Trifluoromethyl substituted perylene bis diimines and preparation method thereof

A technology of perylene bis-diimide and trifluoromethyl, which is applied in the field of organic chemical industry and fine chemical industry to achieve the effect of improving solubility

Inactive Publication Date: 2008-10-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In 2006, the literature reported (Chem.Phys.Lett.2006,417:457) the synthesis of 3,4,9,10-perylene tetracarboxylate, which has good solubility and large extinction coefficient, and has liquid crystal Behavior, but no reports of 3,4,9,10-perylenetetracarboxylate derivatives

Method used

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  • Trifluoromethyl substituted perylene bis diimines and preparation method thereof
  • Trifluoromethyl substituted perylene bis diimines and preparation method thereof
  • Trifluoromethyl substituted perylene bis diimines and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of 1,7-ditrifluoromethyl-N,N'-dibutylperylene bisdiimide

[0035]

[0036] The synthetic route of this compound is shown in the figure above, which is synthesized through the following four steps:

[0037] (1) Synthesis of a mixture of 1,7-dibromoperylenetetracarboxylate tetrabutyl ester and 1,6-dibromoperylenetetracarboxylate tetrabutyl ester, add 820mg perylenetetracarboxylate (1.24mmol), 306mg to a 100mL two-neck bottle K 2 CO 3 (2.2mmol), 60mL CH 2 Cl 2 , Add 4mL liquid bromine (78.4mmol), keep the system at 10℃ under stirring, react for 2h, pass through a silica gel column to obtain 1,7-dibromoperylenetetracarboxylic acid tetrabutyl ester and 1,6-dibromoperylenetetracarboxylic acid tetrabutyl ester 600mg of ester mixture, 60% yield, API-ES-MS, [M+Na] + : 831(m / z); 1 H-NMR (400Mz, CDCl3): δ = 0.85-1.85 (m, 28H), 4.35 (m, 8H), 8.03 (m, 2H, perylene ring), 8.31 (m, 2H, perylene ring), 8.83 (m , 2H, perylene ring); 13 C-NMR(100MHz, CDCl 3 ): δ=14.0...

Embodiment 2

[0043] Example 2: Preparation of tetrabutyl 1-bromoperylenetetracarboxylate

[0044]

[0045] Add 3.0g tetrabutyl perylenetetracarboxylate (4.6mmol) to a 100mL two-necked bottle, 3.0g K 2 CO 3 (22mmol), 50mL CH2Cl2, add 3mL liquid bromine (59mmol), while stirring, keep the system at 20℃, react for 1.5h, and pass through a silica gel column to obtain 900mg of 1-bromoperylenetetracarboxylic acid tetrabutyl ester with a yield of 27%. API- ES-MS, [M+Na] + : 753(m / z); 1 H-NMR (400Mz, CDCl3): δ = 0.85-1.85 (m, 28H), 4.36 (m, 8H), 7.97 (d, 1H, perylene ring), 8.02 (d, 2H, perylene ring), 8.10 (m , 2H, perylene ring), 8.26 (s, 1H, perylene ring), 8.98 (d, 1H, perylene ring); 13 C-NMR(100MHz, CDCl 3 ): δ=13.8, 19.2, 19.3, 30.6, 65.4, 65.5, 65.7, 118.6, 121.6, 122.6, 127.3, 128.0, 129.2, 129.5, 130.0, 130.1, 130.2, 130.4, 130.8, 130.9, 131.6, 132.1, 132.4, 132.5, 137.4.

Embodiment 3

[0046] Example 3: Preparation of 1,6,7-tribromoperylenetetracarboxylic acid tetrabutyl ester and 1,6,7,12-tetrabromoperylenetetracarboxylic acid tetrabutyl ester

[0047]

[0048] Add 410mg tetrabutyl perylenetetracarboxylate (0.62mmol), 552mg K to a 25mL two-neck bottle 2 CO 3 (4mmol), 15mL of chlorobenzene, add 1mL of liquid bromine (19.6mmol), keep the system at 80°C under stirring, react for 48h, and pass through a silica gel column to obtain 110mg of 1,6,7-tribromoperylenetetracarboxylate tetrabutyl ester. Rate 19% API-ES-MS, [M+Na] + :908(m / z) and 1,6,7,12-tetrabromoperylenetetracarboxylic acid tetrabutyl ester 300mg, yield 50%, API-ES-MS, [M+Na] + : 986(m / z).

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Abstract

The invention provides a category of perylene derivatives, that is perylene two-diimine replaced by trifluoromethyl and a preparation method thereof; wherein, the method comprises that perylene four-formate is used as the raw material to synthesize bromination perylene four-formate by brominating liquid bromine; the bromination perylene four-formate and perfluorinated iodoalkane are used as the raw materials to synthesize the perylene four-formate replaced by long chain perfluoroalkyl under the catalysis of copper powders or copper-tin alloy powder, and the bromination perylene four-formate and sodium trifluoroacetate are used as the raw materials to synthesize the perylene four-formate replaced by the trifluoromethyl under the catalysis of cuprous iodide; the long chain perfluoroalkyl or the perylene four-formate replaced by the trifluoromethyl is used as the raw material and hydrolyzed to synthesize the perylene four-formate or perylene four-formate anhydride replaced by the perfluoroalkyl under the function of inorganic alkali or chlorosulfonic acid; the perylene four-formate replaced by the trifluoroacetate and alkylamine or aniline are used as the raw material to synthesize the perylene two-diimine replaced by the trifluoromethyl .

Description

Technical field [0001] The present invention relates to perylene derivatives bromoperylene tetracarboxylate, perfluoroalkyl substituted perylene tetracarboxylate, perfluoroalkyl substituted perylene tetracarboxylic acid and trifluoromethyl substituted perylene bisdiimide and the same The preparation method belongs to the technical field of organic chemicals and fine chemicals. Background technique [0002] 3,4,9,10-perylene tetracarboxylic anhydride is the basic raw material of perylene pigments, dyes and organic semiconductors. The dyes prepared with it are often used in the dyeing and printing of cotton fibers, and have excellent application fastness. The organic pigments have excellent properties and are a high-end variety among organic pigments. At the same time, the large π-π conjugated system in the molecular structure gives it excellent fluorescence and photoelectric properties, making its derivatives useful in electrophotographic and solar cells. , Organic field effect tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
Inventor 肖义袁忠义李政
Owner DALIAN UNIV OF TECH
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