Pyrene type asymmetrical disc-like luminous compound and preparation method thereof

A luminescent compound and asymmetric technology, applied in the field of pyrene-based asymmetric biaxial discotic compounds and its preparation, and disc-shaped electroluminescent compounds, can solve the problems of no fluorescence, achieve strong fluorescence, high luminous efficiency, The effect of broad application prospects

Inactive Publication Date: 2012-05-02
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as an organic fluorescent material, π-π stacking can quench the fluorescence caused by molecular aggregation, and there is basically no fluorescence in solid state or solution.

Method used

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  • Pyrene type asymmetrical disc-like luminous compound and preparation method thereof
  • Pyrene type asymmetrical disc-like luminous compound and preparation method thereof
  • Pyrene type asymmetrical disc-like luminous compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] with R 1 structured as R 2 structured as

[0026] The synthetic method of this compound is introduced as an example

[0027] 1: Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide and place it in a 50mL single-necked bottle, add 1.5mmol p-bromobenzoyl chloride (3.26g), and cool to 0 in an ice bath degree, gradually add 0.02mol aluminum oxide (2.64g); heat and reflux for 14 hours; pour the product into 100mL ice water and stir for 2 hours after cooling, separate the liquid with dichloromethane, dry and filter the organic phase through anhydrous magnesium sulfate and reconstitute Crystallization gave 2.76 g of p-bromobenzoyl chloride monosubstituted pyrene, yellow needle-like crystals, and the yield was 72%.

[0028] 2: Intermediate product bromination reaction: 5mmol p-bromobenzoyl chloride monosubstituted pyrene (1.92g) obtained in step 1 was dissolved in 50mL nitrobenzene, placed in a 100mL single-necked bottle, and ...

Embodiment 2

[0033] with R 1 The structure is: with R 2 The structure is:

[0034] 1: Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide and put it in a 50mL single-necked bottle, add 1.5mmol p-bromobenzoyl chloride (3.26g), and place in an ice bath. After the reaction was stopped, the solvent was distilled off under reduced pressure, and the column developing solvent was a 1:1 mixed solvent of n-hexane and dichloromethane. 1.26 g of pale yellow product was obtained, yield 51%.

[0035] 4: Trimethylsilane removal reaction: Dissolve 1.28 g of 2 mmol of the intermediate product in step 3 in a mixed solution of 5 mL of methanol and 15 mL of tetrahydrofuran, place it in the reactor, add 2 g of potassium carbonate, stir at room temperature for 3 hours, and then depressurize The solvent was distilled off, washed with water and methanol; after vacuum drying for 5 hours, it was directly put into a 100mL two-necked bottle for the next reaction. ...

Embodiment 3

[0038] with R 1 The structure is: with R 2 The structure is:

[0039] The synthetic method of this compound is introduced as an example

[0040] 1: Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide and place it in a 50mL single-necked bottle, add 1.5mmol p-bromobenzoyl chloride (3.26g), and cool to 5mL in an ice bath degree, gradually add 0.02mol aluminum oxide (2.64g); heat and reflux for 12 hours; pour the product into 100mL ice water and stir for 4 hours after cooling, separate the liquid with dichloromethane, dry and filter the organic phase through anhydrous magnesium sulfate, and reconstitute Crystallization gave 2.76 g of p-bromobenzoyl chloride monosubstituted pyrene, yellow needle-like crystals, and the yield was 72%.

[0041] 2: Intermediate product bromination reaction: 5mmol p-bromobenzoyl chloride monosubstituted pyrene (1.92g) obtained in step 1 was dissolved in 50mL nitrobenzene, placed in a 100mL single-nec...

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Abstract

The invention belongs to the technical field of organic synthesis, in particular to a pyrene type asymmetrical disc-like luminous compound and a preparation method thereof. The general structural formula of the compound is shown in the specifications, wherein R1 is shown in the specifications, and n is an integer ranging from 4 to 20; and R2 is shown in the specifications, and n is an integer ranging from 4 to 20. The preparation method of the compound comprises a pyrene Friedel-Crafts acylation reaction, an intermediate product bromination reaction, a Sonogashira coupling reaction, a trimethyl silicane removing reaction and a bromination chain linking reaction. The pyrene type asymmetrical disc-like luminous compound prepared with the method takes a disc as an axis and an asymmetrical bar-shaped molecular chain as an axis, has very high fluorescence and luminous efficiency, and has wide application.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a disc-shaped electroluminescence compound, especially a pyrene-type asymmetric biaxial disc-shaped compound and a preparation method thereof. Background technique [0002] Since the advent of the organic electroluminescent period, organic electroluminescent materials have become popular due to their high luminous brightness and luminous efficiency, rich colors, and easy processing of materials, and the ability to adjust the luminescent color by changing the molecular structure or doping. A new research hotspot in the field of law enforcement officers. The energy structure of an organic compound leads to its fluorescence phenomenon. In most cases, its absorption and fluorescence color depend on the conjugation of the system, that is, it is related to the chemical structure of the molecular chain. When designing and synthesizing organic electroluminescent materials, we sh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/796C07C49/84C07C45/68C09K11/06
Inventor 杨洲梁蓬霞王冬弥永胜金召奎杜政才
Owner UNIV OF SCI & TECH BEIJING
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