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Fluorine-boron fluorescent dye as well as preparation method and application thereof

A fluorescent dye and fluoroboron technology, applied in the field of fluorescent dyes, can solve the problems of unavailable raw materials, small Stokes shift, complicated steps of fluoroboron fluorescent dyes, etc., and achieve the effect of easily available raw materials, simple steps, and excellent fluorescence quantum yield

Inactive Publication Date: 2014-06-18
ANHUI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] The purpose of the present invention is to overcome the defects that the Stokes shift of fluoroboron fluorescent dye is relatively small in the prior art, it is easy to quench fluorescence, and the steps of synthesizing fluoroboron fluorescent dye are complicated, and the raw materials are not easy to obtain, and to provide a brand-new one with higher fluorescence Fluoroboron fluorescent dye with quantum yield and larger Stokes shift and the method for preparing fluoroboron fluorescent dye with simple steps and easy-to-obtain raw materials

Method used

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  • Fluorine-boron fluorescent dye as well as preparation method and application thereof
  • Fluorine-boron fluorescent dye as well as preparation method and application thereof
  • Fluorine-boron fluorescent dye as well as preparation method and application thereof

Examples

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preparation example Construction

[0034] The present invention also provides a preparation method of fluoroboron fluorescent dye, the structure of which is shown in formula (I) or formula (II), wherein the preparation method includes the following steps:

[0035] In the presence of a Lewis acid, after the first contact reaction between the compound represented by the formula (X) and the reactant C, the product after the first contact reaction is obtained, and trifluoro is added to the obtained product after the first contact reaction Carry out the second contact reaction with boron ether;

[0036] The reactant C is selected from compounds of formula (V) or formula (VI),

[0037]

[0038] In formula (X), R 1 is H or halogen; preferably, in formula (X), R 1 For H or Br.

[0039] In formula (V) and formula (VI), R 2 is CN; R 3 , R 4 , R 5 and R 6 Each independently selected from H, halogen, C1-C6 alkyl or C1-C6 alkoxy; V, W, X, Y and Z are each independently CH or N, and in V, W, X, Y Or when Z is N, ...

preparation example 1

[0061] Preparation of raw material 4-bromo-1,8-naphthoimide: Put 0.52g (3.1mmol) of 1,8-naphthoimide in a 50ml round-bottomed flask, add 15ml of chloroform, cool to 0°C, and stir Add 0.16ml (3.1mmol) of bromine dropwise to the solution, drop it within 1min, then place the reaction at 20°C and stir for 24 hours. After the reaction is complete, extract with chloroform and dry to obtain a light yellow solid. The pale yellow solid was detected by H NMR spectroscopy to obtain: 1 H NMR (300MHz, CDCl 3 )δ8.21(d,J=8.1Hz,1H),8.13(d,J=8.1Hz,1H),7.80-7.87(m,2H),7.67(d,J=7.5Hz,1H),6.85( d, J=7.5Hz, 1H).

Embodiment 1

[0063] Preparation of boron fluorescent dye represented by formula (A1):

[0064]

[0065] In a 50ml round-bottomed flask, add 1,8 naphthalimide (60mg, 0.36mmol) and 2-aminopyridine (171mg, 1.8mmol), add 20ml of toluene, put it in an oil bath at 110°C and stir to reflux, then Triethylamine (1ml, 7.17mmol) and titanium tetrachloride (0.3ml, 2.7mmol) were added, and after 12 hours of reaction, boron trifluoride ether (1ml, 8.10mmol) was added, and the reaction was continued for 4 hours. After the reaction, it was cooled, extracted three times with 50 mL of dichloromethane, dried over anhydrous sodium sulfate, distilled under reduced pressure, and silica gel column chromatography was used to obtain a yellow solid with a yield of 42%.

[0066] 1 H NMR (300MHz, CDCl 3 )δ8.45(d,J=6.3Hz,1H),8.30(d,J=7.2Hz,1H),8.10((d,J=5.1Hz,1H),7.93-7.99(m,1H),7.75 -7.80(m,1H),7.54-7.69(m,4H),7.22-7.24(m,1H); 13 C NMR (75MHz, CDCl 3 ) 160.9, 155.3, 141.7, 140.4, 138.6, 131.4, 130.1, 129.5, 1...

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Abstract

The invention discloses a fluorine-boron fluorescent dye as well as a preparation method and application thereof, wherein the structure of the fluorine-boron fluorescent dye is shown as a formula (I) or a formula (II), in the formula (I) and the formula (II), R1 is H or halogen; R2 is CN; R3, R4, R5 and R6 are independently selected from H, halogen, C1-C6 alkyl or C1-C6 alkoxy; V, W, X, Y and Z are independently CH or N, and when V, W, X, Y or Z is N, N has no substituent group. According to the fluorine-boron fluorescent dye and the preparation method thereof, the maximal fluorescence emission wavelength of the fluorine-boron fluorescent dye is 518-600nm, and the fluorine-boron fluorescent dye also has excellent fluorescence quantum yield and Stokes shift, which shows that the fluorine-boron fluorescent dye has good application prospect in the bioanalysis fields of fluorescence labeling, bioimaging and so on; meanwhile, the preparation method is simple in steps, and raw materials can be obtained easily.

Description

technical field [0001] The invention relates to the field of fluorescent dyes, in particular to a fluoroboron fluorescent dye and its preparation method and application. Background technique [0002] Fluoroboron dipyrrole fluorescent dye (BODIPY) is a kind of fluorescent dye molecule with excellent photophysical and chemical properties developed in the past two decades. It has narrow absorption and emission peaks, high molar absorptivity, high Fluorescence quantum yield, good photostability and chemical stability. However, the traditional BODIPY fluorescent dyes have certain defects in application, such as their relatively small Stokes shift and easy fluorescence quenching. [0003] Therefore, it is of great significance to prepare a new fluoroboron fluorescent dye with higher fluorescence quantum yield and larger Stokes shift. At the same time, in the prior art, either step Complicated, or the raw materials are not easy to obtain, multi-step synthesis is required and the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06C07F5/02G01N21/64G01N21/33
Inventor 郝二宏高乃勋焦莉娟
Owner ANHUI NORMAL UNIV
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