| 29% |
Stage #1: pyrrole; 4-tert-Butylbenzaldehyde With iodine In dichloromethane at 40℃; for 0.0833333h; Microwave irradiation;
Stage #2: With chloranil In dichloromethane at 40℃; for 0.0166667h; Microwave irradiation; |
|
| 21% |
With propionic acid for 1.5h; Heating; |
|
| 20% |
With propionic acid at 130℃; for 6h; |
1.1
(1) Put 4-tert-butylbenzaldehyde (16·2 g, 0·1 mol), 100 g of propionic acid and pyrrole (6.71 g, 0.1 mol) into a round bottom flask, and then heat to 130 ° C And stirred for 6 hours. When the reaction was completed, the resultant was cooled to room temperature, 100 g of acetone was added thereto, and the obtained mixture was stirred. The solid compound formed therein was filtered, washed with acetone, and dried to synthesize a porphyrin intermediate (4·2 g, 20%) |
| 16% |
In propionic acid at 90℃; for 1.5h; |
H2T(4-t-Bu)P
18.0 mL of Propionic acid was taken in a100 mL round-bottom (RB) flask and warmed to about 10 min. Tothis, 0.5 mL (3 mmol) of 4-t-butylbenzaldehyde and 0.2 mL(3 mmol) pyrrole were added and then refluxed at 90 °C for 90 min.The reaction mixture was cooled to room temperature and filteredusing G-4 sintered crucible washed and thoroughly with MeOH toremove polypyrrolic impurities. The compound was purifiedthrough silica gel column chromatography using chloroform as aneluent. The solvent was evaporated using rotary evaporator and thecompound was recrystallized using CHCl3/MeOH. The yield wasfound to be 16% (100 mg). UV-Vis. (CH2Cl2, λmax in nm): 420, 517,554, 590, 648. 1H NMR (CDCl3, 400 MHz): δ (ppm) 8.87 (s, 8H, bpyrrole-Ph), 8.15 (d, 8H, J 8 Hz, ortho-Ph), 7.76 (d, 8H, J 8 Hz,meta-Ph), 1.61 (s, 36H, t-Bu-H), -2.74 (s, 2H, -NH proton). Elementalanalysis calcd. for C60H62N4: C, 85.88; H, 7.45; N, 6.68% and found C,85.15; H, 6.22; N, 7.75%. |
| 15% |
at 200℃; for 0.25h; |
|
| 13% |
In propionic acid for 0.5h; Heating; |
|
| 12.89% |
In propionic acid for 0.5h; Reflux; |
5,10,15,20-(Tetra-4-tert-butylphenyl)-21,23-porphin
H2TBPP was synthesized by the procedure from [14].To 100 ml of boiling propionic acid, pyrrol (3.39 g, 32 mmol) and 4-tert-butylbenzaldehyde (5.19 g, 32 mmol) weresuccessively added in drops with constant stirring. After the addition of aldehyde the reaction mass was refluxed with stirringfor 30 min. The solution was cooled to room temperature and placed in a freezer for 12 h. The precipitate formed was filteredoff, washed with methanol (3 times with 10 ml) and hot water (3 times with 30 ml). The obtained purple crystals were driedin the air and then in vacuo. Yield 0.865 g. (12.89%) porphyrin. UV-vis in CHCl3 (λmax, nm): 421, 518, 554, 590, 649. IRspectrum (KBr) ν, cm-1: 3313, 2953, 2920, 2851, 1736, 1461, 1262, 1105, 964, 803, 789, 734, 713. H1 NMR (400 MHz,CDCl3): δ, ppm, (J, Hz) 8.87(s, 8H), 8.17-8.14 (d, J = 8.2 Hz, 8H), 7.77-7.76 (d, J = 8.2 Hz, 8H), 1.62 (s, 36H), -1.38 (s, br,1H), -2.72 (s, br, 1H). |
|
With propionic acid for 1h; Reflux; |
2.1 Synthesis of porphyrins
into a 500 mL round bottom flask added the180mL propionic acid, 15g of 3,5-Di-tert-butylbenzaldehyde, Heated to micro-boiling,than added the drop of 25mL 0.2g pyrrole propionic acid solution, and themixture was refluxed for 1 h; aftergot cooled the reaction solution, added the150 mL of methanol to conductrecrystallization, than allow to stand and we get purple solid after filter, itis known as porphyrin. |
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