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Hexabenzocoronene compound containing thioether in swallowtail side chain and preparation method thereof

A dovetail-shaped, sulfide-containing technology, used in sulfide preparation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problem of high temperature range of liquid crystal phase

Active Publication Date: 2017-03-01
北京广文精细化工研究所
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the liquid crystal phase temperature range of the linear sulfide-containing hexabenzocoronene compound mentioned in the patent is too high

Method used

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  • Hexabenzocoronene compound containing thioether in swallowtail side chain and preparation method thereof
  • Hexabenzocoronene compound containing thioether in swallowtail side chain and preparation method thereof
  • Hexabenzocoronene compound containing thioether in swallowtail side chain and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Embodiment 1: prepare HBC-(CH 2 ) 2 SCH 2 CH(C 6 h 13 )C 8 h 17

[0076] (1) p-bromophenethylmercaptan

[0077] Put p-bromophenethyl bromide (86.87g, 0.33mol), thiourea (30.14g, 0.396mol), and absolute ethanol (120ml) in a round bottom flask, mix and heat to reflux until a white precipitate precipitates, and after filtration , placed in a single-necked bottle and added NaOH (135ml, 5M) aqueous solution, heated under reflux for five hours, after acidification with dilute hydrochloric acid, separated the mercaptan layer, dried over anhydrous sodium sulfate, and distilled under reduced pressure on a 20cm Weiss fractionation column (distillation range 146- 148°C). P-bromophenethyl bromide can be obtained by passing 2-(4'-bromophenyl)ethanol into hydrogen bromide.

[0078] Through NMR analysis, what is obtained is p-bromophenethylmercaptan, and the specific data are: 1 HNMR (300MHz, CDCl 3 ): δ(ppm) δ1.37(t,1H,-),2.76(t,2H,-CH 2 -),2.86(t,2H,-CH 2 -),7.07(d,2H,A...

Embodiment 2

[0093] Embodiment 2: prepare HBC-(CH 2 ) 2 SCH 2 CH(C 8 h 17 )C 10 h 21

[0094] (1) Preparation of 4-bromo-phenethyl (2-octyl dodecyl) sulfide

[0095] Adopt p-bromophenethyl mercaptan (4.93g, 22.7mmol) prepared as embodiment 1 step (1), bromo 2-octyl dodecane (9.86g, 27.3mmol), method is the same as in embodiment 1 Step (2), the productive rate is 85%.

[0096] By nuclear magnetic resonance spectrum analysis, the product obtained is 4-bromo-phenethyl (2-octyl dodecyl) sulfide, and the specific data are: 1 HNMR (400MHz, CDCl 3 ):δ(ppm)δ0.86(t,3H,-CH 3 ),1.27(m,33H,-CH 2 -),2.47(d,2H,-CH 2 -),2.71(t,2H,-CH 2 -),2.81(t,2H,-CH 2 -), 7.07 (d, 2H, ArH), 7.40 (d, 2H, ArH).

[0097] (2) 1,2-bis((2-octyldodecyl)thioethylphenyl)acetylene (TOLAN-(CH 2 ) 2 S CH 2 CH(C 8 h 17 )C 10 h 21 )preparation

[0098] Using p-bromophenethyl(2-octyldodecyl)sulfide (4.14g, 8.3mmol), benzene (30ml), Pd(II) (dichlorobis(triphenylphosphine) palladium, 10% mol), CuI (cuprous iodi...

Embodiment 3

[0108] Embodiment 3: prepare HBC-(CH 2 ) 2 SCH 2 CH(C 10 h 21 )C 12 h 25

[0109] (1) Preparation of p-bromophenethyl (2-decyltetradecyl) sulfide

[0110] Adopt the p-bromophenethylmercaptan (9.77g, 45mmol) prepared as embodiment 1 step (1), bromo 2-decyltetradecane (20.55g, 49mmol), method is with the step in embodiment 1 ( 2), the yield is 82%.

[0111] By nuclear magnetic resonance spectrum analysis, the product obtained is p-bromophenethyl (2-decyltetradecyl) sulfide, and the specific data are 1 HNMR (300MHz, CDCl 3 ):δ(ppm)δ0.87(t,6H,-CH 3 ),1.26(m,41H,-CH 2 -),2.50(d,2H,-CH 2 -),2.72(t,2H,-CH 2 -),2.84(t,2H,-CH 2 -), 7.09 (d, 2H, ArH), 7.40 (d, 2H, ArH).

[0112] (2) 1,2-bis((2-decyltetradecyl)thioethylphenyl)acetylene (TOLAN-(CH 2 ) 2 S CH 2 CH(C 10 h 21 )C 12 h 25 preparation

[0113] Using p-bromophenethyl (2-decyltetradecyl) sulfide 5.54g, 10mmol), benzene (30ml), Pd (II) (dichloro bis (triphenylphosphine) palladium, (10%mol ), CuI (cuprous io...

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Abstract

The invention relates to a hexabenzocoronene compound containing thioether in the dovetail-like side-chain and a preparation method thereof. The structural general formula of the compound is described in the specification, and in the formula, R is a dovetail-like alkyl group. According to the invention, a ring trimerization-ferric trichloride co-coronene process is employed, 2-(4'-bromophenyl)ethanol is used as a raw material; mercaptan is produced after hydroxyl bromination and thiourea salt reaction; then thioether is prepared; a palladium catalyzed direct coupling reaction is selected so as to obtain a diphenylacetylene derivative; the diphenylacetylene derivative undergoes ring trimerization under the catalysis of carbonyl cobalt so as to produce corresponding hexaphenylbenzene; and hexaphenylbenzene is oxidized with ferric chloride anhydrous in dichloromethane and nitromethane and then reduced with a system consisting of iodine and sodium borohydride, then methanol is added, precipitation is carried out so as to obtain a yellow solid, and the yellow solid is purified. The dovetail-like side-chain is favorable for reduction of the melting point of the compound and enables a compound with a certain chain length to have the properties of discotic liquid crystals and to have mesogenic behavior, so reference is provided for designing of discotic liquid crystals. The hexabenzocoronene compound is extensively applied to organic light-emitting diodes, field effect transistors and solar cells.

Description

technical field [0001] The invention relates to a hexabenzocoronene compound with a dovetail-shaped side chain containing sulfide and a preparation method thereof, specifically a side chain of -(CH 2 ) 2 The hexabenzocoronene liquid crystal molecular derivative of SR and its preparation method, R is a saturated alkane with a straight-chain alkane on the second carbon of a straight-chain alkane, referred to as swallowtail, and the R group is CH 2 CH(C n h 2n+1 )C m h 2m+1 Form representation. Background technique [0002] 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. Discotic liquid crystals are a class of compounds composed of disc-shaped rigid hard cores...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C321/20C07C319/20H01L51/00
Inventor 王文广杨明聪蒲嘉陵
Owner 北京广文精细化工研究所
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