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Dibenzothiophene chalcone containing coumarin skeleton and synthesis method and application thereof

A technology of dibenzothiophene and coumarin skeleton, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of unreported photophysical and photochemical properties, and achieve good ultraviolet absorption and fluorescence emission performance. , The synthesis and separation methods are simple, and the stability is good.

Inactive Publication Date: 2012-06-27
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the photophysical and photochemical properties of the A-π-A system formed by coumarin and dibenzothiophene.

Method used

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  • Dibenzothiophene chalcone containing coumarin skeleton and synthesis method and application thereof
  • Dibenzothiophene chalcone containing coumarin skeleton and synthesis method and application thereof
  • Dibenzothiophene chalcone containing coumarin skeleton and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Synthesis of 3-(3-Dibenzothiophene-2-acryl)benzopyran-2-one

[0054] The synthesis proceeds in three steps:

[0055] (1) Synthesis of 3-dibenzothiophenealdehyde

[0056] Dibenzothiophene (1.1 g, 6 mmol) and 20 mL of anhydrous Cl 2 CH 2 Add it to a three-necked flask equipped with a constant pressure funnel, stir and dissolve in an ice-water bath; take 1,1-dichloromethyl methyl ether (1 mL, 12 mmol), use 10 mL of anhydrous Cl 2 CH 2 Dissolve, add to dibenzothiophene; after 10 minutes, take titanium tetrachloride (1.4 mL, 13 mmol) and dissolve it in 20 mL of anhydrous Cl 2 CH 2 , slowly added dropwise to the dibenzothiophene mixed solution, the dropwise addition was completed in about 20 minutes, and the reaction was continued at 25 ° C for 4 hours; the solution was poured into ice water (more ice), vigorously stirred for 1 hour, and the solution was divided into two layers , use anhydrous Cl for the aqueous phase 2 CH 2 Extraction, combine the organic phases, then ...

Embodiment 2

[0066] Synthesis of 3-(3-dibenzothiophene-2-acryloyl)-5,6-benzobenzopyran-2-one

[0067] The synthesis is carried out in three steps:

[0068] (1) Synthesis of 3-dibenzothiophenealdehyde

[0069] With embodiment 1 step (1);

[0070] (2) Synthesis of 3-acetyl-5,6-benzocoumarin

[0071] 2-Hydroxy-1-naphthaldehyde (1.72g, 10mmol) was mixed with ethyl acetoacetate (1.3g, 10mmol) and added to the three-necked flask, then dissolved in 15mL of absolute ethanol solvent, stirred in an ice-water bath, and then added 0.5mL (5mmol) of hexahydropyridine as a The catalyst was stirred in an ice-water bath for 6 hours, filtered with suction, the crude product was washed with deionized water and ethanol, and then recrystallized with absolute ethanol and acetone to obtain a light yellow solid product with a yield of about 76%.

[0072] The structural characterization data of the product is: m.p.189~190℃; 1 H NMR (400MHz, CDCl 3 / TMS)δ: 2.81(s, 3H), 7.51(d, J=9.0Hz, 1H), 7.64(t, J=8.0Hz, ...

Embodiment 3

[0079] Synthesis of 3-(3-dibenzothiophene-2-acryloyl)-7-diethylaminobenzopyran-2-one

[0080] The synthesis is carried out in three steps:

[0081] (1) Synthesis of 3-dibenzothiophenealdehyde

[0082] With embodiment 1 step (1);

[0083] (2) Synthesis of 3-acetyl-7-diethylaminocoumarin

[0084] The 4-N,N-% ethylaminosalicylaldehyde (1.0g, 6.1mmol) and ethyl acetoacetate (0.84g, 6.1mmol) were mixed into the three-necked flask, then dissolved in 15mL absolute ethanol solvent, stirred in an ice-water bath, and then added 0.3mL (3mmol) hexahydrogen Pyridine was used as a catalyst, the reaction was stirred in an ice-water bath for 8 hours, filtered with suction, and the crude product was washed with deionized water and ethanol, and then recrystallized with absolute ethanol and acetonitrile to obtain a bright yellow solid product with a yield of about 69%.

[0085] The structural characterization data of the product are: m.p.151~153℃; 1 H NMR (400MHz, CDCl 3 / TMS)δ: 8.49(s, 1...

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Abstract

The invention belongs to the field of organic light-emitting materials and discloses a dibenzothiophene chalcone containing a coumarin skeleton and a synthesis method and application thereof. The dibenzothiophene chalcone containing the coumarin skeleton has the structure disclosed by formula (I), and the preparation method thereof comprises the following steps: (1) synthesizing 3-dibenzothiophene aldehyde; (2) synthesizing 3-acetyl coumarin derivants; and (3) synthesizing the dibenzothiophene chalcone containing the coumarin skeleton. The dibenzothiophene chalcone containing the coumarin skeleton disclosed by the invention has good stability, thermal decomposition temperature of more than 300 DEG C, good ultraviolet absorption and fluorescence emission performances and small molecular size reaching nanometer level, and can be used as nano material; and the synthesis and separation methods are simple, and raw materials are convenient and easy to obtain.

Description

technical field [0001] The invention belongs to the field of organic luminescent materials, and in particular relates to a dibenzothiophene chalcone containing a coumarin skeleton and a synthesis method and application thereof. Background technique [0002] In recent years, organic materials with strong two-photon fluorescence and two-photon absorption cross-sections have become a research hotspot. As an important organic heterocyclic compound, dibenzothiophene derivatives are used in three-dimensional two-photon microscopy / imaging, two-photon limiting and electrostatic printing, organic field effect transistors, light-emitting diodes, photoluminescence and flash photolysis. , Fluorescence relaxation time calibration, determination of protein antibody and antigen immune response and other fields have been widely used. In addition, D-π-D or A-π-A systems based on dibenzothiophene chromophores have attracted much attention due to their good two-photon absorption. Similarly, ...

Claims

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Application Information

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IPC IPC(8): C07D409/06C09K11/06
Inventor 王辉熊红兰
Owner SOUTH CHINA NORMAL UNIVERSITY
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