1260685-63-9

Basic information

• Product Name: 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• Synonyms: 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione;DPP‐iC20;2,5-Di(OD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole;3,6-bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione DPP-iC20;3,6-Bis(5-bromothien-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-dione;Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-bis(2-octyldodecyl)-;1,4-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-3,6-dione;DPP812-2Br
• CAS NO: 1260685-63-9
• Molecular Formula: C₅₄H₈₆Br₂N₂O₂S₂
• Molecular Weight: 1019.21084
• Mol File: 1260685-63-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 95.0-96.9℃ (hexane toluene )
• Boiling Point: 925.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -5.37±0.60(Predicted)
• CAS DataBase Reference: 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1260685-63-9)
• EPA Substance Registry System: 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1260685-63-9)

Safety Data

• Hazardous Substances Data: 1260685-63-9(Hazardous Substances Data)

Usage

Description

The monomer, 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, contains a DPP moiety. DPP backbone derivatives?as a strong acceptor unit, have a planar conjugated bicyclic structure engaging stronger π–π interactions which allows tuning the band-gap and energy-level of polymer organic semiconductors. Also long alkyl chains, namely 2-octyldodecyl, will allow better solubility for the polymer semiconductor and crystallization and aggregation capacity for the thin-film devices. DPP-containing polymers are considered promising materials for optimizing the performance of organic semiconductors.

Uses

3,6-Bis(5-bromothien-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-dione is an intermediate in the synthesis of DPPT-TT which are organic thin-film transistors.

Upstream product

• 1043023-53-5 9-(iodomethyl)nonadecane 
• 69620-20-8 9-(bromomethyl)nonadecane 
• 5333-42-6 2-octyldodecan-1-ol 
• 1267540-02-2 2,5-bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 
• 1003-31-2 thiophene-2-carbonitrile 

Downstream Products

• 1616696-17-3 C₁₁₄H₁₆₄N₂O₈S₆ 

Relevant articles and documents

Chemical oxidative and solid state synthesis of low molecular weight polymers for organic field effect transistors

Solution processability of the precursor molecules is a major issue owing to their limited solubility for the synthesis of conjugated polymers. Therefore, we favour the solvent free solid state chemical oxidative polymerization route for the synthesis of diketopyrrolopyrrole (DPP) based donor-acceptor (D-A) type conjugated polymers. D-A type polymer Poly(S-OD-EDOT) which contains DPP coupled with EDOT donor units is synthesized via solid state polymerization method. The polymer is employed as an active layer for organic field-effect transistors to measure charge transport properties. The Polymer shows good hole mobility 3.1 × 10?2 cm2 V?1 s?1, with a on/off ratio of 1.1 × 103.

2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-based donor-acceptor alternating copolymer bearing 5,5′-Di(thiophen-2-yl)-2, 2′-biselenophene exhibiting 1.5 cm2·V -1·s-1 hole mobility in thin-film transistors

A novel diketopyrrolopyrrole-based π-conjugated copolymer P(DPP-alt-DTBSe), 5, and a known copolymer P(DPP-alt-QT), 4, have been synthesized in 80-90% yield using the Stille coupling reaction. The molecular weights of 4 and 5 are 58 781 and 19 271 g/mol, respectively, with polydispersity values of 3.25-3.35. A relatively small band gap of 1.32-1.39 eV and excellent solubility in organic solvents were achieved in the two polymers. Thin-film transistors made of 5 exhibit outstanding performance (e.g., μ > 1.0-1.5 cm2·V-1·s-1, I on/Ioff > 105-106) with a conventional n-octyltrichlorosilane-SiO2 gate dielectric.

Processing temperature control of a diketopyrrolopyrrole-alt-thieno[2,3-b]thiophene polymer for high-mobility thin-film transistors and polymer solar cells with high open-circuit voltages

We synthesized a planar pDPPTTi-OD polymer based on diketopyrrolopyrrole (DPP) and thieno [2,3-b]thiophene (TTi) and investigated the electrical properties of the pDPPTTi-OD polymer. pDPPTTi-OD films displayed a low optical bandgap of 1.57?eV, and HOMO and LUMO levels of??5.40 and??3.74?eV, respectively. The 150°C-annealed pDPPTTi-OD films showed a high hole mobility of 0.16?cm2V?1s?1 in organic thin-film transistor (OTFT) devices. The photovoltaic properties of polymer solar cells (PSCs) incorporating the pDPPTTi-OD were also measured. A pDPPTTi-OD:PC71BM blend film was spin-coated at 25, 70 and 90?°C. High-temperature processing significantly improved the power conversion efficiency of PSCs by effectively reducing the PC71BM domain sizes, which improved the miscibility between pDPPTTi-OD and PC71BM. This work demonstrated that the TTi moiety is a useful donor building block for high- performance D–A type polymers in OTFTs and PSCs, and that processing temperatures should be controlled to fully realize the materials’ beneficial intrinsic properties.

A timely synthetic tailoring of biaxially extended thienylenevinylene-like polymers for systematic investigation on field-effect transistors

Considering there is growing interest in the superior charge transport in the ( E )-2-(2-(thiophen-2-yl)-vinyl)thiophene (TVT)-based polymer family, an essential step forward is to provide a deep and comprehensive understanding of the structure-property relationships with their polymer analogs. Herein, a carefully chosen set of DPP-TVT-n polymers are reported here, involving TVT and diketopyrrolopyrrole (DPP) units that are constructed in combination with varying thiophene content in the repeat units, where n is the number of thiophene spacer units. Their OFET characteristics demonstrate ambipolar behavior; in particular, with DPP-TVT-0 a nearly balanced hole and electron transport are observed. Interestingly, the majority of the charge-transport properties changed from ambipolar to p-type dominant, together with the enhanced hole mobilities, as the electron-donating thiophene spacers are introduced. Although both the lamellar d-spacings and π-stacking distances of DPP-TVT-n decreased with as the number of thiophene spacers increased, DPP-TVT-1 clearly shows the highest hole mobility (up to 2.96 cm2 V-11 s-1) owing to the unique structural conformations derived from its smaller paracrystalline distortion parameter and narrower plane distribution relative to the others. These in-depth studies should uncover the underlying structure-property relationships in a relevant class of TVT-like semiconductors, shedding light on the future design of top-performing semiconducting polymers.

Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications

A series of copolymers containing the benzo[1,2-d:4,5-d′]bis(thiazole) (BBT) unit has been designed and synthesised with bisthienyl-diketopyrrolopyrrole (DPP), dithienopyrrole (DTP), benzothiadiazole (BT), benzodithiophene (BDT) or 4,4′-dialkoxybithiazole (BTz) comonomers. The resulting polymers possess a conjugation pathway that is orthogonal to the more usual substitution pathway through the 2,6-positions of the BBT unit, facilitating intramolecular non-covalent interactions between strategically placed heteroatoms of neighbouring monomer units. Such interactions enable a control over the degree of planarity through altering their number and strength, in turn allowing for tuning of the band gap. The resulting 4,8-BBT materials gave enhanced mobility in p-type organic field-effect transistors of up to 2.16 × 10-2 cm2 V-1 s-1 for pDPP2ThBBT and good solar cell performance of up to 4.45% power conversion efficiency for pBT2ThBBT.