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Thiazole[4,5-e]thiophene[2,3-b]pyridine type derivative with fluorescent function and preparation method thereof

A 5-e, 3-b technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as luminescent materials that have not been reported in the literature

Active Publication Date: 2016-07-20
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Through structural modification of thiazo[4,5-e]thiophene[2,3-b]pyridine compounds, a series of organic small molecules with novel skeleton structures and fluorescent functions are obtained, and this type of organic small molecule light-emitting materials No literature report

Method used

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  • Thiazole[4,5-e]thiophene[2,3-b]pyridine type derivative with fluorescent function and preparation method thereof
  • Thiazole[4,5-e]thiophene[2,3-b]pyridine type derivative with fluorescent function and preparation method thereof
  • Thiazole[4,5-e]thiophene[2,3-b]pyridine type derivative with fluorescent function and preparation method thereof

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Experimental program
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Embodiment 1

[0036] Embodiment 1: the synthesis of compound M1-1

[0037] Benzoylacetonitrile (1.45g, 10mmol), sulfur powder (960mg, 30mmol), isovaleraldehyde (860mg, 10mmol), morpholine (4350mg, 50mmol), and absolute ethanol (10mL) were reacted under reflux; After the reaction was completed, cooled to room temperature, added ethyl acetate, washed the organic phase with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, separated and purified by flash column chromatography to obtain 1.8 g of a yellow oil, Yield 75%. MS(EI):m / z(%)=245(55)M + ,230(100); 1 HNMR (300MHz, CDCl 3):δ=7.67-7.64(m,2H,ArH),7.50-7.40(m,3H,ArH),6.93(brs,2H,NH 2 ), 6.51(s, 1H, ArH), 2.92(sept, J=6.8Hz, 1H, CH), 1.23(d, J=6.8Hz, 6H, 2CH 3 ).

Embodiment 2

[0038] Embodiment 2: the synthesis of compound M1-2

[0039] The synthesis method is as in Example 1, o-fluorobenzoylacetonitrile (1.63g, 10mmol), sulfur powder (1.6g, 50mmol), isovaleraldehyde (2.58g, 30mmol), pyridine (1.58g, 20mmol), absolute ethanol (80mL), separated and purified to obtain 1.65g of yellow oil, yield 63%. MS(EI):m / z(%)=263(45)M + ,248(100),228(38),152(37); 1 HNMR (400MHz, CDCl 3 )δ7.52–7.40(m,,2H),7.26–7.20(m,1H),7.20–7.11(m,1H),6.28(d,J=1.5Hz,1H),2.94–2.83(m,1H ), 1.22 (d, J=6.8Hz, 6H). Embodiment 3: the synthesis of compound M1-3

Embodiment 3

[0040] The synthesis method is as in Example 1, o-chlorobenzoylacetonitrile (1.8g, 10mmol), sulfur powder (320mg, 10mmol), isovaleraldehyde (4.3g, 50mmol), triethylamine (1.01g, 10mmol), anhydrous Ethanol (100 mL) was separated and purified to obtain 2.2 g of a yellow oil with a yield of 78%. MS (ESI + ) m / z: 302 (M+Na + ),334(M+MeOH+Na + ); 1 HNMR (300MHz, CDCl 3 ):δ=7.44-7.38(m,1H,ArH),7.37-7.27(m,3H,ArH),6.07-5.92(m,3H,ArH,NH 2 ), 2.83(sept, J=6.8Hz, 1H, CH), 1.18(d, J=6.8Hz, 6H, 2CH 3 ).

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Abstract

The invention provides a thiazole[4,5-e]thiophene[2,3-b]pyridine type derivative shown in the formula (I) (please see the formula in the description), and application of the derivative as a compound with a fluorescent function, and provides a preparation method of the derivative. In the formula, R is selected from hydrogen, chlorine and fluorine, and R' is selected from 4-hydroxy, 2-hydroxy, 2-methyl, 2,6-dimethoxy, 2-hydroxy-5-iodine, 2-hydroxy-5-bromine, 2-hydroxy-3,5-ditertbutyl, 2-hydroxy-4-cyano, 2-hydroxy-4-methoxyl, 2-hydroxy-5-sulfonyl, 2-amino, 2-methanesulfonylamino, 2-p-methylbenzol sulfonylamino, 2-p-methylbenzol sulfonate, 2-(naphthalene-2-sulfonylamino) and 4-benzenesulfonyl.

Description

technical field [0001] The present invention relates to a class of small organic molecules with fluorescent functions, in particular to a class of novel thiazo[4,5-e]thiophene[2,3-b]pyridine derivatives and a preparation method thereof, which simultaneously have a strong liquid Fluorescent and solid fluorescent. Background technique [0002] About 50% of organic compounds belong to heterocyclic compounds in structure (PalwinderSingh.ExpertOpin.Ther.Pat.2011,21(4):437-454). Due to the unique structure of heterocyclic compounds, it is the development of new organic optoelectronic materials in recent years. The basic skeleton of (AngewChemIntEdEngl2014,53(9):2290-310). Therefore, it is of great scientific significance and application value to design and synthesize heterocyclic compounds with novel structures and to study their application in materials science, especially organic light-emitting materials (AccChemRes2012,45(8):1278-93). [0003] As a traditional light-emitting ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/14C09K11/06
CPCC09K11/06C07D513/14C09K2211/1092
Inventor 万一千黄漫娜朱新海余锐娜叶淑娴许可旷实
Owner SUN YAT SEN UNIV
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