Coupled double-BODIPY near-infrared absorption dye and preparation method thereof
A dye-absorbing, near-infrared technology, applied in organic dyes, styryl dyes, chemical instruments and methods, etc., can solve the problems of limited application, many synthesis steps, expensive catalysts, etc., and achieves a simple and easy preparation method, high molar Good extinction coefficient and reaction selectivity
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Embodiment 1
[0024] Under anhydrous and oxygen-free conditions, add dry dichloromethane (50 mL) and 3,5-((4-N,N-diethyl)-divinylbenzene)-8-(1-naphthalene )-BODIPY (100mg, 0.15mmol), the temperature of the reaction system dropped to -78°C, and the FeCl-containing 3 (364mg, 2.25mmol) in nitromethane solution (2.4mL), reacted for 30min; the reaction system was raised to room temperature, and saturated sodium bicarbonate solution was added to quench the reaction, and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and reduced The organic solvent was removed by distillation under pressure, and the residue was separated and purified by silica gel column chromatography with 100% dichloromethane as the eluent to obtain the product I as a dark brown solid (29 mg, 29%). 1 H-NMR (600MHz, CDCl 3 ): δ7.84-7.87(t, J=8.4Hz, 4H), 7.80-7.82(t, J=7.2Hz, 2H), 7.62-7.64(d, J=16.2Hz, 2H), 7.53-7.58( m, 6H), 7.42-7.47(m, 4H), 7.36-7.40(m, 6H), 7.28(s, 1H), 7.18-7.24(m,...
Embodiment 2
[0027] Under anhydrous and oxygen-free conditions, add dry dichloromethane (50 mL) and 3,5-((4-N,N-diethyl)-divinylbenzene)-8-(1-naphthalene )-BODIPY (100mg, 0.15mmol), the temperature of the reaction system dropped to -78°C, and the FeCl-containing 3 (243mg, 1.5mmol) in nitromethane solution (2.0mL), reacted for 30min; the reaction system was raised to room temperature, and saturated sodium bicarbonate solution was added to quench the reaction, and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and reduced The organic solvent was removed by distillation under pressure, and the residue was separated and purified by silica gel column chromatography with 100% dichloromethane as the eluent to obtain the product I as a dark brown solid (18 mg, 18%).
Embodiment 3
[0029] Under anhydrous and oxygen-free conditions, add dry dichloromethane (50 mL) and 3,5-((4-N,N-diethyl)-divinylbenzene)-8-(1-naphthalene )-BODIPY (100mg, 0.15mmol), the temperature of the reaction system dropped to -78°C, and the FeCl-containing 3 (292mg, 1.8mmol) in nitromethane solution (2.4mL), reacted for 20min; the reaction system was raised to room temperature, and saturated sodium bicarbonate solution was added to quench the reaction, and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and reduced The organic solvent was removed by distillation under pressure, and the residue was separated and purified by silica gel column chromatography with 100% dichloromethane as the eluent to obtain the product I as a dark brown solid (22 mg, 22%).
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