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

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

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.

Thieno[3,4-c]pyrrole-4,6-dione Oligothiophenes Have Two Crossed Paths for Electron Delocalization

A new series of electron-deficient oligothiophenes, thieno[3,4-c]pyrrole-4,6-dione oligothiophenes (OTPDn), from the monomer to hexamer, is reported. The optical and structural properties in the neutral states have been analyzed by absorption and emission spectroscopy together with vibrational Raman spectroscopy. In their reduced forms, these molecules could stabilize both anions and dianions in similar ways. For the dianions, two independent modes of electron conjugation of the charge excess were observed: the interdione path and the interthiophene path. The interference of these two paths highlighted the existence of a singlet diradical ground electronic state and the appearance of low-energy, thermally accessible triplet states. These results provide valuable insights into the device performance of TPD-based materials and for the rational design of new high-performance organic semiconductors.

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, characterization and photovoltaic properties of dithienobenzodithiophene-based conjugated polymers

Two new donor-acceptor typed conjugated polymers (P1 and P2) based on the large coplanar and more-extended donor dithieno[2,3-d:2,3-d′]benzo[1,2-b:4,5-b′]dithiphene and thienopyrroledione (TPD) units were synthesized. P1 and P2 have the same polymer backbone, but with different side chains, where P1 has 2-ethylhexyl side chains and P2 has the longer branched 4-ethyoctyl side chains. The solubility measurements show that P2 with longer branched 4-ethyloctyl side chain has better solubility in organic solvents than that of P1. The optical, electrochemical and photovoltaic properties were investigated. P1 and P2 show the very same absorption features in both solution and film states indicating an enhanced molecular planarity of the polymer chains in P1 and P2, which benefits from the large coplanar dithieno[2,3-d:2,3-d′]benzo[1,2-b:4,5-b′]dithiphene unit. The band-gaps of P1 and P2 are at 1.83?eV and 1.74?eV, respectively. The solar cells with P1 or P2 as the electron donor component and PC71BM as the electron acceptor were fabricated and measured under AM 1.5G illumination at 100?mW?cm?2. The results show that the P2/PC71BM-based device showed a moderate power conversion efficiency of 2.86%, which is ～50% improvement in comparison with P1/PC71BM-based device.

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).

A method for synthesizing DBTPD

The invention discloses a synthetic method of 1,3-dibromo-5-alkyl-4H-thiophene [3,4-c]-pyrroles-4,6(5H)-dione (DBTPD), which is characterized by comprising the following steps: taking 3,4-thiophene dimethylbenzene anhydride and alkylamine as raw materials, taking toluene as a solvent, reacting for 15-24 hours under 90-130 DEG C and then cooling to room temperature, then adding thionyl bromide and organic base under 0 DEG C, stirring for 1-5 hours under room temperature, and heating to 110-130 DEG C and reacting for 15-24 hours. The method can realize one-step synthesis, further separation and purification of an intermediate are not required; thionyl bromide during a synthesis process has dehydration effect and has effect as a brominating agent, anhydrous organic base is taken as a catalyst, so that usage of strong acid such as concentrated sulfuric acid and trifluoroacetic acid can be avoided, reaction security is greatly increased, and the products yield by the method can reach 90%.

THIENO, FURO AND SELENOPHENO-[3,4-C]PYRROLE-4,6-DIONE COPOLYMERS

Novel photoactive copolymers based on thieno, furo or selenopheno-[3,4- c]pyrrole-4,6-dione-derivative are described herein. More specifically, the photoactive copolymers comprise repeating units of Formula I -[A1-A2]- I wherein A1 is an electron donating unit such as a mono or polycyclic heteroaryl that is unsubstitued or substituted with one or more C1-20-alkyl or C1-20-alkoxy; and A2 is an alkylfuro or alkylselenopheno-[3,4-c]pyrrole-4,6-dione-derivative. The photoactive copolymers are suitable for use in BHJ solar cells.

Importance of the Donor:Fullerene intermolecular arrangement for high-efficiency organic photovoltaics

The performance of organic photovoltaic (OPV) material systems are hypothesized to depend strongly on the intermolecular arrangements at the donor:fullerene interfaces. A review of some of the most efficient polymers utilized in polymer:fullerene PV devices, combined with an analysis of reported polymer donor materials wherein the same conjugated backbone was used with varying alkyl substituents, supports this hypothesis. Specifically, the literature shows that higher-performing donor-acceptor type polymers generally have acceptor moieties that are sterically accessible for interactions with the fullerene derivative, whereas the corresponding donor moieties tend to have branched alkyl substituents that sterically hinder interactions with the fullerene. To further explore the idea that the most beneficial polymer:fullerene arrangement involves the fullerene docking with the acceptor moiety, a family of benzo[1,2-b:4,5-b]dithiophene-thieno[3,4-c]pyrrole-4,6-dione polymers (PBDTTPD derivatives) was synthesized and tested in a variety of PV device types with vastly different aggregation states of the polymer. In agreement with our hypothesis, the PBDTTPD derivative with a more sterically accessible acceptor moiety and a more sterically hindered donor moiety shows the highest performance in bulk-heterojunction, bilayer, and low-polymer concentration PV devices where fullerene derivatives serve as the electron-accepting materials. Furthermore, external quantum efficiency measurements of the charge-transfer state and solid-state two-dimensional (2D) 13C{1H} heteronuclear correlation (HETCOR) NMR analyses support that a specific polymer:fullerene arrangement is present for the highest performing PBDTTPD derivative, in which the fullerene is in closer proximity to the acceptor moiety of the polymer. This work demonstrates that the polymer:fullerene arrangement and resulting intermolecular interactions may be key factors in determining the performance of OPV material systems.

Enhanced performance of quasi-solid-state dye-sensitized solar cells by branching the linear substituent in sensitizers based on thieno[3,4-c]pyrrole-4, 6-dione

Thieno[3,4-c]pyrrole-4,6-dione-based organic sensitizers with triphenylamine (FNE38 and FNE40) or julolidine (FNE39 and FNE41) as electron-donating unit have been designed and synthesized. A linear hexyl group or a branched alkyl chain, the 2-ethylhexyl group, is incorporated into molecular skeleton of the dyes to minimize intermolecular interactions. The absorption, electrochemical, and photovoltaic properties for these sensitizers were then systematically investigated. It is found that the sensitizers have similar photophysical and electrochemical properties, such as absorption spectra and energy levels, owing to their close chemical structures. However, the quasi-solid-state dye-sensitized solar cells (DSSCs) based on the two types of sensitizers exhibit very different performance parameters. Upon the incorporation of the short ethyl group on the hexyl moiety, enhancements in both open-circuit voltage (Voc) and short-circuit current (J sc) are achieved for the quasi-solid-state DSSCs. The Voc gains originating from the suppression of charge recombination were quantitatively investigated and are in good agreement with the experimentally observed Voc enhancements. Therefore, an enhanced solar energy conversion efficiency (I·) of 6.16 %, constituting an increase by 23 %, is achieved under standard AM 1.5 sunlight without the use of coadsorbant agents for the quasi-solid-state DSSC based on sensitizer FNE40, which bears the branched alkyl group, in comparison with that based on FNE38 carrying the linear alkyl group. This work presents a design concept for considering the crucial importance of the branched alkyl substituent in novel metal-free organic sensitizers. Copyright

Thieno-, furo-, and selenopheno[3,4-c ]pyrrole-4,6-dione copolymers: Effect of the heteroatom on the electrooptical properties

New push-pull conjugated polymers based on furo[3,4-c]pyrrole-4,6-dione (FPD) and selenopheno[3,4-c]pyrrole-4,6-dione (SePD) have been synthesized and compared with their thieno[3,4-c]pyrrole-4,6-dione (TPD) analogues to investigate the effects of the heteroatom on the electrooptical properties. The copolymers were synthesized using either Stille cross-coupling or direct heteroarylation polymerization (DHAP), the latter method giving high molecular weights. Hypsochromic shifts of the band gaps were observed for FPD-based copolymers (sulfur substituted by oxygen) while small bathochromic shift was observed for SePD (sulfur substituted by selenium) when compared to its TPD analogue. These two new classes of conjugated polymers exhibit electrooptical properties that could lead to interesting bulk heterojunction plastic solar cells.