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Pyridine chalcone derivative with aggregation sate fluorescence enhancement and two-photon fluorescence characteristics

A technology of pyridylchalcone and two-photon fluorescence, which is applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of limited application, few types of materials for enhanced fluorescence in aggregated state, etc., and achieve simple preparation process and easy Purification and industrialization, the effect of high yield

Inactive Publication Date: 2010-08-04
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few types of aggregated fluorescence-enhanced materials reported so far, which limits their applications in optoelectronic materials and related fields.

Method used

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  • Pyridine chalcone derivative with aggregation sate fluorescence enhancement and two-photon fluorescence characteristics
  • Pyridine chalcone derivative with aggregation sate fluorescence enhancement and two-photon fluorescence characteristics
  • Pyridine chalcone derivative with aggregation sate fluorescence enhancement and two-photon fluorescence characteristics

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 (WF1): Synthesis of (E)-N,N-diphenyl-4-(2-acryloylpyridyl)aniline.

[0039] (1) Synthesis of N, N-diphenylaminobenzaldehyde: Weigh equimolar amounts of triphenylamine and DMF in a three-necked flask, slowly drop in excess phosphorus oxychloride in an ice bath, and heat up to reflux after dropping for 1 After cooling, slowly pour it into ice water, neutralize it with aqueous sodium hydroxide solution, stir vigorously and let it stand, and filter to obtain the crude product. Finally, light yellow crystals were obtained by vacuum sublimation, which was N, N-diphenylaminobenzaldehyde, with a yield of 89.5%;

[0040] (2) Add self-made N,N-diphenylaminobenzaldehyde (10.8mmol, 2.95g) into 20mL of alcohol (such as methanol, ethanol, etc.), and then add 2-acetylpyridyl (10.8mmol, 1.31 g) and 8mL saturated lye (such as potassium carbonate, NaOH, KOH aqueous solution); stirred at room temperature for 24 hours, filtered the crude product and then rinsed several times wit...

Embodiment 2

[0049] Example 2 (WW1): Synthesis of (E)-N-[4-(2-acryloylpyridyl)]phenylcarbazole.

[0050] (1) Synthesis of N-carbazolylbenzaldehyde: Weigh equimolar amounts of carbazole and p-fluorobenzaldehyde in a three-necked flask, then add excess potassium carbonate and the amount of cetyltrimethyl bromide as catalyst Amine, heated at 136°C in DMF solvent for 3 days, cooled and slowly poured into ice water, stirred and extracted three times with DCM, concentrated to obtain a crude product, and finally obtained a yellow crystal by vacuum sublimation, which is N-carbazolylbenzaldehyde , yield 85.2%;

[0051] (2) Using a method similar to that in Example 1, it is only necessary to change the N,N-diphenylaminobenzaldehyde in step 2 into N-carbazolylbenzaldehyde according to the obtained compound, and the yield is 56.3%;

[0052] (3) Analysis of the obtained compound: yellow, melting point: 200°C, decomposition temperature: 210°C.

[0053] MS (EI), found: 374.1; calculated: 374.14.

[00...

Embodiment 3

[0059] Example 3 (WW2): Synthesis of (E)-N-ethyl-[3-(2-acryloylpyridyl)]carbazole.

[0060] (1) N-ethyl-3-carbazole formaldehyde: the DMF of 3ml is joined in the flask that fills 3.5g (18mmol) N-ethylcarbazole, ice bath and N 2 Under atmosphere, add 0.09 mol of POCl dropwise 3 . After the dropwise addition was completed, the temperature was raised to 90°C to react for 24 hours, cooled to room temperature, the reaction solution was slowly poured into ice water, neutralized with dilute acid, extracted with dichloromethane, anhydrous MgSO 4 After drying, it was purified by silica gel column packing to obtain 2.4 g of N-ethyl-3-carbazole formaldehyde with a yield of 63%.

[0061] (2) The synthetic method is similar to Example 1, only need to change the N,N-diphenylaminobenzaldehyde in step (2) into N-ethyl-3-carbazole formaldehyde according to the compound obtained, and the productive rate is 64.3 %.

[0062] (3) Analysis of the obtained compound: yellow, with a decomposition ...

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Abstract

The invention relates to a pyridine chalcone derivative which has aggregation sate fluorescence enhancement and two-photon fluorescence characteristics and is connected with different aromatic rings or aromatic heteroatomic rings by using allyl acyl-2-pyridyl as a matrix. The pyridine chalcone derivative has a chemical structural formula as shown below, wherein R1 is selected from one of triphenylamine bases, 4-N-carbazole phenyl and 3-(N-ethyl) carbazyl; R2 is selected from one of triphenylamine groups and 4-bromo-triphenylamine group or 3,8-(N-ethyl) carbazyl; and R3 is selected from the triphenylamine group. The pyridine chalcone derivative has important application values in the fields of organic light-emitting diodes (DLED), two-photon fluorescence microscopy, optical switches, biological fluorescence sensors and the like.

Description

technical field [0001] The present invention relates to an organic compound with a pyridychalcone group, in particular to an acryloyl-2-pyridyl group connected with different aromatic rings or aromatic heterocyclic rings with characteristics of enhanced fluorescence in aggregated state and two-photon fluorescence The pyridine chalcone derivatives have important application value in the fields of organic light-emitting diodes (OLEDs), two-photon fluorescence microscopy imaging, optical switches and bioluminescent sensors. Background technique [0002] Many photoluminescent materials have high fluorescence emission intensity in dilute solution, but their luminescence intensity is weak or hardly luminescent in aggregated state and solid state, which is due to aggregation-induced fluorescence quenching. In two-photon fluorescence microscopy for biological imaging, light-emitting molecules are often required to emit light in an aggregated state. In the fabrication of organic elec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D401/10C07D401/06C07D213/50C09K11/06
Inventor 王筱梅陈志刚范丛斌吴莉娜
Owner SUZHOU UNIV OF SCI & TECH
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