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Hexaazabenzophenanthrene trianthraquinone derivative and synthesis method thereof

A technology of trianthracene and synthesis method, applied in the field of hexaazatriphenylene trianthracene derivatives and synthesis thereof, can solve the problems of insignificant improvement effect and the like, achieve mild and easy control of reaction conditions, improve electron withdrawing Ability, the effect of a short synthesis route

Inactive Publication Date: 2020-01-17
CHONGQING TECH & BUSINESS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Azatriphenylene is a structure in which part of the carbon atoms in the central nucleus of triphenylene derivatives are replaced by nitrogen atoms, especially hexaazatriphenylene, whose ability to absorb electrons has been improved compared to triphenylene derivatives It must be improved, but the improvement effect is not obvious

Method used

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  • Hexaazabenzophenanthrene trianthraquinone derivative and synthesis method thereof
  • Hexaazabenzophenanthrene trianthraquinone derivative and synthesis method thereof
  • Hexaazabenzophenanthrene trianthraquinone derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Compound A is 5,6-dodecyl-1,4-naphthoquinone, R is -C 12 h 23 .

[0045] A hexaazatriphenylene trianthraquinone derivative, the structural formula of which is as follows:

[0046]

[0047] The synthetic method of above-mentioned hexaazatriphenanthrene trianthraquinone derivative specifically comprises the following steps:

[0048] (1) Synthesis of 2,3,6,7,10,11-hexa(dibromomethyl)-1,4,5,8,9,12-hexaazatriphenylene

[0049] Add 2.00g 2,3,6,7,10,11-hexamethyl-1,4,5,8,9,12-hexaazatriphenylene and 320mL CH 3 CN / H 2 O mixed solution (wherein CH 3 CN and H 2The volume ratio of O is 99:1), warming up to 85°C, stirring to 2,3,6,7,10,11-hexamethyl-1,4,5,8,9,12-hexaazabenzo After the phenanthrene is completely dissolved, slowly add 48 mL of Br in the reaction system 2 and 80mL CH 3 The mixed solution of CN was maintained at 85°C after the dropwise addition, and refluxed for 72 hours. Cool down to room temperature, add dropwise 300mL 0.50mol / LNaHSO 3 The solution was ...

Embodiment 2

[0053] Compound A is 5,6-bis(n-dodecyl ester group)-1,4-naphthoquinone, R is -COOC 12 h 23 .

[0054] A hexaazatriphenylene trianthraquinone derivative, the structural formula of which is as follows:

[0055]

[0056] Using the 2,3,6,7,10,11-hexa(dibromomethyl)-1,4,5,8,9,12-hexaazatriphenylene synthesized in Example 1 to synthesize the above-mentioned hexaaza Triphenylene trianthraquinone derivatives.

[0057] Vacuumize the 50mL three-neck flask-nitrogen for three cycles, add 0.96g 5,6-bis(n-dodecyl ester)-1,4-naphthoquinone, 0.63g to synthesize 2,3,6,7,10 , 11-hexa(dibromomethyl)-1,4,5,8,9,12-hexaazatriphenylene, 1.12g sodium iodide (NaI) and 20mL N,N-dimethylformamide (DMF ), heated to 90°C, and reacted for 48h under the protection of nitrogen. Cool to room temperature, mix the resulting mixture with 50 mL of acetone and stir for 30 min, filter, wash with deionized water and acetone until the filtrate is colorless, collect the filter cake, dry and column chromatograp...

Embodiment 3

[0059] Compound A is 5,6-bis(n-dodecylamide)-1,4-naphthoquinone, R is -CONHC 12 h 23 .

[0060] A hexaazatriphenylene trianthraquinone derivative, the structural formula of which is as follows:

[0061]

[0062] Using the 2,3,6,7,10,11-hexa(dibromomethyl)-1,4,5,8,9,12-hexaazatriphenylene synthesized in Example 1 to synthesize the above-mentioned hexaaza Triphenylene trianthraquinone derivatives.

[0063] The 50mL three-neck flask was evacuated-nitrogen for three cycles, and 0.95g of 5,6-bis(n-dodecylamide)-1,4-naphthoquinone, 0.63g of 2,3,6,7,10, 11-hexa(dibromomethyl)-1,4,5,8,9,12-hexaazatriphenylene, 1.24 g potassium iodide (KI) and 20 mL N,N-dimethylformamide (DMF), warming To 90 ° C, reacted under nitrogen protection for 48h. Cool to room temperature, mix the resulting mixture with 50 mL of acetone, stir for 30 min, filter, wash with deionized water and acetone until the filtrate is colorless, collect the filter cake, dry and column chromatography to obtain 0.57 g ...

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Abstract

The invention discloses a hexaazabenzophenanthrene trianthraquinone derivative and a synthesis method thereof. The general structural formula of the hexaazabenzophenanthrene trianthraquinone derivative is asshown in the specification. In the general structural formula, R is a C6-C40 alkyl group, C6-C40 alkyl ester, C6-C40 alkylamide; or two ortho-position Rs synthesize C6-C40 substituted imide. The hexaazabenzophenanthrene trianthraquinone derivative can effectively improve the electron absorption capacity of hexaazabenzophenanthrene, and is a novel N-type semiconductor material. Meanwhile, the synthetic method is short in synthetic route, simple and convenient to operate, mild in reaction condition and easy to control, and does not need special equipment.

Description

technical field [0001] The invention belongs to the technical field of organic liquid crystal materials, and in particular relates to a hexaazatriphenylene trianthraquinone derivative and a synthesis method thereof. Background technique [0002] Discotic liquid crystals are widely used in physical devices such as light-emitting diodes, photoconductors, photovoltaic devices, field-effect transistors, and optical storage. [0003] In recent years, more and more triphenylene discotic liquid crystal materials have been synthesized, but due to the limitation of synthesis methods, the flexible side chains of many triphenylene discotic liquid crystal materials are mostly electron-donating groups such as -OR or -SR. The enrichment of charges makes most triphenylene derivatives potential P-type semiconductor materials (hole transport materials), while the discotic liquid crystal N-type semiconductor materials with electron transport function are extremely rare. N-type organic semico...

Claims

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Application Information

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IPC IPC(8): C07D487/14C07D487/22
CPCC07D487/14C07D487/22
Inventor 孙洪飞姚斌
Owner CHONGQING TECH & BUSINESS UNIV
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