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

Uses

Monomer for synthesis of polymers for high power conversion efficiency (PCE) organic solar cells and OFETs through direct arylation polycondensation. Inverted bulk heterojunction solar cells based on PolyDTS-TPD:PC70BM blends or PolyDTG-TPD:PC70BM blends achieved average power conversion efficiencies of from 6.6 - 7.3%. (DTS: dithienosilole; DTG: dithienogermole; TPD: thienopyrrolodione)

Upstream product

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