Beta-phenanthrene azaBODIPY dye and preparation method and application thereof

A technology of fluoroborate dipyrrole and phenanthrene nitrogen, which is applied in the field of β-phenanthreneazepine fluoroborate dipyrrole dye and its preparation, and can solve the problems of unsatisfactory absorption wavelength, few types, poor solubility, etc.

Inactive Publication Date: 2016-11-16
ANHUI NORMAL UNIV
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  • Abstract
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  • Claims
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Problems solved by technology

[0004] In view of the above-mentioned prior art, the purpose of the present invention is to overcome the traditional azafluoroboron dipyrrole fluorescent dyes in the prior art, which cannot meet the near-infrared requirements due to their absorption wavelength, poor solubility, embarrassing position of fluorescence, poor optical selectivity, etc. The disadvantages make it impossible to be applied in some imaging techniques that require long-wave absorption and no fluorescence, and ordinary dyes with long-wave absorption not only have few types, but also have limitations in use, thus providing a relatively Long absorption wavelength and emission wavelength, good optical selectivity, high stability, and simple preparation steps, β-phenanthrene azafluoroboron dipyrrole dye with readily available raw materials and its preparation method and application

Method used

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  • Beta-phenanthrene azaBODIPY dye and preparation method and application thereof

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preparation example Construction

[0035] The present invention also provides a method for preparing a β-phenanthrene azinafluoroboron dipyrrole dye with the structure shown in formula (I), wherein the preparation method comprises:

[0036] 1) In the presence of palladium, the compound represented by formula (II) is subjected to a first contact reaction with arylboronic acid to prepare a mixture M1;

[0037] 2) In the presence of triethylamine, the mixture M1 obtained in step 1) is subjected to a second contact reaction with boron trifluoride ether to obtain a mixture M2;

[0038] 3) The mixture M2 is subjected to a third contact reaction with an oxidizing agent to obtain a β-phenanthreneazepinefluoroboron dipyrrole dye with a structure shown in formula (I);

[0039]

[0040]

[0041] Among them, R 1 Is C1-C6 alkoxy; R 2 and R 4 Each independently selected from C1-C6 alkoxy or C1-C6 alkyl; R 3 and R 5 each independently selected from hydrogen or C1-C6 alkoxy; X is halogen.

[0042] Certainly, the mi...

preparation example 1

[0062] Put 9g of potassium hydroxide in 30g of methanol solution and mix to prepare a methanol solution of potassium hydroxide, add 8g of p-methoxyacetophenone and 8g of p-methoxybenzaldehyde into the above-mentioned methanol solution of potassium hydroxide and react for 30min , a large amount of precipitate was obtained, and the chalcone was obtained by suction filtration; 14 g of the chalcone prepared above was mixed with 6 g of nitromethane, and then 7 g of diethylamine and 50 g of methanol were added and mixed and refluxed for 12 hours to obtain a mixture M1 ; After distilling the solvent in the above-mentioned mixture M1 under reduced pressure, get the solid mixture M2; add 50 g of methanol and 15 g of ammonium acetate to the above-mentioned solid mixture M2 and reflux for 12 hours to obtain a red metallic luster powder M3; The obtained powder M3 was placed in a round-bottomed flask, and 100 g of toluene was added therein to dissolve it and heated to 60°C, then 10 g of tri...

preparation example 2

[0065] Prepare according to the preparation method of Preparation Example 1, except that p-methoxyacetophenone is replaced by p-tert-butylacetophenone, and p-methoxybenzaldehyde is replaced by 3,4,5-trimethoxy Benzaldehyde, compound A2 was obtained. The proton nuclear magnetic spectrum and carbon nuclear magnetic spectrum parameters of the obtained compound A2 are as follows: 1 HNMR (300MHz, CDCl3) δ: 8.07-8.03(m, 8H), 7.08-6.97(m, 8H), 6.92(s, 2H), 3.89(s, 6H), 3.88(m, 6H). 13 C NMR (75MHz, CDCl3) δ: 161.7, 160.7, 157.8, 145.1, 142.8, 131.5, 130.8, 125.5, 124.4, 117.1, 114.2, 55.4.

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Abstract

The invention discloses a beta-phenanthrene azaBODIPY dye and a preparation method and application thereof. The structural formula of the beta-phenanthrene azaBODIPY dye is as shown in the formula (I) (please see the formula in the description), wherein R1 is alkoxy groups of C1-C6, R2 and R4 are independently selected from alkoxy groups of C1-C6 or alkyl groups of C1-C6, and R3 and R5 are independently selected from hydrogen or alkoxy groups of C1-C6. By means of the design, the prepared beta-phenanthrene azaBODIPY dye of the structure shown in the formula (I) has large absorption wavelength in actual use, narrow absorption peaks and emission peaks and excellent molar absorption coefficient, and thereby having potential application in optical sensors and photoacoustic imaging.

Description

technical field [0001] The invention relates to the field of dyes, in particular to β-phenanthreneazepinefluoroborate dipyrrole dyes and a preparation method and application thereof. Background technique [0002] Azafluoroboropipyrrole fluorescent dye (azaBODIPY) has good performances such as near-infrared absorption and narrow absorption and emission peaks, high molar absorptivity, good photostability and chemical stability, making it In the past two decades, it has been widely studied and used in the fields of biological imaging, photosensitizers, and ion probes. However, the traditional azaBODIPY fluorescent dyes have certain defects in application, such as their absorption wavelength cannot meet the near-infrared requirements, poor solubility, and the fluorescence is in an awkward position. And some imaging techniques require long-wave absorption and no fluorescence, such as photoacoustic contrast imaging. But there are few dyes with long-wave (about 800nm) absorption ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00G01N21/64G01N21/33A61K49/22
CPCA61K49/22C07F5/022C09B57/00C09K11/06C09K2211/1096G01N21/33G01N21/64G01N2021/6417
Inventor 盛万乐焦莉娟郝二宏
Owner ANHUI NORMAL UNIV
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