Pyrazoline pyridine-fluorescent coumarin dye derivant, synthesis and uses thereof

A pyrazoline pyridine and fluorescent dye technology, applied in the field of laser dyes and fluorescent dyes, can solve problems such as laser formation and destruction

Active Publication Date: 2009-02-18
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] It was mentioned above that transitions between singlet and triplet states are forbidden, but at the high energy level S 1 The collision of the excited molecule with other surrounding molecules will lead to the inversion of the electron spin, so that the total spin is no longer zero, so there is still a 1 to T 1 the transition
But since T 1 Longer lifespan (10 -3 ~10 -5 s), at T 1 A large number of particles can accumulate on the surface, which will have a destructive effect on the formation of laser light

Method used

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  • Pyrazoline pyridine-fluorescent coumarin dye derivant, synthesis and uses thereof
  • Pyrazoline pyridine-fluorescent coumarin dye derivant, synthesis and uses thereof
  • Pyrazoline pyridine-fluorescent coumarin dye derivant, synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] (1) Synthesis of N, N-diethylcoumarin aldehyde (synthetic method according to J.Med.Chem.2004, 47, 6349)

[0078]

[0079] Add 2mL of phosphorus oxychloride to a 50mL three-necked flask, slowly add 2mL of freshly steamed dimethylformamide (DMF) dropwise under nitrogen protection, and complete the dropwise addition within 30 minutes. The temperature of the reaction solution is controlled at 20-50°C. 10 mL of a DMF solution in which 1.50 g of 7-N,N-diethylaminocoumarin (6.91 mmol) was dissolved was added dropwise thereto. After the dropwise addition was completed, the reaction solution was continued to react at 60° C. for 12 hours. The reaction solution was poured into 100 mL of ice water, and then the pH value of the reaction solution was adjusted with a 20 wt % NaOH aqueous solution, and a large amount of red solids were precipitated. The crude product was filtered, washed several times with water, dried in vacuo, and then recrystallized with absolute ethanol to obt...

Embodiment 2

[0086] Synthesis of Coumarin Derivative (II)-2

[0087]

[0088] The synthesis of N, N-diethylcoumarin aldehyde and intermediate (III)-1 is the same as in Example 1.

[0089] Dissolve 1.63g (0.005mol) of compound (III)-1 and 0.61g (0.005mol) of p-methylphenylhydrazine in 30mL of ethanol, heat and reflux at 90°C for 6 hours, after cooling, a yellow solid precipitates, which is recrystallized after filtration to obtain 1.12 g coumarin derivative (II)-2, yield 54.4%.

[0090] EI-MS, m / e, 413.2[M+1] + .λ ab. max / nm=390nm, λ em max / nm=497nm, Φ f e = 0.97.

Embodiment 3

[0092] Synthesis of Coumarin Derivative (II)-3

[0093]

[0094]

[0095] The synthesis of N, N-diethylcoumarin aldehyde is the same as in Example 1.

[0096] Dissolve 2.45g (0.01mol) of N,N-diethylcoumarin aldehyde and 1.63g (0.01mol) of benzoylacetamide in 30mL of ethanol, add 0.5mL of triethylamine, and heat to reflux at 90°C for 8 hours. After cooling, a yellow solid was precipitated, and 2.16 g of (III)-2 intermediate was obtained by filtration, with a yield of 55.7%. Compound (III)-2 can be directly used in the next reaction without purification.

[0097] Dissolve 1.94g (0.005mol) of compound (III)-2 and 0.54g (0.005mol) of phenylhydrazine in 30mL of ethanol, and heat to reflux at 90°C for 6 hours. After cooling, a yellow solid precipitates, which is filtered and recrystallized to obtain 1.27g of coumarin The yield of prime derivative (II)-3 is 55.2%.

[0098] EI-MS, m / e, 461.2[M+1] + .λ ab. max / nm=392nm, λ em max / nm=515nm, Φ f e = 0.99.

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Abstract

The invention belongs to the field of fluorescent dye and laser dye, and relates to coumarin fluorescent dye and laser dye, in particular to pyrazoline naphthyridine coumarin fluorescent dye derivative, and a synthetic method and an application thereof. The pyrazoline naphthyridine coumarin fluorescent dye derivative has very high fluorescent efficiency with the quantum yield of fluorescence of nearly 100 percent; meanwhile, the fluorescent material has excellent heat, light and electricity chemical stability, and can be used as fluorescent dye, laser dye, organic electroluminescent material, fluorescent marking material, fluorescent chemical sensitive material and the other. The pyrazoline naphthyridine coumarin fluorescent dye derivative has structure as seen in formula I or 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 pyridocoumarin fluorescent dye derivatives and their synthesis methods and uses. Background technique [0002] Since the beginning of the 20th century, organic fluorescent materials have been widely used in textile, plastic coloring and printing pigments. In 1963, Pope et al. in the United States observed the blue electroluminescence of anthracene, which opened the prelude to obtaining electroluminescence with organic fluorescent materials (Pope M., Kallmann H., Magnante P.J.Chem.Phys., 1963, 38: 2042~2049). Small organic molecules used in electroluminescence research have the characteristics of strong chemical modification, wide selection range, easy purification, high fluorescence quantum efficiency, and the ability to produce red, green, blue and other colors of light. The f...

Claims

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Application Information

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