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Quinoline nitrile derivative with aggregation-induced emission performance

A derivative, quinoline nitrile technology, applied in the field of aggregation-induced luminescent compounds, can solve the problems of difficult synthetic routes, fluorescence quenching, etc., and achieve the effect of less synthesis steps, simple synthesis, and obvious aggregation-induced luminescence characteristics

Active Publication Date: 2013-12-25
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the difficulty of the existing synthesis route of DCM derivatives, and the fluorescence is easily quenched in solid state

Method used

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  • Quinoline nitrile derivative with aggregation-induced emission performance
  • Quinoline nitrile derivative with aggregation-induced emission performance
  • Quinoline nitrile derivative with aggregation-induced emission performance

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preparation example Construction

[0024] R in the compound shown in formula I below 2 Taking phenyl or substituted phenyl as an example, the method for the compound shown in the synthetic formula I is further described, and the synthetic method includes the following steps:

[0025] a) with acetonitrile as the reaction solvent, 2-methylquinoline and the corresponding haloalkane (R 1 X, X is Br or I, etc.) kept at reflux for 30 minutes to 12 hours to obtain 2-methyl-quinolinate (compound shown in formula III) substituted on the corresponding N;

[0026] b) In the ethanol / acetic acid system, the compound shown in formula III and malononitrile were kept in a reflux state for 20 hours to 36 hours, and the Michael addition and elimination reaction obtained substituted 2-methyl-quinoline nitrile (formula IV compounds shown);

[0027] c) with acetonitrile as a solvent and piperidine as a catalyst, the compound shown in formula IV and the corresponding benzaldehyde or substituted benzaldehyde are kept in a reflux st...

Embodiment 1

[0034] Synthesis of EP (compound shown in formula I-1)

[0035]

[0036] (1) Synthesis of N-ethyl-2-methylquinoline bromide

[0037] In a 100ml round bottom flask, 2-methylquinoline (7.15g, 50mmol), bromoethane (38.2g, 350mmol) and acetonitrile (50ml) were successively added, and the mixture was refluxed for 2h under Ar protection and magnetic stirrer stirring. After standing and cooling to room temperature, a yellow solid precipitated out, and the solid filter cake was collected by suction filtration to obtain 4.45 g of a yellow solid product, with a yield of 35.3%.

[0038] (2) N-ethyl-2-methyl-4-(α,α-dicyano)methylene-1,4-dihydroquinoline

[0039] In a 100ml round bottom flask, add N-ethyl-2-methylquinoline bromide (4.6g, 18.4mmol), malononitrile (3.04g, 46mmol) and absolute ethanol (35ml) successively, under argon protection , After reflux reaction for 2 hours, the filter cake was obtained by suction filtration as 3.0 g of a yellow product, and the yield was 69.4%.

...

Embodiment 2

[0046] Synthesis of EF (compound shown in formula I-2)

[0047]

[0048] (1) Synthesis of N-ethyl-2-methylquinoline bromide

[0049] In a 100ml round bottom flask, 2-methylquinoline (7.15g, 50mmol), bromoethane (38.2g, 350mmol) and acetonitrile (50ml) were successively added, and the mixture was refluxed for 2h under Ar protection and magnetic stirrer stirring. After standing and cooling to room temperature, a yellow solid precipitated out, and the solid filter cake was collected by suction filtration to obtain 4.45 g of a yellow solid product, with a yield of 35.3%.

[0050] (2) N-ethyl-2-methyl-4-(α,α-dicyano)methylene-1,4-dihydroquinoline

[0051] In a 100ml round bottom flask, add N-ethyl-2-methylquinoline bromide (4.6g, 18.4mmol), malononitrile (3.04g, 46mmol) and absolute ethanol (35ml) successively, under argon protection , After reflux reaction for 2 hours, the filter cake was obtained by suction filtration as 3.0 g of a yellow product, and the yield was 69.4%.

...

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Abstract

The invention relates to a quinoline nitrile derivative. A method comprises the following steps of: reacting 2-methylquinoline serving as an initial raw material with the corresponding alkyl halide to obtain quaternary ammonium salt, performing Michael addition-elimination reaction on the quaternary ammonium salt and malononitrile, and performing Knoevenagel condensation reaction on the obtained compound and the corresponding aromatic aldehyde to obtain a target product. The aggregate or solid substance of the derivative has strong fluorescence and large wavelength, is a good aggregation-induced emission material, and has considerable application prospects in the fields of electroluminescent devices, fluorescent probes, intelligent materials, organism imaging and the like.

Description

technical field [0001] The invention relates to a class of aggregation-induced luminescent compounds containing quinoline nitrile units, in particular to a dicyanomethylene quinoline (quinoline nitrile) derivative. Background technique [0002] In 1989, Deng Qingyun of Kodak Company first reported the use of pyranonitrile derivatives (DCM) as red dye doped electroluminescent devices (C.W.Tang, et al., Electroluminescence of doped organic thin films, J.Appl.Phys ., 1989, 65, 3610-3616). However, when the red light material is solid, it is very easy to cause fluorescence quenching. So far, people have modified DCM to obtain a series of substituted DCM derivatives to solve the problem of solid-state fluorescence quenching. However, these methods usually require cumbersome synthesis steps, and under solid-state conditions, the fluorescence quantum yield is still not high enough (C.T.Chen, Evolution of Red Organic Light-Emitting Diodes: Materials and Devices, Chem.Mater., 2004,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/12C09K11/06
Inventor 朱为宏史川兴郭志前朱世琴邵安东杨金凤管婷祝正阳石文娥
Owner EAST CHINA UNIV OF SCI & TECH
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