Benzanthrone derivative and preparation method thereof and application thereof in functional pigments

A technology for benzanthrone and derivatives is applied in the field of benzanthrone derivatives and their preparation, and achieves the effects of high optical stability, high thermal stability and simple preparation method

Active Publication Date: 2020-07-14
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of a series of benzanthrone derivatives has not been reported in the literature

Method used

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  • Benzanthrone derivative and preparation method thereof and application thereof in functional pigments
  • Benzanthrone derivative and preparation method thereof and application thereof in functional pigments
  • Benzanthrone derivative and preparation method thereof and application thereof in functional pigments

Examples

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preparation example Construction

[0037] Preparation of diaryliodonium salts:

[0038]

[0039] Dissolve 1 equivalent of iodobenzene acetate in 10 mL of dichloromethane, drop TfOH (2 equivalents) into the reaction solution at 0°C, and stir the reaction solution at room temperature for 1 h. After 1h, the reaction solution was lowered to 0°C, benzene (1 equivalent) was dropped into the system, and the reaction was continued at room temperature for 2h. After the reaction was completed, the DCM was spin-dried, and anhydrous ether was added, and a white solid was precipitated. The filter cake was washed with water and ether, and dried in vacuum to obtain compound III-1.

[0040]

[0041] Dissolve mCPBA (85%, 22 mmol, 1.1 equiv) and 4-methyliodobenzene (20 mmol, 1.0 equiv) in 10 mL of dichloromethane, and slowly add toluene (122 mmol, 1.1 equiv) after the ice bath drops to 0°C. Trifluoromethanesulfonic acid (20 mmol, 2.0 equiv) was slowly added dropwise under stirring, and the reaction solution changed from t...

Embodiment 1

[0054]

[0055] Mix 1-naphthoic acid (compound II-1, 0.3mmol, 1 equivalent) and palladium acetate (0.03mmol, 10mol% equivalent), add 4 mL of dichloroethane as solvent, and then add diphenyliodonium trifluoromethanesulfonate Salt (compound III-1, 0.6mmol, 2 equivalents), trifluoromethanesulfonic acid (0.09mmol, 30mol% equivalents), reacted for 24 hours at a temperature of 80 ° C, cooled to room temperature, directly spin-dried, dried Separation and purification by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1) to obtain the yellow solid target product, compound I-1, with a yield of 67%. 1 H NMR (400MHz, CDCl 3 )δ8.71(dd, J=7.3,1.0Hz,1H),8.47(dt,J=12.8,6.4Hz,1H),8.36(d,J=7.4Hz,1H),8.26(d,J=8.1 Hz,1H),8.15(d,J=8.0Hz,1H),7.93(d,J=8.1Hz,1H),7.71(ddd,J=13.5,10.2,4.5Hz,2H),7.60(dd,J =15.4,7.5Hz,1H),7.53(dd,J=11.1,3.9Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ 183.91, 136.22, 135.19, 133.42, 133.00, 131.16, 130.26, 129.83, 128.53, 128.33, 128.16, 127.89, 126.83, ...

Embodiment 2

[0057]

[0058] Mix 4-methyl-1-naphthoic acid (compound II-2, 0.3 mmol, 1 equivalent) and palladium acetate (0.03 mmol, 10 mol% equivalent), add 4 mL of dichloroethane as solvent, and then add diphenyl iodide Onium trifluoromethanesulfonate (compound III-2, 0.6mmol, 2 equivalents), trifluoromethanesulfonic acid (0.09mmol, 30mol% equivalents), reacted at a temperature of 80°C for 24 hours, cooled to room temperature, Direct spin-drying, separation and purification by dry loading column chromatography (eluent: petroleum ether: ethyl acetate = 20:1), the target product (compound I-2) was obtained as a yellow solid with a yield of 65%. 1 H NMR (400MHz, CDCl 3 )δ8.58(d, J=7.5Hz, 1H), 8.46(dd, J=7.9, 1.2Hz, 1H), 8.33(d, J=7.4Hz, 1H), 8.24(d, J=8.1Hz, 1H), 8.06(d, J=8.4Hz, 1H), 7.71–7.65(m, 1H), 7.62–7.57(m, 1H), 7.51(dd, J=12.0, 4.1Hz, 2H), 2.78(s ,3H). 13 C NMR (101MHz, CDCl 3 )δ 183.74, 143.30, 136.32, 133.25, 132.05, 131.10, 129.82, 128.22, 128.01, 127.96, 127.88, 127.16, ...

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Abstract

The invention discloses a benzanthrone derivative and a preparation method thereof. The general formula is shown as a formula I or IV, formula I or IV, R1, R2, R3 is independently selected from hydrogen, halogen, an ester group, an acyl group, a branched-chain or straight-chain C1-C20 alkyl group, a straight-chain or branched-chain C1-C20 alkoxy group, a branched-chain or straight-chain perfluoroC1-C20 alkyl group, a branched-chain or straight-chain perfluoroC1-C20 alkoxy group, a substituted or unsubstituted C4-C40 aryl group, and a substituted or unsubstituted C4-C40 heteroaryl group. The benzanthrone derivative with a novel structure provided by the invention is simple in preparation method, non-toxic and harmless, has yellow fluorescence, can be used as a potential organic functional material, and is an important dye intermediate.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a benzanthrone derivative, a preparation method thereof and its application in functional pigments. Background technique [0002] Benzoanthrone derivatives are an important class of aromatic compounds. Benzoanthrone derivatives have attracted widespread attention because of their important applications in the biomedical field, as optoelectronic materials, and these compounds have now been used in electroluminescent devices. For example, the simplest benzanthrone is a light yellow needle-like crystal. The melting point is 170-174°C. It is reddish brown in concentrated sulfuric acid and has strong orange fluorescence. It is insoluble in water, dilute acid or dilute alkali solution, but soluble in ethanol or other organic solvents. As a dye intermediate, it is used in the production of vat brilliant green FFB, vat olive green B, vat gray M, vat black BBN, et...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/665C07C49/697C07C49/755C07C69/76C07C49/788C07C45/00C07C67/343C07D333/50C09B3/04C09B3/02C09B5/12
CPCC07C49/665C07C49/697C07C49/755C07C69/76C07C49/788C07D333/50C09B3/04C09B3/02C09B5/12
Inventor 韩建伟甘家安程毅
Owner SHANGHAI GANTIAN OPTICAL MATERIALS
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