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N-type star-shaped polycyclic conjugated aromatic hydrocarbon and synthesis method thereof

A synthesis method, N-type star technology, applied in the field of organic liquid crystal materials, can solve the problems of scarcity, etc., and achieve the effect of simple operation, simple and easy-to-obtain raw materials, and short synthesis route

Inactive Publication Date: 2020-01-03
CHONGQING TECH & BUSINESS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[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 charge makes most triphenylene derivatives become potential P-type star-like polycyclic conjugated aromatic hydrocarbons (hole transport materials), while discotic liquid crystals with electron-transport function N-type star-like polycyclic conjugated Aromatics are extremely rare

Method used

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  • N-type star-shaped polycyclic conjugated aromatic hydrocarbon and synthesis method thereof
  • N-type star-shaped polycyclic conjugated aromatic hydrocarbon and synthesis method thereof
  • N-type star-shaped polycyclic conjugated aromatic hydrocarbon and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Compound A is 5,6-di-n-hexyl-1,4-naphthoquinone, R is -C 6 h 13 .

[0042] A kind of N-type star polycyclic conjugated aromatic hydrocarbon, its structural formula is as follows:

[0043]

[0044] The synthesis method of the above-mentioned N-type star-shaped polycyclic conjugated aromatic hydrocarbons specifically comprises the following steps:

[0045] (1) Synthesis of hexabromomethylbenzene

[0046] Add 1.62g of hexamethylbenzene and 30mL of 1,2-dibromoethane to a 100mL single-necked bottle in turn, raise the temperature to 130°C, stir until the hexamethylbenzene is completely dissolved, and slowly add 3.25mL of liquid bromine (Br 2 ) and 10mL of 1,2-dibromoethane, after the dropwise addition, maintain reflux reaction at 130°C for 30h. Then cool down to room temperature naturally, add dropwise 30mL 0.50mol / LNaHSO 3 The solution quenched the reaction to remove excess liquid bromine, filtered, and then washed three times with deionized water and acetone until t...

Embodiment 2

[0050] Compound A is 5,6-bis(4-tert-butylphenyl)-1,4-naphthoquinone, R is

[0051] A kind of N-type star polycyclic conjugated aromatic hydrocarbon, its structural formula is as follows:

[0052]

[0053] Using the hexabromomethylbenzene synthesized in Example 1 to synthesize the above-mentioned N-type star-shaped polycyclic conjugated aromatic hydrocarbons.

[0054] 100mL three-necked flask vacuum-gas three cycles, add 2.11g 5,6-di(4-tert-butylphenyl)-1,4-naphthoquinone, 0.95g hexabromomethylbenzene, 3.37g iodide Sodium (NaI) and 45mL N,N-dimethylformamide (DMF) were heated to 90°C and reacted for 48h under nitrogen protection. Cool to room temperature, add 40 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 0.91 g of a yellow solid, which is the above-mentioned N-type star Polycyclic conjugated aromatic hydrocarbons, yield 43%.

Embodiment 3

[0056]Compound A is 5,6-di(n-hexylcarboxylate)-1,4-naphthoquinone, R is -COOC 6 h 13 .

[0057] A kind of N-type star polycyclic conjugated aromatic hydrocarbon, its structural formula is as follows:

[0058]

[0059] Using the hexabromomethylbenzene synthesized in Example 1 to synthesize the above-mentioned N-type star-shaped polycyclic conjugated aromatic hydrocarbons.

[0060] 100mL there-necked flask was vacuumed-nitrogen for three cycles, and then 2.07g of 5,6-bis(n-hexylcarboxylate)-1,4-naphthoquinone, 0.95g of hexabromomethylbenzene, 3.37g of sodium iodide ( NaI) and 45mL N,N-dimethylformamide (DMF), heated to 90°C, and reacted for 48h under nitrogen protection. Cool to room temperature, add 40 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 1.08 g of yellow solid, which is the above-mentioned N-type star Polycyclic conjugated aromatic h...

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Abstract

The invention discloses N-type star-shaped polycyclic conjugated aromatic hydrocarbon and a synthesis method thereof. The structural general formula of the N-type star-shaped polycyclic conjugated aromatic hydrocarbon is shown in the specification, wherein R in the general formula is C6-C40 alkyl, C6-C40 alkyl ester, C6-C40 alkylamide or a C6-C40 aromatic substituent. The N-type star-shaped polycyclic conjugated aromatic hydrocarbon is a novel N-type star-shaped polycyclic conjugated aromatic hydrocarbon. 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 an N-type star-shaped polycyclic conjugated aromatic hydrocarbon 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 charge makes most triphenylene derivatives become potential P-type star-like polycyclic conjugated aromatic hydrocarbons (hole transport materials), while discotic liquid crystals with electron-transport function N-type star-like polycycl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/22C07D487/14C07C69/76C07C235/84C07C46/00C07C67/343C07C231/12C07B37/10
CPCC07C50/22C07D487/14C07C69/76C07C235/84C07B37/10C07C2603/54
Inventor 孙洪飞姚斌
Owner CHONGQING TECH & BUSINESS UNIV
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