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Naphthalimide derivative and use thereof as fluorescent probe

A naphthalimide, fluorescent probe technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of lack of ion selectivity, low sensitivity, etc., to achieve good selectivity and sensitivity, short response time, The effect of a good linear relationship

Inactive Publication Date: 2012-10-03
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the Ivo Grabchev research group used 4-nitro-1,8-naphthalene anhydride, N,N-dimethylethylenediamine, and diethylenetriamine as the main raw materials to synthesize a structure containing two 1,8-naphthoyl Fluorescent probes with imine fluorophores and two ((2′-N, N-dimethylamino) ethyl) amino recognition groups, although they are enhanced probes, have 3+ ions and Cr 3+ Ions lack selectivity and sensitivity

Method used

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  • Naphthalimide derivative and use thereof as fluorescent probe
  • Naphthalimide derivative and use thereof as fluorescent probe
  • Naphthalimide derivative and use thereof as fluorescent probe

Examples

Experimental program
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Effect test

Embodiment 1

[0026]The molar ratio of N-n-butyl-4-bromo-1,8-naphthalimide to DMEA is 1:45, DMEA is directly used as a solvent, react at 45°C for 24 hours, stop the reaction, cool to room temperature, add an appropriate amount of water to precipitate , stand still, filter with suction, wash with water, and dry the filter cake to obtain a yellow solid (MBN). Yield 90.1%.

Embodiment 2

[0028] The molar ratio of N-n-butyl-4-bromo-1,8-naphthalimide to DMEA is 1:30, DMEA is directly used as a solvent, react at 60°C for 15 hours, stop the reaction, cool to room temperature, add an appropriate amount of water to precipitate , stand still, filter with suction, wash with water, and dry the filter cake to obtain a yellow solid (MBN). Yield 98.1%.

Embodiment 3

[0030] The molar ratio of 4-nitro-1,8-naphthoic anhydride to DMEA was 1:6, DMF was used as solvent, reacted at 120°C for 3h, stopped the reaction to remove solvent, and separated through silica gel column (mobile phase: V CH3OH :V CHCl3 =1:10) to give dark yellow solid (MMN). Yield: 45.3%.

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Abstract

The invention discloses a naphthalimide derivative, which is expressed by a chemical formula shown in the description. The naphthalimide derivative can be synthesized by one-step or two-step reaction under mild condition, and belongs to a fluorescence-enhanced probe; MBN, MMN, EBN and EEN fluorescence can be respectively enhanced by 29.1 times, 24.8 times, 51.1 times and 33.2 times after the derivative is combined with Fe3+ ions, the color is changed to bright yellow green from dark deep yellow, and the change is visible by naked eyes; the probe is used for detecting the Fe3+ ions, has good selectivity and sensitivity, and can quickly respond in real time, and the response time is less than 1 second; and in a range that the concentration of the Fe3+ ions is between 1.0*10<-5>-1.0*10<-4>mol / L, the working curve has good linear relation.

Description

technical field [0001] The invention relates to a naphthalimide derivative, in particular to a naphthalimide derivative which can be used as a ferric ion fluorescent probe. Background technique [0002] Iron is an important trace element necessary for the human body. Anemia caused by iron deficiency is the most common nutritional deficiency in the world, but excessive iron is poisonous to the human body. Therefore, the analysis and detection of Fe3+ ions is very necessary. As a detection method with high sensitivity, less sample volume and practical value, fluorescent probe method is an important means for detecting heavy metal ions. [0003] So far, many literatures have reported that Fe 3+ Ionic fluorescent probes, most of which are fluorescence quenching. There are also reports of fluorescence-enhanced probes using coumarin, rhodamine, and phenanthrene derivatives as fluorophores, but they have disadvantages such as poor water solubility and small Stokes shift. [000...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
Inventor 徐冬梅钱丽丽
Owner SUZHOU UNIV
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