Fe<3+> detection hyperbranched conjugated polymer and preparation method and application thereof

A technology of hyperbranched conjugation and polymers, applied in chemical instruments and methods, measuring devices, fluorescence/phosphorescence, etc., can solve problems such as high production costs, hindering industrial applications, cumbersome synthesis processes, etc., and achieve low detection limits , high selectivity, environment-friendly effect

Inactive Publication Date: 2016-07-20
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At first, due to the highly symmetrical and perfect structure of dendrimers, it first attracted people's attention, but because of its flawless and perfect structure, it often requires multi-step reactions and purifications in the synthesis process, tedious synthesis process and High production cost hampers its industrial application

Method used

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  • Fe&lt;3+&gt; detection hyperbranched conjugated polymer and preparation method and application thereof
  • Fe&lt;3+&gt; detection hyperbranched conjugated polymer and preparation method and application thereof
  • Fe&lt;3+&gt; detection hyperbranched conjugated polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] 0.3g (9.08×10 -4 mol) (2E,2'E) diethyl 4,4'-(5-formyl-1,3-phenylene)-bis(but-2-enoic acid ethyl ester) shown in formula I-1 and 62.16mg (4.09×10 -4 mol) 1,8-diazabicycloundec-7-ene (DBU) was dissolved in 10mL of absolute ethanol, and refluxed for 96 hours. After removing ethanol under reduced pressure, the crude product was dissolved with dichloromethane, and then Washing with aqueous hydrochloric acid and deionized water with a pH value of 2, drying with anhydrous magnesium sulfate and removing dichloromethane under reduced pressure, a hyperbranched conjugated polymer (referred to as M1) was obtained with a yield of 75%. The structural characterization results are as follows:

[0026] 1 HNMR (600MHz, CDCl 3 )δ: 10.01 (-CHO), 8.45-6.32 (=CH), 4.32 (-CH 2 ), 1.24 (-CH 3 ); FT-IR (KBr): CH=: 2914; C=C: 3030, 1635; C=O: 1740.

[0027] As tested by gel permeation chromatography, the polymer has Mn=90676, Mw=105664, and Mw / Mn=1.165.

Embodiment 2

[0029]

[0030] 0.3g (9.92×10 -4 mol) (2E,2'E) dimethyl 4,4'-(5-formyl-1,3-phenylene)-bis(but-2-enoic acid ethyl ester) shown in formula I-2 and 67.93mg (4.09×10 -4 mol) DBU was dissolved in 10 mL of absolute ethanol, and refluxed for 96 hours. After the ethanol was removed under reduced pressure, the crude product was dissolved with dichloromethane, then washed with hydrochloric acid aqueous solution and deionized water with a pH value of 2, and then washed with anhydrous After drying over magnesium sulfate and removing methylene chloride under reduced pressure, a hyperbranched conjugated polymer (referred to as M2) was obtained, and its productive rate was 72%, and the structural characterization results were as follows:

[0031] 1 HNMR (600MHz, CDCl 3 ) δ: 8.38-6.43 (=CH), 4.09 (-CH 3 ), 1.26 (-CH 3 ); FT-IR (KBr): CH=: 2908; C=C: 3004, 1651; C=O: 1745.

[0032] As tested by gel permeation chromatography, the polymer has Mn=57283, Mw=66311, and Mw / Mn=1.158.

Embodiment 3

[0034]

[0035] 0.3g (9.08×10 -4 mol) (2E,2'E) diethyl 4,4'-(5-formyl-1,3-phenylene)-bis(but-2-enoic acid ethyl ester) shown in formula I-1 and 62.16mg (4.09×10 -4 mol) DBU was dissolved in 10 mL of absolute ethanol, and refluxed for 96 hours. After the ethanol was removed under reduced pressure, the crude product was dissolved with dichloromethane, then washed with hydrochloric acid aqueous solution and deionized water with a pH value of 2, and then washed with anhydrous After drying over magnesium sulfate and removing dichloromethane under reduced pressure, the resulting product was dissolved in 8 mL of methanol, and then 8 mL of 2 mol / L NaOH aqueous solution was added, hydrolyzed for 12 hours under reflux conditions, cooled to room temperature, and methanol was removed by rotary evaporation to obtain Conjugated polymers (referred to as M3).

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Abstract

The invention discloses a Fe<3+> detection hyperbranched conjugated polymer and a preparation method and application thereof. A structural unit of the polymer is as shown in the specification, wherein R refers to one of carbomethoxy, carbethoxy, tert-butoxycarbonyl, cyano, nitro and -COONa arbitrarily. By MBH-type reaction synthesis, mild reaction conditions, environment friendliness and freeness of metal catalyst residues are realized; since Fe<3+> ions have an evident quenching effect on fluorescence of a tetrahydrofuran solution or an aqueous solution of the synthesized hyperbranched conjugated polymer, the hyperbranched conjugated polymer can be used for detection of Fe<3+> ions in an aqueous phase or an organic phase and is high in Fe<3+> ion selectivity and low in Fe<3+> ion detection limit.

Description

technical field [0001] The invention belongs to the technical field of high molecular polymers, in particular to a class of novel hyperbranched conjugated polymers containing carbon-carbon double bonds, a preparation method of the polymers and a method for detecting Fe 3+ in the application. Background technique [0002] Due to its highly branched structure, dendritic macromolecules exhibit a series of unique physical and chemical properties such as low viscosity, high rheology, good solubility, and a large number of modifiable terminal functional groups that linear polymers do not have. It has gradually become one of the hot spots in the field of polymer materials research. Due to the special properties of dendritic branched macromolecules, dendritic conjugated polymers have been widely used in the fields of organic electroluminescence, sensors, detectors, biological identification and catalysts. According to their structural characteristics, dendrimers can be divided int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C09K11/06G01N21/64
CPCC08G61/02C08G2261/12C08G2261/132C08G2261/142C08G2261/18C08G2261/312C08G2261/522C09K11/06G01N21/643G01N2021/6417
Inventor 蔡雪刁骆楚欣刘亚婷张婷李玲
Owner SHAANXI NORMAL UNIV
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