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Conjugated micro molecules or conjugated polymer with beta-diketone-containing main chain and preparation method thereof

A technology of conjugated polymers and small molecules, which is applied in the preparation of organic carbonates, organic chemistry, etc., can solve the problems that the coupling reaction cannot be carried out smoothly, and achieve the effects of strong coordination ability, non-toxic effect, and low price

Inactive Publication Date: 2011-02-16
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when using the traditional Sonogashir and Suzuki coupling reaction method to synthesize conjugated small molecules or conjugated polymers containing β-diketones in the main chain, due to the strong coordination ability of β-diketones, enols Interconversion and other characteristics make the coupling reaction not proceed smoothly

Method used

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  • Conjugated micro molecules or conjugated polymer with beta-diketone-containing main chain and preparation method thereof
  • Conjugated micro molecules or conjugated polymer with beta-diketone-containing main chain and preparation method thereof
  • Conjugated micro molecules or conjugated polymer with beta-diketone-containing main chain and preparation method thereof

Examples

Experimental program
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Effect test

example 1

[0045] Add 9,9-di-n-octyl-2-boronate fluorene, and Boc-protected bis(4-bromo)dibenzoylmethane into a two-necked flask equipped with a stirring bar. The above-mentioned flask was dried before use, sealed and evacuated for nitrogen. High-purity nitrogen is treated in a strict water-free and oxygen-free device before use. The catalyst (PPh 3 ) 4 Pd(0) (0.5-2.0 mol%), add toluene and triethylamine with a syringe. Toluene and triethylamine are strictly purified before use to remove some impurities and water. Under the condition of vigorous stirring and avoiding light, the reaction was refluxed. The progress of the reaction was monitored by TLC. After the reaction, the solvent was removed by rotary evaporation and purified by silica gel column chromatography.

example 2

[0047]Add 9,9-di-n-octyl-2-ethynylfluorene and Boc-protected bis(4-bromo)dibenzoylmethane into a two-necked flask equipped with a stirring bar. The above-mentioned flask was dried before use, sealed and evacuated for nitrogen. High-purity nitrogen must be treated in a strict anhydrous and oxygen-free device before use. The catalyst (PPh 3 ) 4 Pd(0) (1.0-3.0 mol%), CuI (3.0-5.0 mol%), tetrahydrofuran and triethylamine were added by syringe. Tetrahydrofuran and triethylamine must be strictly purified before use to remove some impurities and water. The reaction was stirred in the dark and at room temperature. The progress of the reaction was monitored by TLC. After the reaction, the solvent was removed by rotary evaporation and purified by silica gel column chromatography.

[0048] Synthesis of Conjugated Polymers Containing β-Diketones

example 3

[0050] 9,9-di-n-octyl-2,7-diborate fluorene, bis(4-bromo)dibenzoylmethane after Boc protection, 9,9-dioctyl-2,7 -Dibromofluorene is fed into a single-necked flask equipped with a stirring bar in a certain molar ratio. The above-mentioned flask was dried before use, sealed and evacuated for nitrogen. High-purity nitrogen must be treated in a strict anhydrous and oxygen-free device before use. The catalyst (PPh 3 ) 4 Pd(0) (0.5-2.0 mol%), add toluene and triethylamine with a syringe. Toluene and triethylamine must be strictly purified before use to remove some impurities and water. Under the condition of vigorous stirring and avoiding light, the reaction was refluxed for 3 days. After the reaction was complete, it was cooled and the reaction mixture was concentrated, precipitated in methanol, and filtered. Stir vigorously in a mixed solution of hydrazine hydrate:toluene=1:1 for 24h to remove the residual catalyst.

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Abstract

The invention discloses conjugated micro molecules or conjugated polymer with a beta-diketone-containing main chain and a preparation method thereof. The method comprises the following steps of: reacting beta-diketone with halogen with di-tert-butyl dicarbonate in an organic solvent, separating, and performing the Sonogashir and Suzuki coupling reactions of obtained products and an electron-rich monomer or electron-deficient monomer to prepare the conjugated micro molecules or conjugated polymer with the beta-diketone-containing main chain. By utilizing the high coordination capability of the beta-diketone, the conjugated micro molecules are coordinated with different metals to produce different coordination compounds, or the conjugated polymer is blended with different metals to coordinate diketone in the polymer with the metals, so that the photoelectric properties of the conjugated micro molecules or the conjugated polymer can be changed, and the conjugated micro molecules or the conjugated polymer can be applied in the fields such as organic electroluminescence, biosensing, organic electrical storage and the like.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a class of conjugated small molecules or conjugated polymer materials containing β-diketone in the main chain, and relates to the potential application of such materials in the fields of organic electroluminescence, biosensing, and organic electrical storage. Background technique [0002] β-diketone compounds have the characteristics of multiple coordination atoms, tautomerization of ketone form or enol form. Such ligands and metal atoms can form complexes with unique structures through various coordination methods, and their functional complexes show excellent performance in terms of light, electricity, magnetism, molecular carrier and catalytic properties. Therefore, complexes of β-diketones and their derivatives have attracted widespread attention because of their potential applications as new multifunctional materials. However, when using the tradi...

Claims

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Application Information

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IPC IPC(8): C08G61/02C08G61/12C07C69/96C07C68/06C08G61/00
Inventor 凌启淡傅华宋娟
Owner NANJING UNIV OF POSTS & TELECOMM
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