Awesome and Easy Science Experiments about 5,5′-Dibromo-2,2′-bipyridine

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Objects of the present invention are to provide an organic compound having excellent properties, which is excellent in electron-injecting/transporting performances, has hole-blocking ability and is highly stable in a thin-film state, as a material for an organic electroluminescent device having a high efficiency and a high durability; and to provide an organic electroluminescent device having a high efficiency and a high durability using the compound. The invention relates to a compound having a substituted pyridyl group and a pyridoindole ring structure linked through a phenylene group, which is represented by the general formula (1); and an organic EL device comprising a pair of electrodes and at least one organic layer interposed between the electrodes, wherein the at least one organic layer contains the compound: wherein Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; R1 to R14 may be the same or different from each other and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; n represents an integer of 1 to 3; and W, X, Y, and Z respectively represent a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom does not have the substituent of R7, R8, R9, or R10).

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Brief introduction of 5,5′-Dibromo-2,2′-bipyridine

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A linear bis-porphyrin bridged by a 5,5?-diphenyl-2,2?-bipyridine rod-like spacer complexing a [Ru(phen)2]2+ fragment has been synthesized in 7.4% yield by one-pot condensation of 3,5-di-tert-butylbenzaldehyde, 4,4?-dimethyl-3,3?-dihexyl-2,2?-methylenedipyrrole and the [Ru(phen)2]2+ complex of 5,5?-bis(p-formylphenyl)-2,2?-bipyridine, followed by chloranil oxidation. The protected dialdehyde (5,5?-bis[(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]-2,2?-bipyridine) was obtained in 80% yield by Suzuki coupling of 2-[4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]-4,4,5,5-tetramethyl-1, 3-dioxaborolane and 5,5?-dibromo-2,2?-bipyridine, using [Pd(PPh3)4] as catalyst. A new procedure is reported for the preparation of 5,5?-dibromo-2,2?-bipyridine, which is obtained in 80% yield by Stille homocoupling of 2,5-dibromopyridine in the presence of hexamethylditin.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Can You Really Do Chemisty Experiments About 5,5′-Dibromo-2,2′-bipyridine

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A novel class of tetrathiolated aryleneethynylene oligomers was obtained by the Cassar-Heck-Sonogashira coupling between S,S-(5-ethynyl-1,3-phenylene) bis(methylene)diethanethioate (1) and aryl diiodides or dibromides. Although standard coupling conditions are effective in the case of iodo derivatives, the addition of free triphenylphosphane to the reaction mixture was required to overcome the slower reaction rate of dibromoarenes. Oligomers with an extended conjugated system could be obtained starting from a higher homologue of 1 by applying the same synthetic approach. These oligomers represent interesting molecular wires, potentially able to self-assemble on various substrates, including gold and other noble metals in the form of thin films or nanoparticles. The chelating arrangement of the thiol functionalities should ensure stable anchoring and would also represent an interesting novel feature in the study of single molecule conduction with respect to traditional monodentate systems. A novel class of tetrathiolated aryleneethynylene oligomers was obtained bythe Cassar-Heck-Sonogashira coupling ofS,S-(5-ethynyl-1,3-phenylene) bis(methylene)diethanethioate with aromatic halides (bromides and iodides).

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, name: 5,5′-Dibromo-2,2′-bipyridine, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 15862-18-7, Name is 5,5′-Dibromo-2,2′-bipyridine, molecular formula is C10H6Br2N2. In a Article, authors is Zhu, Yuan-Yuan,once mentioned of 15862-18-7

Metal?organic frameworks (MOFs) have been extensively used for single-site catalysis and light harvesting, but their application in multicomponent photocatalysis is unexplored. We report here the successful incorporation of an IrIII photoredox catalyst and a NiII cross-coupling catalyst into a stable Zr12 MOF, Zr12-Ir-Ni, to efficiently catalyze C?S bond formation between various aryl iodides and thiols. The proximity of the IrIII and NiII catalytic components to each other (ca. 0.6 nm) in Zr12-Ir-Ni greatly facilitates electron and thiol radical transfers from Ir to Ni centers to reach a turnover number of 38 500, an order of magnitude higher than that of its homogeneous counterpart. This work highlights the opportunity in merging photoredox and organometallic catalysts in MOFs to effect challenging organic transformations.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

The important role of 5,5′-Dibromo-2,2′-bipyridine

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Six cyclometalated iridium(III) complexes were investigated to assess their potential as photosensitizers for long-range electron transfer, and two of them were incorporated directly into covalent donor-bridge-acceptor molecules. The influence of ligarid substitutions on the excited-state properties and the photoredox behavior of the iridium complexes was explored by optical absorption, steady-state and time-resolved luminescence spectroscopy, as well as by electrochemical methods. Bimolecular electron transfer between the photoexcited complexes and 10-methylphenothiazine and methylviologen was found to be only weakly dependent on the ligand substitutions. Intramolecular long-range electron transfer from phenothiazine to photoexcited iridium(III) in the dyads is slow due to the occurrence of a Coulomb barrier. Consequently, an electron-transfer photoproduct is only observable in the transient absorption spectrum, of a donorbridge-acceptor molecule with a fluorinated photosensitizer that exhibits a very long excited-state lifetime. A flashquench technique is necessary for detection of an electrontransfer product in the dyad with a non-fluorinated photosensitizer. The occurrence of a Coulomb barrier associated with intramolecular (excited-state) long-range electron transfer in the dyads with cyclometalated iridium(III) photosensitizers represents an important difference to previously investigated similar donor-bridge-acceptor molecules with photosensitizers based on d6 metal diimine complexes.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Awesome and Easy Science Experiments about 5,5′-Dibromo-2,2′-bipyridine

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A wide range of ester-substituted oligopyridines, based on pyridine, 1,8-naphthyridine, 1,10-phenanthroline, 2,2′-bipyridine, and 2,2′:6′,6-terpyridine units, has been synthesized and fully characterized. The principal reaction involves the palladium(0)-catalyzed carboalkoxylation of the bromo-, chloro- or triflate-substituted pyridine unit with carbon monoxide in the presence of a primary alcohol as nucleophile and a tertiary amine as base. Monofunctionalization of disubstituted compounds is realized by reaction in ethanol under mild conditions (70 C, 1 atm CO). Stepwise reduction of selected esters with sodium borohydride, followed by Swern oxidation, affords the corresponding carbaldehydes in good yield. Several products are reported for the first time. The synthetic methods reported herein represent a valuable approach to the large-scale preparation of ester-functionalized oligopyridines that can be subsequently transformed to the corresponding alcohols or acids. These procedures also provide a practical methodology to the rational design of ligands bearing different kinds of functionalities.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Some scientific research about 5,5′-Dibromo-2,2′-bipyridine

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We report on the synthesis of 11 pentameric cyclic helicates formed by imine condensation of alkyl monoamines with a common bis(formylpyridine) bipyridyl-derived building block and iron(II) and chloride ions. The cyclic double-stranded helicates were characterized by NMR spectroscopy, mass spectrometry, and in the case of a 2,4-dimethoxybenzylamine-derived pentameric cyclic helicate, X-ray crystallography. The factors influencing the assembly process (reactant stoichiometry, concentration, solvent, nature and amount of anion) were studied in detail: the role of chloride in the assembly process appears not to be limited to that of a simple template, and larger circular helicates observed with related tris(bipyridine) ligands with different iron salts are not produced with the imine ligands. Using certain chiral amines, pentameric cyclic helices of single handedness could be isolated and the stereochemistry of the helix determined by circular dichroism. By employing a particular diamine, a closed-loop molecular pentafoil knot was prepared. The pentafoil knot was characterized by NMR spectroscopy, mass spectrometry, and X-ray crystallography, confirming the topology and providing insights into the reasons for its formation.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Discovery of 15862-18-7

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Sequential synthesis of rigid multi-bipyridine ligands bearing diethynyl/phenyl solubilizing fragments

Reliable and practical synthetic routes for the construction of multitopic bipyridine ligands are presented. The first series contains the chelating fragments connected via an ethynyl function and the second series is built from an alternation of ethynyl/phenyl/bipyridine modules. The synthetic protocol is based on sequential Pd-promoted cross-coupling reactions between selected bis-bpy or ethynyl/phenyl/bpy intermediates of increasing size. The ligands bearing functionalized 1,4-diethynyl-2,5- di(dodecyloxy)benzene subunits are soluble in chlorinated solvents. (C) 2000 Elsevier Science Ltd.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Archives for Chemistry Experiments of 15862-18-7

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A rapidly shuttling copper-complexed [2]rotaxane with three different chelating groups in its axis

Fast and furious: The mobile ring of a copper-complexed [2]rotaxane incorporates an endocyclic but nonsterically hindering bidentate chelate. The rotaxane axis contains three different chelates (see picture), and both terminal coordination sites are separated by about 23 A. The shuttling motion is triggered by oxidation or reduction of the copper center and is as fast as that in a related two-station rotaxane whose terminal stations are 10 A apart.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A phosphorescent iridium complex and its preparation method and application (by machine translation)

The invention relates to a phosphorescent iridium complex and its preparation method and application, belongs to organic photoelectric functional material technical field. In particular relates to a preparation method of the phosphorescence iridium complex molecules and molecular oxygen detection, cell labeling and in the imaging of the application. This kind of complex material consists of a metal-ligand, metal center and benzyl substituted anthracenes auxiliary ligand, general structure are shown in the following, this material has a longer service life of the light-emitting, mild reaction conditions, is easy to be purified, in the anoxic detection, cell imaging and pathological diagnosis in very good application prospect. (by machine translation)

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI