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Coronene compound containing thioether in lateral chain and preparation method thereof

A technology containing thioether and benzocorone, which is applied in the fields of thioether preparation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems that HBC compounds have not been reported, and achieve the effect of high carrier mobility

Active Publication Date: 2012-07-18
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although scholars have made great efforts in the synthesis, the reason why these HBCs cannot be obtained by dehydrocyclization using hexaphenylbenzene as a raw material is still unclear. So far, these types of HBC compounds have not yet been seen. to report

Method used

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  • Coronene compound containing thioether in lateral chain and preparation method thereof
  • Coronene compound containing thioether in lateral chain and preparation method thereof
  • Coronene compound containing thioether in lateral chain and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Embodiment 1: prepare HBC-(CH 2 ) 2 SC 10

[0113] (1) Preparation of p-bromophenethyl decyl sulfide

[0114] Put KOH aqueous solution (15ml, 6M) in the reaction flask, ventilate three times, add decyl mercaptan (10.46g, 60mmol) dropwise under nitrogen protection, after the dropwise addition, add the phase transfer catalyst tetrabutylammonium iodide (amount of catalyst, 0.8 g). Ten minutes later, 50ml of tetrahydrofuran was added, and after being uniform, p-bromophenethyl bromide (5.24g, 20mmol) was slowly added dropwise within ten minutes. The temperature was then raised to 45°C and the reaction was stirred vigorously overnight. After the reaction was completed, the reaction solution was poured into dilute hydrochloric acid (1M), extracted with dichloromethane, dried over anhydrous sodium sulfate, and evaporated to remove the solvent under reduced pressure. Column chromatography gave 6.3 g of a colorless transparent liquid with a yield of 89%.

[0115] Through nu...

Embodiment 2

[0128] (1) Preparation of p-bromophenethyl dodecyl sulfide

[0129] Using dodecylmercaptan (12.12g, 60mmol) and p-bromophenethyl bromide (5.24g, 20mmol), the method was the same as step (1) in Example 1, and the yield was 89%.

[0130] Through nuclear magnetic resonance spectrum analysis, the product obtained is p-bromophenethyl dodecyl sulfide, and the specific data are: 1 HNMR (400MHz, CDCl 3 ): δ (ppm) δ 0.86 (t, 3H, -CH 3 ), 1.29 (m, 16H, -CH 2 -), 1.33 (m, 2H, -CH 2 -), 1.52(m, 2H, -CH 2 -), 2.51(t, 2H, -CH 2 -), 2.73(t, 2H, -CH 2 -), 2.83(t, 2H, -CH 2 -), 7.07 (d, 2H, ArH), 7.40 (d, 2H, ArH). Its H NMR spectrum ( 1 HNMR) such as Figure 19 shown.

[0131] (2) 1,2-bis(dodecylthioethylphenyl)acetylene (TOLAN-(CH 2 ) 2 SC 12 )preparation

[0132] Using p-bromophenethyl dodecyl sulfide (3.85g, 10mmol), benzene (30ml), Pd(II) (dichlorobis(triphenylphosphine) palladium, 10%mol), CuI (iodide Cuprous, 10% mol), DBU (9ml), trimethylsilylacetylene (0.56g), water (0...

Embodiment 3

[0143](1) 1,2-bis(methylthioethylphenyl)acetylene (TOLAN-(CH 2 ) 2 SC 1 )preparation

[0144] Adopt p-bromophenethyl methyl sulfide (2.3g, 10mmol) (also can adopt methylmercaptan, p-bromophenethyl bromide, method is the same as the step (1) in the embodiment 1, prepare p-bromophenethyl methyl sulfide), benzene (30ml), Pd(II) (dichlorobis(triphenylphosphine)palladium, 10%mol), CuI (cuprous iodide, 10%mol), DBU (9ml), Trimethylsilylacetylene (0.56g), water (0.1ml), the method is the same as step (2) in Example 1, and the yield is 87%. Melting point: 146°C.

[0145] By nuclear magnetic resonance spectrum analysis, the product obtained is 1,2-bis(methylthioethylphenyl)acetylene, and the specific data are: 1 HNMR (400MHz, CDCl 3 ): δ, 2.09(t, 6H, -CH 3 ), 2.73(t, 4H, -CH 2 -), 2.90(t, 4H, -CH 2 -), 7.08 (d, 4H, ArH), 7.41 (d, 4H, ArH).

[0146] (2) Hexa(4'-methylthioethylphenyl)benzene (HPB-(CH 2 ) 2 SC 1 )preparation

[0147] Using TOLAN-(CH 2 ) 2 SC 1 (1.31g, 4mm...

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Abstract

The invention relates to coronene compound containing thioether in lateral chain and the preparation method thereof. The structural formula of the compound is shown in the descriptiopn: R refers to alkyl. In the method, ring trimerization- ferric trichloride coronene method, namely 2- (4'- bromophenyl) ethanol is taken as raw material, through hydroxyl bromo, thioether is formed, palladium-catalyzed is selected for direct coupled reaction, so as to obtain diphenylacetypene ramification, under the catalysis of cobalt carbonyl, corresponding hexaphenylbenzene is produced by trimerization cyclization. Anhydrous ferric trichloride is oxidized in methylene dichloride and nitromethane, then reduction is performed by using iodine and sodium borohydride system, and after drying, THF (tetrahydrofuran) is used for recrystal. The synthetic method provided by the invention is simple, is high in yield, and can be extensively used in organic LBD, field-effect tubes and solar batteries.

Description

technical field [0001] The invention relates to a hexabenzocoronene compound containing sulfide in the side chain and a preparation method thereof, in particular to a hexabenzocoronene compound with a side chain of -(CH 2 ) 2 A hexabenzocoronene electron transport compound of SR (R is an alkyl group) and a preparation method thereof, the molecular structure of the compound is as follows: [0002] Background technique [0003] Organic charge transport materials have the advantages of rich material sources, low cost, low toxicity, easy processing and chemical modification, large-area fully flexible thin film devices, and easy disposal. Digital printers, etc.), solar cells, field effect transistors and electroluminescence and other mainstream material systems for optoelectronic devices. [0004] Discotic liquid crystals are a class of compounds composed of disc-like rigid hard cores and surrounding flexible side chains, because they can form columnar superstructures throug...

Claims

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Application Information

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IPC IPC(8): C07C321/20C07C319/20H01L51/54H01L51/30H01L51/46
CPCY02E10/549
Inventor 王文广江宇蒲嘉陵
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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