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1,4-dihydropyridine derivatives as well as preparation method and application thereof

A technology of dihydropyridine and derivatives, which is applied in organic chemistry methods, chemical instruments and methods, and fluid pressure measurement using optical methods, can solve problems such as low luminous efficiency and limit the application of fluorescent materials, and achieve good scientific research value and The effect of industrial application potential

Active Publication Date: 2017-11-24
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 1,4-Dihydropyridine is an excellent traditional structural unit for the construction of various fluorescent compounds, but so far, its derivatives are prone to fluorescence quenching due to the π-π stacking effect in the aggregated state. Limiting its application as a fluorescent material in film-forming or solid-state form, piezoluminescence-chromic materials based on 1,4-dihydropyridine structural units are rarely reported
In order to overcome the defect of low solid-state luminescence efficiency of common 1,4-dihydropyridine derivatives, the present invention designed and synthesized a 1,4-dihydropyridine derivative with aggregation-induced luminescence, polymorphism and piezoluminescence properties. thing

Method used

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  • 1,4-dihydropyridine derivatives as well as preparation method and application thereof
  • 1,4-dihydropyridine derivatives as well as preparation method and application thereof
  • 1,4-dihydropyridine derivatives as well as preparation method and application thereof

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specific Embodiment 1

[0050] 1,4-dihydropyridine derivatives, which have the following structural formula (I):

[0051]

[0052] The 1,4-dihydropyridine derivative of formula (I) is obtained through different recrystallization methods to obtain three different crystalline compounds I-y, I-o and I-r, and the structural formulas of the three crystalline compounds are the same.

[0053] The preparation method of 1,4-dihydropyridine derivative comprises the following steps:

[0054] (1) Preparation of initial samples of 1,4-dihydropyridine derivatives

[0055] (11) Using 2,6-dimethyl-4-pyrone 1 as the starting material, it undergoes an addition-elimination reaction with Michaelis acid to generate intermediate 2;

[0056] (12) Intermediate 2 and 4-dimethylaminobenzaldehyde undergo a condensation reaction to generate intermediate 3;

[0057] (13) Nucleophilic substitution reaction between intermediate 3 and ethylamine to synthesize the initial sample of 1,4-dihydropyridine derivatives;

[0058] The r...

specific Embodiment 2

[0080] Roughly the same as specific embodiment 1, the difference only lies in:

[0081] Step (2) includes the following steps:

[0082] (21) n-hexane and acetone are mixed according to the volume ratio of 5:1 to form a mixed solvent;

[0083] (22) Dissolve the initial sample of 1,4-dihydropyridine derivative in the mixed solvent formed in step (21) to form a solution, then heat the solution to 60°C, maintain this temperature for 5 minutes, and cool to room temperature to obtain emission Yellow fluorescent crystalline compound I-y, wherein:

[0084] The molar ratio of the initial sample of 1,4-dihydropyridine derivative to the mixed solvent is 1:3000.

specific Embodiment 3

[0085] Roughly the same as specific embodiment 1, the difference only lies in:

[0086] Step (2) includes the following steps:

[0087] (21) n-hexane and acetone are mixed according to a volume ratio of 3:1 to form a mixed solvent;

[0088] (22) Dissolve the initial sample of 1,4-dihydropyridine derivatives in the mixed solvent formed in step (21) to form a solution, then heat the solution to 60°C, maintain this temperature for 3 minutes, and cool to room temperature to obtain emission Yellow fluorescent crystalline compound I-y, wherein:

[0089] The molar ratio of the initial sample of 1,4-dihydropyridine derivative to the mixed solvent is 1:1500.

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Abstract

The invention belongs to the field of organic chemical synthesis and application and relates to 1,4-dihydropyridine derivatives as well as a preparation method and an application thereof. The preparation method of the 1,4-dihydropyridine derivatives comprises the following steps: (1) preparing an initial sample of the 1,4-dihydropyridine derivatives; (2) recrystallizing the initial sample of the 1,4-dihydropyridine derivatives in different ways to obtain three different crystalline compounds I-y, I-o and I-r, wherein the step (1) comprises the following steps: (11) forming an intermediate 2 from 2,6-dimethyl-4H-pyran-4-one 1 as an initial material as well as Meldrum's acid through an addition-elimination reaction; (12) forming an intermediate 3 from the intermediate 2 and 4-dimethylaminobenzaldehyde through a condensation reaction; (13) synthesizing the initial sample of the 1,4-dihydropyridine derivatives from the intermediate 3 and ethylamine through nucleophilic substitution.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis and application, and relates to 1,4-dihydropyridine derivatives and their preparation methods and applications. Background technique [0002] Piezoluminescent materials, also known as mechanoluminescent materials or triboluminescent materials, are important smart materials and have great application potential in the fields of fluorescence sensors, pressure sensors or anti-counterfeiting labels. [0003] Organic molecules with aggregation-induced luminescent properties usually have distorted molecular conformations, so they can well overcome the fluorescence quenching effect caused by π-π stacking caused by aggregation (see literature: Chem. Commun., 2001, 1740-1741; J . Mater. Chem., 2001, 11, 2974-2978), expanding its range of applications as fluorescent materials in film-forming or solid-state form. Another noteworthy advantage of organic molecules with aggregation-induced luminescent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C09K11/06C09K9/02G01L1/24G01L11/02
CPCC07B2200/13C07D405/04C09K9/02C09K11/06C09K2211/1029C09K2211/1088G01L1/24G01L11/02
Inventor 黄小波周一斌吴华悦钱乐彬刘妙昌高文霞丁金昌
Owner WENZHOU UNIVERSITY
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