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1,8-naphthalimide derivatives and preparation method thereof

A technology of naphthalimide and derivatives, applied in the field of fluorescent materials, which can solve the problems of low utilization efficiency and mutual interference of fluorophores

Inactive Publication Date: 2011-11-23
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] To this end, Ivo Grabchev et al. used 1,8-naphthalimide derivatives to modify the end groups of low-generation dendritic poly(amide-amine) and poly(propyleneimine) to obtain 4, 8 or 16 The compound of the same 1,8-naphthoimide unit, but it may be that the multi-branched structure of the dendritic macromolecule makes the fluorophore at the end have a greater degree of freedom and is easy to interfere with each other, so that although this type of molecule contains multiple The luminous efficiency of the same 1,8-naphthoimide unit is much lower than that of similar single 1,8-naphthoimide derivatives, that is, the utilization efficiency of the fluorophore is lower

Method used

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  • 1,8-naphthalimide derivatives and preparation method thereof
  • 1,8-naphthalimide derivatives and preparation method thereof
  • 1,8-naphthalimide derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1 prepares EBNP

[0062] Add N-n-butyl-4-bromo-1,8-naphthalimide and ethylenediamine solution to ethylenediamine, the added N-n-butyl-4-bromo-1,8-naphthalimide The molar ratio to ethylenediamine was 1:45, and the mixed solution was stirred and heated at 70°C for 10 hours, then cooled, and water was added to obtain a yellow precipitate.

[0063] The mixture obtained after the reaction was filtered, washed with water, dried in vacuo, and recrystallized from toluene to obtain EBNP as a yellow solid with a yield of 88.0%.

[0064] The EBNPs used in the following examples were all prepared in this example.

Embodiment 2

[0066] Add DIPEA, EBNP and CNC to anhydrous tetrahydrofuran, and the molar ratio of reactants is as follows: n(EBNP):n(CNC):n(DIPEA)=1.8:1.0:2.1. The above mixed solution was placed in an ice-water bath (0-2°C) for 4 h, and then under N 2 Under protection, the temperature was raised to 66°C and the reaction was refluxed for 48h. After natural cooling, the solvent was removed under reduced pressure, and the filtrate was washed with deionized water until the filtrate was colorless, then washed with ethanol and petroleum ether in turn, and dried in vacuum to obtain BCBNT with a yield of 49.6%.

[0067] The product obtained in this example is subjected to infrared spectrum analysis, nuclear magnetic resonance analysis, mass spectrometry and elemental analysis successively, and the analysis results are as follows:

[0068] Infrared spectrum analysis results: 3364.9cm-1 is the stretching vibration of -NH-, 2955.9cm-1 and 2871.0cm-1 are the stretching vibrations of methylene, 1682.5...

Embodiment 3

[0077] Add DIPEA, EBNP and CNC to anhydrous tetrahydrofuran, and the molar ratio of reactants is as follows: n(EBNP):n(CNC):n(DIPEA)=2.2:1.0:2.1. The above mixed solution was placed in an ice-water bath (2-3°C) for 4 h, and the 2 Under protection, the temperature was raised to 65°C and the reaction was refluxed for 48h. After natural cooling, the solvent was removed under reduced pressure, and the filtrate was washed with deionized water until the filtrate was colorless, then washed with ethanol and petroleum ether in turn, and dried in vacuum to obtain BCBNT with a yield of 87.1%.

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Abstract

The invention provides two 1,8-naphthalimide derivatives which respectively have structures of a formula (I) and a formula (II). The 1,8-naphthalimide derivatives which have structures of the formula (I) and the formula (II) respectively contain two and three 1,8-naphthalimide groups. The experiment shows that fluorescence-emission strengths of the derivatives corresponding to the maximum emission wavelength are respectively 1.6 times and 1.9 times as much as the EBNP (4-amino-ethylamino-N-n-butyl-1,8-naphthalimide); and the derivatives have high use rate of fluorogens and have higher fluorescent properties.

Description

technical field [0001] The invention relates to the field of fluorescent materials, in particular to a 1,8-naphthalimide derivative and a preparation method thereof. Background technique [0002] 1,8-naphthoimide derivatives are condensation products of 1,8-naphthalene dioic anhydride and primary amines. 1,8-naphthalimide derivatives contain a very planar naphthalene ring structural unit in the molecule. There is a strong electron-donating group at one end, and a strong electron-withdrawing group at the other end, so there is a large "withdrawing-donating electron conjugated system" in its molecular structure, and electrons in such a system are easily attracted When exposed to light, a transition occurs to produce fluorescence. [0003] At the same time, 1,8-naphthoimide derivatives have a rigid planar structure. First, the rigid planar structure weakens the vibration of molecules, which reduces the interaction between excited state electrons and molecular vibrations, reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K11/06
Inventor 徐冬梅杨亮汪爱丰
Owner SUZHOU UNIV
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