Near infrared fluorescent dyestuff and preparation method and application thereof
A fluorescent dye and near-infrared technology, applied in the field of fluorescence imaging, can solve the problems of severe photobleaching and weak light stability
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[0049] Some specific embodiments of the present invention also provide the preparation method of the above-mentioned near-infrared fluorescent dye, the steps are as follows:
[0050]
[0051] Among them, n 2 is 0 or 1; n 1 is 1, 2 or 3; R 1 , R 2 , R 3 Each is independently selected from a hydrogen atom, an unsubstituted alkyl group, a phenyl-substituted alkyl group or an alkanesulfonic acid group; Z is selected from a halogen group.
[0052] Specifically, the preparation method of the above-mentioned near-infrared fluorescent dye includes:
[0053] (1) Preparation of intermediate (c)
[0054] Compound (b) is dissolved in a solvent, and is added dropwise in an eggplant-shaped bottle filled with compound (a) and a base, and the base is selected from various organic bases and inorganic bases, preferably sodium carbonate, sodium bicarbonate, potassium carbonate , potassium bicarbonate, potassium acetate. The organic solvent is selected from acetic anhydride, acetic acid...
Embodiment 1
[0063] Embodiment 1 compound Rh1018 (R 1 , R 2 , R 3 Both are ethyl n 1 is 3, n 2 For 2) preparation and luminescence properties study
[0064]
[0065] (1) Preparation of intermediate compound C
[0066] Compound A (0.475g, 1mmoL) and potassium acetate (0.098g, 1mmol) were dissolved in a 25mL eggplant-shaped bottle filled with acetic anhydride (5mL), and after stirring for 5min, compound B (0.475, 1mmoL) was added to In the above system, heat the reaction at 50°C for half an hour, pass through the column under the condition of dichloromethane / methanol=20 / 1, and obtain 300 mg of a blue solid product, which is intermediate compound C.
[0067] 1 H NMR (400MHz, MeOD) δ 8.24 (dd, J = 7.6, 1.2Hz, 1H), 7.98 (d, J = 13.8Hz, 1H), 7.85 (d, J = 12.0Hz, 1H), 7.71 (ddt ,J=8.9,7.5,3.7Hz,2H),7.64–7.54(m,3H),7.31(d,J=6.9Hz,2H),7.22(d,J=6.3Hz,1H),7.18(d, J=2.3Hz, 1H), 7.16–7.09(m, 2H), 7.06(d, J=9.5Hz, 1H), 6.48(dd, J=14.2, 12.1Hz, 1H), 5.33(dd, J=13.8 ,11.4Hz,1H),3.70(q,J=7.0Hz,...
Embodiment 2
[0088] Embodiment 2 compound Rh920 (R 1 , R 2 , R 3 Both are ethyl, n 1 is 2, n 2 For 1) preparation and luminescence properties study
[0089]
[0090] (1) Preparation of intermediate compound C-2
[0091] Compound A (0.475g, 1mmoL) and potassium acetate (0.098g, 1mmol) were dissolved in a 25mL eggplant-shaped bottle filled with acetic anhydride (5mL), and after stirring for 5min, compound B-2 (0.258, 1mmoL) was dissolved in batches Add to the above system, heat reaction at 50°C for half an hour, pass through the column under the condition of dichloromethane / methanol=20 / 1, and obtain 600 mg of red solid product, which is intermediate compound C-2.
[0092] (2) Preparation of Compound Rh920
[0093] Intermediate compound C-2 (0.547g, 1mmoL) and potassium acetate (0.098g, 1mmol) were dissolved in acetic anhydride (5mL), and after stirring for 5min, compound D (0.326, 1mmoL) was added to the above system in batches, Heat the reaction at 80° C. for 1 hour, pass through ...
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