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An efficient near infrared fluorescent material and biological applications thereof

A near-infrared and fluorescent dye technology, applied in the application fields of high-efficiency near-infrared fluorescent dyes, bioimaging and fluorescent labeling, can solve the problems of fluorescence analysis technology measurement error, decrease in fluorescence intensity, dye self-quenching, etc., and achieve high solid state Effects of fluorescence quantum efficiency and resistance to photobleaching

Active Publication Date: 2016-11-09
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the small Stokes shift can cause the problem of dye self-quenching, also known as dye self-absorption
This is because the absorption spectrum and the emission spectrum of the dye with a small Stokes shift overlap greatly, so that part of the emitted light of the dye can be absorbed by itself, resulting in a decrease in fluorescence intensity
Another problem is the measurement error caused by the fluorescence analysis technique
This is because the small Stokes shift makes the excitation wavelength too close to the fluorescence detection wavelength, and the excitation wavelength is likely to cause scattered light interference to the fluorescence detection slit

Method used

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  • An efficient near infrared fluorescent material and biological applications thereof
  • An efficient near infrared fluorescent material and biological applications thereof
  • An efficient near infrared fluorescent material and biological applications thereof

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Experimental program
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Effect test

preparation example Construction

[0021] Preparation of precursors

[0022] Compound 1:

[0023] p-Bromophenylacetonitrile (5g, 25.505mmol) and iodine (6.5734g, 25.505mmol) were placed in a 250mL reaction bottle, replaced by argon three times until there was no oxygen and water in the bottle, and 100mL of dry ether was added and stirred to dissolve. Dissolve sodium methoxide (2.8933g, 5.356mmol) in anhydrous methanol (8.680g, 14.613ml), deoxygenate and water, slowly drop into the above solution at -78 degrees Celsius, and keep Argon atmosphere. After the dropwise addition, the temperature was slowly raised to 0°C, and the stirring reaction was continued for 3 hours. After the reaction was completed, the reaction was quenched with 5% dilute hydrochloric acid solution, and then stirred for 12 hours. After the reaction was complete, the solution was filtered with suction, and the filter cake was washed twice with methanol and water. The resulting solid was dried in a vacuum oven. The final product was compou...

Embodiment 1

[0027] Take compound 2 (159.6mg, 0.52mM), p-dianilinostyrene (140mg, 0.52mM), Pd(OAc) respectively 2 (6mg, 0.026mM), Ag 2 CO 3 (85 mg, 0.31 mM) was added to a 50 mL Schlenk tube, about 10 mL of toluene was added, and the reaction was heated at 100 degrees Celsius for 18 hours. After the reaction, the reaction solution was filtered, the filtrate was spin-dried to dry the solvent, and purified by a silica gel column to obtain a deep red powder product compound 3 with a yield of 53.4%. 1HNMR (500MHz, DMSO) δ7.82 (ddd, J = 13.8, 8.6, 6.0Hz, 9H), 7.55 (d, J = 8.7Hz, 2H), 7.43 (s, 1H), 7.39 (s, 1H), 7.33(dd, J=8.3, 7.5Hz, 4H), 7.22(s, 1H), 7.19(s, 1H), 7.11–7.03(m, 6H), 6.96(d, J=8.6Hz, 2H).Ms (m / e): C 36 h 25 N 3 , calcd499.6; found499.6. Elemental analysis experimental value (calculated value): C: 86.6% (86.55%); H: 5.0% (5.04%); N: 8.4% (8.41%).

[0028] Depend on figure 1 It can be seen that the maximum absorption peak of the tetrahydrofuran solution of compound 3 is 45...

Embodiment 2

[0032] Take compound 1 (200mg, 0.52mM), p-dianilinostyrene (280mg, 1.04mM), Pd(OAc) respectively 2 (12mg, 0.052mM), Ag 2 CO 3 (170 mg, 0.62 mM) was added to a 50 mL Schlenk tube, about 10 mL of toluene was added, and the reaction was heated at 100 degrees Celsius for 18 hours. After the reaction was completed, the reaction solution was filtered, the filtrate was spin-dried to dry the solvent, and purified by a silica gel column to obtain compound 4 as a dark red powder with a yield of 62.8%. 1 HNMR (500MHz, DMSO) δ7.87(d, J=8.6Hz, 4H), 7.82(d, J=8.6Hz, 4H), 7.58(d, J=8.8Hz, 4H), 7.43(d, J=8.6Hz, 4H) 16.3Hz, 4H), 7.38–7.33(m, 8H), 7.23(d, J=16.5Hz, 4H), 7.13–7.06(m, 11H), 6.98(d, J=8.7Hz, 4H).Ms( m / e): C 56 h 40 N 4 , calcd768.33; found767.136. Elemental analysis experimental value (calculated value): C: 87.5% (87.47%); H: 5.2% (5.24%); N: 7.3% (7.29%).

[0033] Depend on figure 2 It can be seen that the maximum absorption peak of compound 4 is 472nm, and the maximum e...

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Abstract

Efficient near infrared fluorescent dye having a large Stokes shift and applications thereof in the fields of biological imaging and fluorescent labeling, and other fields are disclosed, and belong to the technical field of organic fluorescent dye and applications. The fluorescent dye adopts fumaronitrile as a basic receptor structure unit in the molecular structure. A donor unit having an electron-releasing ability is connected in a conjugated manner to one side through a double bond or connected in a conjugated manner to two sides through double bonds. The structure formula of the fluorescent dye is shown as follows. The fluorescent dye is novel near infrared fluorescent dye synthesized through a Heck reaction, wherein R represents a donor group. Research finds that the dye emits bright near infrared fluorescence under ultraviolet excitation, and the dye has good photobleaching resistance and a high solid quantum efficiency. The dye has the large Stokes shift, and therefore the dye can be used as a near infrared fluorescent material for the fields of biological imaging and fluorescent labeling, and other fields.

Description

technical field [0001] The invention belongs to the technical field of organic fluorescent dyes and applications, and in particular relates to a high-efficiency near-infrared fluorescent dye with large Stokes shift and its application in the fields of biological imaging, fluorescent labeling and the like. Background technique [0002] The optical microscope in the sixteenth century changed people's understanding of biology and promoted the rapid development of biomedicine. It is known in the art that the size and shape of cells, organelles, chromosomes, etc. can be observed under an optical microscope. The invention of the electron microscope has opened up a new era of research on the ultrastructure of cells, such as the observation of rough endoplasmic reticulum, smooth endoplasmic reticulum, ribosomes, and the analysis of cell molecules with biochemical techniques. With the progress of human society, new imaging equipment and technologies have emerged in recent years, and...

Claims

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Application Information

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IPC IPC(8): C09B23/14C09K11/06G01N21/64
CPCC09B23/14C09B23/141C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 徐斌田文晶闫路林纪光
Owner JILIN UNIV
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