Pyrrole methenyl fluorescent dye and preparation method thereof

A fluorescent dye, pyrromethine technology, applied in the field of pyrromethine fluorescent dyes and its preparation, can solve the problems of complicated separation and purification, difficult to obtain raw materials, and low product yield, and achieve simple operation, easier separation and purification, and short preparation steps Effect

Inactive Publication Date: 2014-01-29
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to overcome the disadvantages of the existing pyrromethine fluorescent dye preparation method, which are cumbersome steps, harsh conditions, difficult to obtain raw materials, complicated separation and purification, and low product yield, and provide a simple, quick, mild and efficient, easy-to-obtain raw material , easy-to-operate, easy-to-purify pyrromethene fluorescent dye and preparation method thereof

Method used

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  • Pyrrole methenyl fluorescent dye and preparation method thereof
  • Pyrrole methenyl fluorescent dye and preparation method thereof
  • Pyrrole methenyl fluorescent dye and preparation method thereof

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preparation example Construction

[0021] The preparation method of the pyrromethene fluorescent dye is as follows: put the cyclopentadienone derivative and the ammonium salt with a molar ratio of 1:4-200 into a sealed tube reactor or an autoclave, add an organic solvent and heat it in a sealed manner, and heat it at 100 React at -140°C for 2-24 hours at 1-10 atmospheres.

[0022] The structural formula of the cyclopentadienone derivative is , where Ar 1 is phenyl, C 1 -C 10 Alkyl substituted phenyl, C 1 -C 10 Halogen partially substituted and fully substituted alkyl phenyl, C 1 -C 10 Alkoxy substituted phenyl, fluorine, chlorine, bromine, iodine substituted phenyl, phenylethynyl or biphenyl; Ar 2 is phenyl, C 1 -C 10 Alkyl substituted phenyl, C 1 -C 10 Halogen partially substituted and fully substituted alkyl phenyl, C 1 -C 10 Alkoxy substituted phenyl, fluoro, chloro, bromo, iodo substituted phenyl, phenylethynyl or biphenyl.

[0023] The ammonium salt is one or more of ammonium acetate, ammoni...

Embodiment 1

[0026] Synthesis of (Z)-2,3,4-triphenyl-5-(phenyl(3,4,5-triphenyl-2H-pyrrole-2-ylidene)methyl)-1H-pyrrole

[0027]

[0028]The following steps are adopted: (1) Add 0.384 grams of tetraphenylcyclopentadienone derivatives in the above picture to a 15 ml sealed tube reactor, add 0.31 grams of ammonium acetate, add 2 ml of acetic acid, heat to 100 ° C, and react for 12 hours . Then cooled to room temperature, the reaction mother liquor was poured into 100ml of water, extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, and the solvent was removed by rotary evaporation. and then separated by column chromatography. Obtained dark red powdery solid 0.28 g, 82%. 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (s, 2H), 7.98 (s, 2H), 7.56 (s, 4H), 7.54 (s, 4H), 7.45 (t, J = 7.3 Hz, 4H), 7.41 (d, J = 7.1 Hz, 4H), 7.37 – 7.29 (m, 15H). MS (MALDI) ( m / z ): 676.2875 (M+).

Embodiment 2

[0030] (Z)-3-(3-methoxyphenyl)-2-((3-methoxyphenyl)(3-(3-methoxyphenyl)-4,5-diphenyl-2H -pyrrole-2-ylidene)methyl)-4,5-diphenyl-1H-pyrrole

[0031]

[0032] The following steps are adopted: (1) Add 0.444 grams of tetraphenylcyclopentadienone derivatives in the above picture to a 15 ml sealed tube reactor, add 1.54 grams of ammonium acetate, add 2 ml of toluene, heat to 110 ° C, and react for 24 hours . Then cooled to room temperature, the reaction mother liquor was poured into 100ml of water, extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, and the solvent was removed by rotary evaporation. and then separated by column chromatography. Obtained dark red powdery solid 0.29 g, 76%. 1 H NMR (400 MHz, CDCl 3 ) δ 14.95 (s, 1H), 7.49 (d, J = 6.5 Hz, 5H), 7.29 (m, 5H), 7.13 (m, 6H), 6.99 (m, 4H), 6.68 (d, J = 8.1 Hz, 2H), 6.44 (d, J = 8.4 Hz, 4H), 6.22 (d, J = 8.3 Hz, 4H), 5.92 (d, J = 7....

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Abstract

The invention relates to a preparation method of a pyrrole methenyl fluorescent dye. Cyclopentenone derivant and ammonium salt with the mole ratio of 1:4-200 are put in a seal tube reactor or an autoclave, the seal tube reactor or the autoclave is sealed and heated after an organic solvent is added, and reaction is carried out for 2-24 hours at the temperature of 100-140 DEG C and 1-10 atmospheres. Compared with the existing synthesis method of deriving from aromatic aldehyde and pyrrole, easy-to-make and easy-to-obtain carbonyl compound-cyclopentenone derivant and inorganic ammonium salt are adopted as raw materials, and compared with the conventional pyrrole preparation way, the preparation method disclosed by the invention has the advantages that the raw material source scope is wide, the whole preparation step is short, the operation is simple, the production rate is high, synthesis steps of protection and deprotection are avoided, multiple substituents can be obtained in one step, and products are easier to separate and purify.

Description

technical field [0001] The invention relates to a pyrromethene fluorescent dye and a preparation method thereof. Background technique [0002] Pyrromethene and its derivatives are a class of very useful and important compounds and intermediates, which have very important applications in fluorescent dyes, lasers, cell staining, and ion detection. For example, it is used to prepare pyrromethene boron difluoride fluorescent dye (BODIPY), (Chem. Rev., 2007, 107, 4891.), which is based on the strong fluorescence, absorption and emission of pyrromethene boron difluoride dye in the visible region The band is relatively narrow, the quantum efficiency is high, and it can be used in many fields such as fluorescent dyes, molecular probes, and cell staining. [0003] In addition, since the discovery of pyrromethene-metal complexes in the early 1990s, research on their structures and properties has become a hot spot in the field of scientific research. This is not only because their ni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/04C09K11/06
Inventor 李继超胡公方吕萍王彦广
Owner ZHEJIANG UNIV
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