1185885-86-2

Usage

Uses

Used in Organic Electronic Materials:
2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is used as a key component in the manufacturing of organic electronic materials due to its high electron mobility and unique chemical structure, which contribute to the improvement of device efficiency and performance.
Used in Field-Effect Transistors:
In the semiconductor industry, 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is utilized as a material for fabricating field-effect transistors. Its high electron affinity and charge transport capabilities make it suitable for enhancing the performance of these transistors.
Used in Organic Photovoltaic Devices:
2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is employed in the production of organic photovoltaic devices, where its electron affinity and charge transport properties are leveraged to improve the efficiency of solar energy conversion.
Used in Organic Light-Emitting Diodes (OLEDs):
In the display industry, 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is used as a material in organic light-emitting diodes. Its ability to facilitate charge transport enhances the brightness, color quality, and overall performance of OLED displays.
Used in Organic Field-Effect Transistors (OFETs):
2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is also utilized in the fabrication of organic field-effect transistors, where its electron mobility and charge transport properties are critical for the operation and efficiency of these transistors in various electronic applications.

InChI:InChI=1S/C30H40N2O2S2/c1-5-9-13-21(7-3)19-31-27(23-15-11-17-35-23)25-26(29(31)33)28(24-16-12-18-36-24)32(30(25)34)20-22(8-4)14-10-6-2/h11-12,15-18,21-22H,5-10,13-14,19-20H2,1-4H3

Upstream product

• 18908-66-2 3-bromomethylheptane 
• 999-64-4 3-bromooctane 
• 1003-31-2 thiophene-2-carbonitrile 

Downstream Products

• 1000623-95-9 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 1308671-90-0 3-(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)dione 
• 1418196-28-7 C₄₄H₅₀N₃O₄S₂^(1-)*Na⁽¹⁺⁾ 
• 1423186-20-2 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 1401967-47-2 2,5-bis(2-ethylhexyl)-3,6-bis(5-(4-methoxyphenyl)thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 
• 1423186-21-3 2,5-bis(2-ethylhexyl)-3,6-bis(5-(p-tolyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 1241836-03-2 (3,6-bis[5-(benzofuran-2-yl)-thiophen-2-yl]-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione) 
• 1404193-07-2 4-(5-(2,5-bis(2-ethylhexyl)-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)thiophen-2-yl)benzaldehyde 

Relevant academic research and scientific papers

Star-shaped magnesium tetraethynylporphyrin bearing four peripheral electron-accepting diketopyrrolopyrrole functionalities for organic solar cells

Magnesium tetraethynylporphyrins bearing four electron-deficient diketopyrrolopyrrole (DPP; Mg-TEP-DPP4) units were synthesized by Sonogashira coupling, and their optical and electrochemical properties were investigated. The energy levels were effectively tuned by DPP with or without electron-withdrawing end-caps. Importantly, all the Mg-TEP-DPP4 molecules have broad absorption bands across the visible and near-infrared regions. The time-dependent excited state features of Mg-TEP-DPP4 and their kinetics were investigated by femtosecond transient absorption spectroscopy in combination with multiwavelength and global/target analyses of time-resolved spectra. Importantly, the charge-separated state was demonstrated to undergo recombination within 253 ps in benzonitrile. Bulk heterojunction organic solar cells fabricated with Mg-TEP-DPP4:PC61BM exhibited a power conversion efficiency of 7.40% after solvent vapor annealing, which enabled balanced charge carrier transport, reduced charge recombination, and favorable charge separation and collection.

High-mobility n-type organic transistors based on a crystallized diketopyrrolopyrrole derivative

A new high-performing small molecule n-channel semiconductor based on diketopyrrolopyrrole (DPP), 2,2′-(5,5′-(2,5-bis(2-ethylhexyl)-3,6- dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-5,2-diyl)) bis(methan-1-yl-1-ylidene)dimalononitrile (DPP-T-DCV), is successfully synthesized. The frontier molecular orbitals in this designed structure are elaborately tuned by introducing a strong electron-accepting functionality (dicyanovinyl). The well-defined lamellar structures of the crystals display a uniform terrace step height corresponding to a molecular monolayer in the solid-state. As a result of this tuning and the remarkable crystallinity derived from the conformational planarity, organic field-effect transistors (OFETs) based on dense-packed solution-processed single-crystals of DPP-T-DCV exhibit an electron mobility (μe) up to 0.96 cm2 V-1 s-1, one of the highest values yet obtained for DPP derivative-based n-channel OFETs. Polycrystalline OFETs show promise (with an μe up to 0.64 cm2 V-1 s-1) for practical utility in organic device applications. Copyright

The effect of side-chain substitution on the aggregation and photovoltaic performance of diketopyrrolopyrrole-alt-dicarboxylic ester bithiophene polymers

Using a dicarboxylic ester bithiophene (DCBT) co-monomer, electron-withdrawing ester groups are introduced on the two central thiophene rings of an alternating donor-acceptor polymer (PDPP4T) consisting of diketopyrrolopyrrole (DPP) and quaterthiophene (4T) to increase the oxidation potential and reduce the photon energy loss in solar cells. To counteract the increased solubility of the PDPPDCBT polymers owing to the ester side chains, linear instead of branched side chains were used on the DPP monomer. The length of the ester side chains was varied to study their effect on the optoelectronic properties, morphology and photovoltaic performance of these polymers in bulk-heterojunction blends with PC71BM as acceptor. The molecular weight of PDPPDCBT is limited, because the bisstannyl-DPP monomer could not be completely purified from mono-functional analogues. By using a non-stoichiometric monomer ratio or a branching unit, the molecular weights were improved to ～35 kDa. A maximum power conversion efficiency of PCE = 5.7% was obtained. Compared to the parent PDPP4T (PCE 7.0%), the photon energy loss for the best PDPPDCBT was reduced from 0.79 to 0.76 eV, but the photon-to-electron quantum efficiency was reduced, as a consequence of a too coarse phase separation, as studied with two-dimensional grazing-incidence X-ray scattering and transmission electron microscopy.

Donor-fullerene dyads for energy cascade organic solar cells

Organic bulk heterojunction (BHJ) solar cells require broad absorption of the incident solar spectrum by the donor and acceptor in the blend. Fullerene derivatives with covalently linked dyes, referred to as dyads, were designed to have strong optical absorption and appropriate electronic levels for electron transfer with common donor polymers in BHJs. Dyads with dyes based on diketopyrrolopyrrole and benzothiadiazole were synthesized using either a methanofullerene or a fulleropyrrolidine linkage. The performance of these dyad acceptors in BHJ solar cells with poly(3-hexylthiophene) (P3HT) and a low optical gap co-polymer of thiophene and diketopyrrolopyrrole (PDPP2FT) were examined. Although the solar power conversion efficiencies were low, charge generation from the molecular dye in the dyad could be observed in BHJs with PDPP2FT. The low power conversion efficiency was attributed to the morphology of the BHJs based on grazing incidence wide angle X-ray scattering patterns. Density functional theory was used to examine the charge transfer states between the donor and the dyad. The lowest energy charge-transfer state was found to be a transition from the donor polymer to the fullerene portion of the dyad.

Substantial photovoltaic response and morphology tuning in benzo[1,2-b:6,5-b′]dithiophene (bBDT) molecular donors

The influence of solubilizing substituents on the photovoltaic performance and thin-film blend morphology of new benzo[1,2-b:6,5-b′]dithiophene (bBDT) based small molecule donor semiconductors is investigated. Solar cells based on bBDT(TDPP)2-PC71BM with two different types of side chains exhibit high power conversion efficiencies, up to 5.53%. This journal is the Partner Organisations 2014.

Diketopyrrolopyrrole (DPP) functionalized tetrathienothiophene (TTA) small molecules for organic thin film transistors and photovoltaic cells

Two novel π-conjugated small molecules based on the electron-deficient diketopyrrolopyrrole (DPP) and the electron-rich fused tetrathienoacene (TTA) frameworks are synthesized and characterized. As verified in the bandgap compression of these chromophores by electrochemistry and density functional theory (DFT) computation, these DPP-TAA derivatives exhibit substantial conjugation and ideal MO energetics for light absorption. The large fused TTA core and strong intermolecular SS interactions enforce excellent molecular planarity, favoring a close-packed thin film morphologies for efficient charge transport, as indicated by grazing incidence wide angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) analysis. Top-gate/bottom-contact thin film transistors based on these systems exhibit hole mobilities approaching 0.1 cm2 V-1 s-1. Organic photovoltaic cells based on DDPP-TTAR:PC71BM blends achieve power conversion efficiencies (PCE) > 4% by systematic morphology tuning and judicious solvent additive selection.

A Phototheranostic Strategy to Continuously Deliver Singlet Oxygen in the Dark and Hypoxic Tumor Microenvironment

Continuous irradiation during photodynamic therapy (PDT) inevitably induces tumor hypoxia, thereby weakening the PDT effect. In PDT-induced hypoxia, providing singlet oxygen from stored chemical energy may enhance the cell-killing effect and boost the therapeutic effect. Herein, we present a phototheranostic (DPPTPE?PEG-Py NPs) prepared by using a 2-pyridone-based diblock polymer (PEG-Py) to encapsulate a semiconducting, heavy-atom-free pyrrolopyrrolidone-tetraphenylethylene (DPPTPE) with high singlet-oxygen-generation ability both in dichloromethane and water. The PEG-Py can trap the 1O2 generated from DPPTPE under laser irradiation and form a stable intermediate of endoperoxide, which can then release 1O2 in the dark, hypoxic tumor microenvironment. Furthermore, fluorescence-imaging-guided phototherapy demonstrates that this phototheranostic could completely inhibit tumor growth with the help of laser irradiation.

A versatile star-shaped organic semiconductor based on benzodithiophene and diketopyrrolopyrrole

We report the synthesis of a new star-shaped π-conjugated oligomer, BDT(DPP)4, containing a benzodithiophene core and four diketopyrrolopyrrole arms. The thermal, electrochemical and optical properties are characterized and the results complemented by computational studies. The utility of the molecule is demonstrated in both solar cell and field-effect transistor devices. In the former, BDT(DPP)4 displays low efficiency when used as an acceptor in blends with poly(3-hexylthiophene) but exhibits promising performance as a donor, in blends with either a fullerene or a non-fullerene acceptor. In field-effect transistors BDT(DPP)4 exhibits typical p-type transistor behavior, which is in accordance with its better donor performance in solar cell devices.

Towards more sustainable synthesis of diketopyrrolopyrroles

The alkylation of 1,4-diketo-3,6-arylpyrrolo[3,4-c]pyrroles (ArDPP) is one of the most important steps in the synthesis of soluble materials based on these molecules and the polymers derived from them (that are employed widely in putative organic solar ce

Family of diazapentalene chromophores and narrow-band-gap polymers: Synthesis, halochromism, halofluorism, and visible-near infrared photodetectivity

A family of pyrrolo[3,4-c]pyrrol-1(2H)-one (PPO) and 2,5-diazapentalene (DAP) chromophores and DAP-containing polymers were synthesized, and their optical and electrochemical properties were studied. PPO and DAP chromophores are readily obtained by chemical transformation of the lactam unit in diketopyrrolopyrrole (DPP) dyes and can be used as versatile building blocks for construction of a variety of conjugated low-band-gap compounds and polymers. In comparison with the DPP chromophores, PPO and DAP chromophores have narrower energy gaps and low-lying HOMO levels in the order DPP > PPO > DAP. Interestingly, the PPO and DAP chromophores exhibit unique visible and near-infrared halochromic and halofluoric properties. The emission spectrum of DAP-containing polymer 6d covers the telecommunication window including the wavelength of 1310 nm. The photodetector with a device configuration of ITO/PEDOT:PSS (35 nm)/active layer (100 nm)/Al (100 nm) was fabricated using a blend of polymer 6d and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) in a weight ratio of 1:3 as the active layer and exhibited photocurrent spectral response from 400 to 1000 nm and the detectivity in an order of 1011 Jones at 800 nm.