1185885-86-2

Basic information

• Product Name: 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• Synonyms: 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione;2, 5-bis(2-ethylhexyl)-3, 6-dithiophene-2-yl-2, 5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione;2,5-Bis(2-ethylhexyl)-3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione;2,5-Bis(2-ethylhexyl)-3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
• CAS NO: 1185885-86-2
• Molecular Formula: C₃₀H₄₀N₂O₂S₂
• Molecular Weight: 524.7808
• Mol File: 1185885-86-2.mol
• Article Data: 46

Chemical Properties

• Melting Point: 127℃
• Boiling Point: 687.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -4.84±0.60(Predicted)
• CAS DataBase Reference: 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1185885-86-2)
• EPA Substance Registry System: 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1185885-86-2)

Safety Data

• Hazardous Substances Data: 1185885-86-2(Hazardous Substances Data)

Usage

General Description

2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is a chemical compound commonly used in the manufacturing of organic electronic materials. It is a type of organic semiconductor that has a high electron affinity and can be used in the fabrication of field-effect transistors and organic photovoltaic devices. Due to its unique chemical structure and high electron mobility, this compound has shown promise in improving the efficiency and performance of electronic devices. Additionally, it has demonstrated potential in applications such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs) due to its ability to facilitate charge transport within these devices.

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 
• 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 
• 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 
• 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 
• 1423186-20-2 2,5-bis(2-ethylhexyl)-3,6-bis(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 

Relevant articles and documents

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.

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.

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.

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.

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

Charge separation and singlet fission in covalently linked diketopyrrolopyrrole derivatives and triphenylamine triad in solution

A covalently linked push-pull type triad containing two unsymmetrical electron donors, triphenylamine (TPA) and benzothiophene (BT), and diketopyrrolopyrrole (DPP), an electron acceptor, through thiophene spacer has been synthesized (BT-DPP-TPA(7)) and ultrafast relaxation dynamics of the triad has been explored in solution phase by various spectroscopic methods. Steady-state and time-resolved emission studies show the efficient fluorescence quenching of the DPP entity of as prepared BT-DPP-TPA(7) triad. The negative free energy values comprising the redox potentials and singlet state energy of BT-DPP-TPA(7) revealed the probability of electron transfer from the singlet ground state of TPA to the excited singlet state of DPP. Femtosecond transient absorption (fsTA) spectroscopic studies confirmed the formation of charge separation state by detecting triphenylamine radical cation as electron-transfer transients. The rate of charge separation, kCS, is (109?108 s?1) observed to be increasing from nonpolar to polar solvents and the rate of charge recombination, kCR, was found to be slower (μs time scale) in polar solvents like DMF and chloroform, than that in hexane, non-polar solvent (ns time scale). This novel aspect could be due to asymmetrically designed push-pull type triad, a feature that was not evident in push-pull triad constructed using symmetric TPA as electron donors. Furthermore, fsTA studies also demonstrate, for the first time, that the DPP derivatives, TDPP(4) and BT-DPP-TPA(7), both undergo singlet fission (SF) event (S→TT) in 100?200 ps time scale in solution phase for the solution of concentration above ～100 μM. These results may pave the new avenue for device design comprising DPP derivatives.

Improved crystallinity of the asymmetrical diketopyrrolopyrrole derivatives by the adamantane substitution

Alkylation of diketopyrrolopyrroles (DPPs) is a powerful tool for increasing the solubility and processability of these pigments. Moreover, alkylation contributes to solid state packing and structural ordering of DPPs. In this study, the influence of the alkylation and solubilization side group engineering to DPPs on the thermal and optical properties was systematically investigated. Two series (each containing 3 derivatives: N,N'-, N,O′- and O,O′-substituted examples) of alkylated DPPs by 2-ethylhexyl and ethyladamantyl substituents were synthesized. Separation of all formed DPP derivatives was accomplished in order to perform an in-depth study of their physicochemical properties. DSC measurements revealed that the O-substitution caused a decrease in the thermal stability of DPP derivatives. On the contrary, an ethyladamantyl side chain, as a rigid alicyclic substituent, contributed very effectively to the increase of the melting point and thermal stability. The new results provide insights into the development of DPP-alkylated regioisomers and their thermal and optical properties.

ORGANIC DYES, COMPOSITIONS AND DYE-SENSITIZED SOLAR CELLS

The present invention relates to a liquid crystal display device. The present invention relates to an organic dye, a composition including the same, and a dye-sensitized solar cell twisted π-spacer and DPP-based core unit introduced therein, and to a composition and a dye-sensitized solar cell including the same.