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

Base Information

• Chemical Name: Benzo[1,2-b:4,5-b']dithiophene-4,8-dione
• CAS No.: 32281-36-0
• Molecular Formula: C10H4O2S2
• Molecular Weight: 220.273
• Hs Code.: 29349990
• Mol file: 32281-36-0.mol

Synonyms:Thieno[2,3-f][1]benzothiophene-4,8-dione;

Chemical Property of Benzo[1,2-b:4,5-b']dithiophene-4,8-dione

Chemical Property:

• Melting Point: 260-262℃
• Boiling Point: 408 °C at 760 mmHg
• Flash Point: 200.6 °C
• PSA: 90.62000
• Density: 1.595 g/cm³
• LogP: 2.58500
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

Benzo[1,2-b:4,5-b'']dithiophene-4,8-dione ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Benzo[1,2-b:4,5-b’]dithiophene is a planar symmetrical molecular structure of the thiophene derivative, enabling a better π-π?stacking and good electron delocalization that encourages charge transport. In recent years, it has been intensively studied for the application of OFETs and OPVs. The incorporation of a low-band-gap unit into the benzo[1,2-b:4,5-b’]dithiophene unit could potentially result in a red-shifted absorption due to its electron-rich properties. Benzo[1,2-b:4,5-b’]dithiophene can be chemically modified to fine-tune its chemical structure and electron properties (e.g. band gap), energy levels, and charge mobility of the small molecule/polymers of interest (at a molecular level).
• Uses: BDTD can be used as an acceptor layer in the fabrication of polymer based solar cells. suzuki reaction

Technology Process of Benzo[1,2-b:4,5-b']dithiophene-4,8-dione

There total 12 articles about Benzo[1,2-b:4,5-b']dithiophene-4,8-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: 86.1%

3-thiophenecarboxylic acid,N,N-diethylamide (73540-75-7) → 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 - 20 ℃; Temperature; Inert atmosphere;

Reference yield: 77.0%

3-thiophene carboxaldehyde (498-62-4) + 3-thiophenecarboxylic acid,N,N-diethylamide (73540-75-7) → 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; 1.) -78 deg C, 1 h, 2.) -78 deg C -> RT, 12 h;

DOI:10.1021/ja00524a059

Reference yield: 77.0%

3-thiophene carboxylic acid chloride (41507-35-1) + 3-thiophenecarboxylic acid,N,N-diethylamide (73540-75-7) → 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -30 - 20 ℃; Inert atmosphere;

DOI:10.1039/c4nj02192d

upstream raw materials:

3-thiophene carboxaldehyde

3-thiophenecarboxylic acid,N,N-diethylamide

n-butyllithium

1H,3H-thieno[3,4-c]furan-1,3-dione

Downstream raw materials:

4,8-didodecyloxybenzo[1,2-b:4,5-b’]dithiophene

4,8-di(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene

C₅₃H₅₈BrNO₇S₃

C₅₄H₅₈BrNO₅S₄

Refernces

• 1、 Pang, Shuting,Wang, Zhiqiang,Yuan, Xiyue,Pan, Langheng,Deng, Wanyuan,Tang, Haoran,Wu, Hongbin,Chen, Shanshan,Duan, Chunhui,Huang, Fei,Cao, Yong. "A Facile Synthesized Polymer Featuring B-N Covalent Bond and Small Singlet-Triplet Gap for High-Performance Organic Solar Cells". supporting information. p. 8813 - 8817. Retrieved 2021/03/16.
• 2、 Aswathy,Sharma, Sushil,Tripathi, Narendra Pratap,Sengupta, Sanchita. "Regioisomeric BODIPY Benzodithiophene Dyads and Triads with Tunable Red Emission as Ratiometric Temperature and Viscosity Sensors". supporting information. p. 14870 - 14880. Retrieved 2019/11/13.