Preparation of near-infrared dye based on aza-fluoroborane and application
A near-infrared dye and heterofluoroborane technology is applied in the field of near-infrared dye azafluoroborane dyes and the preparation thereof, and achieves the effects of deep tissue penetration, convenient industrial production and abundant raw materials
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Embodiment 1
[0036] Example 1: Synthesis of Azafluoroborane Photothermal Dye C
[0037]
[0038] Synthesis of compound 1
[0039] Take a clean two-necked bottle, add magneton, 2.44g of p-hydroxybenzaldehyde (about 20mmol), 19.31g of bromooctane (about 100mmol), 13.82g of potassium carbonate and 50ml of anhydrous magnetic stirring, and react at 80°C 24h. After the reaction was completed, water / dichloromethane was extracted several times, and the organic phases were combined. After separation by chromatography column, 4.68 g of light yellow liquid was obtained (the yield was about 99%).
[0040] Synthesis of Compound 2
[0041] Take a clean two-necked bottle, add magneton, 4.68g of 1 (about 20mmol), 4.1g of 2-bromoacetylthiophene (about 20mmol) and 40ml of ethanol solution. Stir until all the solids are dissolved, then slowly add 5ml of sodium hydride solution (containing 1.00g of sodium hydroxide). The reaction was stirred at room temperature for 24 h, and a yellow solid was precipi...
Embodiment 2
[0053] Example 2: Synthesis of Azafluoroborane Photothermal Dye D
[0054] Synthesis of Compound D
[0055] Take a clean 50ml one-mouth bottle, add magneton, 0.14g (0.15mmol) 5, and 10mL dry dichloromethane to dissolve. At 0°C, after adding 0.107g (0.60mmol) NBS, stir for 6h. After the reaction, the mixed solution was washed with water, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 0.13 g Blue solid product (~80% yield).
[0056] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) = 7.91 (d, J = 4.4Hz, 2H), 7.80 (d, J = 8.8 Hz, 4H), 7.21 (d, J = 4.4Hz, 2H), 6.95 (d, J = 8.8 Hz,4H),4.02(t,J=6.8Hz,4H), 1.86-1.79(m,4H),1.52–1.45(m,4H),1.38–1.29(m,16H),0.92-0.88(m, 6H).
[0057] 13 C NMR (100MHz, CDCl 3 ):δ(ppm)=160.64,148.03,144.68,142.52,135.53,132.51,131.87,131.10,122.87,121.21,114.13,108.82,68.20,33.85,31.90,31.52,30.15,29.56,29.26,26.09,22.69,14.13
[0058] 19 F NMR (37...
Embodiment 3
[0059] Embodiment 3: the test of the molecular weight of C
[0060] Take a small amount of sample C, mix it with the matrix, then apply the sample, and measure it with MALDI-TOF / TOF, as shown in Figure 1, which preliminarily proves the correctness of the C molecule.
[0061] [m / e] (M, MALDI-TOF) theoretical value: 923.62, experimental value: 923.63
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