773881-43-9

Basic information

• Product Name: 5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione
• Synonyms: 5-Octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione;5-Octylthieno[3,4-c]pyrrole-4,6-dione;TPD-octyl;N-n-Octyl-3,4-thiophenedicarboximide;5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione;N-n-Octyl-3,4-thiophenedicarboxiMide
• CAS NO: 773881-43-9
• Molecular Formula: C₁₄H₁₉NO₂S
• Molecular Weight: 265.37116
• Mol File: 773881-43-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 120-122℃ (dichloromethane hexane )
• Boiling Point: 370.9±15.0 °C(Predicted)
• Appearance: /
• Density: 1.160±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Toluene
• PKA: -2.39±0.20(Predicted)
• CAS DataBase Reference: 5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione(773881-43-9)
• EPA Substance Registry System: 5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione(773881-43-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 773881-43-9(Hazardous Substances Data)

Usage

Description

5-Octyl-5H-thieno[3,4-c]pyrrole-4,6-dione is a heterocyclic organic compound that features a thieno[3,4-c]pyrrole core with a 4,6-dione group and an octyl side chain. 5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione is known for its potential use in the synthesis of polymers with high power conversion efficiency (PCE) for organic solar cells and organic field-effect transistors (OFETs).

Uses

Used in Organic Solar Cells:
Used in Organic Field-Effect Transistors (OFETs):
In the field of organic electronics, 5-octyl-5H-thieno[3,4-c]pyrrole-4,6-dione is also used as a monomer for synthesizing polymers that are applied in organic field-effect transistors. These polymers are crucial for the development of flexible and low-cost electronic devices, as they can enhance the performance and efficiency of OFETs.

Upstream product

• 6007-85-8 1H,3H-thieno[3,4-c]furan-1,3-dione 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 6007-82-5 thieno[3,4-c]pyrrole-4,6-dione 
• 111-83-1 1-bromo-octane 
• 3141-26-2 3,4-dibromothiophene 
• 111-86-4 n-Octylamine 
• 201230-82-2 carbon monoxide 
• 18853-32-2 3,4-dicyanothiophene 
• 847052-87-3 4-octylcarbamoylthiophene-3-carboxylic acid 

Downstream Products

• 566939-58-0 1,3-dibromo-5-octylthieno[3,4-c]pyrrole-4,6-dione 

Relevant articles and documents

Direct Imide Formation from Thiophene Dicarboxylic Acids Gives Expanded Side-Chain Selection in Thienopyrrolediones

The synthesis of thienopyrroledione (TPD) has been updated to reduce the number of synthetic steps, remove hazardous and toxic reagents, reduce the amount of byproduct waste, and reduce the use of solvents when unnecessary. Diverse functionalization is possible, introducing 16 examples in yields from 34% to 95%. This reaction scheme was shown to be general for thiophene imides, and a more thorough exploration into side chain engineering is presented with TPD acceptors often used in organic electronic applications.

Facile, one-step synthesis of 5-substituted thieno[3,4-c]pyrrole-4,6-dione by palladium-catalyzed carbonylative amidation

Abstract Described herein is a facile, one-step synthesis of 5-substituted thieno[3,4-c]pyrrole-4,6-diones (TPDs) by a palladium-catalyzed carbonylative amidation of commercially available dibromoaryl compounds under mild conditions. TPDs are important st

Copper-catalyzed direct C-H arylation of thieno[3,4-c]pyrrole-4,6-dione (TPD): Toward efficient and low-cost synthesis of ??-functional small molecules

A series of thieno[3,4-c]pyrrole-4,6-dione (TPD)-based functional small molecules were efficiently synthesized through direct C-H arylations using inexpensive copper salts. In this study, we examined all required reaction parameters including various copper complexes, ligands, bases, and (co)-solvents. Under the optimum reaction conditions, the C-H arylation proceeded smoothly and a variety of functional groups such as ester, nitrile, fluoride, chloride, triazene, and amine were tolerated. This method provides a step-economical and relatively low-cost synthetic alternative to presently used coupling reactions for the preparation of TPD-containing p-functional materials.