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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: 2011-05-04
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-bistrifluoromethyl-N, N'-dibutylperylene bis-diimide

[0035]

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

[0037] (1) Synthesis of tetrabutyl 1,7-dibromoperylene tetracarboxylate and tetrabutyl 1,6-dibromoperylene tetracarboxylate, add 820mg tetrabutyl perylene tetracarboxylate (1.24mmol) to 100mL two-necked bottle, 306mg K 2 CO 3 (2.2mmol), 60mL CH 2 Cl 2 , add 4mL of liquid bromine (78.4mmol), under stirring, keep the system at 10°C, react for 2h, pass through a silica gel column to obtain tetrabutyl 1,7-dibromoperylenetetracarboxylate and tetrabutyl 1,6-dibromoperylenetetracarboxylate Esters mixture 600mg, yield 60%, 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, 19.4, 65....

Embodiment 2

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

[0044]

[0045] Add 3.0g tetrabutyl perylenetetracarboxylate (4.6mmol) in 100mL two-necked bottle, 3.0g K 2 CO 3 (22mmol), 50mL CH2Cl2, add 3mL liquid bromine (59mmol), under stirring, keep the system at 20 ° C, react for 1.5h, pass through a silica gel column to obtain 900mg of tetrabutyl 1-bromoperylenetetracarboxylate, the yield is 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, 1341.6, 13 132.5, 137.4.

Embodiment 3

[0046] Embodiment 3: Preparation of tetrabutyl 1,6,7-tribromoperylenetetracarboxylate and 1,6,7,12-tetrabromoperylenetetracarboxylate

[0047]

[0048] Add 410mg tetrabutyl perylenetetracarboxylate (0.62mmol) in 25mL two-necked bottle, 552mg K 2 CO 3 (4mmol), 15mL of chlorobenzene, add 1mL of liquid bromine (19.6mmol), under stirring, keep the system at 80°C, react for 48h, pass through a silica gel column to obtain 110mg of tetrabutyl 1,6,7-tribromoperylenetetracarboxylate, and collect Yield 19% API-ES-MS, [M+Na] + : 908 (m / z) and 1,6,7,12-tetrabromoperylenetetracarboxylate 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 synthesizethe perylene two-diimine replaced by the trifluoromethyl .

Description

technical field [0001] The present invention relates to perylene derivative bromoperylene tetracarboxylate, perfluoroalkyl substituted perylene tetracarboxylate, perfluoroalkyl substituted perylene tetracarboxylic acid and trifluoromethyl substituted perylene bis-diimide and its The preparation method belongs to the technical field of organic chemical industry and fine chemical industry. Background technique [0002] 3,4,9,10-Perylenetetracarboxylic anhydride is the basic raw material of perylene pigments, dyes and organic semiconductors. The dyes prepared from it are often used in the dyeing and printing of cotton fibers, and have excellent application fastness. The prepared organic pigment has excellent performance and is a high-grade variety in organic pigments. At the same time, the large π-π conjugated system in its molecular structure endows it with excellent fluorescence and photoelectric properties, making its derivatives in electrostatic printing, solar energy Ther...

Claims

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Application Information

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