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A cyanostyrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method

A cyanostyrene and fluorescence detection technology, applied in the direction of 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: 2022-08-09
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 probes to distinguish different polymer materials in polymer blends.

Method used

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  • A cyanostyrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method
  • A cyanostyrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method
  • A cyanostyrene derivative, preparation method and application thereof, polymer detection probe and fluorescence detection method

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preparation example Construction

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

[0061] P-bromophenylacetonitrile, iodine, sodium methoxide solution and the first solvent are mixed, and bimolecular oxidative coupling reaction is carried out to obtain double bromine intermediate product;

[0062] The bis-bromo intermediate product, the compound containing electron donating group, Pd(OAc) 2 , Ag 2 CO 3 It is mixed with the second solvent to carry out a Heck reaction to obtain a cyanostyrene derivative.

[0063] The compound containing the donor group has the structure shown in formula II:

[0064] formula II; in formula II, X is

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

[0066] The present invention mixes p-bromophenylacetonitrile, iodine, sodium met...

Embodiment 1

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

[0096] The electron-donating group-containing compound 4-diphenylaminostyrene (0.52nmol), the bis-bromo intermediate (0.52mmol), Pd(OAc) 2 (0.026mmol) and Ag 2 CO 3 (0.31 mmol) was placed in a 50 mL Schlenk test tube, added to 15 mL of toluene, and the reaction was st...

Embodiment 2

[0099] Prepare double bromine intermediate product according to the method of embodiment 1;

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

[0101] Record it as DOB.

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Abstract

The invention provides a cyanostyrene derivative, a preparation method and application thereof, a polymer detection probe and a fluorescence detection method, belonging to the technical field of polymer detection. The cyanostyrene derivative of the present invention is a typical D-π-A structure, and when dicyanostyrene is connected by double bonds on one side or both sides, a strong electron donor such as methoxy or triphenylamine is introduced, The length of the conjugated chain is increased, which is beneficial to obtain a large two-photon absorption cross-sectional area, and is a high-quality two-photon imaging probe. The cyanostyrene derivatives provided by the present invention have different dispersibility in different polymer phases, so that the fluorescent molecules doped in different polymers have different fluorescence intensities, and the fluorescence method can be used to perform high-contrast imaging and directly distinguish polymerization Phase-separated morphology in blends.

Description

technical field [0001] The present 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 the material 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 microphase 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 the 2D hybrid morphology, but the lack of 3D information...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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