4,8-Di(2-(2-ethylhexyl)thiophene-5-yl)-benzo[1,2-b:4,5-b']dithiophene

Base Information

• Chemical Name: 4,8-Di(2-(2-ethylhexyl)thiophene-5-yl)-benzo[1,2-b:4,5-b']dithiophene
• CAS No.: 1352642-35-3
• Molecular Formula: C34H42S4
• Molecular Weight: 578.971
• Mol file: 1352642-35-3.mol

Synonyms:4,8-Di(2-(2-ethylhexyl)thiophene-5-yl)-benzo[1,2-b:4,5-b']dithiophene

Chemical Property of 4,8-Di(2-(2-ethylhexyl)thiophene-5-yl)-benzo[1,2-b:4,5-b']dithiophene

Chemical Property:

• Boiling Point: 675.5±50.0 °C(Predicted)
• PSA: 112.96000
• Density: 1.133±0.06 g/cm3(Predicted)
• LogP: 13.09080

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,8-Bis[5-(2-ethylhexyl)thiophen-2-yl]benzo[1,2-b:4,5-b']dithiophene >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4,8-Bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b'']dithiophene is a reagent for the synthesis of conjugated copolymer containing tetrafluorophenylene for solar cells application.

Technology Process of 4,8-Di(2-(2-ethylhexyl)thiophene-5-yl)-benzo[1,2-b:4,5-b']dithiophene

There total 5 articles about 4,8-Di(2-(2-ethylhexyl)thiophene-5-yl)-benzo[1,2-b:4,5-b']dithiophene 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: 82.0%

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0) + 2-(2-ethylhexyl)thiophen (4891-44-5) → 4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylhexyl)thiophene-2-yl)benzo[1,2-b:4,5-b']dithiophene (1352642-35-3)

Guidance literature:

2-(2-ethylhexyl)thiophen; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 50 ℃; for 1h; Inert atmosphere;

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione; In tetrahydrofuran; hexane; at 50 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; tin(ll) chloride; In tetrahydrofuran; hexane; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.orgel.2016.07.003

Reference yield:

2-(2-ethylhexyl)thiophen (4891-44-5) + benzo[1,2-b:4,5-b']dithiophene (267-65-2) → 4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylhexyl)thiophene-2-yl)benzo[1,2-b:4,5-b']dithiophene (1352642-35-3)

Guidance literature:

2-(2-ethylhexyl)thiophen; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

benzo[1,2-b:4,5-b']dithiophene;

With hydrogenchloride; tin(II) chloride dihdyrate; In water;

DOI:10.1002/cssc.202100860

Reference yield:

3-bromomethylheptane (18908-66-2) → 4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylhexyl)thiophene-2-yl)benzo[1,2-b:4,5-b']dithiophene (1352642-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: n-butyllithium / Schlenk technique; Inert atmosphere

2: N-Bromosuccinimide / Schlenk technique; Inert atmosphere

3: n-butyllithium / Schlenk technique; Inert atmosphere

With N-Bromosuccinimide; n-butyllithium;

DOI:10.1021/ja403318y

upstream raw materials:

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

2-(2-ethylhexyl)thiophen

2-bromo-5-(2-ethylhexyl)thiophene

3-bromomethylheptane

Downstream raw materials:

1,1′-[4,8-Bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]

2,6-dibromo-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']-dithiophene

Refernces

• 1、 Su, Wenyan,Wang, Yang,Yin, Zhihong,Fan, Qunping,Guo, Xia,Yu, Liyang,Li, Yuxiang,Hou, Lintao,Zhang, Maojie,Peng, Qiang,Li, Yongfang,Wang, Ergang. "13.4 % Efficiency from All-Small-Molecule Organic Solar Cells Based on a Crystalline Donor with Chlorine and Trialkylsilyl Substitutions". . p. 3535 - 3543. Retrieved 2021.
• 2、 Zhang, Shaoqing,Ye, Long,Zhao, Wenchao,Liu, Delong,Yao, Huifeng,Hou, Jianhui. "Side chain selection for designing highly efficient photovoltaic polymers with 2D-conjugated structure". . p. 4653 - 4659. Retrieved 2014.
• 3、 Wu, Haimei,Zhao, Baofeng,Wang, Weiping,Guo, Zhaoqi,Wei, Wei,An, Zhongwei,Gao, Chao,Chen, Hui,Xiao, Biao,Xie, Yuan,Wu, Hongbin,Cao, Yong. "Side chain modification: An effective approach to modulate the energy level of benzodithiophene based polymers for high-performance solar cells". . p. 18115 - 18126. Retrieved 2015.
• 4、 Wang, Yang,Liu, Ying,Chen, Shaojie,Peng, Ruixiang,Ge, Ziyi. "Significant enhancement of polymer solar cell performance via side-chain engineering and simple solvent treatment". . p. 3196 - 3204. Retrieved 2013.
• 5、 Warnan, Julien,Cabanetos, Clement,Bude, Romain,El Labban, Abdulrahman,Li, Liang,Beaujuge, Pierre M.. "Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v". . p. 2829 - 2835. Retrieved 2014.
• 6、 -. "Compound based on benzo [1, 2-b: 4, 5-b '] dithiophene and preparation method thereof". Paragraph 0038; 0045-0048. . Retrieved 2020/09/12.