Fluoroboron fluorescent dye and its preparation method and application

A fluorescent dye, fluorine and boron technology, applied in the field of fluorescent dyes, can solve the problems of unobtainable raw materials, complicated steps of fluorine and boron fluorescent dyes, small Stokes shift, etc., and achieves easy availability of raw materials, excellent fluorescence quantum yield, narrow absorption and emission. peak effect

Inactive Publication Date: 2016-03-30
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Fluoroboron fluorescent dye and its preparation method and application
  • Fluoroboron fluorescent dye and its preparation method and application
  • Fluoroboron fluorescent dye and its preparation method and application

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preparation example Construction

[0028] The present invention also provides a preparation method of fluoroboron fluorescent dye, the structure of the fluoroboron fluorescent dye is shown in formula (III) or formula (IV), characterized in that the preparation method includes the following steps:

[0029] 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;

[0030] The reactant C is selected from compounds of formula (VII) or formula (VIII),

[0031]

[0032] In formula (X), R 1 is H or halogen; preferably, in formula (X), R 1 For H or Br.

[0033] In formula (VII) and formula (VIII), R 2 is CN; R 7 , R 8 Each is independently H or C1-C6 alkyl, R 9 Selected from H, C1-C6 alkyl or C1-C6 alkoxy; V is CH or N, and when V is N, th...

preparation example 1

[0056] 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) 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, pour the mixture into your hand, extract with chloroform, and dry it to light yellow solid.

[0057] The proton nuclear magnetic spectrum detection is carried out to above-mentioned product: 1 HNMR (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).

preparation example 2

[0059] Preparation of raw material 2-amino-6-tert-butylbenzothiazole: Weigh 7.45g of 4-tert-butylaniline and 9g of sodium thiocyanate in a 100ml flask, add 50ml of glacial acetic acid, slowly add 3ml of bromine under stirring , react at 15°C for 3 hours, then pour the mixture into a mixture of 100ml ice water and 100ml ammonia water, stir, a large amount of yellow solid is formed, filter it with suction, wash the solid with water at the same time, and dry it in the air to obtain a yellow solid .

[0060] The proton nuclear magnetic spectrum detection is carried out to above-mentioned product: 1 HNMR (400MHz, CDCl 3 )δ7.6(d, J=2.0Hz, 1H), 7.47(d, J=8.6Hz, 1H), 7.37(m, 1H), 5.30(br, 2H), 1.35(s, 9H).

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Abstract

The invention discloses a fluoroboron fluorescent dye and a preparation method and an application thereof, wherein the structure of the fluoroboron fluorescent dye is shown in a formula (III) or a formula (IV); in the formulae (III) and (IV), R1 is H or halogen, R2 is CN, R7 and R8 are independently H or C1-C6 alkyl, R9 is H, C1-C6 alkyl or C1-C6 alkoxyl, V is CH or N, and when V is N, no substituents are available on N. According to the fluoroboron fluorescent dye provided by the invention, the maximum fluorescent emission wavelength of the fluoroboron fluorescent dye prepared by the method provided by the invention ranges from 518nm to 600nm. Meanwhile, the fluoroboron fluorescent dye further has excellent fluorescence quantum yield and Stokes displacement, which means that the fluoroboron fluorescent dye has a good application prospect in the bioanalysis field such as fluorescence labeling and bioimaging. Meanwhile, the preparation method has simple steps and uses easily available raw materials.

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 brand-new fluoroboron fluorescent dye with higher fluorescence quantum yield and larger Stokes shift. At the same time, the methods for synthesizing novel BODIPY fluorescent dye analogues in the prior art are either complicated in steps , or t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/14C07D513/12C07D513/00C09B57/00C09K11/06G01N21/64
Inventor 郝二宏高乃勋焦莉娟
Owner ANHUI NORMAL UNIV
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