Indole squaraine dye and preparation method and application thereof

A technology of indole squaraine and dyes, which is applied in the field of indole squaraine dyes and its preparation, can solve the problems of low singlet oxygen quantum yield and achieve low singlet oxygen quantum yield and high yield , the effect of good application prospects

Active Publication Date: 2019-08-16
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides an indole squaraine dye and its preparation method and application, which are used to solve the problem of low singlet oxygen quantum yield in the existing squaraine dye used in photodynamic therapy

Method used

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  • Indole squaraine dye and preparation method and application thereof
  • Indole squaraine dye and preparation method and application thereof
  • Indole squaraine dye and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0060] In this example, the compound of formula (III) was prepared by p-iodophenylhydrazine and 3-methyl-2-butanone.

[0061] Dissolve p-iodophenylhydrazine (1.17g, 5mmol) and 3-methyl-2-butanone (0.52g, 6mmol) in 30ml of glacial acetic acid, heat to reflux for 3h for the second reaction, cool to room temperature, and remove by rotary evaporation The solvent was extracted with ethyl acetate and water, and the extracted product was dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation, and then purified with petroleum ether and ethyl acetate (volume ratio of 2:1) to obtain an orange oily liquid that was The compound with the structure shown in (III) was 1.09 g, the purity was 98%, and the yield was 76.5%.

[0062]

[0063] The nuclear magnetic data of the compound of structure shown in formula (III): 1 H NMR (400MHz, CDCl 3 ) δ 7.56–7.49 (m, 2H), 7.20 (d, J=7.9Hz, 1H), 2.16 (s, 3H), 1.18 (s, 6H).

Embodiment 2

[0065] In this example, the compound (SQ) with the structure represented by formula (II) was prepared by the compound represented by formula (III) and squarylium.

[0066] Under nitrogen protection, put squarylium (0.11g, 1mmol) in 10ml of n-butanol and 10ml of toluene in a Dean-Stark apparatus. After heating to reflux for 1h, squarylium was dissolved in a binary solvent system to obtain a reaction solution. The compound (0.57g, 2mmol) with the structure represented by formula (III) was dissolved in 5ml of n-butanol and 5ml of toluene, added dropwise to the reaction solution, and the reaction was stopped after the first reaction for 3h. Cool the first reaction product to precipitate a solid precipitate, add n-hexane to filter and wash the precipitate, then add dichloromethane and water to dissolve and extract the precipitate, dry it with anhydrous sodium sulfate, and rotate it to evaporate, then use a volume ratio of 1:1 The mixed solution of dichloromethane and petroleum ethe...

Embodiment 3

[0070] In this example, SQ-1 was prepared by the compound of formula (II) and aryl boronic acid.

[0071] The compound (324.2 mg, 0.5 mmol) of the structure shown in formula (II) and tetrakis (triphenylphosphine) palladium (57.7 mg, 0.05 mmol) were dissolved in 15 ml of ethylene glycol dimethyl ether, under nitrogen protection, After vacuuming, add phenylboronic acid (134.2mg, 1.1mmol) and saturated sodium bicarbonate solution (168.1mg, 2mmol), heat the temperature to 95°C for 4h Suzuki-Miyaura coupling reaction, Suzuki-Miyaura coupling reaction The product was washed three times with a saturated aqueous solution of ammonium chloride, the solvent was removed by rotary evaporation, extracted with dichloromethane and water, dried with anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and finally the solvent was removed with a volume ratio of 2:1 petroleum ether The mixed solution with dichloromethane was purified by column chromatography to obtain a green ...

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Abstract

The invention belongs to the technical field of squaraine dyes, and particularly relates to an indole squaraine dye and a preparation method and application thereof. The provided indole squaraine dyehas a structural formula shown in the formula (I), wherein R is a phenyl, an anthryl or a pyrenyl. The indole squaraine dye has a high molar extinction coefficient in the near-infrared region, has strong absorption in the near-infrared region, has obvious effects in sensitized singlet oxygen, can be used as a triplet photosensitizer, has a good application prospect in the field of photodynamic therapy, and can solve the problem that the existing squaraine dye has low quantum yield of the singlet oxygen in photodynamic therapy.

Description

technical field [0001] The invention belongs to the technical field of squaraine dyes, in particular to an indole squaraine dye and its preparation method and application. Background technique [0002] At present, the application and research of various squaraine dyes have been reported in many journals and chemical journals. The optical disks used by people are made of squaraine dye coating film, squaraine dye can also be used in liquid crystal display, organic solar cell research, nonlinear optical materials and other fields. The study also found that squaraine dyes have fluorescence emission in the near-infrared region, and this fluorescence emission is very strong, which can be used as a fluorescent probe in the field of life sciences. Moreover, squaraine dyes also have the prospect of being used in photodynamic therapy. [0003] Photodynamic therapy (Photodynamic therapy, PDT) is a new technology that utilizes photodynamic effects for disease diagnosis and treatment. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10A61K41/00
CPCA61K41/0057C09B23/105
Inventor 籍少敏张碧玮霍延平梁亮梁辉
Owner GUANGDONG UNIV OF TECH
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