- A Novel Ratiometric Oxygen Sensor Based On a Sextuple Hydrogen-Bonding Self-Assembly Molecular Heterodimer
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A novel sextuple hydrogen-bonding (HB) self-assembly molecular heterodimer bearing an iridium complex as the indicator dye and two carbazoles as the reference dye, namely 6HB-Irbt-Cz, was synthesized, and its molecular structure was confirmed by1H NMR,13CNMR, TOF-MS and 2D NMR. Because of the inefficient energy transfer process between the carbazole and iridium complex units, 6HB-Irbt-Cz exhibits distinct ?uorescence/phosphorescence dual emission in neat film state. More importantly, the neat film sample of 6HB-Irbt-Cz could display linear ratiometric optical response toward oxygen in the full oxygen concentration range from 0 to 100 vol%, together with good stability, reversibility and rapid response-recovery times. Note that this represents the first discovery of neat-film-based oxygen sensor capable of showing strictly linear ratiometric Stern-Volmer behavior in the oxygen concentration of 0–100 vol%.
- Zeng, Hui,Zhang, Cheng,Huang, Yan,Lu, Zhiyun
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- Synthesis and Properties of Main-Chain Phosphorescent Polymer with Iridium Complex
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The main-chain phosphorescent polymers, PFCzIr(PhStz) and PFOIr(PhStz) with iridium complex (4-BrPhBt)2Ir(Pytz), are synthesized by the Suzuki polycondensation, in which the fluorene-carbazole and fluorene segments are used as a polymer backbon
- Chen, L.,Li, D.,Lin, M.,Ling, Q.,Liu, Ch.,Xing, G.
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- Synthesis of isobornylphenol-containing 3-aryl-1,2,4-triazin-5(4H)-ones
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A method for modification of 3-aryl-1,2,4-triazin-5(4H)-ones with isobornylphenols was proposed. The influence of various acylating agents on the reaction pathway was studied.
- Egorov,Chupakhin,Berezin,Rusinov,Rusinov,Buravlev,Chukicheva,Kuchinc
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- Synthesis, crystal structure, bovine serum albumin binding studies of 1,2,4-triazine based copper(I) complexes
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A series of new copper complexes have been synthesized and completely characterized by pivotal analytical techniques. The coordination geometry around copper(I) complex was best described as distorted tetrahedral geometry. The binding of bovine serum albumin with Cu(I) complexes are also been investigated. The Stern–Volmer analysis on quenching data exhibits the presence of the static quenching mechanism. The binding constants were calculated using modified Stern-Volmer, Lineweaver–Burk and Scatchard plots. All the complexes exhibit the binding constants in the order of 104. Thus, these results can contribute to the development of Cu(I) based drugs.
- Pathaw, Larica,Khamrang, Themmila,Kathiravan, Arunkumar,Velusamy, Marappan
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- Useful preparation of 6-phenyl-2,2′-bipyridine ligands bearing di-n-butylaminophenyl or gallate derivatives substituted in the 3- or 4-positions
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A simple protocol for the efficient preparation of substituted 6-phenyl-2,2′-bipyridine derivatives is described. A reverse type of Diels-Alder reaction between a 6-phenyl-2-pyridyl-1,3,4-triazine and 4-N,N-di-n-butylaminophenyl- or gallate-ethynyl derivatives at high temperature provide a mixture of two products easily separable by column chromatography. A variety of ligands suitable for the synthesis of cyclometalated platinum complexes have been produced. Additional substitution of the Pt-Cl by various donor-acceptor ethynyl fragments is feasible by mean of copper(I) catalysis. Georg Thieme Verlag Stuttgart.
- Diring, Stéphane,Retailleau, Pascal,Ziessel, Raymond
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- The blue phosphorescent iridium complexes containing new triazole ligands for OLEDs
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For the application to organic light-emitting diodes (OLEDs), the blue light emitting iridium complexes containing a new triazole (trzl) ancillary ligand were prepared and their photophysical properties was studied with respect to substituent effect at th
- Ahn, So Youn,Ha, Yunkyoung
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- A Modular Class of Fluorescent Difluoroboranes: Synthesis, Structure, Optical Properties, Theoretical Calculations and Applications for Biological Imaging
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Ten borylated bipyridines (BOBIPYs) have been synthesized and selected structural modifications have been made that allow useful structure–optical property relationships to be gathered. These systems have been further investigated using DFT calculations and spectroscopic measurements, showing blue to green fluorescence with quantum yields up to 41 %. They allow full mapping of the structure to determine where selected functionalities can be implemented, to tune the optical properties or to incorporate linking groups. The best derivative was thus functionalised with an alkyne linker, which would enable further applications through click chemistry and in this optic, the stability of the fluorophores has been evaluated.
- Bachollet, Sylvestre P. J. T.,Volz, Daniel,Fiser, Béla,Münch, Stephan,R?nicke, Franziska,Carrillo, Jokin,Adams, Harry,Schepers, Ute,Gómez-Bengoa, Enrique,Br?se, Stefan,Harrity, Joseph P. A.
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- 1,2,4-Triazole derivatives as host materials for blue and green phosphorescent organic light-emitting devices
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A novel host material, namely 9-(6-(3-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-yl)hexyl)-9H-carbazole (PPHCZ) was designed and synthesized by incorporating 1, 2, 4-triazol as the electron-withdrawing moiety and carbazole as electron-donating moiety using hexyl as bridge. The photophysical, electrochemical, thermal properties and performances in phosphorescent organic light-emitting devices (PhOLED) were thoroughly characterized. PPHCZ with a high triplet energy level (3.01?eV) exhibited an obvious intermolecular interaction in thin film. Green and blue PhOLEDs using fac-tris(2-phenylpyridine)iridium and iridium(III) bis(4,6-difluorophenyl)-pyridinato [Formula presented],C2′]picolinate as phosphorescent dopants have been fabricated.
- Xu, Huixia,Sun, Peng,Wang, Kexiang,Miao, Yanqin,Yang, Tingting,Wang, Hua,Xu, Bingshe,Wong, Wai-Yeung
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- Luminescence comparison of iridium(III) complexes containing symmetric vs. asymmetric quinolinate ligands
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We have focused our research on development of the iridium complexes, especially with respect to blue and red emission for OLED. Previously, we prepared bis-[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(acetylacetonate) [Ir(2,3-dpqx-F2)2/
- Park, Hye Rim,Ha, Yunkyoung
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- Synthesis, structural, DFT calculations and biological studies of rhodium and iridium complexes containing azine Schiff-base ligands
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The reaction of [Cp*MCl2]2(M?=?Rh/Ir) with N–N′ azine Schiff-base ligands (L1–L4) leads to the formation of mononuclear cationic half-sandwich complexes having the general formula [Cp*M(L)Cl]+(1–8), (M?=?Rh/Ir and L?=?(2-hydroxy-4-methoxybenzylidene)2-pyridylamidrazone (L1), (2-hydroxybenzylidene)2-pyridylamidrazone (L2), (1-(2-hydroxyphenyl)ethylidene)2-pyridylamidrazone (L3) and (1-phenylethylidene)2-pyridylamidrazone (L4). All these complexes were isolated as their hexafluorophosphate salts and fully characterized by spectroscopic and analytical techniques. The molecular structure of complexes (1), (3), (4), (7) and (8) have been determined by single crystal X-ray crystallographic studies which displayed the coordination of the ligand to the metal in a bidentate N∩N fashion through nitrogen atom of pyridine and one azine nitrogen. The chemo-sensitivity activities of the complexes were evaluated against HT-29 (human colorectal cancer) cell line and non-cancer cell line ARPE-19 (human retinal epithelial cells) which revealed that the complexes are moderately cytotoxic to cancer cells over human cells although complex 5 was the most potent among all the compounds. Theoretical studies carried out using DFT and TD-DFT at B3LYP level shows good agreement with the experimental results.
- Adhikari, Sanjay,Sutradhar, Dipankar,Shepherd, Samantha L.,Phillips, Roger M.,Chandra, Asit K.,Rao, K. Mohan
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- Novel light-emitting electrophosphorescent copolymers based on carbazole with an Ir complex on the backbone
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Novel light-emitting phosphorescent polymers based on 3,6-carbazole with an iridium complex on the backbone were synthesized by Suzuki polycondensation of A-A and B-B type monomers. Three difluoro-substituted phenylpyridine iridium complexes with differen
- Zhen, Hongyu,Luo, Jie,Yang, Wei,Chen, Qiliang,Ying, Lei,Jianhua, Zou,Wu, Hongbin,Cao, Yong
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- The blue phosphorescent iridium complexes containing the pyridyltriazole derivatives as a main ligand
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The titled iridium compounds involving the electron-withdrawing pyridyltriazole derivative as a main ligand were synthesized. The main ligand, 2-(5-methoxy-methyl)-2H-1,2,4-triazol-3-yl)pyridine (trzl-CH2OMe), was designed for development of the blue light-emitting iridium complexes. The ligand involves the electron-withdrawing moiety, N, which may contribute to lowering the HOMO energy level of the complex. In this paper, the new homoleptic complex, tris-(2-(5-(methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridinato)iridium (Ir(trzl-CH2OMe)3), was synthesized with trzl-CH 2OMe as the main ligand. The heteroleptic complexes containing trzl-CH2OMe and other ancillary ligands were also prepared, where the ancillary ligands, acac and pic, represent acetylacetonate and picolinate, respectively. The photophysical properties of the iridium complexes prepared herein, Ir(trzl-CH2OMe)3, Ir(trzl-CH2OMe) 2(acac), Ir(trzl-CH2OMe)2(pic) were investigated. Their photoluminescence maximum appeared at 445nm, 460nm and 472nm, respectively. We also investigated the electrochemical properties of these iridium complexes for the possible application to organic light-emitting diodes.
- Park, Hye Rim,Ha, Yunkyoung,Yi, Ye Young
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- Highly sensitive iridium(III) complex-based phosphorescent probe for thiophenol detection
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A cyclometalated iridium(iii) complex (Ir-DNBS) was designed and synthesized as a high-performance phosphorescent thiophenol probe. Ir-DNBS displays a distinct phosphorescence off-on response toward thiophenol with high selectivity, high sensitivity (detection limit: 2.5 nM) and fast response (10 min). It is noteworthy that the signaling phosphore of Ir-DNBS possesses relatively high photoluminescence quantum efficiency (ΦPL = 0.21) together with relatively long lifetime (τ = 2.07 μs), indicative of its potential in achieving high temporal resolution. Ir-DNBS is also applicable to the detection of thiophenol in actual water samples with high recovery rate. Photophysical and spectral characterization results revealed that the probing mechanism of Ir-DNBS toward thiophenol lies in the thiolate-mediated cleavage reaction, resulting in suppressed photo-induced excited state electron transfer process in the reaction product.
- Xiong, Li,Yang, Lin,Luo, Shuai,Huang, Yan,Lu, Zhiyun
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- A rational protocol for the synthesis of arylated bipyridine ligands via a cycloaddition pathway
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(Chemical Equation Presented) A generic design principle for the preparation of a variety of substituted phenyl-polypyridine ligands is described. These ligands are readily prepared by a regioselective [4+2] cycloaddition between electron-deficient dienes, such as 2,6-disubstituted-1,3, 4-triazines, and ethynyl-arenes or ethynyl-alkanes. Exceptional reactivity is found with electron-rich dienophiles bearing ethynylgallate or ethynylphenyldibutylamino groups. Two regioisomers are formed, the meta being preferred due to favorable π-π interactions in the transition state, while the para isomers are formed in low yields in most cases. The use of tert-butylacetylene or N,N-dimethylamino-2-propyne, however, drives the reaction exclusively to the para isomer. Di-N,N-dibutylaminophenyl or isoquinoline ligands can also be produced in a single step by reverse Diels-Alder reactions. Cross-coupling reactions of iodo-substituted ligands or their platinum(II) complexes under Pd(0) catalysis gives branched ligands and complexes bearing paraffin chains, electron-donor or electron-acceptor groups. The use of a chloro-Pt(II) complex of an iodo-functionalized ligand allows both halogens to be replaced by ethynyl groups by using different catalysts. This methodology readily accommodates various functional groups and has been successfully extended to systems containing a variety of donor/acceptor frameworks. All ligands strongly absorb in the near-UV and luminesce in solution at rt with quantum yields ranging from 0 to 66%. Excited state lifetimes are in the nanosecond range and the solvent effects are in keeping with singlet excited states mixed with charge-transfer character. As deduced from spectroscopic and electrochemical studies, the di-n-butylamino derivatives are strong reductants in the excited state.
- Diring, Stephane,Retailleau, Pascal,Ziessel, Raymond
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- Multimodal Probes: Superresolution and Transmission Electron Microscopy Imaging of Mitochondria, and Oxygen Mapping of Cells, Using Small-Molecule Ir(III) Luminescent Complexes
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We describe an Ir(III)-based small-molecule, multimodal probe for use in both light and electron microscopy. The direct correlation of data between light- and electron-microscopy-based imaging to investigate cellular processes at the ultrastructure level
- Shewring, Jonathan R.,Cankut, Ahmet J.,McKenzie, Luke K.,Crowston, Bethany J.,Botchway, Stanley W.,Weinstein, Julia A.,Edwards, Elizabeth,Ward, Michael D.
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- Palladium(II)complexes of ambidentate and potentially cyclometalating 5-aryl-3-(2′-pyridyl)-1,2,4-triazine ligands
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The 5-aryl-3-(2′-pyridiyl)-1,2,4-triazine ligands under study [5-phenyl-(PyTZPh)L1 5-(3-methoxyphenyl)-(PyTZ3Me-OPh)L2 5-(4-methoxyphenyl)-(PyTZ4MeOPh)L3 5-(4-trifluoromethylphenyl)-(PyTZ4CF3Ph)L4 5-(4-fluorophenyl)-(PyTZ4FPh)L5 and tris-3,5,6-(2′-pyridyl)-1,2,4-triazine (Py3TZ)L6] react with [(COD)PdCl2] (COD = 1,5-cyclooctadiento form complexes [(L1-6)PdCl2] with N,N bidentate binding ligands, also including the potentially N,N,N tridentate ligand L6. This was concluded from an in-depth NMR spectroscopic study of the new complexes and from comparison with Pd-terpy complexes [(R′ terpy)PdCl]Cl [R′terpy = 4′-R′-2,2′:6′,2′′-terpyridine R′ = H or SMe], showing definite tridentate N,N,N coordination, and with the Pd-bpy complexes [(bpy)Pd(Mes)Cl] and [(bpy)PdCl2], show-ing definite bidentate N,N binding. The new ligands and complexes were fully characterised by multinuclear NMR spectroscopy, IR spectroscopy and mass spectrometry. No evidence for the parent triazine complexes is observed in EI-MS instead, cyclometalated complexes (HCl eliminatiowere detected in all cases. TDA/TG experiments support this assumption. Attempts to prepare the cyclometalated derivatives as substances failed, in line with the unfavourable binding mode. Detailed electrochemical measurements reveal ligand-centred reductions at very moderate potentials, in line with UV/Vis absorption spectroscopy and DFT calculations, revealing very low-lying triazine-centred LUMOs. Results from cyclic voltammetry also support the composition of [(Py3TZ)PdCl2].
- Zvirzdinaite, Maryte,Garbe, Simon,Arefyeva, Natalia,Krause, Maren,Von Der Stück, René,Klein, Axel
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- Homoleptic platinum(ii) complexes with pyridyltriazole ligands: Excimer-forming phosphorescent emitters for solution-processed OLEDs
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Two new homoleptic platinum(ii) complexes are reported that feature aryl-appended 5-(2-pyridyl)-1,2,4-triazole chelates acting as N^N- ligating ions, PtL12 and PtL22. Readily prepared from easily accessible proligands, they offer good solubility in organic solvents, allowing them to be incorporated into OLEDs through solution processing. Crystal structures reveal staggered, face-to-face packing of the π systems in adjacent complexes, but with no close Pt?Pt interactions. The complexes display bright unimolecular phosphorescence: for PtL12 and PtL22 respectively, λmax = 502 and 514 nm; Φ = 0.21 and 0.48; τ = 5.1 and 4.6 μs in deoxygenated CH2Cl2 at 295 K. Both complexes show a strong propensity to form intensely emissive excimers at higher concentrations: λmax = 585 and 625 nm for PtL12 and PtL22. The photophysical properties in doped and neat thin films have been investigated using steady-state and time-resolved methods. These studies highlight the presence of different environments of bimolecular excited states with different lifetimes, those emitting at lowest energy apparently having the longest lifetimes, contrary to what is normally found for unimolecular emitters through the effects of vibrational deactivation. The prototype solution-processed OLEDs gave EQEs of 9.6-12.5% for PtL12 and 8.8-11.4% for PtL22, impressive values for solution-processed devices incorporating such simple complexes and only a little inferior to the EQE of 15% achieved using PtL12 in a device prepared by evaporation. Compounds of this type have potential to provide the red and green components for white light OLEDs, due to their tunable, uni- and bimolecular excited state emission.
- Walden, Melissa T.,Pander, Piotr,Yufit, Dmitry S.,Dias, Fernando B.,Williams, Gareth J.A.
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- Synthesis of 2-pyridylpyridines via aza-Diels-Alder reactions between 3-pyridyl-1,2,4-triazines and some vinyl alkanoates
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New synthetic procedure for 2,ω-bipyridines involving aza-Diels-Alder reaction between 3-(ω-pyridyl)-1,2,4-triazine and vinyl octanoate or decanoate as a dienophile is described. Copyright
- Shintou, Taichi,Ikeuchi, Fumiaki,Kuwabara, Hirokazu,Umihara, Ken,Itoh, Isamu
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- Discovery of a potent phenolic N1-benzylidene- pyridinecarboxamidrazone selective against Gram-positive bacteria
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As part of a study into antimycobacterial compounds a set of phenolic N1-benzylidene-pyridinecarboxamidrazones was prepared and evaluated. This report describes the unexpected discovery of a potent compound with a pronounced selectivity for Gram-positive bacteria over Gram-negative micro-organisms. In addition, this compound is active against various drug-resistant Gram-positive bacteria.
- Rathbone, Daniel L.,Parker, Katy J.,Coleman, Michael D.,Lambert, Peter A.,Billington, David C.
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- Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones
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The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.
- Dong, Guangbin,Xu, Yan,Zhou, Xukai
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supporting information
p. 20042 - 20048
(2021/12/03)
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- LED can be used for blue light excitation temperature in the cationic iridium (III) complex preparation (by machine translation)
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The invention relates to a novel can be blue light excitation used for preparing warm white light emitting diode (LED) red luminescent material - of cationic organic iridium (III) complex, the material can be with the Y3 Al5 O12 : Ce3 + (YAG: Ce) yellow fluorescent powder mixed doped package, the use of GaN blue light chip (λEm, max =455 nm) excited by warm white light, specific content relates to cationic organic iridium (III) complex synthesis and device preparation, to finally obtain excellent temperature or temperature of the light-emitting efficiency of the light emitting diode. In order to GaN blue light chip as the excitation light source, varied temperature in the increase of the content of illumination material, LED by cold white light changing into a warm white light. With only the use of the YAG: Ce is a light-emitting material compared with the preparation of the LED device, the invention uses YAG: Ce with the red luminescent material mixed doped the preparation of the color temperature of the LED device there can be substantially reduced. The temperature in the light-emitting material of good chemical and thermal stability, high luminous efficiency, easy synthesis and purification, low cost, and simple operation when applied to the LED, and has better application prospect. (by machine translation)
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Paragraph 0014
(2018/03/24)
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- N - hexyl carbazole substituted phenyl and [...] (III) complex and its preparation
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The invention discloses an N-hexyl carbazole substituted phenyl benzothiazole iridium (III) complex. The complex has a structure represented in a general structural formula (I). The complex emits organic yellow light, has double polarity and better solubility, and can be taken as a phosphorescent luminescence material for preparation of an organic light-emitting device with a wet method.
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Paragraph 0041; 0054-0055
(2020/02/07)
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- Redox Series of Cyclometalated Nickel Complexes [Ni((R)Ph(R′)bpy)Br]+/0/-/2- (H-(R)Ph(R′)bpy = Substituted 6-Phenyl-2,2′-bipyridine)
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New organonickel complexes [Ni((R)Ph(R′)bpy)Br] carrying various substituted derivatives of the tridentate -C∧N∧N ligand 6-(phenyl-2-ide)-2,2′-bipyridine (-Phbpy) were synthesized from the precursor [Ni(COD)2] (COD = 1,5-cyclooctadiene) and the protoligands (ligand precursors) Br-(R)Ph(R′)bpy. Several synthetic routes for the protoligands were studied and compared. All new compounds have been analyzed and spectroscopically characterized. From several complexes crystal and molecular structures were obtained from XRD experiments. UV-vis absorption spectroscopy and detailed electrochemical measurements reveal the impact of the various substituents on the electronic structure of the complexes. Quantum chemical DFT calculations illustrate the composition of highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) and support the assignment of the single-electron reduction and oxidation products as bpy-localized ligand radical species and transient nickel(III) intermediates, respectively.
- Sandleben, Aaron,Vogt, Nicolas,H?rner, Gerald,Klein, Axel
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supporting information
p. 3332 - 3341
(2018/09/27)
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- NOVEL OXABOROLE ANALOGS AND USES THEREOF
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This application describes compounds, compositions, and methods which are useful in treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a parasite.
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Paragraph 0261
(2018/09/21)
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- Cyclization of Methyl-Coumalate-Derived Methyl 1-Benzamido-6-oxo-1,6-dihydropyridine-3-carboxylates: Assembly of the [1,2,4]Triazolo[1,5-a]pyridine Ring System
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An efficient three-step synthesis of a series of fused bicyclic s-[1,2,4]triazolo[1,5-a]pyridines 1 was accomplished utilizing novel intermediates derived from inexpensive, commercially available hydrazides A and methyl coumalate B. A significant feature of this approach was the formation of a dihydrazide intermediate 2, bypassing the need for oxidative N-N bond formation in the 1,2,4-triazole synthesis. Further purification of the dihydrazides 2, beyond simple isolation, proved to be unnecessary owing to the impurity rejection afforded by the crystalline oxadiazolium salts 3. Additionally, the prepared oxadiazolium perchlorate salts showed excellent moisture stability, an unusual feature in compounds of this type.
- Moloney, Harold,Magnus, Nicholas A.,Buser, Jonas Y.,Embry, Matthew C.
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p. 6279 - 6288
(2017/06/23)
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- 1,2,4-triazole derivative-based dark blue fluorescent material and preparation method thereof
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The invention discloses a 1,2,4-triazole derivative-based dark blue fluorescent material which is as shown in the structural general formula (I). A 1,2,4-triazole derivative is used as a receptor unit, and phenylcarbazole or triphenylamine is used as a donor unit, thus forming the dark blue fluorescent material through conjugated benzene ring connection. The structural characteristic of the fluorescent material is favorable for forming a charge transfer excited state in a molecule, increasing the radiation excitor utilization rate and breaking through the limit that the excitor utilization rate of the fluorescent material is 25 percent to obtain the dark blue fluorescent material. The chromaticity coordinate of an OLED device prepared from the fluorescent material is less than that of standard blue light.
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Paragraph 0049; 0050
(2017/07/19)
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- 1,2,4-Triazole acceptor-based thermally activated delayed fluorescence material
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The invention discloses a 1,2,4-riazole acceptor-based thermally activated delayed fluorescence material with the structure represented by general formula (I) and capable of realizing dark blue lights. The material is formed through connecting the para-position of 3-substituted phenyl group of a 1,2,4-triazole derivative used as an acceptor unit with an N-containing donor unit. The thermally activated delayed fluorescence material has small singlet-triplet energy level difference, can meet requirements of the thermally activated delayed fluorescence material, allows a dark blue fluorescence material to be obtained, and improves the luminous efficiency of TADF type OLED devices.
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Paragraph 0043; 0044
(2017/09/01)
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- Bipolar hosts and non-doped deep-blue emitters (CIE: Y = 0.04) based on phenylcarbazole and 2-(2-phenyl-2 H -1,2,4-triazol-3-yl)pyridine groups
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We have designed and synthesized four bipolar materials, TAZ-1Cz, TAZ-2Cz, TAZ-3Cz and TAZ-4Cz, using 2-(2-phenyl-2H-1,2,4-triazol-3-yl)pyridine (TAZ) as an electron-withdrawing group and phenylcarbazole as an electron-donating group. Their rigid molecular structures improve their thermal stability with high glass transition temperatures: 99 °C for TAZ-2Cz, 100 °C for TAZ-3Cz and 103 °C for TAZ-4Cz. Employing TAZ-1Cz, TAZ-2Cz, TAZ-3Cz and TAZ-4Cz as hosts, green phosphorescent organic light-emitting devices (PhOLEDs) with fac-tris(2-phenylpyridine)iridium as an emitter display maximum external quantum efficiencies (EQEs) of 15.8, 15.5, 16.0 and 13.0%, respectively. And blue PhOLEDs hosted by TAZ-1Cz, TAZ-2Cz and TAZ-3Cz achieved maximum current efficiencies of 8.6, 11.0 and 10.6 cd A-1, respectively. Furthermore, non-doped OLEDs using TAZ-1Cz and TAZ-4Cz as emitters exhibit electroluminescence (EL) peaks at 400 and 412 nm with CIE coordinates of (0.16, 0.04) and (0.15, 0.04), which are located in the deep-blue region.
- Xu, Huixia,Sun, Peng,Wang, Kexiang,Li, Jie,Wang, Fang,Miao, Yanqin,Wang, Hua,Xu, Bingshe,Wong, Wai-Yeung
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p. 4455 - 4462
(2017/07/11)
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- ALIPHATIC-AROMATIC HETEROCYCLIC COMPOUNDS AND USES THEREOF IN METAL EXTRACTANT COMPOSITIONS
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The invention relates to an aliphatic-aromatic heterocyclic compound A which comprises at least two heterocyclic rings B and C, to a metal extractant composition E comprising this aliphatic-aromatic heterocyclic compound A and an organic acid D having at least one carboxylic, sulfonic, sulfuric, phosphinic, phosphonic, or phosphoric acid group, and to a process to extract one or more metals M selected from the group consisting of Ni and Co from an aqueous acidic leach solution PL comprising ions of at least one of the metals M, and further, at least one kind of further ions selected from the group consisting of Fe ions, Al ions, Cu ions, Mg ions, Mn ions, and also silicate anions, by mixing the solution PL with an extractant composition E, separating the organic and aqueous phases, and recovering the metal M from the separated organic phase.
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Paragraph 0168-0169
(2016/09/26)
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- Antimycobacterial activity of new N1-[1-[1-aryl-3-[4-(1H-imidazol-1-yl)phenyl]-3-oxo]propyl]-pyridine-2-carboxamidrazone derivatives
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N1-[1-[1-aryl-3-[4-(1H-imidazol-1-yl)phenyl]-3-oxo]propyl]-pyridine-2-carboxamidrazone derivatives were design, synthesized and tested for their in vitro antimycobacterial activity. The new compounds showed a moderate antimycobacterial activity
- Zampieri, Daniele,Mamolo, Maria Grazia,Vio, Luciano,Romano, Maurizio,Skoko, Nata?a,Baralle, Marco,Pau, Valentina,De Logu, Alessandro
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supporting information
p. 3287 - 3290
(2016/07/12)
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- A novel high-efficiency white hyperbranched polymer derived from polyfluorene with green and red iridium(III) complexes as the cores
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A new kind of single triple-color hyperbranched polymer PF-Ir(ppy)2(pytzph)m-Ir(piq)2(pytzph)n was designed and synthesized, in which green and red iridium(III) complexes acted as cores and blue polyfluorene acted as backbone. PF-Ir(ppy)2(pytzph)m-Ir(piq)2(pytzph)n (m = 5, n = 5 and m = 25, n = 5) had higher quantum efficiency than PF-Ir(piq)2(pytzph)5. The energy transfer from green core bis(2-phenylpyridine)[3-(2-pyridyl)-5-phenyl-1,2,4-triazole]iridium(III) [Ir(ppy)2(pytzph)] with high triplet energy level (ET = 2.58 eV) to red core bis(1-phenylisoquinolinato)[3-(2-pyridyl)-5-phenyl-1,2,4-triazole]iridium(III) [Ir(piq)2(pytzph)] (ET = 2.12 eV) could realize by intermediate poly(9,9-dioctylfluorene) (PF) segments. A typical single emitting-layer device with the configuration of ITO/PEDOT:PSS (40 nm)/PF-Ir(ppy)2(pytzph)m-Ir(piq)2(pytzph)n (80 nm)/TPBi (40 nm)/LiF (0.8 nm)/Al (100 nm) was fabricated. Among the white polymers, PF-Ir(ppy)2(pytzph)5-Ir(piq)2(pytzph)5 exhibited excellent electroluminescent properties with a Commission Internationale Ed I'eclairage (CIE) coordinate of (0.32, 0.34) and a maximum luminous efficiency of 11.49 cd/A.
- Sun, Jing,Wang, Hua,Xu, Huixia,Zhang, Tiaomei,Li, Lu,Li, Jie,Wu, Yuling,Xu, Bingshe,Zhang, Xinwen,Lai, Wenyong
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p. 191 - 201
(2016/04/05)
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- Ir(III) phosphors modified with fluorine atoms in pyridine-1,2,4-triazolyl ligands for efficient OLEDs possessing low-efficiency roll-off
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Five neutral heteroleptic Ir(III) complexes 1-5 using the same cyclometalated ligand and different pyridine-1,2,4-triazolyl derivatives as ancillary ligands with fluorine substituents attached, were rationally designed and prepared. Their photophysical, electrochemical, and thermal properties were studied, and theoretical calculations were performed to understand the emission behaviors as well. Introducing fluorine atoms has little effect on the photophysical and thermal properties, but the performances of the resulting devices can be fine-tuned. Among them, a heavy doping level device employing a phosphor with five fluorine atoms delivers superior device efficiencies with ηc = 32.6 cd A-1 and ηp = 27.6 lm W-1, respectively, which is higher than those of other counterparts. Importantly, such a device exhibits almost negligible roll-off in luminance efficiency. Despite nondoped devices achieving good EL performance, more fluorine atoms lead to a relatively higher efficiency roll-off. The results suggest that rational incorporation of fluorine atoms into the ancillary ligands can significantly improve the performance of devices with features of high efficiency and small roll-off.
- Mao, Hui-Ting,Zang, Chun-Xiu,Wen, Li-Li,Shan, Guo-Gang,Sun, Hai-Zhu,Xie, Wen-Fa,Su, Zhong-Min
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supporting information
p. 3870 - 3877
(2016/12/07)
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- Bipolar blue phosphorescent host material based on carbazole and 1,2,4-triazole
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The invention discloses a bipolar blue phosphorescent host material which is as shown in a structural general formula (I) and takes carbazole and 1,2,4-triazole as a donor and a receptor respectively. The triplet-state energy level of the host material is
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Paragraph 0030
(2016/12/22)
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- Efficient Preparation of Pyridinyl-1,2,4-Triazines via Telescoped Condensation with Diversely Functionalized 1,2-Dicarbonyls
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The development of materials for efficient chemoselective extraction of minor actinides remains at the forefront of research efforts in the area of separation science. Lewis basic complexants derived from nitrogen-donor scaffolds are often employed in this area due to favorable complexation with the transuranic element americium. In the present work an efficient procedure for the preparation of eight useful 3-pyridin-2-yl-1,2,4-triazines (2 novel) is demonstrated via telescoped condensation with the requisite 1,2-dicarbonyl in two-pots without additives, differentially extractive work-up procedures, or recrystallization. Additional efforts in this area have demonstrated the utility of polar aprotic solvents for the preparation of nine functionalized pyridinyl-2,6-bis-1,2,4-triazines (4 novel) directly from the requisite 2,6-pyridine dicarbonitrile in 49–99% yield over four total steps. The streamlined preparation of these important materials and detailed synthetic procedures is reported herein.
- Tai, Serene,Marchi, Sydney V.,Carrick, Jesse D.
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p. 1138 - 1146
(2016/07/29)
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- Bidentate NHC pyrozolate ligands in luminescent platinum(ii) complexes
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A bidentate C^N donor set derived from an N-heterocyclic carbene (NHC) precursor linked to a trifluoromethyl (CF3) functionalized pyrazole ring is described for the first time. The ligands have been employed to prepare four new phosphorescent complexes by the coordination of platinum(ii) centres bearing cyclometalated phenyl-pyridine/triazole-pyridine chelates. The electronic and steric environments of these complexes were tuned through the incorporation of suitable substituents in the phenyl-pyridine/triazole-pyridine ligands, wherein the position of the phenyl-ring substituent (a CF3 group) also directs the selective adoption of either a trans or a cis configuration between the CNHC and the Cphenyl donor atoms. Molecular structures obtained by X-ray diffraction for three of the complexes confirm a distorted square-planar configuration around the platinum centre, and DFT calculations show that the substituents have a significant influence on the energies of the frontier orbitals. Moreover, a platinum(ii) complex featuring the new bidentate NHC^pyrazolate ligand and a bulky adamantyl functionalized pyridine-triazole luminophore was observed to be highly emissive and exhibiting a sky-blue luminescence (λEm = 470 nm) with photoluminescence quantum yields as high as 50% in doped PMMA matrices. A complete photophysical investigation of all of the complexes in solution as well as in the solid state is herein reported.
- Naziruddin, Abbas Raja,Galstyan, Anzhela,Iordache, Adriana,Daniliuc, Constantin G.,Strassert, Cristian A.,De Cola, Luisa
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p. 8467 - 8477
(2015/05/20)
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- Sterically Hindered Luminescent PtII-Phosphite Complexes for Electroluminescent Devices
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PtII complexes with one bulky, sterically demanding, tertiary phosphite ancillary ligand and a coordinating chromophore are herein presented. The phosphite ligand, tris(2,4-di-tert-butylphenyl) acts as a bidentate ligand coordinating the platin
- Mydlak, Mathias,Yang, Cheng-Han,Polo, Federico,Galstyan, Anzhela,Daniliuc, Constantin G.,Felicetti, Michael,Leonhardt, Jens,Strassert, Cristian A.,De Cola, Luisa
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p. 5161 - 5172
(2015/03/30)
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- Synthesis and photoelectric properties of a solution-processable yellow-emitting iridium(iii) complex
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A solution-processable yellow-light-emitting heteroleptic phosphorescent Ir(iii) complex of (CzhBTZ)2Ir(fpptz) [CzhBTZ: (2-[2-(6-(9-carbazolyl)hexyl)phenyl]benzothiazole) fpptz: (2-(5-(4-fluorophenyl)-2H-1,2,4-triazol)-3-yl)] was synthesized. Its photophysical, thermal and electroluminescence properties were investigated. Phosphorescent organic light-emitting diodes (PhOLEDs) using (CzhBTZ)2Ir(fpptz) doping in (4,4′-bis(N-carbazolyl)-1,1′-biphenyl) as the emitting layer were prepared by spin-coating with a maximum peak at 533 nm, and International Commission on Illumination (CIE) coordinates of (0.42, 0.56).
- Wu, Yuling,Xu, Huixia,Yang, Junli,Li, Jie,Liang, Wenqing,Sun, Jing,Wang, Hua,Xu, Bingshe
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p. 8908 - 8914
(2015/11/10)
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- Synthesis and characterization of blue-to-green electrophosphorescence emitter based on pyrazole iridium complexes
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To overcome the roll-off efficiency of electrophosphorescent organic light-emitting devices, Ir(III) complexes of (ppz)2Ir(N?N) were synthesized and named for (ppz)2Ir(tfmpptz), (ppz) 2Ir(fpptz), (ppz)2Ir(tfmptz) and (ppz)2Ir(pybi) (ppz: 1-phenylpyrazolato; N?N: N, N′-heteroaromatic). Their molecular structures, photophysical properties and cyclic voltammetric data were reported. The crystals of (ppz)2Ir(tfmpptz), (ppz) 2Ir(fpptz) are monoclinic, space group P2(1)/n, and (ppz) 2Ir(tfmptz) is triclinic, space group P-1. The emission maximum peaks of (ppz)2Ir(tfmpptz), (ppz)2Ir(fpptz), (ppz) 2Ir(tfmptz) and (ppz)2Ir(pybi) at room temperature appear at 486, 497, 473 and 530 nm, respectively. The devices with architecture of ITO/NPB (30 nm)/CBP: (ppz)2Ir(N?N) (6%, 30 nm)/BAlq(10 nm)/Alq3(30 nm)/LiF(1 nm)/Al (100 nm) were fabricated by thermal evaporation. The results indicate that the larger steric hindrance of ancillary ligands efficiently suppressed the roll-off of efficiency at high current density.
- Huixia, Xu,Yan, Yue,Litao, Qu,Yuying, Hao,Hua, Wang,Liuqing, Chen,Bingshe, Xu
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- Structure-reactivity relationships in the hydrogenation of carbon dioxide with ruthenium complexes bearing pyridinylazolato ligands
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Pyridinylazolato (N-N') ruthenium(II) complexes of the type [(N-N')RuCl(PMe3)3] have been obtained in high yields by treating the corresponding functionalised azolylpyridines with [RuCl 2(PMe3)4] in the presence of a base. 15N NMR spectroscopy was used to elucidate the electronic influence of the substituents attached to the azolyl ring. The findings are in agreement with slight differences in the bond lengths of the ruthenium complexes. Furthermore, the electronic nature of the azolate moiety modulates the catalytic activity of the ruthenium complexes in the hydrogenation of carbon dioxide under supercritical conditions and in the transfer hydrogenation of acetophenone. DFT calculations were performed to shed light on the mechanism of the hydrogenation of carbon dioxide and to clarify the impact of the electronic nature of the pyridinylazolate ligands. Copyright
- Muller, Keven,Sun, Yu,Heimermann, Andreas,Menges, Fabian,Niedner-Schatteburg, Gereon,Van Wuellen, Christoph,Thiel, Werner R.
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p. 7825 - 7834
(2013/07/05)
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- Discovery of a new molecular probe ML228: An activator of the hypoxia inducible factor (HIF) pathway
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Hypoxia and ischemia are linked to several serious public health problems that affect most major organ systems. Specific examples include diseases of the cardiovascular, pulmonary, renal, neurologic, and musculoskeletal systems. The most significant pathw
- Theriault, Jimmy R.,Felts, Andrew S.,Bates, Brittney S.,Perez, Jose R.,Palmer, Michelle,Gilbert, Shawn R.,Dawson, Eric S.,Engers, Julie L.,Lindsley, Craig W.,Emmitte, Kyle A.
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experimental part
p. 76 - 81
(2012/02/16)
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- Organic Compound, Benzoxazole Derivative, and Light-Emitting Element, Light-Emitting Device, and Electronic Device Using Benzoxazole Derivative
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Novel benzoxazole derivatives are provided to reduce driving voltage of light-emitting elements, and to reduce power consumption of light-emitting elements, light-emitting devices, and electronic devices. A benzoxazole derivative represented by the general formula (G1) is provided. Since the benzoxazole derivative represented by the general formula (G1) has an electron-injecting property, the benzoxazole derivative can be suitably used for light-emitting elements, light-emitting devices, and electronic devices.
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Page/Page column 60-61
(2012/07/27)
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- New blue phosphorescent iridium complexes containing phenylpyridine and triazole ligands: Synthesis and luminescence studies
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The synthesis and luminescence of iridium(III) complexes containing new phenylpyridine (C∧N) ligands, 4-Me-4'-F-ppy, 4-Me-4'-CF3-ppy and 4-OMe-4'-CF3-ppy, were studied. These ligands were designed for development of the blue light-em
- Ahn, So Youn,Lee, Hyun Shin,Ha, Yunkyoung
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scheme or table
p. 4414 - 4418
(2012/06/16)
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- Pyridyltriazole as a main ligand in the iridium complexes for blue phosphorescence
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New blue-phosphorescent iridium complexes containing pyridyltriazole derivatives (trzl-CH2OMe) as main ligands and benzyldiphenylphosphines (bdp) as ancillary ligands were synthesized and their photophysical properties were investigated. As a m
- Ahn, So Youn,Ha, Yunkyoung
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experimental part
p. 68 - 74
(2011/07/30)
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- FUSED PYRIMIDINES
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Compounds of formula (I), or an N-oxide, a salt, a tautomer or a stereoisomer of said compound, or a salt of said N-oxide, tautomer or stereoisomer, wherein ring B and the pyrimidine to which it is fused, R4, R5, R6, R7, m and n have the meanings as given in the description and the claims, which are effective inhibitors of the Pi3K/Akt pathway, processes for their production and their use as pharmaceuticals.
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Page/Page column 150
(2010/09/03)
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- FUSED PYRIMIDINES AS AKT INHIBITORS
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The present invention relates to compounds of formula (I), a N-oxide or tautomer or stereoisomer thereof, or a salt thereof, wherein ring B and the imidazole to which it is fused, R4, R6, R7, R10, m and n have the meanings as given in the description and the claims, which are effective inhibitors of the Pi3K/Akt pathway, processes for their production and their use as pharmaceuticals.
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Page/Page column 60
(2010/09/03)
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- Organic Compound, Benzoxazole Derivative, and Light-Emitting Element, light-Emitting Device, and Electronic Device Using the Benzoxazole Derivative
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Novel benzoxazole derivatives are provided to reduce driving voltage of light-emitting elements, and to reduce power consumption of light-emitting elements, light-emitting devices, and electronic devices. A benzoxazole derivative represented by the general formula (G1) is provided. Since the benzoxazole derivative represented by the general formula (G1) has an electron-injecting property, the benzoxazole derivative can be suitably used for light-emitting elements, light-emitting devices, and electronic devices.
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- Acenaphthopyridine Derivative, Material of Light-Emitting Element, Light-Emitting Element, Light-Emitting Device, and Electronic Appliance
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It is an object to provide a new compound which is suitable for a material of an electron-transporting layer of a light-emitting element. In particular, it is an object to provide a compound which can be used for forming a light-emitting element capable of emitting light at a low drive voltage. An acenaphthopyridine derivative represented by the following general formula (G1) is provided. In the formula, Het represents a pyridyl group or a quinolyl group.
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Page/Page column 15
(2009/10/06)
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- A convenient synthesis of pyridine and 2,2′-bipyridine derivatives
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α-Chloro-α-acetoxy-β-keto-esters 9 were readily prepared from β-keto-esters 6 in good overall yields. These compounds reacted as α,β-diketo-ester equivalents 2 with amidrazones 1 yielding triazines 3, generally in good yields. Picolinates 10 provided an alternative source of α,β-diketo-ester equivalents 2 when treated with copper(II) acetate. A 'one-pot' reaction of the α,β-diketo-ester equivalents 2 with amidrazones 1 in the presence of 2,5-norbornadiene 5 in boiling ethanol yielded the pyridines 4 and 2,2′-bipyridines 4 (R1=2-pyridyl) directly without the need to isolate the corresponding triazines 3. Triazine 3c reacted with the aza-dienophiles 13 and 17 affording the products 16 and 18, respectively, in good yields.
- Altuna-Urquijo, Marta,Gehre, Alexander,Stanforth, Stephen P.,Tarbit, Brian
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body text
p. 975 - 984
(2009/04/10)
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- FUSED IMIDAZOLES FOR CANCER TREATMENT
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Compounds of Formula (I), a tautomer or stereoisomer thereof, or a salt thereof,wherein ring B and the imidazole to which it is fused, R4, R6 and R7 have the meanings as given in the description and the claims, are effective inhibi tors of the Pi3K/Akt pathway.
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Page/Page column 45-46
(2009/04/25)
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- FUSED BICYCLIC IMIDAZOLES
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Compounds of formula (I) a tautomer or stereoisomer thereof, or a salt thereof, wherein ring B and the imidazole to which it is fused, R4, R6 and R7 have the meanings as given in the description and the claims, are effective inhibitors of the Pi3K/Akt pathway.
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Page/Page column 18
(2009/07/03)
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- GHRELIN MODULATING COMPOUNDS AND COMBINATIONS THEREOF
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Compounds that modulate GHS-R are described, for examples compounds formula (I).
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Page/Page column 130-131
(2009/01/20)
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- Synthesis of 6-phenyl-2,2′-bipyridine ligands bearing polyaromatic substituents
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A simple protocol for the efficient preparation of substituted 6-phenyl-2,2′-bipyridine derivatives is described. An inverse Diels-Alder reaction between a 3-phenyl-5-pyridyl-1,2,4-triazine and an electron-rich ethynyl species at high temperature provides a mixture of two products easily separable by column chromatography. The most encumbered isomer is favoured, likely due to favourable π-π stacking interactions in the transition state. A variety of those ligands suitable for the synthesis of cyclo-metallated complexes have been produced.
- Diring, Stéphane,Retailleau, Pascal,Ziessel, Raymond
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p. 8069 - 8073
(2008/03/14)
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