Acridone derivatives and synthesis method thereof

A derivative, acridone technology, applied in the field of organic chemical synthesis, can solve the problem of large fluorescence influence, and achieve the effect of good fluorescence intensity

Active Publication Date: 2014-04-02
ZHENGZHOU SIGMA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As we all know, the conjugated system in the molecule has a great influence on the fluorescence. Increasing the length of the π-electron conjugated system in the molecule can improve the fluorescence efficiency. As the number of rings increases, the fluorescence intensity tends to be stronger. Therefore, acridone derivatives with multi-conjugated systems must have stronger fluorescence properties than existing acridone derivatives, which can be used for further research on new acridone derivatives. Fluorescence-like materials provide useful reference, but there is no related report

Method used

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  • Acridone derivatives and synthesis method thereof
  • Acridone derivatives and synthesis method thereof
  • Acridone derivatives and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0037] Synthetic compound (1)

[0038] ① Add 160g dimethyl sulfoxide into a reaction flask with a thermometer and a reflux tube, and add (b) 156g (1mol), 70g potassium carbonate, CuFe while stirring. 2 O 4 Magnetic powder 6g and (a) 94g (1mol), react at 100~105℃, TLC tracking shows that the raw material has reacted completely, add cooling water to cool the system to 60~80℃, add 2g activated carbon and 2g sodium sulfide nonahydrate, continue stirring until After the system is uniform, filter, then add concentrated hydrochloric acid to adjust the pH of the filtrate between 1 and 2, filter the precipitate, wash with water, and dry to obtain 190g of white solid powder intermediate (c);

[0039] ② Add 1000g of toluene, 100g (0.47mol) of intermediate (c) and 80g of p-toluenesulfonic acid into the reaction flask, and react at 100~110℃. TLC tracking shows that the reaction of the raw materials is completed and the temperature is reduced to 20~25℃ to precipitate the result. 80g of yellow-gr...

Embodiment 2

[0042] The compound (2) was synthesized using the same method, with a purity of 99.3% and a yield of 76%, MS: [M+1]: 605; 1 HNMR (DMSO- d 6 )Δ: 7.80 (d, 1H), 7.62 (s, 1H), 7.22 (m, 2H), 7.46 (d, 4H), 7.21 (m, 10H), 6.80 (m, 1H), 6.62 (m, 2H) ),6.53 (d,4H),6.20 (d,4H), 2.30(s,3H); Anal. Calcd for C 44 H 32 N 2 O: C 87.39, H 5.33, N 4.63; found C 87.40, H 5.33, N 4.60.

Embodiment 3

[0044] Compound (3) was synthesized using the same method, with a purity of 99.5% and a yield of 72%, MS: [M+1]: 605; 1 HNMR (DMSO- d 6 )Δ: 7.81 (d,1H), 7.66 (s,1H), 7.45 (d,4H), 7.32 (m,1H), 7.21 (m,10H), 6.70 (m,3H), 6.55 (d,4H) ), 6.30(s,1H), 6.21 (d,4H), 2.35(s,3H); Anal. Calcd for C 44 H 32 N 2 O: C 87.39, H 5.33, N 4.63; found C 87.39, H 5.34, N 4.63.

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Abstract

The invention discloses novel compounds containing an acridone structure, and particularly relates to acridone derivatives and a synthesis method thereof, belonging to the technical field of organic chemical synthesis. The structure of the acridone derivatives is shown in the specification, wherein R1 and R2 are independently selected from H, methoxy, C1-10 alkyl and C1-10 haloalkyl. The compounds have higher fluorescence and can be used for organic luminescent materials.

Description

technical field [0001] The invention relates to a class of compounds containing an acridone structure, in particular to acridone derivatives, and belongs to the technical field of organic chemical synthesis. Background technique [0002] Luminescent materials run through the long history of human civilization, and are widely used in high-tech fields such as communications, satellites, optical computers, biomolecular probes, etc., especially in today's information age, the development of luminescent materials that meet various information display needs Especially fast. Among them, organic light-emitting materials have attracted more and more interest in recent years because of their higher luminous efficiency, wider range of luminous color choices, and the advantages of easy large-area film formation. Whether an organic compound can emit light, as well as its wavelength and efficiency mainly depend on its chemical structure. Fluorescence usually occurs in molecules with rig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/14C09K11/06
CPCC07D219/14C09K11/06C09K2211/1029
Inventor 王建莉杨勇石田丽徐亚娟
Owner ZHENGZHOU SIGMA CHEM
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