1267540-02-2

Usage

Uses

Used in Organic Electronics:
2,5-Bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is used as a key component in organic electronics due to its high electron mobility and good film-forming properties, which contribute to the development of efficient and stable devices.
Used in Solar Cell Applications:
In the solar cell industry, 2,5-Bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is utilized as an active layer material for creating organic photovoltaic devices. Its properties allow for the production of solar cells with improved efficiency and stability.
Used in Solution-Processed Electronic Devices:
The solubility provided by the long alkyl side chains of 2,5-Bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione makes it suitable for use in solution-processed electronic devices, where its processability and performance are highly valued.

Upstream product

• 69620-20-8 9-(bromomethyl)nonadecane 
• 1003-31-2 thiophene-2-carbonitrile 
• 1043023-53-5 9-(iodomethyl)nonadecane 
• 5333-42-6 2-octyldodecan-1-ol 

Downstream Products

• 1260685-63-9 3,6-bis(5-bromothiophene-2-yl) 22,5-bis(2-octyl-1-dodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 1351986-34-9 2,5-bis(2-octyldodecyl)-3,6-bis(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 1224430-28-7 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-decyltetradecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 

Relevant academic research and scientific papers

Incorporation of fused tetrathiafulvalene units in a DPP-terthiophene copolymer for air stable solution processable organic field effect transistors

A new terthiophene-diketopyrrolopyrrole (DPP) copolymer has been synthesised in which the central thiophene ring within the terthiophene repeat unit is attached to a fused tetrathiafulvalene (TTF). The electrochemical and absorption data of the polymer, p(DPP-TTF), are presented, and the multi-redox states are investigated by UV-vis spectroelectrochemistry. Bottom gate/bottom contact field effect transistors were fabricated from films of p(DPP-TTF) annealed at 200 °C. The material, which under these conditions forms a fibrous structure, exhibited hole mobilities of 4 ± 2 × 10 -2 cm2 V-1 s-1 with an on/off ratio of 1 × 104. The transistors showed little sign of degradation over 15 days of exposure under ambient conditions, demonstrating excellent air-stability. This characteristic is attributed to the incorporation of the TTF unit into the polymer.

A highly crystalline low band-gap polymer consisting of perylene and diketopyrrolopyrrole for organic photovoltaic cells

A new, low band-gap donor-acceptor-type conjugated polymer, PDPP-PER, comprising 3,9-perylene (PER) and diketopyrrolo[3,4-c]pyrrole (DPP) was synthesized. The crystallinity of the synthesized polymer film significantly improved with thermal annealing to 150°C. The PCE of the PDPP-PER device reached 6.35% with a high open-circuit voltage of 0.79 V.

Rational design of pyrrolopyrrole-aza-BODIPY-based acceptor-donor-acceptor triads for organic photovoltaics application

Acceptor-donor-acceptor triads consisting of diketopyrrolopyrrole (DPP) or pyrrolopyrrole aza-BODIPY (PPAB) or both as acceptors and cyclopentadithiophene as a donor were rationally designed for near infrared (NIR) photovoltaics application. Among them, the PPAB-based triad exhibited the highest power conversion efficiency of 3.88% owing to the panchromatic absorption in the UV/vis/NIR regions.

Diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, and preparation methods thereof

The invention provides a diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on the conjugated oligomer, and preparation methods thereof. The general structural formula of the conjugated oligomer is shown as a formula I in the specification. The diphenyl-pyrrolo-pyrrolidinedione with good light stability and strong electron withdrawing ability is used as a construction unit,a simple coupling reaction is used as a connection method, and the method for preparing the conjugated oligomer with controllable polymer, long light absorption wavelength and high photo-thermal conversion efficiency is provided. Meanwhile, the invention provides a preparation method of the nanoparticles based on the conjugated oligomer, and a new material and method are provided for the application of the conjugated oligomer as a photo-thermal reagent in biological treatment.

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.

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.

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.

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.

Synthesis and optical properties of photovoltaic materials based on the ambipolar dithienonaphthothiadiazole unit

Dithieno[3′2′:5,6;2′′,3′′:7,8]naphtho[2,3-c][1,2,5]thiadiazole (DTNT) was designed to control the band energies of the polymers for photovoltaic materials. Electrochemical analysis showed that DTNT acts as both an electron donor and an electron acceptor, revealing the ambipolar nature of the DTNT unit. The direct arylation polymerization of DTNT with 2,2′-bithiophene (BTh) and 3,6-bis(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) afforded four polymers that differed in either the unit of copolymerization or the chosen side chains. In the PDTNT-BTh series, a shoulder absorption band was observed at a longer wavelength than the intense absorption band. The PDTNT-DPP series exhibited a narrow band gap of less than 1.4 eV and a low HOMO energy of -5.43 eV. An organic photovoltaic cell that contained a PDTNT-BTh polymer with 2-ethylhexyl groups and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an active layer afforded the best performance among the studied compounds, with a JSC of 6.98 mA cm-3, a VOC of 0.758 V, a FF of 0.52, and a PCE of 2.76%.

Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors

Four π-conjugated benzo[1,2-b:4,5-b′]dithiophene (BDT) based polymers were synthesized for application in polymer solar cells. These polymers possessed desirable HOMO/LUMO levels for polymer photovoltaic applications. PBDTT-TTz and PBDTT-DTBT displayed strong absorption in the range of 300-650 nm, while PBDTT-DPP and PBDTT-TTDPP showed a further 100 nm extended absorption band. The lowest unoccupied molecular orbital energy levels of polymers were tuned effectively from -3.34 eV to -3.81 eV by fusing with different accepting units. A maximum power conversion efficiency of 2.60% was obtained from photovoltaic cells with a PBDTT-TTz:PC61BM (1:2, w/w) blend film as the active layer, with a short circuit current density of 8.37 mA cm-2, an open circuit voltage of 0.70 V, and a fill factor of 44.3%. This journal is