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Triarylamine compound containing pyridazo quinazolone and preparation method and application thereof

A technology of pyridoquinazolinones and compounds, which is applied in the field of triarylamine compounds, can solve problems such as few reports, and achieve good photoelectric conversion efficiency

Active Publication Date: 2019-03-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, pyridoquinazolones are also a typical class of nitrogen-containing rigid aromatic heterocyclic compounds, which have good hole transport ability and unique photoelectric properties, but their application in dyes has rarely been reported.

Method used

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  • Triarylamine compound containing pyridazo quinazolone and preparation method and application thereof
  • Triarylamine compound containing pyridazo quinazolone and preparation method and application thereof
  • Triarylamine compound containing pyridazo quinazolone and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of the compound represented by the formula (WL4) in Example 1:

[0022] 1) Synthesis of compound represented by formula (II-1)

[0023] Under nitrogen protection, add 2-bromopyridoquinazolinone (0.275g, 1mmol), biboronic acid pinacol ester (0.253g, 1mmol), 1,1'-bis(diphenylphosphine) to the there-necked flask Ferrocene palladium chloride (the molecular formula is PdCl 2 (dppf), 0.022g, 0.03mmol), potassium acetate (0.294g, 3mmol) and 1,4-dioxane (15mL), heated and refluxed for stirring for 10h, after the reaction was completed, 100mL of water was added to the reaction solution, Then 30 mL of dichloromethane was added for extraction, left to stand for stratification, and the organic layer and the aqueous layer were obtained by liquid separation. The organic layer was washed with saturated brine and anhydrous Na 2 SO 4 Dry, then concentrate and evaporate the solvent to obtain the crude product I, which is directly used for the next reaction.

[0024] Under n...

Embodiment 2

[0032] The synthesis of compound shown in embodiment 2 formula (WL5):

[0033] 1) Synthesis of compound represented by formula (II-2)

[0034]Under nitrogen protection, compound of formula (IV) (0.434g, 1 mmol), potassium carbonate (0.276g, 2 mmol), tetrakistriphenylphosphine palladium (0.11 g, 0.1 mmol) and compound of formula (I) (0.32 g, 1 mmol) was dissolved in 50 mL of solvent (the solvent was V toluene: V methanol: V water=6:1:2), heated and refluxed for stirring for 10 h, after the reaction was completed, the reaction solution was cooled to room temperature, filtered, and the filtrate was evaporated The solvent, the residue after the solvent was evaporated was dissolved in dichloromethane, washed with saturated sodium chloride solution, anhydrous Na 2 SO 4 Drying, then concentrating and distilling off dichloromethane, the concentrate was separated by column chromatography to obtain 0.32 g of the compound represented by formula (II-2) as an orange powder (yield 58%), w...

Embodiment 3

[0041] The synthesis of compound shown in embodiment 3 formula (WL6):

[0042] 1) Synthesis of compound represented by formula (II-3)

[0043] Under nitrogen protection, add 2-bromopyridoquinazolinone (0.275g, 1mmol), biboronic acid pinacol ester (0.253g, 1mmol), PdCl to the there-necked flask 2 (dppf) (0.022g, 0.03mmol), potassium acetate (0.294g, 3mmol) and 1,4-dioxane (15mL), heated and refluxed for stirring for 10h, after the reaction was completed, 100mL of water and 30mL of dichloromethane, extracted, left to stand for stratification, separated to obtain an organic layer and an aqueous layer, the organic layer was washed with saturated brine in turn, anhydrous Na 2 SO 4 Dry, then concentrate and evaporate the solvent to obtain the crude product I, which is directly used for the next reaction.

[0044] Under nitrogen protection, crude product I (0.148 g, 0.4 mmol), compound represented by formula (V) (0.322 g, 1 mmol), Pd (PPh) 3 ) 4 (0.15g, 0.13mmol) and K 2 CO 3 ...

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Abstract

The invention discloses a triarylamine compound containing pyridazo quinazolone and a preparation method and application thereof. The molecular structure of the triarylamine compound containing the pyridazo quinazolone is as shown in a formula (WL4), a formula (WL5), a formula (WL6) or a formula (WL7) (as shown in the specification). The triarylamine compound containing the pyridazo quinazolone isused as a donor, a double bond or thiophene is used as a bridge, and a cyanoacetic acid is used as an acceptor to synthesize the triarylamine compound containing the pyridazo quinazolone. The triarylamine compound containing the pyridazo quinazolone can be used as a dye sensitizer, and the dye-sensitized solar cells assembled by the compound as a dye sensitizer have good photoelectric conversionefficiency, so that a new applicable substance is added for the screening of dye sensitizers.

Description

technical field [0001] The present invention relates to a pyridoquinazolinone-containing triarylamine compound and a preparation method and application thereof. Background technique [0002] Dye-sensitized solar cells (DSSCs) are considered to be a better alternative to traditional expensive and low-efficiency monocrystalline silicon solar cells due to their ease of fabrication, high efficiency, and low cost. [0003] Among the components of dye-sensitized solar cells, dye sensitizers with excellent light absorption properties and electron transport properties are the most important factors to ensure the photoelectric conversion efficiency of DSSCs. The research on dye sensitizers at home and abroad is mainly divided into two categories, one is organometallic complexes with a typical structure of functional polypyridine ruthenium compounds, and the second is non-metallic organic dyes. Among them, non-metal organic dyes have the advantages of high extinction coefficient, sim...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C09B23/14C09B23/04H01G9/20
CPCC07D471/04C07D519/00C09B23/04C09B23/14H01G9/2059Y02E10/542
Inventor 韩亮陈元熹吴靓蒋绍亮叶青李郁锦崔艳红
Owner ZHEJIANG UNIV OF TECH
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