3,7-disubstituted phenoxazine derivatives and preparation method thereof

A phenoxazine and disubstituted technology, which is applied in the field of 3,7-disubstituted phenoxazine derivatives and their preparation, can solve the problems of structural rigidity, limited application space, and inability to connect with other units to achieve nitration The effect of mild reaction conditions, simple synthesis method and safe operation

Inactive Publication Date: 2019-11-12
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, since the six-membered heterocyclic ring in the middle of the molecular structure of phenoxazine and the benzene rings on both sides form a special conjugated large Π bond system, the molecular structure of phenoxazine is stable, and it is often caused by structural rigidity during use. It cannot be connected with other units in use, thus limiting its application space

Method used

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  • 3,7-disubstituted phenoxazine derivatives and preparation method thereof
  • 3,7-disubstituted phenoxazine derivatives and preparation method thereof
  • 3,7-disubstituted phenoxazine derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The preparation method of 3,7-dinitro-N-(4-nitrophenyl) phenoxazine comprises the steps:

[0050] (1) Preparation of N-(4-nitrophenyl) phenoxazine:

[0051] Weigh 16.4mmol of phenoxazine, 17.2mmol of 4-fluoronitrobenzene and 17.2mmol of cesium fluoride, dissolve them in 30mL of dry dimethyl sulfoxide, and heat and stir the mixture at 120°C for 18h in a nitrogen atmosphere , then cooled to room temperature, poured into a mixed solution of ethanol and deionized water, filtered, and washed with water to obtain N-(4-nitrophenyl)phenoxazine, a red solid, with a yield of 92%; 1 H-NMR (400MHz, DMSO, ppm): 8.499-8.477 (d, 2H), 7.773-7.750 (d, 2H), 6.844-6.706 (m, 6H), 6.054-6.031 (d, 2H);

[0052] The preparation process is as follows:

[0053]

[0054] The preparation method of 3,7-dinitro-N-(4-nitrophenyl) phenoxazine, the steps are as follows:

[0055] Weigh 6mmolCu(NO 3 ) 2 ·3H 2 O, measure 10 mL of acetic acid and 10 mL of acetic anhydride, stir and mix at room te...

Embodiment 2

[0059] The preparation method of 3,7-diamino-N-(4-aminophenyl) phenoxazine comprises the steps:

[0060] Weigh 2.54 mmol of 3,7-dinitro-N-(4-nitrophenyl) phenoxazine prepared in Example 2, 9.58 mmol of tin particles and 20 mL of concentrated hydrochloric acid with a mass concentration of 38% and put them into the reaction In the bottle, first reflux at 85°C for 12h in a nitrogen atmosphere, then reflux at 95°C for 12h, then cool to room temperature, add sodium hydroxide solution to adjust the pH to 7, stand still, filter and wash with water to obtain the crude product, and dissolve the crude product In tetrahydrofuran, petroleum ether was added thereto until a large amount of solids were precipitated to obtain 3,7-diamino-N-(4-aminophenyl)phenoxazine as an orange-red powder with a yield of 38.18%, in which 3, The yield of 7-dinitro-N-(4-nitrophenyl)phenoxazine to 3,7-diamino-N-(4-aminophenyl)phenoxazine can reach 83%; 1 H-NMR (400MHz, DMSO, ppm): 6.889-6.869 (d, 2H), 6.708-6....

Embodiment 3

[0064] The preparation method of 3,7-diacetyl-N-(4-formic acid methyl ester phenyl) phenoxazine comprises the steps:

[0065] (1) the preparation of N-(4-formic acid methyl phenyl) phenoxazine:

[0066] Take 5mmol of phenoxazine, 10mmol of methyl 4-iodobenzoate and 6mmol of potassium carbonate, dissolve them in 30mL of dry N,N-dimethylformamide, and stir the mixture in an oil bath at 220°C in a nitrogen atmosphere 6h, then cooled to room temperature, poured into dichloromethane, dissolved organic matter with dichloromethane, then filtered to remove inorganic matter, column chromatography (wherein the volume ratio of ethyl acetate to n-hexane was 1:10), to obtain N -(4-methyl formate phenyl)phenoxazine, light yellow crystalline solid, yield 94%; 1 H-NMR (400MHz, DMSO, ppm): 8.282-8.250 (d, 2H), 7.462-7.430 (d, 2H), 6.706-6.702 (d, 6H), 6.654-6.650 (d, 2H), 6.599-6.594 (d, 2H), 3.974(s, 3H), 5.934-5.911(2d, 2H);

[0067] The preparation process is as follows:

[0068]

[...

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Abstract

The invention relates to the technical field of phenoxazine derivatives, and particularly relates to 3,7-disubstituted phenoxazine derivatives and a preparation method thereof. Phenoxazine adopted asa raw material is subjected to a coupling reaction to synthesize N-(4-aminophenyl) phenoxazine; the N-(4-aminophenyl) phenoxazine is subjected to a nitration reaction to synthesize 3,7-dinitro-N-(4-nitrophenyl) phenoxazine; the 3,7-dinitro-N-(4-nitrophenyl) phenoxazine is subjected to reduction to synthesize 3,7-diamino-N-(4-aminophenyl) phenoxazine. The obtained 3,7-dinitro-N-(4-nitrophenyl) phenoxazine and the 3,7-diamino-N-(4-aminophenyl) phenoxazine can be structurally modified easily, and novel compounds having different functions can be easily synthesized from the same. The synthesized phenoxazine derivatives can be widely applied in materials, dye, photosensitized solar cells, and other fields.

Description

technical field [0001] The invention relates to the technical field of phenoxazine derivatives, in particular to a class of 3,7-disubstituted phenoxazine derivatives and a preparation method thereof. Background technique [0002] As early as more than 100 years ago, scientists began to study phenoxazine. Because phenoxazine molecules contain nitrogen atoms and oxygen atoms, both nitrogen atoms and oxygen atoms are electron-rich atoms, making phenoxazine a strong electron-donating unit. At the same time, the six-membered heterocyclic ring in the middle and the benzene rings on both sides form a special conjugated large Π bond system, which makes the molecule have high delocalization, rigidity, flexibility and stability. Based on the structural characteristics of phenoxazine, the molar extinction coefficient of phenoxazine is high, the absorption wavelength is in the near-infrared region, it has good water solubility and low biological toxicity, so it has been a hot spot in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/38C09B19/00
CPCC07D265/38C09B19/00
Inventor 邹如意肖莉春杨月赵玉芬
Owner ZHENGZHOU UNIV
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