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

Base Information

• Chemical Name: 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• CAS No.: 1185885-86-2
• Molecular Formula: C30H40N2O2S2
• Molecular Weight: 524.792
• Mol file: 1185885-86-2.mol

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

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

Chemical Property:

• Melting Point: 127℃
• Boiling Point: 687.5±55.0 °C(Predicted)
• PKA: -4.84±0.60(Predicted)
• PSA: 100.48000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 8.44240
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

2,5-Bis(2-ethylhexyl)-3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 7 articles about 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.4%

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione + 3-bromomethylheptane (18908-66-2) → 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione (1185885-86-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 145 ℃; for 15h;

Reference yield: 41.0%

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione + 3-bromomethylheptane (18908-66-2) → 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione (1185885-86-2) + 2-(2-ethylhexyl)-4-(2-ethylhexyloxy)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrol-1(2H)-one (1380497-22-2) + C30H40N2O2S2

Guidance literature:

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione; With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 1h;

3-bromomethylheptane; In N,N-dimethyl-formamide; at 105 ℃; for 2.83333h;

DOI:10.1016/j.dyepig.2019.108141

Reference yield: 32.0%

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione + 3-bromooctane (999-64-4) → 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione (1185885-86-2)

Guidance literature:

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione; With potassium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 1h;

3-bromooctane; In N,N-dimethyl-formamide; at 130 ℃; for 12h;

upstream raw materials:

3-bromomethylheptane

thiophene-2-carbonitrile

3-bromooctane

Downstream raw materials:

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

3,6-bis(2,2'-bithiophene-5-yl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

2,5-bis(2-ethylhexyl)-3,6-bis[5-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)thiophene-2-yl]-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

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

Refernces

• 1、 Yoon, Won Sik,Park, Sang Kyu,Cho, Illhun,Oh, Jeong-A,Kim, Jong H.,Park, Soo Young. "High-mobility n-type organic transistors based on a crystallized diketopyrrolopyrrole derivative". . p. 3519 - 3524. Retrieved 2013.
• 2、 Cowart, John S.,Liman, Christopher,Garnica, Amanda,Page, Zachariah A.,Lim, Eunhee,Zope, Rajendra R.,Baruah, Tunna,Hawker, Craig J.,Chabinyc, Michael L.. "Donor-fullerene dyads for energy cascade organic solar cells". . p. 192 - 202. Retrieved 2017.
• 3、 Zhou, Nanjia,Vegiraju, Sureshraju,Yu, Xinge,Manley, Eric F.,Butler, Melanie R.,Leonardi, Matthew J.,Guo, Peijun,Zhao, Wei,Hu, Yan,Prabakaran, Kumaresan,Chang, Robert P. H.,Ratner, Mark A.,Chen, Lin X.,Facchetti, Antonio,Chen, Ming-Chou,Marks, Tobin J.. "Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells". . p. 8932 - 8941. Retrieved 2015.
• 4、 He, Qiao,Shahid, Munazza,Panidi, Julianna,Marsh, Adam V.,Huang, Wentao,Daboczi, Matyas,Kim, Ji-Seon,Fei, Zhuping,Anthopoulos, Thomas D.,Heeney, Martin. "A versatile star-shaped organic semiconductor based on benzodithiophene and diketopyrrolopyrrole". . p. 6622 - 6629. Retrieved 2019.
• 5、 Qian, Gang,Qi, Ji,Davey, James A.,Wright, James S.,Wang, Zhi Yuan. "Family of diazapentalene chromophores and narrow-band-gap polymers: Synthesis, halochromism, halofluorism, and visible-near infrared photodetectivity". . p. 2364 - 2372. Retrieved 2012.
• 6、 Bangal, Prakriti Ranjan,Chakali, Madhu,Dyaga, Bharath,Mandal, Haraprasad,Rao, V. Jayathirtha,Venkatesan, Munisamy. "Charge separation and singlet fission in covalently linked diketopyrrolopyrrole derivatives and triphenylamine triad in solution". . . Retrieved 2020/11/26.
• 7、 Almenningen, David Moe,Gautun, Odd Reidar,Hoff, B?rd Helge,Venkatraman, Vishwesh,Yemene, Amsalu Efrem. "Synthesis of novel 3,6-dithienyl diketopyrrolopyrrole dyes by direct C-H arylation". . . Retrieved 2020/05/29.