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Pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives, synthesis method of same, and application of same

A technology of benzocoumarin and pyrazoline pyridine, applied in the field of laser dyes and fluorescent dyes

Inactive Publication Date: 2009-09-09
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some inorganic lasers can emit electromagnetic waves in the ultraviolet, visible, near-infrared, and far-infrared, these lasers can only excite very limited wavelengths of narrow wavelengths.

Method used

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  • Pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives, synthesis method of same, and application of same
  • Pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives, synthesis method of same, and application of same
  • Pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives, synthesis method of same, and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthesis of Benzocoumarin Derivative (I)-1

[0052]

[0053] The synthesis of 9-N, N-diethylaminobenzocoumarin aldehyde is referred to in the literature (J.Org.Chem.2007, 72, 2088-2096; J.Med.Chem.2004, 47, 6349).

[0054] Dissolve 2.95g (0.01mol) of 9-N,N-diethylaminobenzocoumarin aldehyde and 1.01g (0.01mol) of acetoacetamide in 30mL of ethanol, add 0.5mL of triethylamine, 90°C Heated to reflux for 8 hours, solid precipitated after cooling, and filtered to obtain 1.94 g of (III)-1 intermediate, with a yield of 51.6%. Compound (III)-1 can be directly used in the next reaction without purification.

[0055] Dissolve 1.88g (0.005mol) of compound (III)-1 and 0.23g (0.005mol) of methylhydrazine in 30mL of ethanol, heat and reflux at 90°C for 6 hours, and precipitate a solid after cooling, recrystallize after filtration to obtain 1.05g of benzo Coumarin derivative (I)-1, yield 54.4%.

[0056] EI-MS, m / e, 387.2[M+1] + .λ ab. max / nm(CH 2 Cl 2 ) = 470nm, λ em ma...

Embodiment 2

[0058] Synthesis of Benzocoumarin Derivative (I)-2

[0059]

[0060] The synthesis of 9-N, N-diethylaminobenzocoumarin aldehyde and intermediate (III)-1 is the same as in Example 1.

[0061] Dissolve 1.88g (0.005mol) of compound (III)-1 and 0.74g (0.005mol) of phenylhydrazine in 30mL of ethanol, heat to reflux at 90°C for 6 hours, and precipitate a solid after cooling, recrystallize after filtration to obtain 1.15g of benzoin Soybean derivative (I)-2, the yield is 55.6%.

[0062] EI-MS, m / e, 415.2[M+1] + .λ ab. max / nm(CH 2 Cl 2 )=465nm,λ em max / nm(CH 2 Cl 2 ) = 580nm, Φ f e = 0.93.

Embodiment 3

[0064] Synthesis of Benzocoumarin Derivative (II)-1

[0065]

[0066] The synthesis of 9-N, N-diethylaminobenzocoumarin aldehyde and intermediate (III)-1 is the same as in Example 1.

[0067] Dissolve 1.88g (0.005mol) of compound (III)-1 and 0.54g (0.005mol) of phenylhydrazine in 30mL of ethanol, heat to reflux at 90°C for 6 hours, and precipitate a solid after cooling, recrystallize after filtration to obtain 1.26g of benzoin Soybein derivative (II)-1, the yield is 56.3%.

[0068] EI-MS, m / e, 449.2[M+1]+ .λ ab. max / nm(CH 2 Cl 2 ) = 475nm, λ em max / nm(CH 2 Cl 2 ) = 588nm, Φ f e = 0.95.

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Abstract

The invention belongs to the field of fluorescent dyes and laser dyes, and relates to coumarin fluorescent dyes and laser dyes, in particular to pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives, a synthesis method of the same, and application of the same. The pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives have longer emission wavelength and extremely high luminous efficiency, and the fluorescence quantum efficiency of the derivatives is approximately 100 percent; at the same time, a luminescent material of the derivatives has excellent thermo, photo and electrochemical stability, and can be used as fluorescent dyes, laser dyes, organic electroluminescent materials, fluorescent labeling materials, fluorescent chemosensitive materials and the like. The pyrazoline naphthyridine benzocoumarin fluorescent dye derivatives have a structure shown in a formula (I) or a formula (II).

Description

field of invention [0001] The invention belongs to the field of fluorescent dyes and laser dyes, and relates to a class of coumarin-based fluorescent dyes and laser dyes, in particular to pyrazoline pyridobenzocoumarin fluorescent dye derivatives and their synthesis methods and uses. Background technique [0002] In the past ten years, organic fluorescent dyes have been applied in various fields of industry and civil use. Organic fluorescent solvent dyes have been widely used in organic fluorescent pigments and coatings, fluorescent dyes for plastics and artificial fibers, optical brighteners, organic scintillators, flaw detection for rockets and ships and large equipment, organic fluorescence in chemical and electrochemiluminescent bodies sources, fluorescent chemical analysis, fluorescent tracers in biology and medicine, and fluorescent sources in military and other fields. At present, the application of fluorescent dyes in biology and medicine is a huge and constantly ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/02C09K11/06H05B33/14G01N33/533
Inventor 汪鹏飞刘卫敏代青张文军李述汤
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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