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Naphthalene-based highly condensed ring-aza[6]helicene compounds and methods for their synthesis

A synthesis method and compound technology, applied in the field of highly condensed ring aza[6]helicene compounds and their synthesis, achieving the effects of simple reaction operation, reduced cost, and easy popularization and application

Inactive Publication Date: 2016-01-06
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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  • Naphthalene-based highly condensed ring-aza[6]helicene compounds and methods for their synthesis
  • Naphthalene-based highly condensed ring-aza[6]helicene compounds and methods for their synthesis
  • Naphthalene-based highly condensed ring-aza[6]helicene compounds and methods for their synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: Preparation of 7-hexyl-7-aza[6]helicene (Ia)

[0069] Specific steps are as follows:

[0070] (1) Purify the organic solvent benzene by atmospheric distillation, and store it under an inert atmosphere until use;

[0071] (2) trans-9-hexyl-3-(2-naphthylvinyl)carbazole (Ⅱa, 0.45mmol) and iodine (I 2 , 0.46mmol) into the purified 500ml organic solvent benzene in step (1), stir rapidly while dissolving, after completely dissolving, pass inert gas for 30 minutes;

[0072] (3) Under continuous stirring, add 18ml of propylene oxide into the solution obtained in step (2), so that the concentration of propylene oxide in the solution is 0.51 mol / liter;

[0073] (4) Use a 500W high-pressure mercury lamp to irradiate the solution obtained in step (3) through quartz glass for 10 minutes until the reaction is completed to obtain a crude product;

[0074] (5) The solvent is evaporated in vacuo, and the obtained crude product is dissolved in chloroform, and the mass fra...

Embodiment 2

[0082] Embodiment 2: Preparation of 10-bromo-7-hexyl-7-aza[6]helicene I (b)

[0083] The chemical reaction formula is as follows:

[0084]

Embodiment 3

[0085] Example 3: Preparation of 10-bis(trimethylphenyl)boryl-7-hexyl-7-aza[6]helicene I (c)

[0086] The chemical reaction formula is as follows:

[0087]

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Abstract

The invention provides a naphthalene-based high condensed ring-aza [6] helicene compound (I) and a synthesis method thereof, and belongs to the technical field of chemical engineering. The naphthalene-based high condensed ring-aza [6] helicene compound with a photoelectricity function is successfully prepared from naphthalene and a carbazole derivative serving as raw materials by adopting a photocatalysis ring-closing method. The naphthalene-based high condensed ring-aza [6] helicene compound has the advantages of high yield, short time, simple operation and the like. A common low-cost reagent is used, so that the preparation cost is reduced, and the naphthalene-based high condensed ring-aza [6] helicene compound is easy to popularize and apply. The naphthalene-based high condensed ring-aza [6] helicene compound (I) has very good solubility in different organic solvents, so that the purification of the compound and the preparation of a membrane by using the compound are facilitated. Multiple high condensed ring-aza [6] helicene compounds can be obtained by inserting different substituent groups. The naphthalene-based high condensed ring-aza [6] helicene compound (I) is expected to be widely applied in the fields such as organic electroluminescence, organic field-effect transistors, organic second-order nonlinear or chiral liquid crystal, biological medicines and the like.

Description

technical field [0001] The invention relates to a naphthalene-based highly condensed-ring aza[6]helicene compound and a synthesis method thereof, in particular to the preparation of an aza[6]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 organic electroluminescence, organic field effect transistors, organic second-order nonlinearity, chiral liquid crystals, 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 synthes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80C07F5/02C07D401/04
CPCC07D209/80C07D401/04C07F5/027
Inventor 刘陟华万鸣张保杰郭巍陶绪堂崔得良
Owner SHANDONG UNIV
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