* 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.
Reference:
[1] Journal of the American Chemical Society, 2013, vol. 135, # 12, p. 4656 - 4659
[2] Journal of the American Chemical Society, 2014, vol. 136, # 27, p. 9608 - 9618
5
[ 4282-29-5 ]
[ 566939-58-0 ]
Reference:
[1] Organic Letters, 2004, vol. 6, # 19, p. 3381 - 3384
[2] Advanced Functional Materials, 2011, vol. 21, # 4, p. 718 - 728
[3] Chemistry of Materials, 2012, vol. 24, # 7, p. 1346 - 1356
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 18, p. 3758 - 3766
[5] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19035 - 19042
[6] Journal of the American Chemical Society, 2013, vol. 135, # 12, p. 4656 - 4659
[7] Journal of the American Chemical Society, 2014, vol. 136, # 27, p. 9608 - 9618
[8] RSC Advances, 2015, vol. 5, # 94, p. 77460 - 77468
[9] Organic Letters, 2017, vol. 19, # 5, p. 996 - 999
[10] Journal of Materials Chemistry A, 2017, vol. 5, # 34, p. 18088 - 18094
6
[ 847052-87-3 ]
[ 566939-58-0 ]
Reference:
[1] Organic Letters, 2004, vol. 6, # 19, p. 3381 - 3384
[2] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19035 - 19042
[3] RSC Advances, 2015, vol. 5, # 94, p. 77460 - 77468
[4] Journal of Materials Chemistry A, 2017, vol. 5, # 34, p. 18088 - 18094
7
[ 6007-85-8 ]
[ 566939-58-0 ]
Reference:
[1] Organic Letters, 2004, vol. 6, # 19, p. 3381 - 3384
[2] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19035 - 19042
[3] RSC Advances, 2015, vol. 5, # 94, p. 77460 - 77468
[4] Journal of Materials Chemistry A, 2017, vol. 5, # 34, p. 18088 - 18094
8
[ 18853-32-2 ]
[ 566939-58-0 ]
Reference:
[1] Organic Letters, 2004, vol. 6, # 19, p. 3381 - 3384
[2] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19035 - 19042
Reference:
[1] Chemistry of Materials, 2012, vol. 24, # 7, p. 1346 - 1356
12
[ 190723-12-7 ]
[ 566939-58-0 ]
Reference:
[1] Journal of the American Chemical Society, 2013, vol. 135, # 12, p. 4656 - 4659
[2] Journal of the American Chemical Society, 2014, vol. 136, # 27, p. 9608 - 9618
With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h;Reflux;
This compound was prepared according to the literature procedure [33]. Compound 1 (4.20 g, 10 mmol) was dissolved into dry THF (200 mL), 2-(tributylstannyl)thiophene (9.35 g, 25 mmol), and bis(triphenylphosphine) palladium (II) dichloride (150 mg) were added to the reaction mixture. The solution was refluxed for 24 h then cooled and poured into water. The mixture was extracted twice with dichloromethane. The organic phased were combined, washed with brine, and dried over anhydrous magnesium sulphate. The solvent was removed under reduce pressure and the crude product was purified by column chromatography using dichloromethane:hexanes as the eluent (ratio 1:1) to afford 3.0 g of the product as a yellow powder (Yield: 70%). MS (EI): m/z = 429. 1H NMR (400 MHz, CDCl3, δ): 8.02 (d, 2H), 7.16 (d, 2H), 7.14 (t, 2H), 3.76 (t, 2H), 1.87 (m, 2H), 1.70 (m, 2H), 1.37 (m, 10H), 0.91 (m, 3H). 13C NMR (400 MHz, CDCl3, δ): 161.38, 134.20, 132.57, 130.10, 128.77, 127.64, 115.67, 37.64, 30.70, 28.16, 28.13, 27.40, 25.90, 21.58, 13.06.
64%
With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 100℃; for 12h;Inert atmosphere;
Well-dried 500 mL three-necked round bottom flask was charged with 1,3-dibromo-5-octyl -4H- thieno [3,4-c] pyrrole -4,6 (5H) - dione(7.50 g, 17.73 mmol) and Tributyl (thiophene-2-yl) stacking of four(16.53 g, 44.32 mmol) toPut dissolved in 300 mL of toluene. Using a balloon filled with nitrogen, it keeps the stream of nitrogen for 10 minutes. Pd (PPh3) 2Cl2 (0.37 g, 0.53 mmol) toInsert, after raising the temperature to 100 , was stirred for 12 hours under a nitrogen flow. The mixture was extracted with chloroform and the organicAfter the base layer was washed with water and then dried with MgSO4, using a rotary evaporator to remove the solvent. n- hexane / dichlorideRomero shot; separated by column chromatography using (volume ratio 4: 1) solvent, 4.88 g of yellow solid CompoundIt was obtained in yield of 64%.
60%
With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 100℃; for 12h;Inert atmosphere;
A well-dried 500 mL three-neck round bottom flask was charged with 1,3-dibromo-5-octyl-4H-thieno [3,4-c] pyrrole-4,6 (5H)(10.0 g, 23.63 mmol) and tributyl (thiophen-2-yl) stannane (21.16 g, 56.71 mmol)It dissolved. Using a balloon containing nitrogen, the mixture was kept under a nitrogen stream for 10 minutes, and pd (PPh3) 2Cl2 (1.65 g, 2.36Mmol), the temperature was raised to 100 DEG C, and the mixture was stirred for 12 hours under a nitrogen stream. The mixture was washed with chloroformThe organic layer was washed with water, dried over MgSO4, and then eluted with a rotary evaporator to remove the solventLt; / RTI & gt; This was separated by column chromatography using a mixed solvent of n-hexane / dichloromethane (4/1)6.1 g (60%) of a yellow solid compound were obtained.
1-bromo-5-octyl-thieno[3,4-c]pyrrole-4,6-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
30.9%
A total of 6.35 g (15 mmol) of Br2-TPD was mixed with 150 mL ofethanol, 30 mL of acetic acid and 1 mL of hydrochloric acid (12 N) in a250-mL flame-dried three-neck round-bottom flask equipped with awater condenser and then heated to 70 C to completely dissolve thesolid. Next, 981 mg (15 mmol) of zinc dust was added (in one portion).The mixture was stirred at 85 C for 2 h. After cooling down, the solidresidue was filtered off and the solvent removed under reduced pressureto afford a crude yellow solid. The crude product was dissolved in diethyl ether and washed with water (2 times) and sodium bicarbonate.The organic phase was separated and dried over magnesium sulfate.Purification was accomplished by silica gel column chromatographyusing a dichloromethane and hexane (1:4) mixture as the eluent. Thecollected solution was dried by evaporation to afford a white solid.Recovered yield: 1.6 g (2.4 mmol, 30.9%). 1H-NMR (500 MHz, chloroform-d, δ): 7.71 (s, 1H, CH), 3.59 (t, J=7.3 Hz, 2H, CH2), 1.63 (m,J=7.3 Hz, 2H, CH), 1.33-1.23 (br m, 10H, CH2), 0.87 (t, J=7.0 Hz,3H, CH3). HRMS (EI) m/z, calculated for C14H18BrNO2S (M+): 343;found: 343.
With thionyl chloride; at 90℃; for 12h;Inert atmosphere;
General procedure: Acetic anhydride (7.6 mL) was added to 1 (0.50 g, 1.52 mmol) under a nitrogen atmosphere. The mixture was heated to 140 C for 12 h and then cooled to room temperature. The volatile compounds were removed in vacuo and the crude product was used in the next step without purification. After the brown solid was dissolved in toluene (1 mL), 4-trifluoromethylaniline (294 mg, 1.83 mmol) was added to the solution and the mixture was heated under reflux for 24 h. After removing the volatile components, thionyl chloride was added to the residue and the reaction mixture was stirred at 90 C for 12 h. The volatile components were removed in vacuo and the residue was extracted with chloroform. The organic phase was dried with anhydrous sodium sulfate and the solvent was removed under a reduced pressure. The crude product was purified by column chromatography with silica gel using chloroform as the eluent. The product was recrystallized from ethanol to afford TPD1 as an off-white solid with a yield of 81%.
(5′-hexyl-[2,2′-bithiophen]-5-yl)trimethylstannane[ No CAS ]
[ 1603829-49-7 ]
Yield
Reaction Conditions
Operation in experiment
53%
With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 100℃; for 12h;Inert atmosphere;
Well-dried three-necked 100mL round bottom flask, 1,3-dibromo-5-octyl-4H-wrapped in no [3,4-c] pyrrole -4,6 (5H) - dione (1.01g, 2.38mmol )and(5'-hexyl-2,2Oppenheimer Bar itty-yl) trimethyl put a four star (1.97g, 4.77mmol) was dissolved in toluene 40ml.Using a balloon filled with nitrogen, it keeps the stream of nitrogen for 10 minutes.After that, insert the Pd (PPh3) 2Cl2 (0.05g, 0.07 mmol) as a catalyst, and then raise the temperature to 100 , was stirred for 12 hours under a nitrogen flow. After the mixture is extracted with chloroform and the organic layer was washed with water and then dried with MgSO4 gave, rotary increasedUsing the erection and the solvent was removed. n- hexane / chloroform: using (volume ratio at a ratio of 2: 1) solvent separated by column chromatography to obtain a yellow solid compound with yield of 0.96g (53%).