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Type I boron fluoride complex dipyrromethene dye, and preparation method and application thereof

A technology of dipyrrole methine and boron fluoride, applied in the directions of methine-based/polymethine-based dyes, chemical instruments and methods, organic dyes, etc., can solve the problems of uneasy operation of reaction process, difficult synthesis of raw materials, low yield, etc. Good photostability, high molar extinction coefficient, simple reaction steps

Inactive Publication Date: 2011-05-18
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In addition, Niko et al. used the asymmetric condensation of pyrrole containing free carboxyl groups and another molecule of substituted pyrrole to finally generate BODIPY fluorescent dyes with active carboxyl groups. However, the raw materials of this method are difficult to synthesize, and the entire reaction process is also not easy to operate. , the yield is also lower

Method used

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  • Type I boron fluoride complex dipyrromethene dye, and preparation method and application thereof
  • Type I boron fluoride complex dipyrromethene dye, and preparation method and application thereof
  • Type I boron fluoride complex dipyrromethene dye, and preparation method and application thereof

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preparation example Construction

[0076] The preparation method of the present invention is different from the traditional synthetic method of using aldehydes or acid chloride compounds to react with substituted pyrroles to prepare dyes, but uses acid anhydrides to directly react with substituted pyrroles, and the synthetic method is improved and optimized, so that the yield Up to 25%.

[0077] The boron fluoride complexed dipyrromethene fluorescent dye containing carboxylic acid and its derivatives of the present invention has a fluorescence quantum yield of 0.6-0.8, and the maximum ultraviolet absorption and fluorescence emission wavelengths are respectively at 495 ± 10nm and 510±10nm, the Stokes shift is between 10-20nm.

[0078] The boron fluoride complexed dipyrromethene fluorescent dye containing carboxylic acid and its derivatives of the present invention, when M in the fluorescent dye II, III or IV is a hydrogen proton, due to the presence of carboxylic acid groups, this type of dye is Low concentrati...

Embodiment 1

[0098] Synthesis of compound IIa:

[0099]

[0100] In the dry 250ml single-necked round bottom flask, add 204mg (1.8mmol) glutaric anhydride successively, 201mg (3mmol) pyrrole, then inject absolutely anhydrous fresh tetrahydrofuran 75ml with a syringe under nitrogen protection, control the reaction temperature as 55°C, magnetic stirring overnight, the color of the reaction solution is light brown; after cooling to room temperature and evaporating half of the solvent, slowly add 1.2g (12mmol) of anhydrous triethylamine under ice bath, after vigorously stirring for 10 minutes, drop Add 1.28g (9mmol) boron trifluoride ether solution. Keep stirring rapidly, and after the reaction solution returns to normal temperature, continue stirring for 4-8 hours. The whole reaction process was followed by TLC. After the reaction is complete, the mother liquor is poured into a separatory funnel, extracted with dichloromethane, washed with deionized water, and repeated three times, the o...

Embodiment 2

[0105] Synthesis of compound IIIa:

[0106]

[0107] In a 250mL single-necked round-bottom flask, add 160mg (1.6mmol) succinic anhydride and 201mg (3mmol) 1-hydropyrrole in sequence, then inject 10mL of dry acetonitrile and 50mL of DCM with a syringe under nitrogen protection, and stir rapidly with magnetic force to make the solid Dissolve (ultrasound or heating can also be used to promote dissolution), and then set up a condensing device and replace the reaction system with nitrogen for 3-5 times under vacuum, heat in an oil bath and reflux for overnight reaction; The mother liquor was cooled to room temperature, placed in an ice-water bath, and 2.4 g (24 mmol) of anhydrous triethylamine was slowly added dropwise. After vigorous stirring for 10 minutes, 2.56 g (18 mmol) of boron trifluoride ether solution was added dropwise. Keep stirring rapidly, after the reaction solution returns to normal temperature, slowly heat to 50°C, and continue stirring until no more fluorescent...

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Abstract

The invention relates to a type I boron fluoride complex dipyrromethene fluorescent dye. The fluorescent dye is shown as a general formula I, wherein R1, R2, R3, R5, R6 and R7 are H or C1-C8 alkyl respectively; R8 is a radical of a structural formula X, Y, Z or P; M is H, Na, K, N (R9R10R11R12) or N-succinimido; and R9, R10, R11 and R12 are H, C1-C8 alkyl or C1-C8 alkyl with substituent group-OH, an ether bond or carboxyl. The dye is synthesized by directly reacting substituted pyrrole with anhydride, has a high photo-physical property, stability, cell penetration capability and intracellular dissolving capability and is particularly suitable for bioluminescence analysis and biological marking.

Description

technical field [0001] The invention relates to a class of novel boron fluoride complexed dipyrromethene fluorescent dyes that can be used in the field of biological fluorescence analysis, and a preparation method and application thereof. Background technique [0002] Fluorescence analysis technology, as a traditional analysis method, has been greatly developed especially with the emergence and application of new fluorescence analysis technology in recent years. These new technologies have the advantages of high sensitivity, good selectivity, less sampling volume, fast and simple methods, etc., and have become an important tool for trace and ultra-trace or even molecular level analysis in various research fields. Fluorescence analysis methods can provide various physical parameters including excitation spectrum, emission spectrum and three-dimensional spectrum as well as fluorescence intensity, fluorescence efficiency and fluorescence lifetime. These parameters reflect vari...

Claims

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Application Information

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IPC IPC(8): C09B23/04C09K11/06G01N21/64G01N33/52
Inventor 彭孝军王东川樊江莉王丽孙世国张剑洲
Owner DALIAN UNIV OF TECH
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