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Naphthalimide derivative and application thereof

A technology of naphthalimide and derivatives, which is applied in the application field of naphthalimide derivatives as pH fluorescent molecular switches, can solve problems such as interference, and achieve the effect of short synthesis route and mild reaction conditions

Inactive Publication Date: 2012-11-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the reported 4-amino-1,8-naphthoimide-based hydrogen ion fluorescent probes or sensors whose fluorescence intensity varies with pH value are generally interfered by the coexistence of metal ions in the system.

Method used

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  • Naphthalimide derivative and application thereof
  • Naphthalimide derivative and application thereof
  • Naphthalimide derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment one: the preparation of intermediate NETB

[0029] With absolute ethanol as solvent, the molar ratio of 4-bromo-1,8-naphthalic anhydride (BNA) to tris(2-aminoethyl)amine (TAEA) n(BNA):n(TAEA)=3.0: 1. First, BNA was dispersed in absolute ethanol in a three-necked flask, stirred, and then TAEA was dropped into it, and mixed evenly. After the addition was completed, the temperature was raised to 60 °C for 4 h. Cool to room temperature, filter, and wash the filter cake with water and absolute ethanol successively to obtain a tan solid, which is dried in vacuo. Separation by silica gel column (mobile phase, V CH3OH :V CHCl3 =1:60) to obtain a pale yellow solid, which was heated to reflux with acetone to wash, filtered while hot to remove the solvent, and a white powder NETB was obtained. Yield 55.5%.

Embodiment 2

[0030] Embodiment two: the preparation of intermediate NETB

[0031] With absolute ethanol as the solvent, the molar ratio of 4-bromo-1,8-naphthalic anhydride (BNA) to tris(2-aminoethyl)amine (TAEA) n(BNA):n(TAEA)=3.1: 1. First, BNA was dispersed in absolute ethanol in a three-necked flask, stirred, and then TAEA was dropped into it, and mixed evenly. After the addition was completed, the temperature was raised to 70 °C for 5 h. Cool to room temperature, filter, and wash the filter cake with water and absolute ethanol successively to obtain a tan solid, which is dried in vacuo. Separation by silica gel column (mobile phase, V CH3OH :V CHCl3 =1:60) to obtain a pale yellow solid, which was heated to reflux with acetone to wash, filtered while hot to remove the solvent, and a white powder NETB was obtained. Yield 59.2%.

Embodiment 3

[0032] Embodiment three: the preparation of intermediate NETB

[0033] With absolute ethanol as the solvent, the molar ratio of 4-bromo-1,8-naphthalic anhydride (BNA) to tris(2-aminoethyl)amine (TAEA) n(BNA):n(TAEA)=3.1: 1. First, BNA was dispersed in absolute ethanol in a three-necked flask, stirred, and then TAEA was dropped into it, and mixed evenly. After the addition was completed, the temperature was raised to 78 °C for 5 h. Cool to room temperature, filter, and wash the filter cake with water and absolute ethanol successively to obtain a tan solid, which is dried in vacuo. Separation by silica gel column (mobile phase, V CH3OH :V CHCl3 =1:60) to obtain a pale yellow solid, which was heated to reflux with acetone to wash, filtered while hot to remove the solvent, and a white powder NETB was obtained. Yield 56.2%.

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PUM

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Abstract

The invention discloses a naphthalimide derivative and an application thereof; the naphthalimide derivative contains three 1,8-naphthalimide fluorophores; 4-bromo-1,8-naphthalic anhydride is dispersed in absolute ethyl alcohol, and then tri(2-aminoethyl)amine is dropped into the mixture to obtain white powder after treatment; the obtained white powder and N,N-Dimethylethylenediamine are mixed to dissolve according to a mole ratio of 1: (160-298); and the naphthalimide derivative can be obtained after the reaction for 24-72 hours at the temperature of 75-95 DEG C. The naphthalimide derivative disclosed by the invention can be used as a pH iuminophor switch, and the action of the switch is not influenced by various co-existing ions.

Description

technical field [0001] The invention relates to a naphthalimide derivative and the application of the naphthalimide derivative as a pH fluorescent molecular switch. Background technique [0002] 1,8-Naphthimide compounds have flexible derivatization methods at the 4-position and imide, high fluorescence quantum yield, long fluorescence emission wavelength, large Stockes shift, and good photostability , so it is widely used in fluorescent molecular probes and sensors, dye-sensitized solar cells, organic electroluminescent materials, data storage materials and other fields. Hydrogen ions are the most widely distributed cations in nature, which exist in almost all aqueous solutions and affect the properties of aqueous solutions. Therefore, the detection of hydrogen ions is of great significance. [0003] 1,8-Naphthoimide introduces amino groups or substituted amino groups at the 4-position and the imide. The derivatives obtained are typical hydrogen ion (proton, pH) fluorescen...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
Inventor 徐冬梅杨亮
Owner SUZHOU UNIV
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