1260685-63-9

Usage

Uses

Used in Organic Thin-Film Transistors (OTFT) Industry:
3,6-Bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is used as an intermediate in the synthesis of DPPT-TT, which are organic thin-film transistors. Its strong acceptor unit and planar conjugated structure contribute to the optimization of the performance of organic semiconductors in TFT applications, while the long alkyl chains improve solubility and thin-film device properties.

Upstream product

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

Downstream Products

• 1616696-17-3 C₁₁₄H₁₆₄N₂O₈S₆ 

Relevant academic research and scientific papers

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.

Annealing-free high-mobility diketopyrrolopyrrole-quaterthiophene copolymer for solution-processed organic thin film transistors

A donor-acceptor polymer semiconductor, PDQT, comprising diketopyrrolopyrrole (DPP) and β-unsubstituted quaterthiophene (QT) for organic thin film transistors (OTFTs) is reported. This polymer forms ordered layer-by-layer lamellar packing with an edge-on orientation in thin films even without thermal annealing. The strong intermolecular interactions arising from the fused aromatic DPP moiety and the DPP-QT donor-acceptor interaction facilitate the spontaneous self-assembly of the polymer chains into close proximity and form a large π-π overlap, which are favorable for intermolecular charge hopping. The well-interconnected crystalline grains form efficient intergranular charge transport pathways. The desirable chemical, electronic, and morphological structures of PDQT bring about high hole mobility of up to 0.97 cm2/(V·s) in OTFTs with polymer thin films annealed at a mild temperature of 100 °C and similarly high mobility of 0.89 cm2/(V·s) for polymer thin films even without thermal annealing.

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.

Modulation of electronic properties of π-conjugated copolymers derived from naphtho[1,2-b:5,6-b′]dithiophene donor unit: A structure-property relationship study

A set of three donor-acceptor conjugated (D-A) copolymers were designed and synthesized via Stille cross-coupling reactions with the aim of modulating the optical and electronic properties of a newly emerged naphtho[1,2-b:5,6-b′] dithiophene donor unit for polymer solar cell (PSCs) applications. The PTNDTT-BT, PTNDTT-BTz, and PTNDTT-DPP polymers incorporated naphtho[1,2-b:5,6- b′]dithiophene (NDT) as the donor and 2,2′-bithiazole (BTz), benzo[1,2,5]thiadiazole (BT), and pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP), as the acceptor units. A number of experimental techniques such as differential scanning calorimetry, thermogravimetry, UV-vis absorption spectroscopy, cyclic voltammetry, X-ray diffraction, and atomic force microscopy were used to determine the thermal, optical, electrochemical, and morphological properties of the copolymers. By introducing acceptors of varying electron withdrawing strengths, the optical band gaps of these copolymers were effectively tuned between 1.58 and 1.9 eV and their HOMO and LUMO energy levels were varied between -5.14 to -5.26 eV and -3.13 to -3.5 eV, respectively. The spin-coated polymer thin film exhibited p-channel field-effect transistor properties with hole mobilities of 2.73 × 10-3 to 7.9 × 10-5 cm2 V-1 s-1. Initial bulk-heterojunction PSCs fabricated using the copolymers as electron donor materials and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) as the acceptor resulted in power conversion efficiencies in the range of 0.67-1.67%.

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.

Photocontrolled Synthesis of n-Type Conjugated Polymers

Current approaches to synthesize π-conjugated polymers (CPs) are dominated by thermally driven, transition-metal-mediated reactions. Herein we show that electron-deficient Grignard monomers readily polymerize under visible-light irradiation at room temperature in the absence of a catalyst. The product distribution can be tuned by the wavelength of irradiation based on the absorption of the polymer. Conversion studies are consistent with an uncontrolled chain-growth process; correspondingly, chain extension produces all-conjugated n-type block copolymers. Preliminary results demonstrate that the polymerization can be expanded to donor–acceptor alternating copolymers. We anticipate that this method can serve as a platform to access new architectures of n-type CPs without the need for transition-metal catalysis.

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.

Effects of Chemical Composition, Film Thickness, and Morphology on the Electrochromic Properties of Donor-Acceptor Conjugated Copolymers Based on Diketopyrrolopyrrole

A series of diketopyrrolopyrrole (DPP) and propylenedioxythiophene (ProDOT)-containing random copolymers with different donor-to-acceptor ratios is synthesized through Stille coupling polymerizations. The low-bandgap polymers display dark tones with colors ranging from magenta to blue, and reveal reversible colored-to-transmissive electrochromism in absorption/transmission-type devices with high optical contrasts (up to 48 and 77 in the visible and near-infrared regions, respectively), modest switching speeds (a few to tens of seconds) and coloration efficiencies (267-5742C-1), as well as good long-term ambient redox stabilities. The structure-performance relationship of the polymers, in particular, the role of donor-to-acceptor ratio, is investigated, and it is shown that an increase in the amount of acceptor in the polymers leads to slower oxidative but faster reductive switching, accompanied with enhancement of the redox stability. In addition, further study on the influence of film thickness and film morphology reveals that devices with higher optical contrasts are attainable from thicker polymer films at the expense of switching speeds; films with high uniformity and connectedness together with open, loose structures at submicron to micron scale are favorable for achieving good electrochromic performance. On and off: A series of electrochromic diketopyrrolopyrrole-based conjugated polymers are synthesized and characterized. Reversible colored-to-transmissive optical changes with high contrasts and ambient redox stabilities are observed (see figure). The influences of donor-to-acceptor ratio and film morphology on the electrochromic performance are addressed.

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.

NOVEL COMPOUND AND PHOTOELECTRIC CONVERSION DEVICE HAVING THE SAME

The present specification of the photoelectric conversion element is the life, efficiency, electrochemical stability and thermal stability can be compound, said compound number. under public affairs including photoelectric conversion element. Specifically photoelectric conversion region of. under public affairs number organic solar cell. (by machine translation)