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CAS No. : | 871696-12-7 | MDL No. : | MFCD30187269 |
Formula : | C30H43B2NO4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | VUJPSYQJTJSPOI-UHFFFAOYSA-N |
M.W : | 503.29 | Pubchem ID : | 25150161 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 80℃; for 18.0h;Inert atmosphere; | Porphyrin 5 (50 mg, 0.08 mmol), borylated carbazole 18 (190 mg, 0.38 mmol), and K3PO4 (322 mg, 1.52 mmol) were charged to a 50 mL Schlenk tube and dried under high vacuum for 20 min. THF (10 mL) was added and the solution was degassed via three freeze-pump-thaw cycles. Pd(PPh3)4 (8.8 mg, 0.01 mmol) was added, the reaction heated to 80 °C under argon and left to stir at this temperature for 18 h. Solvents removed in vacuo, the residue dissolved in CH2Cl2 and washed with saturated NaHCO3, brine and H2O. Organic layers dried over MgSO4 and solvents removed in vacuo. Residue filtered through a plug of silica using CH2Cl2/hexane (1:1) and CH2Cl2 as eluent to give three fractions. Solvents removed to yield purple product 20 (40 mg, 55percent, 0.04 mmol). Mp=220 °C; 1H NMR (400 MHz, CDCl3): deltaH=-2.67 (s, 2H, NH), 0.78 (t, 3JH-H=14.2 Hz, 3H, CH3), 0.87-0.92 (m, 2H, CH2), 1.25-1.30 (m, 4H, CH2), 1.49 (s, 12H, CH3), 1.96-2.02 (m, 2H, CH2), 2.73 (s, 6H, tolyl-CH3), 2.75 (s, 3H, tolyl-CH3), 4.49 (t, 3JH-H=14.2 Hz, 2H, CH2), 7.56-7.60 (m, 6H, tolyl-H), 7.87 (d, 3JH-H=7.8 Hz, 1H, carbazole-H), 8.07 (s, 1H, carbazole-H), 8.14 (d, 3JH-H=8.3 Hz, 6H, tolyl-H), 8.29 (s, 1H, carbazole-H), 8.38 (d, 3JH-H=7.8 Hz, 1H, carbazole-H), 8.45 (d, 3JH-H=7.8 Hz, 1H, carbazole-H), 8.87-8.92 (m, 8H, beta-H) ppm; 13C NMR (100 MHz, CDCl3): deltaC=13.9, 21.6, 22.6, 25.0, 27.1, 29.7, 31.6, 43.2, 83.9, 115.6, 115.9, 118.4, 119.9, 120.2, 120.8, 121.9, 125.4, 126.7, 127.4, 130.9, 134.5, 137.3, 139.3, 139.9, 130.4, 140.7 ppm; FT-IR (ATR): nu=3316, 2922, 2853, 1725, 1625, 1560, 1451, 1333, 1259, 1143, 1080, 965, 798, 733, 687 cm-1; UV-vis (CH2Cl2): lambdamax (log )=424 (5.60), 518 (4.49), 553 (4.36), 592 (4.27), 649 nm (4.26); HRMS (ESI) [C65H63N5O2B+H]: calcd 956.5075, found 956.5072. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 80℃; for 18.0h;Inert atmosphere; | Porphyrin 4 (50 mg, 0.08 mmol), borylated carbazole 18 (90 mg, 0.18 mmol), and K3PO4 (343 mg, 1.62 mmol) were charged to a 50 mL Schlenk tube and dried under high vacuum for 20 min. THF (10 mL) was added and the solution was degassed via three freeze-pump-thaw cycles. Pd(PPh3)4 (9.4 mg, 0.01 mmol) was added, the reaction heated to 80 °C under argon and left to stir at this temperature for 18 h. Solvents removed in vacuo, the residue dissolved in CH2Cl2 and washed with saturated NaHCO3, brine, and H2O. Organic layers dried over MgSO4 and solvents removed in vacuo. Residue subjected to column chromatography (CH2Cl2/hexane 1:1) to yield purple product, which was recrystallized from CH2Cl2/MeOH to give purple crystals 19 (46 mg, 62percent, 0.05 mmol). Mp=231 °C; 1H NMR (600 MHz, CDCl3): deltaH=-2.65 (s, 2H, NH), 0.78 (t, 3JH-H=13.6 Hz, 3H, CH3), 0.88-0.92 (m, 2H, CH2), 1.23-1.28 (m, 2H, CH2), 1.56 (s, 12H, CH3), 1.97-2.02 (m, 4H, CH2), 4.47-4.50 (m, 2H, CH2), 7.63 (d, 3JH-H=8.3 Hz, 1H, carbazole-H), 7.76-7.80 (m, 9H, Ph-H), 7.87 (d, 3JH-H=7.6 Hz, 1H, carbazole-H), 8.16 (d, 3JH-H=7.9 Hz, 2H, carbazole-H), 8.26 (d, 3JH-H=7.6 Hz, 6H, Ph-H), 8.38 (d, 3JH-H=7.6 Hz, 1H, carbazole-H), 8.45 (d, 3JH-H=7.6 Hz, 1H, carbazole-H), 8.86-8.88 (m, 6H, beta-H), 8.93 (d, 3JH-H=3.8 Hz, 2H, beta-H) ppm; 13C NMR (150 MHz, CDCl3): deltaC=13.9, 22.4, 24.8, 26.8, 29.0, 31.4, 43.1, 83.7, 107.7, 114.9, 115.3, 115.8, 118.3, 118.9, 119.5, 120.0, 120.9, 121.7, 121.8, 125.0, 125.3, 126.5, 127.5, 131.1, 134.4, 139.7, 140.1, 140.6, 140.7, 142.1 ppm; FT-IR (ATR): nu=3311, 3053, 2927, 2855, 1624, 1597, 1560, 1430, 1332, 1243, 1143, 1078, 964, 797, 727, 699, 686 cm-1; UV-vis (CH2Cl2): lambdamax (log )=422 (5.13), 515 (4.22), 552 (4.17), 592 (4.15), 655 nm (4.09); HRMS (MALDI LD+) [C62H57N5O2B+H]: calcd 914.4605, found 914.4604. |