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Boro-isoindole fluorescent dye and preparation method and applications thereof

A fluorescent dye, isoindole boron technology, applied in the field of fluorescent dyes, can solve the problems of cumbersome preparation process, complicated method, and low quantum yield

Active Publication Date: 2017-07-14
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, the preparation process of most isoindolebora near-infrared fluorescent dyes is cumbersome and complicated, and the obtained isoindolebora near-infrared fluorescent dyes have poor spectral selectivity, low quantum yield and poor water solubility. Well, not good for further application

Method used

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  • Boro-isoindole fluorescent dye and preparation method and applications thereof
  • Boro-isoindole fluorescent dye and preparation method and applications thereof
  • Boro-isoindole fluorescent dye and preparation method and applications thereof

Examples

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preparation example Construction

[0048] The present invention also provides a method for preparing the above-mentioned isoindole bora fluorescent dye, wherein the preparation method comprises the following steps:

[0049] In the presence of a solvent, the halogenated hydrocarbon (R13-X) and the compound represented by the formula (II) are stirred at 20-25°C for 12-15h in the dark according to the molar ratio of 1:5-10, and then purified. Promptly obtain the isoindole bora fluorescent dye shown in formula (I);

[0050]

[0051] Wherein, R1, R2, R3, R4 are each independently hydrogen, C1-C12 alkyl, halogen or C1-C12 alkoxy;

[0052] R5, R6, R7, R8 are each independently hydrogen, C1-C12 alkyl, halogen, C1-C12 alkoxy, cycloalkyl or aryl;

[0053] R9 is hydrogen, alkenyl or C1-C12 alkyl;

[0054] R10 and R11 are each independently hydrogen, C1-C12 alkyl, halogen or alkenyl;

[0055] R12 is hydrogen, C1-C12 alkyl, halogen, alkenyl or C1-C12 alkoxy;

[0056] The R13 is a C1-C12 alkyl group, and X is a haloge...

preparation example 1

[0077] Preparation of raw material 1-(3-bromo-1H-isoindol-1-ylidene)-N,N-dimethylmethylamine: 1.5g (5.24mmol) POBr 3 Place in a 250ml round bottom flask, add 50ml of dichloromethane, cool to 0°C, add 0.27ml (3.49mmol) DMF dropwise to the solution under stirring, drop it within 5min, then place the reaction at 20°C and stir After 0.5 hours, cool to 0° C., weigh 1.0 g (7.5 mmol) of isoindol-1-one, dissolve it in dichloromethane, place it in a constant-pressure dropping funnel, and add it dropwise to the above mixture. After the dropwise addition was completed, it was transferred to an oil bath at 60°C and heated to reflux, and the plate was spotted by TLC. After 2.5 hours, the reaction was complete. After cooling to room temperature, 100ml of ice water was added, and the pH value was adjusted to 8 with sodium carbonate, extracted, concentrated, passed through a column, and recrystallized to obtain a light yellow solid.

preparation example 2

[0079] Preparation of raw material (2-hydroxyphenyl)-2H-isoindole-1-carbaldehyde: Weigh 1-(3-bromo-1H-isoindole-1-ylidene)-N,N-dimethylformaldehyde Amine 400mg (1.66mmol), 2-hydroxyphenylboronic acid 331mg (3.5mmol) Na 2 CO 3 (1M, 5mL) in a 100ml Schlenk reactor, add Pd(PPh 3 ) 4 60mg, (0.05mmol), after flushing three times and releasing three times, moved to a 75°C oil bath and heated and stirred for 12h. After cooling to room temperature, it was extracted with water, and the organic phase was collected, dried over anhydrous sodium sulfate, and evaporated with a rotary evaporator to obtain a yellow solid. After dissolving with absolute ethanol, add saturated sodium hydroxide solution and heat to reflux for 3h. After removing ethanol, extract with water and ethyl acetate, neutralize with dilute HCl (3M) to pH 7, collect the organic phase, dry over anhydrous sodium sulfate, rotary evaporate with a rotary evaporator, and recrystallize to obtain a yellow solid

[0080] (2-H...

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Abstract

The invention discloses a boro-isoindole fluorescent dye and a preparation method and applications thereof. The structure of the boro-isoindole fluorescent dye is represented by the formula (I). The provided boro-isoindole fluorescent dye has the advantages of good spectral selectivity, excellent fluorescence quantum yield, and good solubility, can carry out derivation through Knoevenagel reactions, has high water solubility and a good cell penetrating performance after salt forming, and can be applied to imaging for positioning mitochondria at the same time.

Description

technical field [0001] The invention relates to the field of fluorescent dyes, in particular to isoindole bora fluorescent dyes and their preparation methods and applications. Background technique [0002] Near-infrared fluorescent dyes have been widely used in bioimaging, photodynamic therapy photovoltaics and optoelectronics due to their excellent performance, and have received extensive attention in recent years (Chem. Rev., 2012, 112, 4391). For example, near-infrared fluorescent dyes can be used in biological imaging, which has the advantages of low background interference and strong sample penetration, and can realize real-time in situ online non-destructive detection of cells and sub-cells in some biological samples such as living tissues, and can be used in Monitoring biomolecules and their movement processes in living cells and living bodies has shown good application prospects in chemical biology and clinical examination and diagnosis. At present, there are very l...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/02C09K11/06C09K2211/1007C09K2211/1029C09K2211/104C09K2211/1055G01N21/6486
Inventor 焦莉娟陈娜于长江郝二宏
Owner ANHUI NORMAL UNIV
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