Synthon and method for preparing dibenzocoronene compounds by same

A technology of synthons and compounds, which is applied in the field of preparation, can solve the problem of no report on synthetic methods

Active Publication Date: 2014-02-12
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The present invention studies a synthon and the preparation of imide-containing dibenzocoronene deriv

Method used

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  • Synthon and method for preparing dibenzocoronene compounds by same
  • Synthon and method for preparing dibenzocoronene compounds by same
  • Synthon and method for preparing dibenzocoronene compounds by same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] 1. 1,7-bis(3,3',4,4'-di-n-dodecyloxyphenyl)-N,N'-bis(n-dodecyl)-3,4:9,10 -Perylene diimide——Compound (A)

[0131]

[0132] in N 2 environment, 1.2g (1mmol) Pd (PPh 3 ) 4 A solution of toluene (160ml) was added to a round bottom flask containing 8.8g (10mmol) of 1,7-dibromobis-n-dodecylperyleneimide, and then 2M Na 2 CO 3 solution (40ml) and 10.8g (22mmol) of 3,4-n-dodecyloxyphenylboronic acid in CH 3 OH (60ml) solution, stirred at 70°C for 48hrs. Cool to room temperature, add 5ml NH 3 water and 2N Na 2 CO 3 solution (15ml) to stop the reaction, CHCl 3 Extraction, washed with water, anhydrous Na 2 SO 4 Dry, filter, evaporate most of the solvent, add methanol to precipitate, if necessary, use a silica gel column (CHCl 2 : petroleum ether=10:1) purification, from CHCl 3 / methanol recrystallization to obtain dark blue powder 13.0g, yield rate is 80%, Mp. is: 95.30 ℃;

[0133] Through proton nuclear magnetic resonance spectrum analysis, the specific data are...

Embodiment 2

[0148] 1. 1,7-bis(3,3',4,4'-di-n-dodecyloxyphenyl)-N,N'-bis(2-octyldodecyl)-3,4: 9,10-Perylene Diimide - Compound (1)

[0149]

[0150] Using 1,7-dibromobis-2-octyldodecylperyleneimide (11.09g, 10mmol), Pd(PPh 3 ) 4 (Tetrakis(triphenylphosphine)palladium, 1.2g, 1mmol), toluene (160ml), 2M Na 2 CO 3 Solution (40ml), 3,4-dodecyloxyphenylboronic acid (10.8g, 22mmol), methanol (60mml), the method was the same as that of Example 1 to prepare compound (A) in Step 1, and the yield was 80%.

[0151] Through proton nuclear magnetic resonance spectrum analysis, the specific data are: 1 HNMR (CDCl 3 )δ: 0.82-0.88 (m, 24H, CH 3 ), 1.21-1.39 (m, 138H, CH 2 ), 1.41 (m, 4H, CH 2 ), 1.56 (m, 4H, CH2 ), 1.89 (m, 6H, CH 2 ), 3.92(m, 4H, NCH 2 ), 4.07-4.13 (m, 8H, OCH 2 ), 6.94 (m, 2H, ArH), 7.02 (m, 4H, ArH), 7.82 (d, 2H, PerH), 8.13 (d, 2H, PerH), 8.52 (s, 2H, Per-H). Its H NMR spectrum ( 1 HNMR) such as Figure 13 shown.

[0152] 2. 1,7-bis(3,3',4,4'-dihydroxyphenyl)-N,N'-bi...

Embodiment 3

[0166] 1. 1,7-bis(3,3',4,4'-dihexadecyloxyphenyl)-N,N'-bis(1-butyldodecyl)-3,4: 9,10-Perylene Diimide - Compound (5)

[0167]

[0168] Phenylphosphine)palladium, 1.2g, 1mmol), toluene (160ml), 2M Na 2 CO 3 Solution (40ml), 3,4-Di-n-hexadecyloxyphenylboronic acid (13.26, 22mmol), methanol (60mml), the method was the same as that of Example 1 to prepare compound (A) in step 1, and the yield was 80%.

[0169] Through proton nuclear magnetic resonance spectrum analysis, the specific data are: 1 HNMR (CDCl 3 )δ: 0.85-0.90 (m, 24H, CH 3 ), 1.22-1.85 (m, 154H, CH 2 ), 1.93 (m, 4H, CH 2 ), 2.26 (m, 4H, CH 2 ), 3.99(t, 4H, OCH 2 ), 4.11(t, 4H, OCH 2 ), 5.12 (m, 2H, NCH), 7.09 (s, 2H, ArH), 7.15 (m, 4H, ArH), 7.96 (d, 2H, PerH), 8.20 (s, 2H, PerH), 8.68 (d , 2H, PerH). Its H NMR spectrum ( 1 HNMR) such as Figure 19 shown.

[0170] 2. 1,7-bis(3,3',4,4'-dihydroxyphenyl)-N,N'-bis(1-heptyloctyl)-3,4:9,10-perylenediyl imine (6)

[0171]

[0172] Using 1,7-bis(3,3',4,...

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Abstract

The invention relates to a synthon and a method for preparing dibenzocoronene compounds by the same. The synthon is a tetrahydroxy-substituted perylene bisimide compound, and has a structure as shown in general formula (I), wherein R is a C1-C18 linear chain primary alkyl or a primary alkyl with a branched chain. According to the invention, dibromo-perylene anhydride or mixtures are used for preparing dibromo-imide; dibromo-imide and phenylboronic acid substituted by alkoxys at 3 and 4 positions are subjected to a Suzuki coupling reaction under the catalysis of Pd(PPh3)4 to prepare aryl-substituted perylene bisimide compounds; further dealkylation reaction is carried out under the action of boron tribromide so as to form tetrahydroxy-substituted perylene bisimide compound synthon; then the synthon is used as a raw material to synthesize charge transfer compounds of coronene compounds with imide groups at two sides of the molecule. The synthetic method of the invention is simple, high in yield, and widely applicable to organic light-emitting diodes, field effect transistors, and solar cells. The general formula (I) is shown in the description.

Description

technical field [0001] The present invention relates to a synthon and a method for preparing a dibenzocoronene compound by using a synthon, specifically, a synthetic module molecule (the structure of which is as follows) is used as a raw material to synthesize a compound containing imide groups on both sides of the molecule. Process for the preparation of charge transport compounds. [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 printing machines, 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 thr...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K19/34H01L51/54H01L51/30H01L51/46
CPCY02E10/549C09K19/3483C07D471/06H10K85/621H10K85/731
Inventor 蒲嘉陵王文广杨滕州
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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