A kind of near-infrared bodipy fluorescent dye and preparation method thereof
A fluorescent dye and near-infrared technology, which is applied in the field of organic compound synthesis, can solve the problems of many synthesis steps, poor solubility, and high difficulty, and achieve the effects of good solubility, less pollution, and good reaction selectivity
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Embodiment 1
[0032] Equipped with a water trap in the single-neck round bottom flask, 1,3,5,7-tetramethyl-8(2,4,6-trimethylbenzene)-BODIPY (146.4mg, 0.40mmol), 2-formyl Indene (0.862g, 1.60mmol) and p-toluenesulfonic acid (68mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux at 140°C, TLC was followed to detect the complete reaction of the raw materials, and the solvent was collected until evaporated to dryness. The reactant was concentrated and subjected to silica gel column chromatography, and the eluent was (petroleum ether / CH 2 Cl 2 =6:4), to obtain dark green solid A (182.0 mg, 32.33%). Esi-MS: calcd for C 102 h 106 BF 2 N 2 1407.8417, found: 1407.8459 (M+H + )( figure 1 ); 1 HNMR: (600MHz, CDCl 3 )δ8.46(d, J=4.20Hz, 2H), 8.40(d, J=7.20Hz, 4H), 7.93(d, J=16.2Hz, 2H), 7.83(d, J=8.40Hz, 2H) , 7.67(s, 1H), 7.54-7.52(m, 2H), 7.50-7.48(m, 2H), 7.46-7.42(m, 6H), 7.38-7.33(m, 4H), 7.03(s, 2H) , 6.74(s, 2H), 3.15-3.03(m, 12H), 2.40(s, 3H), 2.31...
Embodiment 2
[0034] Equipped with a water trap in the round bottom flask, 1,3,5,7-tetramethyl-2,6-diiodo-8(2,4,6-trimethylbenzene)-BODIPY (247.2mg, 0.40mmol) , tripolyindene formaldehyde (0.862g, 1.60mmol) and p-toluenesulfonic acid (68mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux at 140 ° C, TLC traced and detected that the reaction of the raw materials was complete, and the solvent was collected until evaporated to dryness. The reactant was concentrated and subjected to silica gel column chromatography, and the eluent was (petroleum ether / CH 2 Cl 2 =8:2), to obtain green solid B (196.2mg, 29.54%). Esi-MS: calcd for C 102 h 103 BF 2 I 2 N 2 1658.6272, found: 1658.6218 (M + )( Figure 5 ); 1 H NMR: (600MHz, CDCl 3 )δ8.46(d, J=8.40Hz, 2H), 8.39(t, J=8.40Hz, 6H), 7.95(d, J=16.2Hz, 2H), 7.88(d, J=7.20Hz, 2H) , 7.69(s, 2H), 7.49-7.33(m, 12H), 7.06(s, 2H), 3.14-2.99(m, 12H), 2.43(s, 3H), 2.33-2.13(m, 18H), 1.56 (s, 6H), 0.34-0.23 (m, 36H) (...
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