2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Base Information

• Chemical Name: 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
• CAS No.: 365547-21-3
• Molecular Formula: C25H36Br2S2
• Molecular Weight: 560.49
• Hs Code.: 2934999090
• Mol file: 365547-21-3.mol

Synonyms:DBCPDP;DTC26-2Br;2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;2,6-dibromo-4,4-di-(2-ethylhexyl)-4H-cyclopenta[2,1-b;2,6-DibroMo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b;2,6-DibroMo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b';2,6-DibroMo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene;2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene;4H-Cyclopenta[2,1-b:3,4-b']dithiophene, 2,6-dibroMo-4,4-bis(2-ethylhexyl)-;2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene >

Chemical Property of 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Chemical Property:

• Boiling Point: 552.1±50.0 °C(Predicted)
• PSA: 56.48000
• Density: 1.297
• LogP: 10.81410
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene >99.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene, with two thiophene units confined to one plane, cyclopenta[2,1-b;3,4-b′]dithiophene compounds allow?more effective conjugation if embedded into semiconducting polymers which in turn will have lowers the band gap. Furthermore, the planar structure will have greater effect on the morphology for the thin film devices to allow a well packed polymer?to polymer?backbones?which will bring the third-dimension into play. Take PCPDTBT for example, the planar structure improves the hole mobility of the device to 1 x 10-3 cm2/Vs.
• Uses: suzuki reaction

Technology Process of 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

There total 12 articles about 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-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: 98.0%

4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-20-2) → 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-21-3)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere; Darkness;

DOI:10.1039/d0cc00398k

Reference yield: 91.0%

3-bromomethylheptane (18908-66-2) + 2,6-dibromo-4H-cyclopenta-[2,1-b:3,4-b’]dithiophene → 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-21-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In water; at 75 ℃; for 0.75h;

DOI:10.1039/c4ra08119f DOI:10.1039/c4ra08119f

Reference yield: 36.0%

4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-20-2) → 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-21-3) + 4,4-bis(2-ethylhexyl)-2H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6(4H)-dione (1423124-61-1)

Guidance literature:

4,4-bis(2-ethylhexyl)-4H-cyclopenta(2,1-b:3,4-b’)-dithiophene; With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere; Darkness;

With water; In N,N-dimethyl-formamide; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.01.026

upstream raw materials:

4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

3-thiophene carboxaldehyde

4H-cyclopenta[2,1-b;3,4-b']dithiophene

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Downstream raw materials:

2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene

4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Refernces

• 1、 Feng, Ru,Sato, Narumi,Yasuda, Takuma,Furuta, Hiroyuki,Shimizu, Soji. "Rational design of pyrrolopyrrole-aza-BODIPY-based acceptor-donor-acceptor triads for organic photovoltaics application". supporting information. p. 2975 - 2978. Retrieved 2020/03/19.
• 2、 -. "POLYMER COMPOUND". Paragraph 0235. . Retrieved 2016/10/07.