3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione Chemical Properties

Boiling point:

742.2±60.0 °C(Predicted)

Density 

1.45

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

-5.35±0.60(Predicted)

color 

Dark red/purple

InChIKey

JVVGLKKTAZYUQU-UHFFFAOYSA-N

SMILES

N1(CC(CC)CCCC)C(C2SC(Br)=CC=2)=C2C(=O)N(CC(CC)CCCC)C(C3SC(Br)=CC=3)=C2C1=O

3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione Usage And Synthesis

Description

3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP-EH-2ThBr) is a building block containing a?DPP backbone as a strong acceptor unit. It has a planar conjugated bi-cyclic structure engaging stronger π–π interactions. Due to its electron-deficient nature,?DPP-EH-2ThBr and its derivatives are used for the synthesis of small molecules and low band-gap polymer semiconductors?with OPV, OLED and perovskite solar cells.

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 3,6-bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-C]pyrrole-1,4-diones was carried out using 2,5-bis(2-ethylhexyl)-3,6-bis(thiophen-2-yl)pyrrolo[3,4-C]pyrrole-1,4-diones as starting material as follows: in a 100 mL single-necked round-bottomed flask was charged with compound 3 (1.01 g, 2.05 mmol) and 50 mL of CHCl3. The reaction mixture was cooled to 273 K and N-bromosuccinimide (NBS) was added in batches under stirring. After NBS was completely added, the mixture was slowly warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the mixture was poured into water and extracted with CHCl3. The organic phases were combined and evaporated to remove CHCl3. The resulting red solid was purified by column chromatography using CHCl3/petroleum ether as eluent. The final isolation afforded 0.95 g of the target product 4 in 71% yield. The structure of the product was confirmed by 1H NMR, 13C NMR and FTIR.1H NMR (500 MHz, CDCl3) δ (ppm): 8.30 (d, J = 3.7 Hz, 2H), 6.62 (d, J = 3.7 Hz, 2H), 3.99 (m, 4H), 1.78-1.68 (m, 2H), 1.39-1.24 ( m, 16H), 0.92 (t, J = 7.5 Hz, 6H), 0.88 (t, J = 7.0 Hz, 6H).13C NMR (75 MHz, CDCl3) δ (ppm): 161.1, 146.4, 132.9, 126.4, 122.4, 115.7, 106.4, 46.4, 40.2, 30.7 28.9, 23.9, 23.3, 14.2, 10.8. FTIR (KBr) νmax: 3422, 3084, 2957, 2926, 2859, 1657, 1556, 1504.9, 1450, 1406, 1308, 1261, 1233, 1165, 1100, 1072, 1027, 967, 833, 810, 731. 833, 810, 731, 709, 635, 466, 430 cm-1.

References

[1] Journal of the American Chemical Society, 2010, vol. 132, # 44, p. 15547 - 15549
[2] Australian Journal of Chemistry, 2014, vol. 67, # 8-9, p. 1330 - 1337
[3] RSC Advances, 2015, vol. 5, # 25, p. 19520 - 19527
[4] Journal of Materials Chemistry A, 2013, vol. 1, # 8, p. 2795 - 2805
[5] Journal of Fluorescence, 2016, vol. 26, # 6, p. 1939 - 1949

3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione(1000623-95-9)Related Product Information

• Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-
• 3,6-Di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
• 3,4-Dimethoxythiophene
• 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole
• 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 3,6-DIBROMOTHIENO[3,2-B]THIOPHENE
• 3,6-Di(thieno[3,2-b]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 3,6-bis(5-broMo-4-(2-ethylhexyl)thiophen-2-yl)-1,2,4,5-tetrazine
• 3,6-Bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4-dione
• 4,4'-Dibutoxy-2,2'-bis(trimethylstannyl)-5,5'-bithiazole
• DPP‐iC12
• 3,4-Dibromothiophene