Near-infrared fluorescent dye with large stokes shift and synthesis method and application

The technology of a fluorescent dye and a synthesis method, applied in the field of specific fluorescence detection, can solve the problems of self-quenching of the dye and the reduction of the fluorescence intensity of the dye, and achieve the effects of easy purification, stable fluorescence intensity and high yield

Active Publication Date: 2015-03-25
SHANDONG NORMAL UNIV
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AI Technical Summary

Problems solved by technology

At present, some fluorescent dyes have relatively close fluorescence absorption peaks and emission peaks, and the Stokes shift is small, such as about 10-15nm. The small Stokes shift has a large overlap between the absorption spectrum and the emission spectrum. , so that part of the emitted light of the dye can be absorbed by itself, resulting in a decrease in the fluorescence intensity of the dye, resulting in the self-quenching of the dye; and a large Stokes shift can effectively reduce the reabsorption of photons emitted by the fluorophore

Method used

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  • Near-infrared fluorescent dye with large stokes shift and synthesis method and application
  • Near-infrared fluorescent dye with large stokes shift and synthesis method and application
  • Near-infrared fluorescent dye with large stokes shift and synthesis method and application

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Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 fluorescent dye

[0038] Synthesis of Compound 1:

[0039] (1) Synthesis of intermediate c:

[0040] Get raw materials a and b (the amount of a and b added is 1mmol) (indole iodine salt a and condensing agent b are prepared with reference to the prior art, references: Tang, B.; Yu, F.; Li, P. ; Tong, L.; Duan, X.; Xie, T.; Wang, X.J.Am Chem.Soc.2009,131,3016-3023.), dissolved in 20ml of toluene-acetic acid mixture (volume ratio of toluene and acetic acid 15:5), reacted at 110°C for 2h; after the reaction was completed, concentrated under reduced pressure at 60°C for 30min, removed the solvent, and carried out column separation using a thin-layer chromatographic column (the stationary phase in the chromatographic column was silica gel). The eluent is a dichloromethane-methanol mixture, and in the mixture, the volume ratio of dichloromethane to methanol is 50:1; a black-red solid is obtained, which is intermediate c (60% yield);

[0041] (...

Embodiment 2

[0047] The synthesis of embodiment 2 fluorescent dyes

[0048] Synthesis of Compound 2:

[0049] The synthetic method of Compound 2 is the same as that of Compound 1 in Example 1, except that the raw material in step (2) is changed from acetophenone to 4-methylacetophenone. Fluorescent dye compound 2 (R is Me) is a black-red solid with a yield of 68%.

[0050] Concrete synthetic route is as follows:

[0051]

[0052] The infrared, NMR and mass spectrometry of compound 2 are characterized as follows:

[0053] Compound 2: IR:v C＝O =1639.25cm -1 ,v C-H =2926.57cm -1 . 1 H NMR (600MHz, CDCl 3 ):1.26(t,J=6.0Hz,4H),1.69(m,6H),1.87(s,3H),5.50(q,1H),6.65(d,J=2.4Hz,1H),6.90(t ,J=6.0Hz,1H),6.95(d,J=12.0Hz,1H),7.17(t,J=6.0Hz,2H),7.25(t,J=5.4Hz,7H),7.62(d,J =12.0Hz,1H),7.84(d,J=6.0Hz,3H),7.89(d,J=12.0Hz,3H). 13 C NMR (150MHz, CDCl 3 ):11.1,21.3,21.6,26.2,27.3,28.0,28.1,29.3,29.7,36.9,46.2,92.6,106.2,109.9,120.2,121.7,124.3,127.2,127.7,128.4,128.8,129.1,136.9 139.3, 140.9, ...

Embodiment 3

[0054] Example 3 Synthesis of fluorescent dyes

[0055] Synthesis of compound 3:

[0056] The synthetic method of Compound 3 is the same as that of Compound 1 in Example 1, except that the raw material in step (2) is changed from acetophenone to 4-methoxyacetophenone. Fluorescent dye compound 3 is a black-red solid with a yield of 74%.

[0057] The synthetic route is as follows:

[0058]

[0059] The infrared, NMR and mass spectrometry of compound 3 are characterized as follows:

[0060] Compound 3: IR:v C＝O =1672.52cm -1 ,v C-H =2934.26cm -1 ,v C-H =2839.52cm -1 . 1 H NMR (600MHz, CDCl 3 ):1.25(t,J=6.0Hz,3H),1.64(s,6H),1.87(t,J=6.0Hz,2H),2.57(m,4H),3.70(m,2H),3.85(m ,3H),5.48(d,J=12.0Hz,1H),6.64(d,J=7.8Hz,1H),6.80-6.90(m,4H),7.18(t,J=7.8Hz,2H),7.61 (d,J=13.8Hz,1H),7.99(d,J=9.0Hz,2H),8.34(d,J=15.0Hz,1H). 13 C NMR (150MHz, CDCl 3 ):11.1,21.3,26.2,27.3,28.1,30.0,36.9,46.2,55.43,55.46,92.6,106.2,110.0,113.6,119.9,120.2,121.2,124.3,127.2,127.7,128.6,1390.2,5, 140...

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Abstract

The invention discloses a near-infrared fluorescent dye with a large stokes shift and a synthesis method and an application. A structural formula of the fluorescent dye is as shown in the specification. The preparation method of the fluorescent dye comprises the following steps: (1) dissolving an indole iodized salt a and a condensing agent b at the mass ratio of 0.5:1 to 1.5:1 into a toluene-acetic acid mixed liquor, reacting at 110 DEG C for two hours, concentrating to remove a solvent after reaction is ended, and carrying out column separation to obtain an intermediate body c; and (2) dissolving the intermediate body c, and acetophenone, 4-methylacetophenone or 4-methoxyacetophenone at the mass ratio of 1:3 to 1:1 into a potassium hydroxide solution-methanol mixed liquid, reacting at 60-100 DEG C for 15-30 hours, carrying out reduced pressure concentration at 30-60 DEG C for 20-50 minutes after reaction is ended to remove the solvent, and separating through a column, so as to obtain the near-infrared fluorescent dye with the large stokes shift. The fluorescent dye disclosed by the invention has the maximal near-infrared emission wavelength, and has the large stokes shift.

Description

technical field [0001] The invention relates to a class of near-infrared fluorescent dyes with a large Stokes shift, a synthesis method and application thereof, and belongs to the technical field of specific fluorescence detection. Background technique [0002] At present, fluorescence imaging technology has developed into the most important means for dynamic monitoring of living cells and biomolecular events in vivo. The development of new fluorescent imaging sensors has greatly promoted the progress of cell biology and medical diagnostic imaging. [0003] near-infrared emission (E m >650nm) fluorescent dyes are widely used in the field of biological imaging because of their advantages such as low photodamage to biological tissue samples, deep tissue penetration ability, and low biological background fluorescence interference. At present, some fluorescent dyes have relatively close fluorescence absorption peaks and emission peaks, and the Stokes shift is small, such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10C09K11/06G01N21/64
Inventor 唐波李平肖海滨张雯
Owner SHANDONG NORMAL UNIV
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