A kind of asymmetric benzofluoroboron dipyrrole fluorescent dye and its preparation method
A technology of benzofluoroborate dipyrrole and fluorescent dyes, which is applied in the field of fluorescent dyes and can solve problems such as limiting structural diversity
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Embodiment 1
[0014]
[0015] In a (200 mL) dry round bottom flask, add 2-bromo BODIPY (50 mg, 0.129 mmol), tolan (69 mg, 0.387 mmol), anhydrous sodium carbonate (28 mg, 0.260 mmol), lithium bromide (8 mg, 0.090 mmol), palladium acetate (3mg, 0.013mmol), under nitrogen protection, add N,N-dimethylformamide 40mL, tricyclohexylphosphine (7mg, 0.026mmol), and stir at 110°C for about 24h, then the reaction ends , washed with saturated brine, extracted with ethyl acetate, and N,N-dimethylformamide was removed, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the obtained crude product was purified by silica gel column chromatography (20% ethyl acetate / petroleum ether) to obtain product 1A.
[0016] The identification results are as follows: 1 H NMR (400MHz, CD 2 Cl 2 )δ8.49(s,1H),7.42(s,1H),7.30–7.24(m,5H),6.88–6.85(m,3H),6.81(dt,J=8.6,2.9Hz,2H),6.76 –6.70(m,4H),6.67–6.63(m,2H),6.53–6.47(m,4H),6.38(s,2H),6.16(dd,J=3.8,2.3Hz,1H),5.72(d ,J=3.0Hz,1H),2.14(s,3H),1.82(...
Embodiment 2
[0021]
[0022] In a (200 mL) dry round bottom flask, add 2-bromoBODIPY (50 mg.0.129 mmol), 4-fluorotolan (83 mg, 0.387 mmol), anhydrous sodium carbonate (28 mg, 0.260 mmol), lithium bromide ( 8mg, 0.090mmol), palladium acetate (3mg, 0.013mmol), under the protection of nitrogen, add N,N-dimethylformamide 40mL, tricyclohexylphosphine (7mg, 0.026mmol), stir at 110℃ for about 24h After the reaction is over, wash with saturated brine, extract with ethyl acetate, remove N,N-dimethylformamide, and use anhydrous Na 2 SO 4 After drying, the obtained crude product was purified by silica gel column chromatography (20% ethyl acetate / petroleum ether) to obtain product 1B.
[0023] The identification results are as follows: 1 H NMR (500MHz, CD 2 Cl 2 )δ8.49(s,1H),7.47(s,1H),7.23–7.19(m,2H),7.02(t,J=8.7Hz,2H),6.76–6.72(m,2H),6.63(t ,J=8.8Hz,2H),6.53–6.45(m,8H),6.38(t,J=8.8Hz,2H),6.19(dd,J=3.7,2.2Hz,1H),5.74(d,J= 3.6Hz,1H),2.19(s,3H),1.85(s,6H). 13 C NMR (100MHz, CD 2 Cl 2)δ163.0...
Embodiment 3
[0028]
[0029] In a (200 mL) dry round bottom flask, add 2-bromoBODIPY (50 mg, 0.129 mmol), 4-methoxytolan (92 mg, 0.387 mmol), anhydrous sodium carbonate (28 mg, 0.260 mmol), Lithium bromide (8mg, 0.090mmol), palladium acetate (3mg, 0.013mmol), under nitrogen protection, add N,N-dimethylformamide 40mL, tricyclohexylphosphine (8mg, 0.026mmol), stir at 110°C After about 24 hours, the reaction was completed, washed with saturated brine, extracted with ethyl acetate, and N,N-dimethylformamide was removed, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the obtained crude product was purified by silica gel column chromatography (20% ethyl acetate / petroleum ether) to obtain product 1C.
[0030] The identification results are as follows: 1 H NMR (400MHz, CD 2 Cl 2 )δ8.49(s,1H),7.42(s,1H),7.30–7.24(m,5H),6.88–6.85(m,3H),6.81(dt,J=8.6,2.9Hz,2H),6.76 –6.70(m,4H),6.67–6.63(m,2H),6.53–6.47(m,4H),6.38(s,2H),6.16(dd,J=3.8,2.3Hz,1H),5.72(d ,J=3.0Hz,1H),2.14...
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