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A kind of fluorophenylquinoline phosphine oxide flame-retardant and luminescent bifunctional material and its preparation method

A technology of substituted phenylquinoline and bifunctional materials, applied in the direction of luminescent materials, chemical instruments and methods, phosphorus organic compounds, etc., can solve the problems of few types, no new flame retardant materials involved, limited research, etc., and achieve good dissolution high performance, synergistic flame retardant, and achieve the effect of ternary synergy

Active Publication Date: 2019-03-01
INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-cyclopropyl-4-(4-fluorophenyl) quinoline-3-carbaldehyde is an important intermediate in the synthesis of drug pitavastatin, and its research in the prior art is mostly limited to synthetic methods, process research, and as Application of pharmaceutical intermediates in the synthesis of pitavastatin
However, the research on this type of compound is very limited and there are few types, and the research on this type of compound as a new type of flame retardant material has not been involved.
In particular, the functional structural unit fluorophenylquinoline and phosphine oxide groups are simply and effectively combined to form a fluorophenylquinoline phosphine oxide compound with dual functions of flame retardancy and light emission. Not yet reported in

Method used

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  • A kind of fluorophenylquinoline phosphine oxide flame-retardant and luminescent bifunctional material and its preparation method
  • A kind of fluorophenylquinoline phosphine oxide flame-retardant and luminescent bifunctional material and its preparation method
  • A kind of fluorophenylquinoline phosphine oxide flame-retardant and luminescent bifunctional material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of Fluorophenylquinoline Phosphine Oxide Flame Retardant Luminescent Bifunctional Material (Compound I)

[0032] Dissolve 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (compound II, 0.10mol) and bis(p-methylphenyl)phosphine oxide (compound III, 0.10mol) in In 100 ml of toluene, stirred and refluxed for 4-6 hours, the solvent was removed by rotary evaporation, and a white solid was precipitated. The crude product was recrystallized with methanol and dried in vacuo to obtain the target product with a yield of 73%. The melting point by DSC was 209.66°C (peak).

[0033] 1 H NMR(300MHz,DMSO-d6 / TMS)δ:0.19(m,1H),0.79(m,1H),0.95(m,1H),1.06(m,1H),2.30(s,3H),2.36( s,3H),2.81(m,1H),5.70-5.76(m,1H),6.72-6.81(m,1H),6.99-7.07(m,2H),7.14-7.40(m,10H),7.59- 7.66 (m, 3H), 7.81 (d, J=8.4Hz, 1H). IR(KBr)ν: 3061, 2921, 2865, 1602, 1569, 1556, 1512, 1490, 1411, 1225, 1159, 1115, 1095, 1075, 1047, 1020, 900, 842, 806, 764, 718, 653, 549cm-1. Its infrare...

Embodiment 2

[0035] Example 2: Preparation of Fluorophenylquinoline Phosphine Oxide Flame Retardant Luminescent Bifunctional Material (Compound I)

[0036] Dissolve 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (compound II, 0.10mol) and bis(p-methylphenyl)phosphine oxide (compound III, 0.12mol) in In 100 ml of dioxane, stirred and refluxed for 4-6 hours, the solvent was removed by rotary evaporation, and a white solid was precipitated. The crude product was recrystallized with methanol-toluene, dried in vacuo, and the target product was obtained with a yield of 71%.

Embodiment 3

[0037] Example 3: Preparation of Fluorophenylquinoline Phosphine Oxide Flame Retardant Luminescent Bifunctional Material (Compound I)

[0038] Dissolve 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (compound II, 0.10mol) and bis(p-methylphenyl)phosphine oxide (compound III, 0.08mol) in In 100 milliliters of toluene-methanol (volume ratio is 3:1), stirred and refluxed for 4-6 hours, the solvent was removed by rotary evaporation, and a white solid was precipitated. The crude product was recrystallized with methanol-tetrahydrofuran and dried in vacuo to obtain the target product. The yield was 67%.

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Abstract

The invention discloses a fluorinated pheoylquinoline and phosphine oxide material with double functions of flame retardancy and light emitting shown in formula I and a preparation method thereof. A novel fluorinated pheoylquinoline and phosphine oxide compound with double functions of flame retardancy and light emitting is formed by combining two functional structure units, such as cyclopropyl fluorinated pheoylquinoline and phosphine oxide groups, so that a new variety of flame retardant agent and ultraviolet light emitting material is increased. The preparation method has the advantages that the technology is simple, the safety and environment-friendly effects are realized, and the preparation method is suitable for industrial production. The prepared luorinated pheoylquinoline and phosphine oxide material with double functions of flame retardancy and light emitting shown has the advantages that the dissolvability is good, the thermal stability and chemical stability are high, the processing property is good, the double functions of flame retardancy and light emitting are realized, the multi-element synergistic action of fluorine, phosphor and nitrogen is realized, the better flame-retardant efficiency is realized, the excellent solid ultraviolet light emitting characteristic is realized, and the application range is wide.

Description

Technical field: [0001] The invention relates to the technical fields of flame-retardant materials and organic light-emitting materials, in particular to a fluorophenylquinoline phosphine oxide flame-retardant and light-emitting dual-functional material and a preparation method thereof. Background technique: [0002] Flame retardants are widely used in electronic appliances, communications, nuclear power, aerospace, transportation, building materials, interior decoration, textiles and other fields, and are one of the important measures for scientific fire prevention and control. With the development of society and the advancement of science and technology, the application fields of flame retardants continue to expand. Countries around the world have increasingly stringent requirements for the flame retardancy of materials and products in various fields, and new requirements have been put forward for the research and development and application technology of flame retardants. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/60C09K11/06C09K21/12C08K5/5397C08L63/00C08L67/00C08L77/00
CPCC07F9/60C08K5/5397C08L63/00C08L67/00C08L77/00C09K11/06C09K21/12C09K2211/1022C09K2211/1029
Inventor 孙一峰汪昭玮柳亚玲刘梦影吉国强叶小机潘文龙牟德海
Owner INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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