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Fluorene conjugated polymer film based on cyclodextrin side chain and its preparation method and application

A conjugated polymer, cyclodextrin technology, applied in fluorescence/phosphorescence, material excitation analysis, etc., can solve the problems of cumbersome synthesis methods, limited wide use, etc., to improve the emission wavelength, increase the Stokes shift, and simplify complex methods. Effect

Inactive Publication Date: 2018-09-25
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Unfortunately, cumbersome synthetic methods for polymerizing "fluorescent donors" and "fluorescent acceptors" in the backbone of fluorene-based conjugated polymers limit their widespread use

Method used

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  • Fluorene conjugated polymer film based on cyclodextrin side chain and its preparation method and application
  • Fluorene conjugated polymer film based on cyclodextrin side chain and its preparation method and application

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preparation example Construction

[0051] The preparation method of the cyclodextrin side chain i.e. propargyl-cyclodextrin is as follows:

[0052] Disperse the cyclodextrin (3.2-12.8 mmol) in water, and slowly add an aqueous solution of sodium hydroxide (3.2-12.8 mmol) dropwise in an ice-water bath to completely dissolve the cyclodextrin. At this time, p-toluenesulfonyl chloride (4.6-18.4 mmol) was dissolved in acetonitrile solution and slowly added dropwise to the above-mentioned clear liquid, during which white precipitates were formed. After the mixture was reacted at room temperature for 4 h, the pH value was adjusted to 6 with 1-3 mol / L saline solution, filtered, and recrystallized in water to obtain the target product. Dissolve the obtained product mono-6-deoxy-6-p-toluenesulfonyl-cyclodextrin (1~3mmol) and propargylamine (2~6mmol) in DMF, and react at 100~110°C for 4h under nitrogen protection . After the reaction, the solution was cooled to room temperature and settled in acetone. The solid was colle...

Embodiment 1

[0055] The main chain of the fluorene conjugated polymer, that is, the end group of the side chain is -N 3 The preparation method of the fluorene conjugated polymer comprises the steps:

[0056] (1) 1mmol of 2,7-dibromofluorene is added to 50mL of mass fraction in 50% NaOH aqueous solution, then 1mmol of phase transfer catalyst tetrabutylammonium bromide, 10mmol of 1,6-dibromohexane is added, After reacting at 75°C for 4h, cool to room temperature, pass CH 2 Cl 2 Extraction, and then washed with 0.5mL dilute hydrochloric acid aqueous solution and water, anhydrous MgSO 4 Drying, followed by silica gel column purification, eluent is n-hexane / dichloromethane (volume ratio 10:1), to obtain white solid 9,9'-bis(bromohexyl)-2,7-dibromofluorene, this step The yield was 52%.

[0057] (2) 5 mmol of compound 9,9'-di(bromohexyl)-2,7-dibromofluorene, 15 mmol of NaN 3 Dissolve in 35 mL of DMSO, react for 4 h under nitrogen protection, 75 °C, cool to room temperature, add 150 mL of wat...

Embodiment 2

[0064] The main chain of the fluorene conjugated polymer, that is, the end group of the side chain is -N 3 The preparation method of the fluorene conjugated polymer comprises the steps:

[0065] (1) 1mmol of 2,7-dibromofluorene is added to 50mL of mass fraction in 50% NaOH aqueous solution, then 1mmol of phase transfer catalyst tetrabutylammonium bromide, 10mmol of 1,6-dibromohexane is added, After reacting at 75°C for 4h, cool to room temperature, pass CH 2 Cl 2 Extraction, and then washed with 0.5mL dilute hydrochloric acid aqueous solution and water, anhydrous MgSO 4 Drying, followed by silica gel column purification, eluent is n-hexane / dichloromethane (volume ratio 10:1), to obtain white solid 9,9'-bis(bromohexyl)-2,7-dibromofluorene, this step The yield was 52%.

[0066] (2) 5 mmol of compound 9,9'-di(bromohexyl)-2,7-dibromofluorene, 15 mmol of NaN 3 Dissolve in 35 mL of DMSO, react for 4 h under nitrogen protection, 75 °C, cool to room temperature, add 150 mL of wat...

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Abstract

The invention discloses a fluorene type conjugated polymer membrane based on a cyclodextrin side chain, as well as a preparation method and application of the fluorene type conjugated polymer membrane. According to the invention, a cyclodextrin molecule is modified on a side chain of a fluorene type conjugated polymer, and the characteristic that a cyclodextrin cavity is used for cladding micromolecules of a fluorescent dye is adopted, so that fluorescence micromolecules are fixed to positions near a main chain of the fluorene type conjugated polymer, fluorescence resonance energy transfer is generated between the fluorene type conjugated polymer and the micromolecules of the fluorescent dye, the Stokes displacement of the fluorene type conjugated polymer membrane is enlarged, and the transmitted wave length of the membrane is prolonged. According to the fluorene type conjugated polymer membrane as well as the preparation and application thereof disclosed by the invention, the transmitted wave length of the membrane is adjusted and controlled, a conventional complex method for enlarging the transmitted stoke displacement of the membrane by using a donor and a receptor in the main chain is simplified, and a new thinking and a new method are provided for adjusting and controlling conjugated polymer transmitted light.

Description

technical field [0001] The invention relates to the technical field of aromatic hydrocarbon explosives, in particular to a cyclodextrin side chain-based fluorene conjugated polymer film and its preparation method and application. Background technique [0002] The detection of aromatic hydrocarbon explosives is an important direction of fluorescent sensing detection. In fluorescent sensing detection, fluorescent conjugated polymers are widely used due to their characteristics of "one-point contact, multi-point response". As an important class of fluorescent conjugated polymers, fluorene conjugated polymers have good application prospects in the field of explosive detection. [0003] In order to increase the Stokes shift of the fluorene conjugated polymer film, reduce the interference of the excitation light on the detection signal, and improve the detection sensitivity of the target analyte, relevant researchers have developed a series of methods to regulate the fluorene conj...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08L87/00C08G81/00C08J5/18C08J7/00G01N21/64
CPCC08G81/00C08J5/18C08J7/00C08J2387/00C08L87/005C08L2203/16G01N21/64
Inventor 赵川德范桂娟王晓川刘小乐于谦
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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