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Pyrrole pyridine hydrazine difluoroboron fluorescent dye and its preparation method and application

A technology of pyrrole pyridine hydrazine and fluorescent dyes, applied in hydrazone dyes, luminescent materials, fluorescence/phosphorescence, etc., can solve problems such as undiscovered two-photon performance

Active Publication Date: 2020-05-05
ANHUI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this type of BOPHY fluorescent dye has not been found to have the corresponding two-photon performance

Method used

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  • Pyrrole pyridine hydrazine difluoroboron fluorescent dye and its preparation method and application
  • Pyrrole pyridine hydrazine difluoroboron fluorescent dye and its preparation method and application
  • Pyrrole pyridine hydrazine difluoroboron fluorescent dye and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0052] Synthesis of Pyrropyridinehydrazine Difluoroboron Fluorescent Dye 1aa:

[0053]

[0054] 2-Pyrrole aldehyde (190mg, 2mmol) and pyridine hydrazine (230mg, 2.1mmol) were dissolved in 2-dichloroethane (60ml), and p-toluenesulfonic acid (87mg, 0.05mmol) was added. The reaction mixture was heated to reflux for 6 h, followed by TLC spot plate. When the 2-pyrrole aldehyde derivative disappears on the silica gel plate, that is, when the reaction is complete, add 2-10 mL of N,N-diisopropylethylamine into the reaction system. After the reaction mixture was stirred for 10 min, boron trifluoride ether (3-20 ml) was added, and the reaction system was stirred and refluxed for 1-24 h. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, and dichloromethane and water were added. The organic phase was separated, the corresponding aqueous phase was extracted several times with dichloromethane, and the organic layers were combined. Wash wit...

Embodiment example 2

[0057] Synthesis of pyrrolizidine difluoroboron fluorescent dye 1ba:

[0058]

[0059] According to the method of Example 1, the difference is that starting from 2,4-dimethylpyrrole aldehyde (246mg, 2mmol) and pyridine hydrazine (230mg, 2.1mmol), the yield of 1ba was 42% (260mg). 1 H NMR (300MHz, CDCl 3 ): δ=7.88(d, J=5.4Hz, 1H), 7.82(t, J=8.1Hz, 1H), 7.65(s, 1H), 7.48(d, J=8.7Hz, 1H), 6.88(t ,J=6.6Hz,1H),6.15(s,1H),2.49(s,3H),2.29(s,3H). 13 C NMR (75MHz, CDCl 3 ): δ=152.0, 147.8, 142.9, 136.6, 136.0, 129.1, 122.9, 117.7, 114.4, 111.3, 14.0, 10.9. 19 F NMR (470MHz, CDCl 3 ): δ=-141.5(d, J=30.6Hz, 1F), -141.7(d, J=30.1Hz, 1F), -145.7(d, J=24.0Hz, 1F), -145.8(d, J= 24.4Hz,1F).HRMS(APCI)Calcd.For C 12 h 13 B 2 f 4 N 4 [M+H] + :311.1262, found 311.1260.

Embodiment example 3

[0061] Synthesis of pyrrolizidine difluoroboron fluorescent dye 1ca:

[0062]

[0063] Carry out according to the method of embodiment case 1, difference is to set out from 2,4-dimethyl-3-ethylpyrrole aldehyde (304mg, 2mmol) and pyridine hydrazine (230mg, 2.1mmol), the productive rate of preparation 1ca is 46 % (310 mg). 1 H NMR (300MHz, CDCl 3 ): δ=7.88(d, J=5.7Hz, 1H), 7.80(t, J=7.5Hz, 1H), 7.61(s, 1H), 7.48(d, J=8.7Hz, 1H), 6.87(t ,J=6.6Hz,1H),2.49-2.42(m,5H),2.23(s,3H),1.08(t,J=7.5Hz,3H). 13 C NMR (125MHz, CDCl 3 ): δ=151.9, 146.2, 142.7, 136.0, 133.4, 130.7, 128.5, 122.1, 114.2, 111.3, 17.2, 14.8, 12.0, 9.2. 19 F NMR (470MHz, CDCl 3 ):δ=-141.3(d,J=26.3Hz,1F),-141.5(d,J=29.1Hz,1F),-145.7(d,J=23.0Hz,1F),-145.8(d,J=23.0Hz,1F) 23.5Hz,1F).HRMS(APCI)Calcd.For C 14 h 16 B 2 f 3 N 4 [M-F] + :319.1513,found319.1522.

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Abstract

The invention discloses a pyrrolidine double-fluorine-boron strong fluorescent dye and a preparation method and application thereof, wherein the structure is as shown in formula (1), R1, R2 and R3 areH or C1-C6 linear or branched alkyl group, R5 is H, Cl, xylylene group, nonane group, benzene ring group, OR9, NR9R10, or SR9. R4, R6, R7 and R8 are each independently H, C1-C6 linear or branched alkyl, C1-C6 linear or branched cycloalkane group; wherein R9 and R10 are each independently H, CH2COOEt, oxo group, xylyl group, C1-C6 linear or branched alkyl or C1-6 linear or branched cycloalkane group; the pyrrolidine double-fluorine-boron strong fluorescent dye has the advantages of up to 998 GM double-photon absorption cross section at 700-900nm, high molar absorption coefficient, high fluorescence quantum yield, high light stability and double photon fluorescence and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis and preparation of fluorescent dyes, in particular to pyrrole pyridine hydrazine difluoroboron fluorescent dye and its preparation method and application. Background technique [0002] In recent years, two-photon confocal fluorescence microscopy can effectively avoid photobleaching and phototoxicity by virtue of its ability to use infrared laser excitation with relatively strong penetrating power. It is used in super-resolution tomography and three-dimensional imaging of living cells and biological tissues It has higher spatial resolution and tomographic imaging capabilities, which has aroused great interest. Therefore, it is of great significance to design and develop two-photon fluorescent dyes with practical value, large two-photon absorption cross section, high photophysical and chemical stability and good chemical diversity. [0003] Organoboron fluorescent dyes have attracted much attention...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09B26/02C09K11/06G01N21/64
CPCC07F5/022C09B26/02C09K11/06C09K2211/107G01N21/6486
Inventor 于长江郝二宏焦莉娟黄维扬
Owner ANHUI NORMAL UNIV
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