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Dibenz tetraaza [14] annulene compound and preparation method and application thereof

A compound and tetraaza technology, applied in the field of rotaxene compounds and their preparation, can solve the problems of high production cost, single solvent selectivity, low light stability and the like

Inactive Publication Date: 2008-04-09
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor thermal stability and light stability of the above-mentioned materials, it is necessary to add a light stabilizer during actual use, and it is necessary to use expensive tetrafluoropropanol as a solvent, and the solvent has a single selectivity, resulting in higher production costs and poor procedures. more complicated

Method used

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  • Dibenz tetraaza [14] annulene compound and preparation method and application thereof
  • Dibenz tetraaza [14] annulene compound and preparation method and application thereof
  • Dibenz tetraaza [14] annulene compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0087] Example 1, preparation of dibenzotetraazepine [14] annulene compound of formula VIII

[0088] Take 0.2 mol of 4-methyl-o-phenylenediamine, 0.2 mol of acetylacetone and 0.1 mol of nickel acetate tetrahydrate, put them in a 500 mL three-neck flask, add 250 mL of ethanol, protect with nitrogen gas, heat and reflux for 40 hours, the solution is dark green, and store in the refrigerator cooled to 0°C, filtered, washed twice with ethanol at 0°C, and finally washed with water, and the filter cake was dried to obtain 34.5 g of nickel annulenene complex with a yield of 80.4%.

[0089] Dissolve 0.05mol of anrocene nickel complex in 150ml of toluene, add 0.1mol of oxalyl chloride, stir, and heat properly to make the reaction appear dark red. After 15 minutes of reaction, add 0.2mol of 2,2,4,4-tetramethyl-3 - Pentanol, heated to reflux for 1 hour, the solution gradually became green and darkened, added 20ml triethylamine, continued to reflux for 1 hour, filtered after cooling, remo...

Embodiment 2

[0095] Embodiment 2, the dibenzotetraazepine [14] annulene compound of preparation formula IX structural formula

[0096] Take 0.2 mol of 4-methyl-o-phenylenediamine, 0.2 mol of acetylacetone and 0.1 mol of nickel acetate tetrahydrate, put them in a 500 mL three-neck flask, add 250 mL of ethanol, protect with nitrogen gas, heat and reflux for 40 hours, the solution is dark green, and store in the refrigerator cooled to 0°C, filtered, washed twice with ethanol at 0°C, and finally washed with water, and the filter cake was dried to obtain 34.5 g of nickel annulenene complex with a yield of 80.4%.

[0097]Dissolve 0.05mol of anrocene nickel complex in 150ml of toluene, add 0.1mol of oxalyl chloride, stir, and heat properly to make the reaction appear dark red. After reacting for 15 minutes, add 0.2mol of 2,4-dimethyl-3-pentanol, Heat to reflux for 1 hour, the solution gradually turns green and deepens, add 20ml triethylamine, continue to reflux for 1 hour, filter after cooling, r...

Embodiment 3

[0103] Example 3, preparation of dibenzotetraazepine [14] annulene compound of formula X

[0104] Take 0.2 mol of 4-methyl-o-phenylenediamine, 0.2 mol of acetylacetone and 0.1 mol of nickel acetate tetrahydrate, put them in a 500 mL three-neck flask, add 250 mL of ethanol, protect with nitrogen gas, heat and reflux for 40 hours, the solution is dark green, and store in the refrigerator cooled to 0°C, filtered, washed twice with ethanol at 0°C, and finally washed with water, and the filter cake was dried to obtain 34.5 g of nickel annulenene complex with a yield of 80.4%.

[0105] Dissolve 0.05mol of the anrocene nickel complex in 150ml of toluene, add 0.1mol of oxalyl chloride, stir, and heat properly to make the reaction appear dark red. After reacting for 15 minutes, add 0.2mol of 2,6-di-tert-butyl p-cresol, and heat Reflux for 1 hour, the solution gradually turns green and deepens, add 20ml triethylamine, continue to reflux for 1 hour, filter after cooling, remove toluene b...

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Abstract

The invention discloses a kind of dibenzo tetraaza (14) annulene compounds, of which a preparation method and the application in the aspect of a optical recording media. The structural general formula of the compounds is indicated as formula I. The dibenzo tetraaza (14) annulene materials which are provided by the invention have the advantages of high luminous sensitivity, good thermal stability (TG decomposition temperature is more than 250 DEG C), high solubility, easy dissolution and good crystallization resistance. The compounds can be dissolved in the ether solvent, and the solubility in the alcohol or in the ether solvent can be more than 6 percent. The light stabilizer does not need to be added during the production process, only such materials are used alone. The usage of the dibenzo tetraaza (14) annulene materials which are provided by the invention for the optical disk production can not only significantly reduce the production cost of the optical disks, but also greatly improve the recording performance of the disks at the same time of meeting the requirement of current BD-R and HD DVD-R optical disks on the recording media.

Description

technical field [0001] The invention relates to a class of annulene compounds and a preparation method and application thereof, in particular to dibenzotetraaza[14]annulene compounds. Background technique [0002] In recent years, with the rapid development of the information industry, the traditional storage methods have undergone revolutionary changes. The development and progress of the society has led to the rapid expansion of the amount of information. How to effectively store, manage and utilize various information has become an important issue in people's daily work and life. Due to the advantages of high storage density, high fidelity, high definition, long life, and fast data access speed, optical discs have been widely used in production and office automation, education, scientific research, document storage and retrieval, advertising, software , audio-visual entertainment and other fields. Originally, the content of the CD disc was copied in when the disc was pr...

Claims

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Application Information

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IPC IPC(8): C07D257/00C07F17/02G11B7/242
Inventor 宾月景张复实易家祥
Owner TSINGHUA UNIV
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