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Water-dispersible hyperbranched conjugated polymer fluorescent nanoparticles as well as preparation method and application thereof

A hyperbranched conjugated, fluorescent nanotechnology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problem of low sensitivity of nitroaromatics, improve detection sensitivity, realize post-functionalization reaction, quench The effect of increasing the extinction constant

Active Publication Date: 2016-01-20
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention provides a water-dispersed hyperbranched conjugated polymer fluorescent nanoparticle and its preparation method and application in order to solve the technical problem of low sensitivity of detecting nitroaromatics in the water phase by using conjugated polymers

Method used

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  • Water-dispersible hyperbranched conjugated polymer fluorescent nanoparticles as well as preparation method and application thereof
  • Water-dispersible hyperbranched conjugated polymer fluorescent nanoparticles as well as preparation method and application thereof
  • Water-dispersible hyperbranched conjugated polymer fluorescent nanoparticles as well as preparation method and application thereof

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preparation example Construction

[0047] The preparation method of the water-dispersed hyperbranched conjugated polymer fluorescent nanoparticles provided by the present invention, the specific steps are as follows:

[0048] Step 1: Dissolve the emulsifier completely in deoxygenated deionized water under argon atmosphere. Monomers A3, B2, palladium catalyst were dissolved in deoxygenated toluene and transferred to the stirred emulsifier solution. After ultrasonically oscillating the reactor at 40-50°C for 5-20 minutes, add K with a concentration of 2M under stirring. 2 CO 3 aqueous solution, and then continue to ultrasonic 5 ~ 10min. The obtained reaction mini-emulsion is placed in a 80-90°C oil bath, and stirred for 24-48 hours. Add boric acid end-capping agent 4-(4,4,5,5-4methyl-[1,3,2]dioxaborolan-2-yl)phenol and react for 3-4 hours, add bromo end-capping agent Reagent 4-bromophenol continued to react for 3-4 hours. After cooling, the reaction emulsion was poured into 200 mL saturated NaCl aqueous solu...

Embodiment 1

[0059] Water-dispersed hyperbranched conjugated polymer fluorescent nanoparticles with triphenylbenzene and fluorene as conjugated structural units were prepared. Its synthetic route is as follows:

[0060]

[0061] Among them, the monomers 1,3,5-tris(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolane)phenyl)benzene and 9,9- Dihexyl-2,7-dibromofluorene was synthesized by referring to literature method.

[0062] Step 1: Under argon atmosphere, completely dissolve CTAB5.82g (16mmol) in 90mL deoxygenated deionized water in a 250mL two-necked bottle. Monomer 1,3,5-tris(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolane)phenyl)benzene 164mg (0.24mmol), 9 , 9-dihexyl-2,7-dibromofluorene 177mg (0.36mmol) and catalyst Pd (PPh 3 ) 4 2 mg was dissolved in 6 mL of deoxygenated toluene. The toluene solution of monomer and catalyst was transferred by syringe into the stirred CTAB solution. Place the reactor in an ultrasonic water bath at 50°C, and after ultrasonic oscillation for 20 min, add 3 ...

Embodiment 2

[0069] Water-dispersed hyperbranched conjugated polymer fluorescent nanoparticles with triphenylamine and fluorene as conjugated structural units were prepared. Its synthetic route is as follows:

[0070]

[0071] Among them, the monomer tris(4-bromophenyl)amine and 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-di Hexylfluorene was synthesized according to literature method.

[0072] Step 1: Dissolve CTAB8.76g (24mmol) completely in 90mL deoxygenated deionized water in a 250mL two-necked bottle under argon atmosphere. Monomer tris(4-bromophenyl)amine 164mg (0.24mmol), 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9, 9-dihexylfluorene 181mg (0.36mmol), catalyst Pd (PPh 3 ) 4 2 mg was dissolved in 6 mL of deoxygenated toluene. The toluene solution of monomer and catalyst was transferred by syringe into the stirred CTAB solution. Place the reactor in an ultrasonic water bath at 50°C, and after ultrasonic oscillation for 20 min, add 3 mL of K with a concentratio...

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Abstract

The invention relates to water-dispersible hyperbranched conjugated polymer fluorescent nanoparticles as well as a preparation method and an application thereof and aims to solve the technical problem of low sensitivity of conjugated polymers used currently during detection of nitro-aromatic compounds in a water phase. An internal hydrophobic cavity structure and a terminal hydrophilic structure of each nanoparticle are a hyperbranched conjugated polymer core part composed of conjugated structure units Ar1 and Ar2 and sodium oxypropyl sulfonate or sodium oxybutyl sulfonate generated through a reaction between terminal hydroxyl of precursors of the hyperbranched conjugated polymer fluorescent nanoparticles and 1,3-cyclopropane sultone or 1,4-cyclobutyl sultone respectively. The nanoparticles prepared with the method are effectively combined with TNT molecules through a hydrophobic enrichment function, and the detection sensitivity is remarkably improved. The quenching coefficient and the detection limit of the hyperbranched conjugated polymer fluorescent nanoparticles can be improved by several magnitudes in comparison with traditional linear conjugated polymers and nanoparticles of the traditional linear conjugated polymers, and the selective detection of TNT in an aqueous solution can be realized.

Description

technical field [0001] The invention relates to a nano particle, in particular to a water-dispersed hyperbranched conjugated polymer fluorescent nano particle and a preparation method and application thereof. Background technique [0002] Nitroaromatic explosives such as 2,4,6-trinitrotoluene (TNT) and 2,4,6-trinitrophenol (PA) are highly explosive and play an important role in national defense and military fields. At the same time, these explosives have also been used by terrorist organizations to carry out terrorist attacks in recent years, posing a serious threat to the safety of the country and people, and becoming one of the security issues of global concern. On the other hand, with the development of industry, such highly toxic substances are currently widely used in many industrial fields, and their irregular use or excessive discharge as industrial waste will cause serious pollution of air, soil and water sources, and endanger human health. For example, TNT pollutes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C08G61/12C09K11/06G01N21/64
Inventor 王利祥童辉吴晓甫李海波徐玉祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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