1423186-20-2

Basic information

• Product Name: 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• Synonyms: 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• CAS NO: 1423186-20-2
• Molecular Weight: 676.987
• Mol File: 1423186-20-2.mol

Chemical Properties

• CAS DataBase Reference: 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1423186-20-2)
• EPA Substance Registry System: 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1423186-20-2)

Safety Data

• Hazardous Substances Data: 1423186-20-2(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 1185885-86-2 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione 
• 108-86-1 bromobenzene 

Relevant articles and documents

Solvent-Free Pd-Catalyzed Heteroaryl-Aryl Coupling via C-H Bond Activation for the Synthesis of Extended Heteroaromatic Conjugated Molecules

Direct arylation of thienopyrrolodione, diketopyrrolopyrroles, benzodithiophene derivatives, and fluorinated heteroarenes with functionalized aryl iodides is proven in solvent-free and non-anhydrous conditions. The reaction is performed in the presence of air and tolerates several functional groups on both the coupling partners, enabling a convenient synthesis of extended heteroaromatic conjugated molecules.

Diketopyrrolopyrrole based highly crystalline conjugated molecules for application in small molecule donor-polymer acceptor nonfullerene organic solar cells

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Diketopyrrolopyrrole (DPP) derivatives are an important class of high-performance pigment used in inks, paints, plastics, and organic electronics. Until now, DPP derivatives containing sophisticated aryl units at the DPP core have usually been obtained via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this work, a series of DPP-based π-conjugated molecules bearing diverse aryl substituents on the thiophene- or benzene-DPPs were facilely synthesized in moderate to excellent yields through the Pd-catalyzed direct arylation of C-H bonds. The synthetic procedures feature advantages over traditional C-C cross-coupling reactions such as: (1) avoidance of the use of organometallic reagents in the starting materials leading to simpler byproducts and higher atom economy, (2) fewer synthetic steps, (3) higher yields, (4) better compatibility with chemically sensitive functional groups, and (5) simpler catalytic systems free of phosphine ligands. These advantages make the present protocol an ideal and versatile strategy for the synthesis of DPP derivatives, especially for structurally complicated DPPs that may possess chemically sensitive functionalities. The optical and electrochemical properties of the synthesized DPPs (17 compounds) were systematically investigated using UV-vis spectroscopy, steady-state fluorescence spectroscopy, and cyclic voltammetry (CV).