Boracic polyacetylene derivative suitable for fluorinion detection and preparation method thereof

A technology of polyacetylene and fluoride ions, applied in the field of anion detection, to achieve the effects of flexible molecular design, increased sensitivity, and improved bonding efficiency

Inactive Publication Date: 2014-03-05
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, fluorescence-enhanced and naked-eye-visible boron-containing conjugated polymer detectors for fluoride ion detection have not been reported.

Method used

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  • Boracic polyacetylene derivative suitable for fluorinion detection and preparation method thereof
  • Boracic polyacetylene derivative suitable for fluorinion detection and preparation method thereof
  • Boracic polyacetylene derivative suitable for fluorinion detection and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Synthesis of poly-4-{bis(2,4,6-trimethylphenyl)boronyl}-4'-ethynylbiphenyl

[0033] Synthesis of 4-bromo-4'-trimethylsilylethynylbiphenyl. Take a 250ml dried three-necked flask with a rotor, add 4,4'-dibromobiphenyl under the protection of Ar gas, and pump it three times. Add 50ml THF, 20ml i-Pr through the three-way valve 2 NH, add TMSA after the solid is dissolved, and tighten the three-way valve. Ar gas protection, 45 ℃, overnight reaction. The mixture was spun dry, ether was added, washed first with 1M HCl, then three times with distilled water. The resulting organic phase was dried over anhydrous magnesium sulfate for one hour, filtered and spin-dried. The primary product was separated by silica gel chromatography with petroleum ether as the eluent. 2.35 g of white crystals were obtained (yield 35.4%). 1 H-NMR (400 Hz, CDCl 3 ), δ (ppm): 7.425-7.566 (m, 8H), 0.269 (s, 9H).

[0034] Synthesis of 4-{bis(2,4,6-trimethylphenyl)boronyl}-4'-trimethylsil...

Embodiment 2

[0037] Example 2 Synthesis of poly-9,9-dimethyl-4-{bis(2,4,6-trimethylyl)boronyl}-7-ethynylfluorene

[0038] Synthesis of 9,9-dimethyl-4-{bis(2,4,6-trimethylphenyl)boronyl}-7-ethynylfluorene. This monomer has the same synthesis process as the monomer in Example 1, except that the starting reactant 4,4'-dibromobiphenyl is replaced with 9,9-dimethyl-4,7-dibromobiphenyl Fluorene. White crystals were obtained. 1 H NMR (400MHz, CDCl3)δ7.71–7.47(m,6H), 6.84(s,4H), 3.13(s,1H), 2.32(s,6H), 2.02(s,12H), 1.43(s, 6H). 13 C NMR (100MHz, CDCl3), δ154.9, 153.6, 145.6, 142.2, 142.1, 141.1, 139.7, 138.7, 136.4, 131.5, 131.0, 128.4, 126.8, 121.5, 120.8, 120.0, 84.6, 77.7, 47.0, 21.4. Elemental Analysis (C 35 H 35 B) Calculated value) / %: C: 90.12, H: 7.56, measured value / %: C: 90.15, H: 7.54. The synthesis of the polymer in this example is the same as the synthesis method of the polymer in Example 1. The molecular weight of the polymer is 7.15×10 6 g / mol, molecular weight distributio...

Embodiment 3

[0039] Example 3 Detection of F- by poly-4-{bis(2,4,6-trimethylphenyl)boronyl}-4'-ethynylbiphenyl solution

[0040] Configuration concentration 2.9×10 -6 mol / L Bu4NF tetrahydrofuran solution, the concentration prepared in Example 1 is 3.2×10 -6 mol / L polymer poly-4-{bis(2,4,6-trimethylphenyl)boronyl}-4'-ethynylbiphenyl solution and the same concentration of 4-{bis(2, 4,6-Trimethylphenyl)boronyl}-4'-ethynylbiphenyl tetrahydrofuran solution. will Bu 4 NF tetrahydrofuran solution was added dropwise to the solution of monomer and polymer, and the fluorescence change of monomer and polymer after adding fluoride ion was measured by UV-fluorescence photometer. exist figure 1 In the fluorescence spectrum shown, it can be observed that obvious fluorescence quenching phenomenon occurs after the monomer is added dropwise with fluoride ions, while the maximum emission wavelength is blue-shifted after the dropwise addition of fluoride ions to the polymer, but the fluorescence intensity...

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Abstract

The invention relates to a boracic polyacetylene derivative suitable for fluorinion detection and a preparation method thereof, belonging to the technical field of anion detection. The boracic polyacetylene derivative is characterized thatcarbene is taken as the main chain, and the side chain has three-coordination boracic substituent groups for fluorinion detection. The preparation method comprises steps of firstly, synthesizing an alkyne monomer containing the three-coordination boracic substituent group; then, polymerizing in the presence of a catalyst, so as to obtain the designed boracic polyacetylene derivative having the function of detecting fluorinion through fluorescence. According to a polymer sensor, due to the introduction of different Ar groups with electronic transmission function, the molecular designing is more flexible, and the polymer as the detector can improve the detection sensitivity and enhances the stability and processibility of a probe.

Description

technical field [0001] The invention belongs to the technical field of anion detection, and relates to a boron-containing polyacetylene derivative with a fluorescence detection function for fluoride ions and a preparation method thereof. Background technique [0002] Fluoride ion has many unique biological and chemical properties. It is one of the essential trace elements for the human body and an indispensable element for the formation of bones and teeth. However, excessive intake of fluoride will cause fluorosis, which will cause great harm to the human body, resulting in diseases such as dental fluorosis, fluorosis and bone cancer, and will also cause low immunity and affect the growth and development of organisms. With the development of industry, fluorine pollution is becoming more and more serious, so the detection of fluoride ion has become a hot field. For example, Chinese patents CN102241698A, CN101007821A, CN1730485A, CN102466635A, etc. have all reported a series ...

Claims

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Application Information

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IPC IPC(8): C08F238/00G01N21/64
Inventor 胡雁鸣赵忠夫白雪张春庆李战胜
Owner DALIAN UNIV OF TECH
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