- Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds
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A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4′-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.
- Ahn, Mina,Kim, Min-Ji,Cho, Dae Won,Wee, Kyung-Ryang
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p. 403 - 413
(2020/12/23)
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- Fluorene compound and organic electroluminescent device thereof
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The invention provides a fluorene compound and an organic electroluminescent device thereof. Belong to organic electroluminescence technical field. When the fluorene compound is used as a cover layer material, light can be effectively inhibited from being scattered from the cathode composite layer to a far distance from the cathode composite layer, light can be scattered from different directions of the cathode of the organic electroluminescent device, light transmittance of the device can be effectively weakened. Fluorene compound and organic electroluminescent device thereof The utility model has good application effect and industrialization prospect.
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Paragraph 0134-0137; 0172-0174
(2021/11/03)
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- Aromatic amine derivatives having fluorenyl moiety and organic light-emitting diode including the same
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The present invention relates to aromatic amine derivatives with a fluorene structure and a light-emitting element including the same, and more specifically, to an organic light-emitting compound expressed as [Formula A] and a light-emitting element containing the same. [Formula A] In [Formula A], X1 or X8 and Ar1, Ar2 are specifically defined in the description of the invention.
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Paragraph 0268-0270
(2020/03/24)
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- Compound, display panel and display device
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The invention belongs to the technical field of OLEDs and provides a compound as shown in a chemical formula I which is described in the specification. In the chemical formula I, Ar1, Ar2, Ar3 and Ar4are mainly selected from C6-C40 aryl groups and C5-C40 heteroaryl groups; R and R are mainly selected from -C(R)2-,-N(R)-,-O- and -S-; X1, X2 and X3 are selected from C atoms or N atoms; L1 andL2 are selected from phenylene, naphthylene and biphenylene; and Y1 and Y2 represent electron withdrawing groups and are mainly selected from nitrogen-containing heterocyclic substituents and cyano-containing substituents. In the compound disclosed by the invention, electron donating groups are connected to two substitution sites of a benzene ring or a nitrogen heterocyclic ring where X1, X2 andX3 are located, so the compound has the capability of transporting holes; and an amino group containing an electron withdrawing unit is connected to the other substitution site, so the compound has the capability of transporting electrons; and thus, the compound has the capability of transporting holes and electrons at the same time. By introducing a bipolar transmission main body, charge transmission balance in a light-emitting layer is facilitated, an exciton recombination region can be broadened, a device structure is simplified, and device efficiency is improved. The invention further provides a display panel and a display device.
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Paragraph 0075-0081
(2020/06/17)
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- Electron Push-Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning
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A series of perylene-based donor-acceptor-donor (D-A-D) compounds, 3,9-bis(p-(R)-diphenylamino)perylene (R: CN (2a), F (2b), H (2c), Me (2d), and OMe (2e)), was synthesized using 3,9-dibromoperylene with p-(R)-diphenylamine, and the intramolecular charge transfer (ICT) on the D-A-D system with regard to the electron push-pull substituent effect was investigated. By introducing various p-(R)-diphenylamine derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of the D-A-D compounds were systematically controlled and the emission colors were efficiently tuned from green to red. As expected, the steady state emission spectra of all D-A-D compounds were observed, as well as the emission color controlled, depending on the Hammett substituent constants (σp). In the Lippert-Mataga plots, a different charge-transfer character was observed depending on the electron push-pull substitution, which showed gradually increased ICT characters from the electron-withdrawing to donating substitution. However, exceptionally, the strong electron-withdrawing group of CN-substituted 2a did not correlate with the other R group compounds. From the experimental data and density functional theory calculations, we assume that there is a constraint on emission color tuning to generate higher energy of blue emission in the D-A-D molecular system, due to the reverse charge-transfer property caused by the strong electron-withdrawing group.
- Ahn, Mina,Kim, Min-Ji,Wee, Kyung-Ryang
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p. 12050 - 12057
(2019/10/11)
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- CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
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In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
- Mohammadinezhad, Arezou,Akhlaghinia, Batool
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p. 15525 - 15538
(2019/10/19)
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- Tripod with two handles shape tetramine pi and preparation method, tripod with two handles shape tetramine pi film modified electrode and its preparation method (by machine translation)
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The invention relates to a tripod with two handles shape tetramine pi and preparation method, tripod with two handles shape tetramine pi film modified electrode and its preparation method, which belongs to the electrode surface modification material technical field, in the prior art of interface modifying method adopts the bridged the molecular system synthesis difficult, poor stability and surface adsorption efficiency is low. The tripod with two handles shape tetramine pi, has the following structure, the 1, 3, 6, 8 - four bromines pi two fragrant amines derivatives with catalytic palladium catalyst under the coupling reaction. The invention provides a tripod with two handles shape tetramine pi can be used for modifying the electrode. (by machine translation)
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Paragraph 0083; 0086
(2018/03/26)
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- 4-(Phenoxy) and 4-(benzyloxy)benzamides as potent and selective inhibitors of mono-ADP-ribosyltransferase PARP10/ARTD10
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Human Diphtheria toxin-like ADP-ribosyltranferases (ARTD) 10 is an enzyme carrying out mono-ADP-ribosylation of a range of cellular proteins and affecting their activities. It shuttles between cytoplasm and nucleus and influences signaling events in both compartments, such as nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling and S phase DNA repair. Furthermore, overexpression of ARTD10 induces cell death. We recently reported on the discovery of a hit compound, OUL35 (compound 1), with 330 nM potency and remarkable selectivity towards ARTD10 over other enzymes in the human protein family. Here we aimed at establishing a structure-activity relationship of the OUL35 scaffold, by evaluating an array of 4-phenoxybenzamide derivatives. By exploring modifications on the linker between the aromatic rings, we identified also a 4-(benzyloxy)benzamide derivative, compound 32, which is potent (IC50 = 230 nM) and selective, and like OUL35 was able to rescue HeLa cells from ARTD10-induced cell death. Evaluation of an enlarged series of derivatives produced detailed knowledge on the structural requirements for ARTD10 inhibition and allowed the discovery of further tool compounds with submicromolar cellular potency that will help in understanding the roles of ARTD10 in biological systems.
- Murthy, Sudarshan,Desantis, Jenny,Verheugd, Patricia,Maksimainen, Mirko M.,Venkannagari, Harikanth,Massari, Serena,Ashok, Yashwanth,Obaji, Ezeogo,Nkizinkinko, Yves,Lüscher, Bernhard,Tabarrini, Oriana,Lehti?, Lari
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- Selective Cross-Coupling of (Hetero)aryl Halides with Ammonia to Produce Primary Arylamines using Pd-NHC Complexes
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Herein we report the first example of (hetero)arylation of ammonia using a monoligated palladium-NHC complex. The new, rationally designed, precatalyst (DiMeIHeptCl)Pd(allyl)Cl featuring highly branched alkyl chains has been shown to be effective in selective aminations across a range of challenging substrates, including nitrogen-containing heterocycles and those featuring base-sensitive functionality. The less bulky Pd-PEPPSI-IPentCl precatalyst performs well for ortho-substituted aryl halides, giving monoarylated products in high yield with good selectivity.
- Lombardi, Christopher,Day, Jonathan,Chandrasoma, Nalin,Mitchell, David,Rodriguez, Michael J.,Farmer, Jennifer L.,Organ, Michael G.
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supporting information
p. 251 - 254
(2017/04/26)
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- Charge instability of symmetry broken dipolar states in quadrupolar and octupolar triphenylamine derivatives
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The quadrupolar and octupolar cyano triphenylamines shows symmetry broken dipolar charge transfer state, however, its stability can be controlled by the rotation of N-C bond of amino and phenylene moiety. the Partner Organisations 2014.
- Easwaramoorthi, Shanmugam,Thamaraiselvi, Pichandi,Duraimurugan, Kumaraguru,Beneto, Arockiam Jesin,Siva, Ayyanar,Nair, Balachandran Unni
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supporting information
p. 6902 - 6905
(2014/06/23)
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- Amination with Pd-NHC complexes: Rate and computational studies involving substituted aniline substrates
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The amination of aryl chlorides with various aniline derivatives using the N-heterocyclic carbene-based Pd complexes Pd-PEPPSI-IPr and Pd-PEPPSI-IPent (PEPPSI=pyridine, enhanced precatalyst, preparation, stabilization, and initiation; IPr=diisopropylphenylimidazolium derivative; IPent= diisopentylphenylimidazolium derivative) has been studied. Rate studies have shown a reliance on the aryl chloride to be electron poor, although oxidative addition is not rate limiting. Anilines couple best when they are electron rich, which would seem to discount deprotonation of the intermediate metal ammonium complex as being rate limiting in favour of reductive elimination. In previous studies with secondary amines using PEPPSI complexes, deprotonation was proposed to be the slow step in the cycle. These experimental findings relating to mechanism were corroborated by computation. Pd-PEPPSI-IPr and the more hindered Pd-PEPPSI-IPent catalysts were used to couple deactivated aryl chlorides with electron poor anilines; while the IPr catalysis was sluggish, the IPent catalyst performed extremely well, again showing the high reactivity of this broadly useful catalyst. Copyright
- Hoi, Ka Hou,Calimsiz, Selcuk,Froese, Robert D. J.,Hopkinson, Alan C.,Organ, Michael G.
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supporting information; experimental part
p. 145 - 151
(2012/02/04)
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- Optimization of the central linker of dicationic bis-benzimidazole anti-MRSA and anti-VRE agents
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A series of bis-benzimidazole diamidine compounds containing different central linkers has been synthesized and evaluated for in vitro antibacterial activities, including drug-resistant bacterial strains. Seven compounds have shown potent antibacterial activities. The anti-MRSA and anti-VRE activities of compound 1h were more potent than that of the lead compound 1a and vancomycin.
- Hu, Laixing,Kully, Maureen L.,Boykin, David W.,Abood, Norman
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scheme or table
p. 3374 - 3377
(2010/02/28)
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- Palladium-Catalyzed Animation of Aryl Halides on Solid Support
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(Matrix Presented) The first examples of the Pd(0)-catalyzed amination of aryl halides using Rink-resins as nitrogen source are described. Pd2dba3/BINAP/NaO-t-Bu was found to be the most efficient catalyst/base system, while a solvent mixture of dioxane and tert-butyl alcohol was shown to enhance the selectivity toward the desired monoarylation. Moderate to good yields and excellent purities of the amination products were found with electron-poor aryl halides, while electon-rich aryl halides failed to react under these conditions.
- Weigand, Klaus,Pelka, Sylvie
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p. 4689 - 4692
(2007/10/03)
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- Aromatic Nitro group Displacement Reactions. Part 2. The Synthesis of Diarylamines and some Heteroaromatic Analogues.
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In dipolar aprotic solvents, activated aromatic nitro-groups can usually be displaced by anilines of enhanced N-acidity in the presence of the heavier alkali-metal carbonates.When catalysed by potassium t-butoxide, however, attack occurs preferentially at other reactive centers in the molecule, except where the nitro-group is highly activated.Some of the resulting diarylamines (the term is here expanded to include arylaminoxanthen-9-ones) are intermediates in the synthesis of heterocycles.
- Gorvin, John H.
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p. 1662 - 1681
(2007/10/02)
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- The Synthesis of Di- and Tri-arylamines through Halogen Displacement by Base-activated Arylamines: Comparison with the Ullmann Condensation
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In dipolar aprotic solvents, nitranions derived from anilines of enhanced N-acidity displace fluorine from activated aromatic compounds at room temperature.Diarylamines thus produced are free from triarylamines, which are formed at higher temperatures when diarylamines, after N-deprotonation by potassium t-butoxyde or by the heavier alkali metal carbonates, similarly displace activated fluorine.Certain diarylamines can also be prepared by chlorine displacement in the presence of alkali metal carbonates.It is confirmed that such carbonates play only an auxiliary role in the Ullmann (copper-assisted) diarylamine synthesis conducted in dipolar aprotic solvents; they may indeed impede the reaction in some instances.
- Gorvin, John H.
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p. 1331 - 1336
(2007/10/02)
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