1231160-83-0

Basic information

• Product Name: 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• Synonyms: 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione;1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione;1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole- 4,6(5H)-dione 97%;2,5-Dibromo-N-(2-ethylhexyl)-3,4-thiophenedicarboximide;2,5-Dibromo-N-(2-ethylhexyl)-3,4-thiophenedicarboximide;TPD26-2Br
• CAS NO: 1231160-83-0
• Molecular Formula: C₁₄H₁₇Br₂NO₂S
• Molecular Weight: 423.16328
• Mol File: 1231160-83-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 115-117℃
• Boiling Point: 452.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.618
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -3.36±0.20(Predicted)
• CAS DataBase Reference: 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(1231160-83-0)
• EPA Substance Registry System: 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione(1231160-83-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 1231160-83-0(Hazardous Substances Data)

Usage

Description

1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is a thienopyrrolodione (TPD) based electron acceptor material (n-type semiconductor) that is widely used in the field of organic photovoltaics (OPV). 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione possesses a powerful electron withdrawing capability, which makes it a valuable component in the development of efficient solar energy conversion systems.

Uses

Used in Organic Photovoltaic (OPV) Applications:
1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is used as an electron acceptor material in the synthesis of low band gap polymers for various OPV devices, including bulk heterojunction solar cells. Its strong electron withdrawing capability contributes to the high power conversion efficiency (PCE) observed in these solar cells, with reported values as high as 7.3%.
Used in Polymer Solar Cells:
In the polymer solar cell industry, 1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is utilized as a key component in the development of n-type semiconductor materials. These materials play a crucial role in enhancing the performance and efficiency of solar cells by facilitating the separation and transport of photogenerated charge carriers.
Used in Suzuki Reaction:
1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione is also employed in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are essential in the synthesis of various complex organic molecules, including those with potential applications in pharmaceuticals, materials science, and other industries.

InChI:InChI=1S/C14H17Br2NO2S/c1-3-5-6-8(4-2)7-17-13(18)9-10(14(17)19)12(16)20-11(9)15/h8H,3-7H2,1-2H3

Upstream product

• 1231160-82-9 5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 
• 104-75-6 2-Ethylhexylamine 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 6007-85-8 1H,3H-thieno[3,4-c]furan-1,3-dione 
• 190723-12-7 2,5-dibromo-3,4-dicarboxylic acid thiophene 
• 1015423-45-6 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde 
• 1231160-81-8 4-[[1-(2-ethylhexyl)amino]carbonyl]-3-thiophenecarboxylic acid 

Downstream Products

• 1420835-19-3 5-(3-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)-5-(2-ethylhexyl)-4,6-dioxo-5,6-dihydro-thieno[3,4-c]pyrrol-1-yl)thiophene-2-carbaldehyde 

Relevant articles and documents

Development of novel naphtho[1,2-b:5,6-b′]dithiophene and thieno[3,4-c]pyrrole-4,6-dione based small molecules for bulk-heterojunction organic solar cells

Two new small molecules, composed of naphthodithiophene (NDT) donor core and thienopyrroledione (TPD) group acceptor group end-capped with and without an alkyl-bithiophene, defined as NDT(TPD)2 and NDT(TPDTT)2 were designed and synthesized by stille coupling reactions. The thermal and electrochemical analyses carried out for both the small molecules revealed good thermal stability along with high decomposition temperature (>350?°C). NDT(TPD)2 showed a deep HOMO level (?5.38?eV), compared to slightly upshifted HOMO (?5.26?eV) of NDT(TPDTT)2. While X-ray diffractometry suggests crystalline and amorphous nature of NDT(TPD)2 and NDT(TPDTT)2 respectively, the space charge limited current analysis revealed high hole mobility in the former and appreciable charge balance in the later. The conventional organic solar cell (OSC) devices fabricated using NDT(TPD)2 and NDT(TPDTT)2 as donor show power conversion efficiency (PCE) of 0.26% and 0.8% respectively. While NDT(TPDTT)2 device after blending with additive, owing to the improved D-A heterojunction yielded maximum PCE of 1.31% resulting from enhanced Jsc 3.32?mA/cm2, Voc 0.75?V and FF of 52.44.

Structural Insight into Aggregation and Orientation of TPD-Based Conjugated Polymers for Efficient Charge-Transporting Properties

In this study, we obtained a new structural insight into the charge-transporting properties in TPD-based polymers that cannot be solely explained in terms of the type of orientation. We synthesized two types of copolymers comprising mono-TPD or bis-TPD as the accepting unit. Although the planarity and energy levels are similar with the mono-TPD unit, the aggregation state is quite different, and the X-aggregation tendency seems to be stronger when the bis-TPD unit is incorporated. In the case of TPD1, an effective π-πorbital overlap is found to originate from the H-aggregates, and 3D charge transport pathways are formed with a bimodal orientation of edge-on and face-on, resulting in an efficient charge transportation (1.84 cm2·V-1·s-1 of hole and 0.31 cm2·V-1·s-1 of electron). In contrast, despite the well-aligned edge-on orientation of TPD2, it exhibited a relatively very low mobility and splitted emission characteristics in photoluminescence spectra because of the tilted intermolecular stacking pattern with an X-shape (0.015 cm2·V-1·s-1 for hole and 0.16 cm2·V-1·s-1 for electron). An overall characterization of the semiconducting polymers was performed, and it was found that the type of aggregation in the final thin films, such as H- or X-aggregation, is indeed important and perhaps more important than the orientation to obtain polymers with a high charge carrier mobility.

Synthesis of TPD–thiophene-based small molecule donor for organic photovoltaic cells

The donor–acceptor–donor (D–A–D) type small molecule, TPD2T, was synthesized by the Stille coupling reaction and consisted of the electron-withdrawing thiene[3,4-c]pyrrole-4,6-dione (TPD) unit as an electron-accepting (A) core and electron-rich bithiophene units as electron-donating (D) groups. The absorption maximum of the TPD2T film was observed at 460?nm, and was broader and red-shifted compared to that in solution (λmax = 450?nm). Organic photovoltaic cells fabricated with the conventional and inverted structures both exhibited similar power conversion efficiencies of 0.14–0.15%. Despite the low short-circuit current values, the TPD2T devices showed high open-circuit voltages of over 1.0?V owing to the relatively low-lying HOMO level of TPD2T (?5.4?eV).