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Carbazolophenanthridine compounds with diaza aromatic fused ring structure and synthesis method thereof

A carbazolophenanthridine and synthesis method technology, which is applied in the field of azaaromatic fused ring compounds and their synthesis, can solve the problems of enhanced interaction force and poor solubility, and achieve improved solubility, simple reaction operation, and easy Promoted app performance

Inactive Publication Date: 2016-03-23
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the increase of the conjugated system, the interaction force between aromatic fused ring molecules with rigid planar structure is enhanced, resulting in poor solubility.

Method used

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  • Carbazolophenanthridine compounds with diaza aromatic fused ring structure and synthesis method thereof
  • Carbazolophenanthridine compounds with diaza aromatic fused ring structure and synthesis method thereof
  • Carbazolophenanthridine compounds with diaza aromatic fused ring structure and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1: Preparation of 14-hexyl-carbazolophenanthridine (Ia)

[0065]

[0066] Specific steps are as follows:

[0067] (1) Purify the organic solvent benzene by atmospheric distillation, and store it under an inert atmosphere until use;

[0068] (2) Combine trans-9-hexyl-3-(2-quinoline-vinyl)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;

[0069] (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;

[0070] (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;

[0071] (5) The solvent is evaporated in vacuo, and the obtained crude product is dissolved in ...

Embodiment 2

[0077] Embodiment 2: Preparation of 11-bromo-14-hexyl-carbazolophenanthridine I (b)

[0078] The chemical reaction formula is as follows:

[0079]

Embodiment 3

[0080] Example 3: Preparation of 11-bis(trimethylphenyl)boryl-14-hexyl-carbazolophenanthridine I (c)

[0081] The chemical reaction formula is as follows:

[0082]

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Abstract

The invention provides carbazophenanthridine compounds (1) with a diazo-aromatic condensed ring structure and a synthetic method thereof. The diazo-aromatic condensed ring compounds can be prepared successfully from carbazole and quinoline derivatives as the raw materials by a photocatalytic closed-loop method. The synthetic method of the carbazophenanthridine compounds with the diazo-aromatic condensed ring structure is simple, and a common and cheap reagent is utilized so that the cost of the preparation can be reduced and the preparation method can be popularized and applied easily. The compounds (I) have good solubility in different organic solvents so that the compounds can be purified and formed into films conveniently; a plurality of diazo-aromatic condensed ring compounds can be obtained by introducing different substituent groups. The compounds (I) are expected to be widely applied in the fields of organic field effect tubes, organic light-emitting diodes, photovoltaic cells, organic nonlinear optics, fluorescence probes and laser dyes.

Description

technical field [0001] The invention relates to a class of azaaromatic condensed ring compounds based on carbazole and quinoline and a synthesis method thereof, in particular to the preparation of 14-hexyl-carbazolophenanthridine compounds by using a photocatalytic ring-closing reaction method, and belongs to the technical field of chemical industry. Background technique [0002] Aromatic fused ring compounds are formed by the fusion of multiple aromatic rings; these compounds have a large conjugated system, planarity and rigid structure. Aromatic fused ring compounds are widely used in fields such as organic field effect transistors, organic light-emitting diodes, photovoltaic cells, organic nonlinear optics, fluorescent probes, and laser dyes because of their special structures and physical and chemical properties. For example, CN103108875A provides a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic de...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07F5/02C09K11/06
CPCC07D471/04C07D471/14C07F5/027
Inventor 刘陟华万鸣张保杰郭巍陶绪堂崔得良
Owner SHANDONG UNIV
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