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Compound with hemicyanine-naphthalimide structure, and preparation method and application thereof

A naphthalimide and compound technology, which is applied in the field of compounds with a hemicyanine-naphthalimide structure, can solve the problems of poor biocompatibility of dyes, easy to be affected by biological internal environmental factors, and easy to produce cytotoxicity, etc.

Inactive Publication Date: 2015-11-11
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these classic fluorophores have certain limitations due to their structural characteristics, such as the fluorescence emission wavelength region is easily affected by biological internal environmental factors, the dyes have poor biocompatibility, and are prone to cytotoxicity, etc.

Method used

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  • Compound with hemicyanine-naphthalimide structure, and preparation method and application thereof
  • Compound with hemicyanine-naphthalimide structure, and preparation method and application thereof
  • Compound with hemicyanine-naphthalimide structure, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0029] A compound with half cyanine-naphthalimide structure, its structural formula is as follows:

[0030] .

[0031] The specific synthetic route of above-mentioned compound is referred to as follows:

[0032]

[0033] The synthesis steps are as follows:

[0034] (1) Synthesis of Compound 1

[0035] Add 4-bromo-1,8 naphthalene anhydride (5.54g, 20.0mmol) and n-butylamine (2.4mL, 24mmol) into a 500mL round bottom flask, add solvent ethanol 200mL, reflux for 12 hours under nitrogen protection, until the solution is clear, and depressurize Part of the solvent was distilled off and cooled to room temperature, and light yellow crystals were precipitated, which were recrystallized from ethanol to obtain light yellow crystals with a yield of 84.9%. Compound 1 1 See HNMR figure 1 , 1 HNMR (400MHz, CDCl 3 )δ: 8.65 (1H,d, J =7.3Hz),8.56(1H,d, J =8.5Hz),8.41(1H,d, J =7.9Hz),8.03(1H,d, J =7.9Hz),7.84(1H,t, J =7.9Hz),4.17(2H,t, J =7.5Hz),1.76–1.68(2H,m,),1.50–1.40(2H,m...

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Abstract

The invention relates to a compound with a hemicyanine-naphthalimide structure, and a preparation method and an application thereof. The structural formula of the compound is shown in the specification. The dissolvability, the maximum absorption, the optimum fluorescence emission wavelength and the quantum yield of the compound are tested in the spectrum property experiment of the compound; a solvent effect experiment of the fluorescence emission of the compound shows that the fluorescence emission of the compound has a substantial solvent effect; experiments of response of the compound to ions show that the absorption peak nearby 600nm gradually enhances with increase of the trifluoroacetic acid concentration, and the absorption peak at 490nm decreases with the increase of the trifluoroacetic acid concentration until disappearance, so the structure of the compound changes after trifluoroacetic acid is added; and fluorescence spectrum detection finds that the maximum emission spectrum intensity enhances with the addition of trifluoroacetic acid, so the compound can be used as an acidic fluorescence probe. The preparation method of the compound has the characteristics of simple operation, mild conditions and high reaction yield.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and specifically relates to a compound with a semicyanine-naphthalimide structure, its preparation method and application. Background technique [0002] Fluorescent dye-based assays have been widely used in important fields such as analytical chemistry, environmental detection, biological imaging, and disease diagnosis. Fluorescent molecular probe technology has many advantages such as simple operation, non-destructive sample, fast analysis speed, high sensitivity, and the ability to realize in situ detection and visual detection of biological samples. At present, the research work on fluorescent probes based on classic fluorescent nuclei such as rhodamine, coumarin, naphthalimide, cyanine, and boron pyrrole mainly focuses on heavy metal ions in samples, endogenous biological The detection of active small molecules, especially the structure of cyanine and fluoropyrrole, has the charac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64
CPCC07D471/06C09K11/06C09K2211/1466G01N21/64
Inventor 王建红侯旭锋要冲张树峰甘莹赵瑾
Owner HENAN UNIVERSITY
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