2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3, 6dimethylformamide (DMF) in 250 ml dithiol2yl2, 5dihydropyrrolo[3, 4c]pyrrole1, 4dione(3, 6Dithiophen2yl2, 5dihydropyrrolo[3, 4c]pyrrole1, 4dione, put 13.0 g, 43.3 mmol) and potassium carbonate (K2CO3, 24.0g) was added at atemperature of 145 ° c good It was dissolved. The 2ethylhexylbromide (2ethylhexylbromide, 38.6g, 200mmol) was put in the solution at a time by using a syringe. 145Stirred over 15 hours at ° C and then lowered to room temperature and stirred to give poured over 500ml of cold water andgives the filter washed several times with water and alcohol. After drying, the silica column (silica column, eluent Hexane:Methylene chloride = 1: 10) through a solid was obtained of a dark purple powder.Under a nitrogen atmosphere, 3, 6-dithiophen-2-yl-2, 5-dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione (13 g, 43.3 mmol) dissolved in 300 mL of dimethylformamide (DMF) was added to a 500 ml two-necked round bottom flask. After stirring the mixture with heating, potassium carbonate (K2CO3) (4 eq.) was added and stirred at 140°C. Then, 2-ethylhexylbromomide (4.6 eq.) was added thereto and stirred for 12 hours. After stopping the reaction by thin film chromatography (TLC) confirmation, the resulting mixture was washed with ice water and solids were filtered through a filter and purified by silica column eluted with chloroform to obtain 2, 5-diethylhexyl-3, 6-dithiophen-2-ylpyrrolo[3, 4-c]pyrrole-1, 4-dione (18.01 g, Y=79percent).in a nitrogen atmosphere of formula (5) Compound 5 (3. 00g, 9. 99mmol), anhydrous potassium carbonate (6. 22g, 45mmol) was added to a solution containing 50ml N, N- dimethylformamide (DMF ) the reaction flask was heated to 120 ° C, and then dissolved in a minimum of DMF of 1-bromo-2-ethylhexanoate was added dropwise to the burning reaction flask while adding a small amount of 18-crown-6 ether, dropwise after the addition is complete warm to 150 ° C, for 12 hours. Then cooled to room temperature, the reaction solution was poured into four volumes of distilled water, the aqueous phase was extracted with methylene chloride to colorless, and then the organic phase was washed three times with distilled water, the organic solvent was removed under reduced pressure after boiling range 60 ° C -90 ° C petroleum ether as eluent over a silica gel column, to give the formula shown in (5) compound 6 3. 77g, yield 72percent. ;3, 6-Dithiophen-2-yl-2, 5-dihydropyrrolo[3, 4-c]pyrrole-1, 4-(2H, 5H)-dione (cmpd describedhere above)(3.922 g, 13.06 mmol) and potassium carbonate (7.226 g, 52.28 mmol, 4 equiv) were dried under vacuum. DMF (65 mL) was added and the medium was stirredat 145 °C for 10 min resulting in a deeper purple color medium. 2-Ethylhexylbromide (11.6 mL, 65.23 mmol, 5 equiv) was added slowly at 100 °C. The medium was stirred further at 145 °C overnight, then cooled to rt.The reaction medium was quenched with an ice/water solution (150 mL), then extracted with CH2Cl2 andwashed with water, finally dried with brine and over Na2SO4. Purification by column chromatography onsilica using a gradient of CH2Cl2/petroleum ether as eluent (50/50 to 100/0) afforded cmpd 1 as a purple solid(4.336 g, 63percent).Charge a 500-ml eggplant-shape flask with the above- prepared compound (a) (5.0 g, 13.3 mmol), 2-ethylhexyl bromide (8.0 g, 41.6 mmol), dry DMF (100 ml), and potassium carbonate (6.0 g). Agitate the flask content all night long at 70° C. Afier distilling the solvent away under reduced pressures, add a mixed solvent of methanol and water (MeOH/water=1/1, 100 ml) to the flask. Separate the precipitate by filtration and purify it by a silica gel colunm chromatography (solvent: toluene). Thus, a red powder (4.5g, 52.4percent) is obtained. mlz=525.3 (M+H)The compound 1 (10.0g, 33.3mmol), 2- ethylhexyl bromide ( 19. 3g, 99.9mmol), and K2CO3 (18.4g, 133mmol) dry DIt was mixed in MF (300mL), stirred for 24 hours at 120. ° C. . After cooling to room temperature , precipitationThe reaction mixture was poured into a large amount of ice water to form a palace compound . The resulting precipitate was times by filtrationTo yield , and washed with water and methanol .The resulting product was purified by silica gel column chromatography ( eluent : CHCl3 / hexaDown = 1: 1, v purified on / v ) , then recrystallized from CHCl3 / methanol , and dried under vacuumTo give compound 2 as a red- brown solid ( 8.89 g , yield = 51percent ) .Compound 2(3.36 g, 10.8 mmol) and 100 mL of dry DMF were added to a 250 mL two-neck round–bottom flask, equipped with a condenserand stir-bar and placed under N2 atmosphere. The mixturewas heated to 393 K, stirred for 30 min, and 2-ethylhexylbromide (6.05 g, 31.3 mmol) was then addedquickly (while at 393 K).The reaction mixture was subsequently stirred at 413 K forca. 6 h, and cooled to room temperature. The organic phasewas extracted with diethyl ether and washed with water. Thediethyl ether was evaporated, and the resulting tacky solid(red) was purified by column chromatography using CHCl3as eluent. 1.30 g of 3 was isolated (25 percent yield). 1H NMR(500MHz, CDCl3): (ppm) = 8.33 (d, J = 3.6 Hz, 2 H), 7.61 (d, J = 1.3 Hz, 2 H), 6.69 (dd, J = 1.7 Hz, 3.6 Hz, 2 H), 4.04 (d, J = 7.8 Hz, 4 H), 1.80–1.68 (m, 2 H), 1.39–1.26 (m, 16 H), 0.95–0.85 (m, 12 H). 13C (75 MHz, CDCl3): (ppm) = 161.4, 145.0, 144.8, 134.1, 120.4, 113.6, 106.6, 46.3, 40.1, 30.7, 28.8, 24.0, 23.2, 14.2, 10.9.General procedure: This compound was synthesized according to a literature procedure [41] 3, 6-Di(thiophen-2-yl)pyrrolo[3, 4-c]pyrrole-1, 4(2H, 5H)-dione (3) (0.45 g, 1.5 mmol) and KIn a 100 mL flask was added compound 14 (available from Osaka Kikoki K.K.) (1.50 g, 5.0 mmol), Anhydrous potassium carbonate (3.46 g, 25.0 mmol) and N, N-dimethylformamide (50 mL)Heating to 120 ° C was added after 1 hour of reaction Bromo-n-octane (2. 2 mL, 12.5 mmol), Maintain the reaction at 130 ° C for 12 hours. After the reaction, the mixture was cooled to room temperature, poured into a large amount of water, filtered and the cake was separated by silica gel column chromatography using petroleum ether: chloroform (V: V = 1: 1)To give a reddish-brown solid 15 (0.85 g, 32percent).

Molecular Weight:524.8
XLogP3:7.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:14
Exact Mass:524.25312087
Monoisotopic Mass:524.25312087
Topological Polar Surface Area:97.1
Heavy Atom Count:36
Complexity:797
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes