparation method thereof

A fluorescent molecular probe and name technology, applied in the field of organic analysis and photochemistry, to overcome the influence of acid-base environment, broad industrial application prospects and scientific research value

Inactive Publication Date: 2014-08-13
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since thiol (-SH) contains active hydrogen, it is the most chemically active group in cells; at the same time, it contains 1,3,4- Compounds with oxadiazole-2-mercapto functional groups are mostly used as intermediates in the synthesis of drugs or in the synthesis of organometallic complexes with electroluminescent properties, but have not been developed as pH fluorescent probes.

Method used

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  • Novel pH-responsive fluorescent molecular probe and preparation method thereof
  • Novel pH-responsive fluorescent molecular probe and preparation method thereof
  • Novel pH-responsive fluorescent molecular probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 1mmol of formula (II) compound, 3mmol of KOH, 20mL of ethanol and 2mL of water into the reaction flask, stir, and heat to reflux until clear; then add 4.9mmol of CS 2 , continue heating to reflux, TLC tracking. Cool after reacting for 10 hours, pour into 200mL water, adjust the pH to 5-6 with 10% hydrochloric acid with a mass percent concentration, separate out a large amount of solids, filter with suction, and recrystallize the filter cake with ethyl acetate to obtain the compound of formula (I): Yellow solid, yield 81.3%.

Embodiment 2

[0037] Add 1mmol of formula (II) compound, 2mmol of KOH, 15mL of ethanol and 1mL of water into the reaction flask, stir, and heat to reflux until clear; then add 4mmol of CS 2 , continue heating to reflux, TLC tracking. Cool after reacting for 12 hours, pour into 200mL water, adjust the pH to 5-6 with 10% hydrochloric acid with a mass percent concentration, separate out a large amount of solids, filter with suction, and recrystallize the filter cake with ethyl acetate to obtain the compound of formula (I): Yellow solid, yield 78.6%.

Embodiment 3

[0039] Add 1mmol of formula (II) compound, 4mmol of KOH, 25mL of ethanol and 2.5mL of water into the reaction flask, stir, and heat to reflux until clear; then add 7mmol of CS 2 , continue heating to reflux, TLC tracking. Cool after reacting for 10 hours, pour into 200mL water, adjust the pH to 5-6 with 10% hydrochloric acid with a mass percent concentration, separate out a large amount of solids, filter with suction, and recrystallize the filter cake with ethyl acetate to obtain the compound of formula (I): Yellow solid, yield 77.4%.

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Abstract

The invention relates to a pH-responsive fluorescent molecular probe with a chemical name, namely, 5-(2-phenyl-pyrrolo[2,1,5-cd]indolizine-5-yl)-1,3,4-oxadiazole-2-thiophenol, as well as a preparation method and application thereof. According to the preparation method, a mercapto group is adopted as an identifying group and an indolizine group is adopted as a signal group for the first time to successfully prepare the compound. By virtue of the fluorescent probe molecules, a sensitive identification of H<+1> under different pH values is realized, the types of the pH-responsive fluorescent molecular probe are enriched, and a novel use of the mercapto functional group is opened up. The pH-responsive fluorescent molecular probe has very broad industrial application prospects and provides valuable reference to make a scientific research.

Description

technical field [0001] The present invention relates to a novel pH-responsive fluorescent molecular probe, a preparation method and its use, more specifically to a chemical name of 5-(2-phenylpyrrolo[2,1,5-cd]indolizine -5-yl)-134- A pH-responsive fluorescent molecular probe of oxadiazole-2-thiophenol, a preparation method and an application thereof belong to the fields of organic analysis and photochemistry. Background technique [0002] pH is an important parameter that affects the physical and chemical properties and reaction performance of substances, and it has important biological significance. The most widely used pH measurement methods are pH colorimetric indicators and glass electrodes. Since it was found that the litmus test solution has the characteristic dependence of color change with the change of pH value, various acid-base indicators have been widely used, but this method also has defects, that is, it cannot be used for live cell imaging in vivo, and Colo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D471/16G01N21/64
Inventor 顾玮瑾江玉亮宋香云王炳祥
Owner NANJING NORMAL UNIVERSITY
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