1392422-47-7

Basic information

• Product Name: 2,5-Bis(2-ethylhexyl)-3,6-bis(5-(trimethylstannyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• Synonyms: 2,5-Bis(2-ethylhexyl)-3,6-bis(5-(trimethylstannyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• CAS NO: 1392422-47-7
• Molecular Formula: C₃₆H₅₆N₂O₂S₂Sn₂
• Molecular Weight: 850.39204
• EINECS: 200-258-5
• Mol File: 1392422-47-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 779.3±70.0 °C(Predicted)
• Appearance: /
• PKA: -4.84±0.60(Predicted)
• CAS DataBase Reference: 2,5-Bis(2-ethylhexyl)-3,6-bis(5-(trimethylstannyl)thiophen-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-(trimethylstannyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1392422-47-7)
• EPA Substance Registry System: 2,5-Bis(2-ethylhexyl)-3,6-bis(5-(trimethylstannyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1392422-47-7)

Safety Data

• Hazardous Substances Data: 1392422-47-7(Hazardous Substances Data)

Usage

General Description

2,5-Bis(2-ethylhexyl)-3,6-bis(5-(trimethylstannyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is a complex and long chemical compound. It contains two 2-ethylhexyl groups, two trimethylstannyl groups, and multiple thiophene and pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione groups. 2,5-Bis(2-ethylhexyl)-3,6-bis(5-(trimethylstannyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is commonly used in the development of organic electronic materials, such as solar cells and transistors. It has unique optical and electronic properties, making it suitable for use in various technological applications. However, due to its complex structure and potentially toxic stannyl groups, proper handling and disposal procedures are necessary when working with this chemical.

Upstream product

• 18908-66-2 3-bromomethylheptane 
• 1185885-86-2 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione 
• 1066-45-1 trimethyltin(IV)chloride 

Relevant articles and documents

A diketopyrrolopyrrole molecule end-capped with a furan-2-carboxylate moiety: The planarity of molecular geometry and photovoltaic properties

We designed and synthesized a diketopyrrolopyrrole (DPP) molecule with a fully-planar molecular geometry, 3,6-bis{5-[(ethylfuran-2-carboxylate)-2-yl] thiophene-2-yl}-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP(CF)2), for solution-processable organic solar cells (OSCs). It is theoretically calculated that the dihedral angles between the two furan-2-carboxylate end-groups and the DPP core are both only 0.56°. Due to this negligible steric distortion, the molecular conformation of DPP(CF) 2 can be considered fully coplanar, leading to a higher crystallinity for the DPP(CF)2 film. As a result, the hole mobility of DPP(CF)2 is one order of magnitude higher than that of the DPP derivative with thiophene-2-carboxylate as the end-group (DPP(CT)2). DPP(CF)2 exhibits both a low optical band gap (Eg) of 1.60 eV and a low-lying highest occupied molecular orbital (HOMO) energy level of -5.33 eV, implying that DPP(CF)2 is a promising electron donor for OSCs. OSCs with DPP(CF)2 or DPP(CT)2 as the electron donor and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the electron acceptor were fabricated. It is found that the DPP(CF) 2-based devices exhibit much better photovoltaic performance than the DPP(CT)2-based devices, with the highest power conversion efficiency of 5.37% and a short-circuit current density of 11.4 mA cm-2. This phenomenon can be ascribed to the superior charge-transporting ability of DPP(CF)2 due to its fully-planar molecular geometry. This journal is the Partner Organisations 2014.

Diketopyrrolopyrrole-based acceptor-acceptor conjugated polymers: The importance of comonomer on their charge transportation nature

Besides the donor-acceptor (D-A) type, acceptor-acceptor (A-A) polymers are another class of important alternative conjugated copolymers, but have been less studied in the past. In this study, two kinds of A-A polymers, P1 and P2, have been designed and synthesized based on diketopyrrolopyrrole in combination with the second electron-deficient unit, perylenediimide or thieno[3,4-c] pyrrole-4,6-dione. UV-vis absorption spectroscopy revealed that these two kinds of polymers have a band gap of 1.28-1.33 eV. Their highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels are around -5.6 and -4.0 eV for P1 polymers, whereas -5.4 and -3.7 eV for P2 polymers, respectively. Density functional theory study disclosed that P1 backbone is in a vastly twisting state, whereas that of P2 is completely planar. Furthermore, organic field-effect transistor devices were fabricated using these two kinds of polymers as the active material. Of interest, the devices based on P1 polymers displayed n-channel behaviors with an electron mobility in the order of 10 -4 cm2 V-1 s-1. In contrast, the P2-based devices exhibited only p-channel charge transportation characteristics with a hole mobility in the order of 10-3 cm2 V -1 s-1.