566939-56-8

Basic information

• Product Name: 1,3-DibroMo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• Synonyms: 1,3-DibroMo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• CAS NO: 566939-56-8
• Molecular Formula: C₁₂H₁₃Br₂NO₂S
• Molecular Weight: 395.11012
• Mol File: 566939-56-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,3-DibroMo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DibroMo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(566939-56-8)
• EPA Substance Registry System: 1,3-DibroMo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(566939-56-8)

Safety Data

• Hazardous Substances Data: 566939-56-8(Hazardous Substances Data)

Usage

General Description

1,3-Dibromo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is a chemical compound that belongs to the class of pyrrole-4,6(5H)-dione derivatives. It is a synthetic organic compound that is commonly used in the field of organic chemistry and material science. 1,3-DibroMo-5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is known for its potential application as a pigment in the production of organic electronic devices and as a semiconductor material in the development of organic photovoltaic cells. Its unique molecular structure and properties make it a promising candidate for various technological applications. Additionally, this compound has been studied for its potential biological activities, including its antimicrobial and antitumor properties, making it of interest for pharmaceutical research.

Upstream product

• 6007-85-8 1H,3H-thieno[3,4-c]furan-1,3-dione 
• 111-26-2 hexan-1-amine 
• 566939-54-6 5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 
• 1015423-45-6 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 18853-32-2 3,4-dicyanothiophene 

Downstream Products

• 1379800-01-7 C₃₉H₃₂N₂O₃S₃ 
• 1379800-05-1 C₄₂H₃₃N₃O₄S₃ 

Relevant articles and documents

Push-pull thiophene-based small molecules with donor and acceptor units of varying strength for photovoltaic application: Beyond P3HT and PCBM

Here is reported an expedient synthesis implementing enabling technologies of a family of thiophene-based heptamers alternating electron donor (D) and acceptor (A) units in a D-A′-D-A-D-A′-D sequence. The nature of the peripheral A groups (benzothiadiazole vs. thienopyrrole-dione vs. thiophene-S,S-dioxide) and the strength of the donor units (alkyl vs. thioalkyl substituted thiophene ring) have been varied to finely tune the chemical-physical properties of the D-A oligomers, to affect the packing arrangement in the solid-state as well as to enhance the photovoltaic performances. The optoelectronic properties of all compounds have been studied by means of optical spectroscopy, electrochemistry, and density functional theory calculations. Electrochemical measurements and Kelvin probe force microscopy (KPFM) predicted a bifunctional behaviour for these oligomers, suggesting the possibility of using them as donor materials when blended with PCBM, and as acceptor materials when coupled with P3HT. Investigation of their photovoltaic properties confirmed this unusual characteristic, and it is shown that the performance can be tuned by the different substitution pattern. Furthermore, thanks to their ambivalent character, binary non-fullerene small-molecule organic solar cells with negligible values of HOMO and LUMO offsets were also fabricated, resulting in PCEs ranging between 2.54-3.96%. This journal is

A method for synthesizing DBTPD

The invention discloses a synthetic method of 1,3-dibromo-5-alkyl-4H-thiophene [3,4-c]-pyrroles-4,6(5H)-dione (DBTPD), which is characterized by comprising the following steps: taking 3,4-thiophene dimethylbenzene anhydride and alkylamine as raw materials, taking toluene as a solvent, reacting for 15-24 hours under 90-130 DEG C and then cooling to room temperature, then adding thionyl bromide and organic base under 0 DEG C, stirring for 1-5 hours under room temperature, and heating to 110-130 DEG C and reacting for 15-24 hours. The method can realize one-step synthesis, further separation and purification of an intermediate are not required; thionyl bromide during a synthesis process has dehydration effect and has effect as a brominating agent, anhydrous organic base is taken as a catalyst, so that usage of strong acid such as concentrated sulfuric acid and trifluoroacetic acid can be avoided, reaction security is greatly increased, and the products yield by the method can reach 90%.

Linear side chains in benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c] pyrrole-4,6-dione polymers direct self-assembly and solar cell performance

While varying the size and branching of solubilizing side chains in π-conjugated polymers impacts their self-assembling properties in thin-film devices, these structural changes remain difficult to anticipate. This report emphasizes the determining role that linear side-chain substituents play in poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers for bulk heterojunction (BHJ) solar cell applications. We show that replacing branched side chains by linear ones in the BDT motifs induces a critical change in polymer self-assembly and backbone orientation in thin films that correlates with a dramatic drop in solar cell efficiency. In contrast, we show that for polymers with branched alkyl-substituted BDT motifs, controlling the number of aliphatic carbons in the linear N-alkyl-substituted TPD motifs is a major contributor to improved material performance. With this approach, PBDTTPD polymers were found to reach power conversion efficiencies of 8.5% and open-circuit voltages of 0.97 V in BHJ devices with PC71BM, making PBDTTPD one of the best polymer donors for use in the high-band-gap cell of tandem solar cells.