Cyano styrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method

A technology of cyanostyrene and derivatives, which is applied in fluorescence/phosphorescence, measurement devices, photovoltaic power generation, etc., to achieve the effect of improving the depth of fluorescence imaging and large two-photon absorption cross-sectional area

Active Publication Date: 2021-12-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is currently a lack of efficient fluorescent prob

Method used

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  • Cyano styrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method
  • Cyano styrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method
  • Cyano styrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method

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preparation example Construction

[0060] The present invention provides the preparation method of cyanostyrene derivative described in above-mentioned technical scheme, comprises the following steps:

[0061] P-bromophenylacetonitrile, iodine, sodium methylate solution and the first solvent are mixed to carry out bimolecular oxidative coupling reaction to obtain double bromo intermediates;

[0062] The bisbromine intermediate product, electron-donating group compound, Pd(OAc) 2 、Ag 2 CO 3 Mix with the second solvent, carry out Heck reaction, obtain cyanostyrene derivative.

[0063] The monad-containing compound has a structure shown in formula II:

[0064] Formula II; In formula II, X is

[0065] In the present invention, unless otherwise specified, the required preparation materials are commercially available products well known to those skilled in the art.

[0066] The present invention mixes p-bromophenylacetonitrile, iodine, sodium methoxide solution and a first solvent to carry out a bimolecula...

Embodiment 1

[0095] Dissolve p-bromophenylacetonitrile (5.00g, 25.5mmol) and iodine (6.57g, 25.5mmol) in dry ether (100mL), dissolve sodium methoxide (2.89g, 5.3mmol) in methanol solution (8.68g, 14.61 mL), mixed the obtained ether mixture with sodium methoxide solution, stirred in a dry ice bath for 0.5 h, raised the temperature to 0°C, replaced the dry ice bath with ice water, and stirred for 4 h. % of hydrochloric acid to quench the reaction; after stirring the resulting mixed material for 12 hours, the resulting material was filtered, and the solid separated from the resulting product was washed with methanol at 0°C and then rinsed with water, and then the resulting mixture was dried to obtain a bis-bromo intermediate ;

[0096] The electron-donating group compound 4-dianilino-styrene (0.52nmol), the bisbromo intermediate (0.52mmol), Pd(OAc) 2 (0.026mmol) and Ag 2 CO 3 (0.31mmol) was placed in a 50mL Schlenk test tube, added in 15mL toluene, stirred and reacted at 110°C for 18h, and...

Embodiment 2

[0099] Prepare according to the method for embodiment 1 and obtain two bromine intermediates;

[0100] The electron-donating group compound 4-methoxystyrene (1.04nmol), the bisbromo intermediate (0.52mmol), Pd(OAc) 2 (0.052mmol) and Ag 2 CO 3 (0.62mmol) was placed in a 50mL Schlenk test tube, added in 15mL toluene, stirred and reacted at 110°C for 18h, the resulting product system was purified on a silica gel column, and the reagents used were dichloromethane and petroleum ether (volume ratio: 1:1), Obtain cyanostyrene derivatives, the structural formula is:

[0101] Recorded as DOB.

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Abstract

The invention provides a cyano styrene derivative, a preparation method and application thereof, a polymer detection probe and a fluorescence detection method, which belong to the technical field of polymer detection. The cyano styrene derivative is of a typical D-pi-A structure, strong electron donors such as methoxyl or triphenylamine are introduced to one side or two sides of dicyanostyrene through double bond connection, meanwhile, the length of a conjugated chain is increased, and a high-quality two-photon imaging probe with a large two-photon absorption sectional area can be obtained. The cyano styrene derivative provided by the invention has different dispersibility in different polymer phases, so that fluorescent molecules doped in different polymers have different fluorescence intensities, and a fluorescence method can be utilized to carry out high-contrast imaging and directly distinguish phase separation forms in polymer blends.

Description

technical field [0001] The invention relates to the technical field of polymer detection, in particular to a cyanostyrene derivative, a preparation method and application thereof, a polymer detection probe and a fluorescence detection method. Background technique [0002] The polymer blending method has the characteristics of simplicity and good repeatability, and is an important means of polymer modification. For blending, the properties of materials are affected not only by the chemical composition and structure of the various polymers, but also by the microscopic phase separation obtained during the forming process. In order to study the relationship between the microscopic phase separation morphology and macroscopic mechanical properties of polymer blends, transmission electron microscopy (TEM) and scanning electron microscopy (SEM) are widely used. Images obtained by these techniques provide information about 2D hybrid morphology, but the lack of 3D information may lea...

Claims

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Application Information

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IPC IPC(8): G01N21/64
CPCG01N21/643G01N2021/6432Y02E10/549
Inventor 徐斌武志远田文晶
Owner JILIN UNIV
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