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Polymerization fluorescent dye, preparation method and application thereof

A fluorescent dye and dye technology, applied in anthracene dyes, luminescent materials, organic dyes, etc., can solve the problems of slow polymerization process and few systems, and achieve the effect of high photostability and high fluorescence quantum yield.

Active Publication Date: 2012-06-27
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescent matrix is ​​easy to quench free radicals in the process of free radical polymerization of olefins, and acts as a termination of the polymerization inhibitor, thereby slowing down the polymerization process [Y.J.He and H.Tian, ​​Acta Polymerica Sinica (2000) 379-381; Pan Zuren. Polymer Chemistry [M]. Chemical Industry Press, 2007: 108]
Therefore, there are fewer systems reported at present, which has become one of the difficulties in this field.

Method used

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  • Polymerization fluorescent dye, preparation method and application thereof
  • Polymerization fluorescent dye, preparation method and application thereof
  • Polymerization fluorescent dye, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of polymerizable fluorescent dye 3:

[0042]

[0043] Synthesis of intermediate 2: 4-bromo-N-methylthrapyridone (1, 4.9g, 14.4mmol), anhydrous copper sulfate (0.2g, 10mol%) and 1,6-hexanediamine (2g, 17.2mmol) was dissolved in 100mL ethylene glycol monomethyl ether, and anhydrous potassium carbonate (3g, 21.6mmol) was added as an acid-binding agent. After reflux for 24 hours, potassium carbonate and copper sulfate were removed by filtration. The filtrate was freed of solvent using rotary evaporation to give a red solid. The solid was washed with ethanol to remove excess 1,6-hexanediamine. Silica gel column separation (ethyl acetate:methanol=10:1 as eluent), the yield was 51%.

[0044] 1 H-NMR (400MHz, CDCl 3 )δ10.49(m, 1H, NH), 8.46(d, J=7.7Hz, 1H, ArH,), 8.30(d, J=7.9Hz, 1H, ArH), 8.20(d, J=7.9Hz, 1H, ArH), 7.83-7.62 (m, 4H, ArH, CH 2 ), 3.86(s, 3H, CH3), 1.71-1.60(nb, 12H, CH 2 ).MS(TOF MS ES+) calculated for [C 23 h 26 N 3 o 2 ] + : 376.2020...

Embodiment 2

[0048] Synthesis of polymerizable fluorescent dye 5:

[0049] Polymerizable naphthalimide fluorescent dyes were prepared from 4-bromo-1,8-naphthalene anhydride as starting material.

[0050]

[0051] Synthesis of intermediate 4: 4-bromo-1,8-naphthalene anhydride (5.5g, 19.9mmol) and 1,6-hexanediamine (4.6g, 39.7mmol) were dissolved in 200mL ethylene glycol monomethyl ether, reflux After 5h, a large amount of yellow solid precipitated out. After the reaction, the reaction solution was poured into 500 mL of water, filtered, and the filter cake was washed with cold ethanol to remove residual 1,6-hexanediamine. After drying, 5.1 g of yellow solid was obtained with a yield of 63%, which was used for the synthesis of dye 5 without further purification.

[0052] Dye 5 can be obtained by amidation of intermediate 4, and the reaction steps refer to the process of synthesis of dye 3.

[0053] 1 H-NMR (400MHz, CDCl 3 )δ8.57(d, 1H, J=4.0, ArH), 8.45(d, 1H, J=8.0, ArH), 8.29(d, 1H,...

Embodiment 3

[0055] Synthesis of polymerizable fluorescent dye 8:

[0056]

[0057] Synthesis of Intermediate 6: 4-bromo-1,8-naphthalene anhydride (2.7g, 10mmol) and 3-octylamine (1.5g, 12mmol) were dissolved in 100mL ethanol solution, heated to reflux for 10h, no raw material was detected by TLC 4-Bromo-1,8-naphthalene anhydride was cooled to room temperature, and a large amount of khaki solids precipitated out. The reaction solution was filtered, and the filter cake was washed with a small amount of cold ethanol solution until the filtrate had no yellow color. After drying, 3.0 g of an earthy yellow product was obtained, with a crude yield of 88%.

[0058] Synthesis of Intermediate 7: Intermediate 6 (3.0g, 7.7mmol) and anhydrous piperazine (5.0g, 58mmol) were dissolved in 100mL of ethylene glycol monomethyl ether, heated to 100°C, the reaction solution turned yellowish brown, After continuing to react for 6h, it was cooled to room temperature. The reaction solution was poured into 4...

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Abstract

The invention relates to polymerization fluorescent dye, a preparation method and application thereof. The polymerization fluorescent dye has the structure of the following general formula, wherein D is a fluorescent dye base body, Z is a connection group containing functional groups capable of polymerizing, and n is 1 or 2. The polymerization fluorescent dye has the advantages of being high in photostability and fluorescence quantum yield and can be used under severe conditions of laser reading, laser scanning, neon lamp lighting, outdoor conditions and the like. Fluorescent nanometer microballoon obtained through preparation can be widely applied to application of the fields of biological detecting, lighting material, printing or coating. The preparation of emulsion polymerization uses olefin double bond free radical polymerization, can embed the fluorescent dye into polymer conveniently, and can not fall. Simultaneously, monomer with benzyl chloride ethylene is led in, and chemical crosslink locus forming can be conducted. The fluorescent nanometer microballoon capable of being functionalized and prepared through the emulsion polymerization can meet the requirements.

Description

technical field [0001] The invention belongs to the field of organic polymer materials, in particular to a class of polymerizable fluorescent dyes and applications thereof. Background technique [0002] Functional polymer nanospheres have attracted extensive research interest due to their potential applications in materials, fluorescent sensors, and biomedical detection. Compared with fluorescent dyes in the molecular state, fluorescent microspheres have the advantages of good stability and high luminous efficiency; compared with inorganic fluorescent particles, fluorescent polymer microspheres have the characteristics of good monodispersity, uniform particle size, and good sphericity. Therefore, it has good prospects for application in the fields of standards, metrology, immunomedicine, biochemistry, analytical chemistry, and biomedicine. [0003] Fluorescent microspheres are prepared by conventional methods, and the fluorescent dye is adsorbed on the carrier [Z.L.Zhang, Y...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B69/10C09B57/08C09B5/14C09B5/62C08F220/60C08F212/32C08F212/34C08F2/24
CPCC08F2/24C08F12/22C08F12/26C08F20/60C08F212/32C09B5/14C09B5/62C09B57/08C09B69/102C09B69/109C09K11/06C08F220/603
Inventor 彭孝军强新新樊江莉宋锋玲孙世国
Owner DALIAN UNIV OF TECH
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