Fluorescent dye based on aggregation-induced luminescence near-infrared, large Stokes shift, and photostability, and its preparation method and application
A technology of aggregation-induced luminescence and fluorescent dyes, applied in the field of mitochondrial fluorescent labeling, fluorescent dyes and their preparation, can solve the problems of failing to provide mitochondrial number, shape, prone to photobleaching, and difficult long-term tracer of mitochondria
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Embodiment 1
[0046] (1) Synthesis of Dye I-1:
[0047]
[0048] In a 50mL round bottom flask, add 2-(1-dodecyl-2,6-lutidine-4(1H)-ylidene) malononitrile (350mg, 1.03mmol, compound V-1) , ethanol (20mL), (2-(2-formylphenoxy)ethyl)triphenylphosphine bromide (1.52g, 3.09mmol, compound VI-1), triethylamine 1.0mL, under the protection of argon , Reflux reaction 1h. Cool, remove the solvent by rotary evaporation under reduced pressure, and perform column chromatography (DCM:EA:MeOH=4:3:2, v / v / v) to obtain 630 mg of solid (dye I-1), with a yield of 47.6%.
[0049] 1 H NMR (400MHz, DMSO-d 6 ,ppm): δ7.84(m,24H,phenyl-H),7.63-7.59(m,6H,phenyl-H),7.38-7.30(m,4H,phenyl-H),7.15(t,J=10.2 Hz, 4H, phenyl-H), 7.03-7.01 (d, J = 8.0Hz, 2H, alkene-H), 7.17 (t, J = 15.0Hz, 2H, alkene-H), 6.48-6.44 (d, J =16.0Hz, 2H, alkene-H), 4.05-3.96(m, 6H, -CH 2 -),3.66(t,J=14.8Hz,4H,-CH 2 -),1.43-1.26(m,20H,-CH 2 -),0.88(t,J=8.0Hz,3H,-CH 3 ).
[0050] Mass spectrometry(ESI-MS,m / z):[M-2Br] 2+ calcd for C 76 ...
Embodiment 2
[0082] Absorption and Fluorescence Spectra of Dye I-7 in Aggregated State
[0083] The dye I-7 prepared in Example 1 was dissolved in analytically pure dimethyl sulfoxide to make 1.0 × 10 -2 stock solution of M. Then, 2 mL of a THF / water mixed solvent having a tetrahydrofuran (THF) content of 99% was prepared. Take 2 μL of the above stock solution and add it to the prepared THF / water mixed solvent, mix well and transfer to an optical quartz cuvette (10×10 mm) to test its absorption and fluorescence spectra. Such as figure 1 As shown, the dye I-7 exhibits a broad absorption peak at 350-650nm, and the maximum absorption wavelength is located at 520nm; with 520nm as the excitation wavelength, the maximum emission peak of the dye I-7 is located at about 685nm and is located in the near-infrared region. The Kex shift reaches 165nm; and the aggregation of the dye I-7 in the mixed solvent leads to the enhancement of its fluorescence, which has typical fluorescence enhancement char...
Embodiment 3
[0085] Dye I-7 photostability test
[0086] Photostability is one of the important performance indicators for evaluating dyes in practical applications such as long-term imaging. We evaluated the photostability of the dye by continuously illuminating the dye and then monitoring its fluorescence intensity, and selected the commercial dye Mitotracker Green as a reference dye. Such as figure 2 As shown, as the illumination time increases, the fluorescence intensity of Mitotracker Green decreases sharply. When the illumination time is about 6 minutes, Mitotracker Green produces serious photobleaching, indicating that its photostability is poor; however, under the same illumination conditions, the fluorescence intensity of dye I-7 Slowly decreased, when the light time reached 15min, its fluorescence intensity was 75% of the initial fluorescence intensity, indicating that the dye I-7 has excellent photostability.
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