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Carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound and synthetic method thereof

A synthesis method and a diazepine technology are applied in the field of highly condensed ring diaza[7]helicene compounds and their synthesis, and the effects of simple reaction operation, easy popularization and application, and cost reduction are achieved.

Inactive Publication Date: 2012-07-25
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No such helicene compounds have been reported in the existing materials

Method used

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  • Carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound and synthetic method thereof
  • Carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound and synthetic method thereof
  • Carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of 2,12-dihexyl-2,12-diaza[7]helicene (Ia)

[0062] The chemical reaction formula is as follows:

[0063]

[0064] Specific steps are as follows:

[0065] (1) the organic solvent benzene is purified by atmospheric distillation, and stored under an inert atmosphere for later use;

[0066] (2) trans-1,2-bis(9-hexyl-3-carbazole)ethylene (IIa, 0.45mmol) and iodine (I 2 , 0.46mmol) join in the 500ml organic solvent benzene that step (1) purifies, stir rapidly while dissolving, after dissolving completely, logical inert gas 30 minutes;

[0067] (3) under the continuous stirring situation, 18ml propylene oxide is added in the solution of step (2) gained, make the concentration of propylene oxide in the solution be 0.51 mol / liter;

[0068] (4) irradiating the solution obtained in step (3) through quartz glass with a high-pressure mercury lamp of 500W for 10 minutes to the end of the reaction to obtain a crude product;

[0069] (5) The solven...

Embodiment 2

[0081] Embodiment 2: 2,12-dihexyl-5,15-dibromo-2,12-diaza[7]helicene (Ib) preparation reaction formula:

[0082]

[0083] The specific steps are the same as in Example 1, except that the main raw material for the reaction is trans-1,2-bis(9-hexyl-6-bromo-3-carbazole)ethylene (IIb).

[0084] The yield of the obtained compound was 80.1%.

Embodiment 3

[0085] Example 3: Preparation of 2,12-dihexyl-5,15-diphenyl-2,12-diaza[7]helicene (Ic):

[0086]

[0087] The specific steps are the same as in Example 1, except that the main raw material for the reaction is trans-1,2-di(9-hexyl-6-phenyl-3-carbazole)ethylene (IIc).

[0088] The yield of the obtained compound was 79.6%.

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Abstract

The invention provides a carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound (I) and a synthetic method thereof, belonging to the technical field of chemical industry. A high-condensed ring dinitrogen-aza[7]helicene compound with high solubility is prepared successfully by taking a cheap carbazole derivative with a plurality of active spots as a raw material by a photocatalysis loop closing method. The method has the advantages of high yield, short time, easiness for operating and the like; and moreover, the use of an expensive reagent is avoided, so that the preparation cost is reduced, and popularization and application are easy. The carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound (I) is recrystallized in different solvents, so that an inclusion compound crystal comprising different solvents is obtained. The high-condensed ring dinitrogen-aza[7]helicene compound can be widely applied in the fields of super molecular chemistry, asymmetric catalysis, chiral liquid crystals, organic two-order nonlinearity, organic electroluminescence, biological medicine and the like.

Description

technical field [0001] The invention relates to a carbazole-based highly condensed ring diaza[7]helicene compound and a synthesis method thereof, in particular to the preparation of a diaza[7]helicene compound by using a photocatalytic ring-closing reaction method, and belongs to the technical field of chemical industry. Background technique [0002] Helicene is a class of polycyclic aromatic compounds with a helical structure formed by the ortho-condensation of multiple aromatic rings. There are twisted faces in such molecules, which are typical chiral helical molecules. Helicene and its derivatives are widely used in the fields of asymmetric catalysis, chiral liquid crystals, organic second-order nonlinearity, organic electroluminescence, and biomedicine because of their unique structures and special physical and chemical properties. [0003] The photocatalytic ring closure reaction is a very important reaction for the synthesis of helicene derivatives. The precursor synt...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 刘陟石龙强陶绪堂崔得良郭巍
Owner SHANDONG UNIV
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