Awesome and Easy Science Experiments about 4-Bromo-2,2′-bipyridine

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Synthesis and characterization of beta-diketonato ruthenium(II) complexes with two 4-bromo or protected 4-ethynyl-2,2?-bipyridine ligands

Two new mononuclear mixed-ligand ruthenium(II) complexes with acetylacetonate ion (2,4-pentanedionate, acac) and functionalized bipyridine (bpy) in position 4, [Ru(bpyBr)2(acac)](PF6) (2; bpyBr = 4-Bromo-2,2?-bipyridine, acac = 2,4-pentanedionate ion) and [Ru(bpyOH)2(acac)](PF6) (3; bpyOH = 4-[2-methyl-3-butyn-2-ol]-2,2?-bipyridine) were prepared as candidates for building blocks. The 1H NMR, 13C NMR, UV-Vis, electrochemistry and FAB mass spectral data of these complexes are presented.

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

Extracurricular laboratory:new discovery of 4-Bromo-2,2′-bipyridine

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Columnar/Lamellar Packing in Cocrystals of Arylbipyridines with Diiodoperfluorobenzene

Stimulated by strongly directional C-I?N noncovalent halogen bonding, pi-hole?pi and pi-pi interactions, cocrystals of nonplanar 4-arylated-2,2?-bipyridine (ArB) derivatives with 1,4-diiodo-tetrafluorobenzene (D) were generated which exhibit a promising columnar/lamellar packing arrangement. Hirshfeld surface, quantum theory of atoms in molecules, and electrostatic potential surface analyses were employed to examine the weak intermolecular interactions governing the packing arrangement in ArB crystals and corresponding cocrystals with D (ArB¡¤D). Cocrystals of 4-phenyl-2,2?-bipyridine (PhB) and 4-(naphthalen-1-yl)-2,2?-bipyridine (NaB) with D [PhB¡¤D1, PhB¡¤D2, (NaB)2¡¤D2.5, and (NaB)3¡¤D2] exhibited C-I?N directed infinite one-dimensional chains of alternate ArB and D units. In contrast, C-I?N interactions guide the formation of termolecular complexes in the cocrystal of 4-(phenanthren-9-yl)-2,2?-bipyridine with D (PhenB¡¤D0.5). Successful implementation of C-I?N interactions aided by 2,2?-bipyridine and D enabled the tuning of three-dimensional close packing in planar polyaromatic hydrocarbons into a columnar/lamellar arrangement suitable for optoelectronic devices.

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

The important role of 4-Bromo-2,2′-bipyridine

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Conjugated polymers with 2,2?-bipyridine and diethinylenebenzene units: Absorption and luminescence properties

Alternating oligomers and polymers consisting of 2,2?-bipyridine and diethinylenebenzene units and corresponding model compounds were synthesized and investigated in dilute solutions by absorption spectroscopy and by stationary and time-resolved emission spectroscopy. The strictly linear (rod-like) pi-chain oligomers/polymers were compared with the angularly linked oligomers/polymers and with related model compounds. The model compounds which already show the essential spectroscopic properties of the oligomers/polymers consist of three (hetero)aromatics linearly connected by two diethenylene groups. These models exhibit fluorescence quantum yields close to unity and short fluorescence decay times around 1 ns. Fluorescence anisotropy and rotational relaxation times are consistent with the Stokes-Einstein equation and the Perrin equation. The absorption and emission spectra of the polymers and their radiative rate constants determined by fluorescence quantum yield and lifetime and according to the Strickler/Berg equation show a conjugation length of one to two repetition units. The conjugation along the chain is stronger in linear than in angular polymers and stronger in alkoxy-substituted than in unsubstituted polymers. In angular polymers at least two different emitting segments were found. The shortened mean lifetimes and the reduced fluorescence quantum yields and anisotropies of the oligomers/polymers indicate an additional radiationless deactivation channel which is opened by energy migration along the chain. Rates of energy transfer calculated for linear and angular polymers correlate with rates of radiationless deactivation. Copyright

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

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Minimizing Side Product Formation in Alkyne Functionalization of Ruthenium Complexes by Introduction of Protecting Groups

The synthesis of alkyne functionalized bipyridine ruthenium complexes are reported. The improved synthetic approach through application of stable protecting groups prevents formation of possible side products while facilitating purification. By applying copper-catalysed azide-alkyne cycloaddition reactions (CuAAC) pyrene units with flexible alkyl linkers are introduced at the periphery of the complex, opening up various applications including surface immobilization and DNA intercalation. All complexes are characterized structurally as well as photophysically, especially regarding the influence of the introduced alkyne and triazolyl substituents on their photophysical behavior.

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

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Synthesis of new dendritic antenna-like polypyridine ligands

An efficient synthesis of multidentate polypyridine ligands, 3,5-bis(2,2?-bipyridin-4-ylethynyl)benzoic acid and 3,5-bis(2,5-bis(2- pyridyl)-pyridin-4-ylethynyl)benzoic acid, with potential application in the production of ruthenium dyes for dye-sensitised solar cells was developed. Isolation of intermediate products and final compounds is simple and the yields are very high. The ligands obtained can be used in the synthesis of dendritic analogues of well known and very efficient N3 dye and “black dye”.

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

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A high molar extinction coefficient mono-anthracenyl bipyridyl heteroleptic ruthenium(II) complex: Synthesis, photophysical and electrochemical properties

In our quest to develop good materials as photosensitizers for photovoltaic dye-sensitized solar cells (DSSCs), cis-dithiocyanato-4-(2,3-dimethylacrylic acid)-2,2′- bipyridyl-4-(9-anthracenyl-(2,3-dimethylacrylic)-2,2′-bipyridyl ruthenium(II) complex, a high molar extinction coefficient charge transfer sensitizer, was designed, synthesized and characterized by spectroscopy and electrochemical techniques. Earlier studies on heteroleptic ruthenium(II) complex analogues containing functionalized oligo-anthracenyl phenanthroline ligands have been reported and documented. Based on a general linear correlation between increase in the length of p-conjugation bond and the molar extinction coefficients, herein, we report the photophysical and electrochemical properties of a Ru(II) bipyridyl complex analogue with a single functionalized anthracenyl unit. Interestingly, the complex shows better broad and intense metal-to ligand charge transfer (MLCT) band absorption with higher molar extinction coefficient (deltamax = 518 nm, sigma = 44900 M-1cm-1), and appreciable photoluminescence spanning the visible region than those containing higher anthracenyl units. It was shown that molar absorption coefficient of the complexes may not be solely depended on the extended p-conjugation but are reduced by molecular aggregation in the molecules.

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

New explortion of 4-Bromo-2,2′-bipyridine

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Photon Funnels for One-Way Energy Transfer: Multimetallic Assemblies Incorporating Cyclometallated Iridium or Rhodium Units Accessed by Sequential Cross-Coupling and Bromination

The generation of multimetallic assemblies is a widely explored theme, owing to the relevance of controlling energy and electron transfer between metal centres to many fields of contemporary importance. Boronic acid substituted coordination and organometallic complexes have been shown to be useful synthons in the formation of such structures through cross-coupling with halogenated complexes. In this work we used such a methodology to generate an octanuclear mixed-metal compound of composition Ir7Ru having a dendrimer wedge-like structure. The method combined cross-coupling with regiospecific bromination of phenylpyridine (ppy) ligands at the position para to the C?Ir bond. The propensity of Ir(ppy)2-based complexes to electrophilic bromination was found to be deactivated by the introduction of fluorine atoms. The coupling methodology was extended to rhodium-containing systems, exemplified by a tetranuclear system of composition Rh2Ir1Ru1. The synthesis required the use of boronic acid appended RhIII complexes, which could be accessed by the introduction of a neopentyl boronate ester appended bipyridine into the coordination sphere of RhIII. The excited-state energies of the constituent metal units in the resulting multinuclear complexes are such that unidirectional energy transfer occurs from the RhIII/IrIII branches to the RuII core. The luminescence thus resembles that of an isolated [Ru(bpy)3]2+ unit, but the ability of the structure to collect light is greatly enhanced.

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

Can You Really Do Chemisty Experiments About 4-Bromo-2,2′-bipyridine

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Synthesis of rigid-rod linkers to anchor chromophores to semiconductor nanoparticles

Four rigid-rod sensitizers, made of a phenylethynyl spacer substituted with a chromophore and two COOR binding groups, were prepared to study dynamics of electron injection at the interface of metal oxide semiconductor nanoparticles. Dimethyl Ru(bpy)2(5-(5-1,10-phenanthrolinyl)ethynyl)isophthalate) 2+ (4a), dimethyl Ru(bpy)2(5-(4-(2,2?-bipyridinyl)ethynyl)isophthalate) 2+ (4b), dimethyl 5-(1-pyrenylethynyl)isophthalate (4c), and dimethyl 5-(9-anthracenylethynyl)isophthalate (4d), were synthesized and characterized. Their absorption spectra, emission spectra, and electrochemical properties have been studied in acetonitrile and hexane solutions at room temperature.

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

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Bipyridyl? and pyridylquinolyl?phenothiazine structures as potential photoactive ligands: Syntheses and complexation to palladium

Three new bipyridyl? and pyridylquinolyl?phenothiazine structures were synthesized through Pd-catalyzed C?N couplings between phenothiazine and the corresponding bromo-heteroaryls. For the 2-(N-phenothiazine)-bipyridine, boat conformation was determined for the phenothiazine moiety by X-ray diffraction analysis. Single well-defined palladium acetate complexes were observed by 1H NMR analysis with the 4-(N-phenothiazine)-bipyridine and the pyridyl-5-(N-phenothiazine)-quinoline. Compared to the naked ligands, the UV?visible absorption spectra showed, in these cases, significantly red shifted lambdamax upon coordination. Preliminary modeling experiments with the free and the coordinated 4-(N-phenothiazine)-bipyridine suggested for both the occurrence of electronic transfers from the phenothiazine to the bipyridine. Potentially enabling the tuning of the electron density of the coordinating moiety upon near-UV irradiation, this bipyridyl?phenothiazine structure could be the origin of a novel class of photo-active ligands for applications in organometallic catalysis.

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

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14162-95-9,4-Bromo-2,2′-bipyridine,as a common compound, the synthetic route is as follows.,14162-95-9

General procedure: In a tube were added 6-bromo-2,2-bipyridine (70.5mg, 0.3mmol, 1equiv.), phenothiazine (77.7mg, 1.3equiv.), RuPhos-Pd-G2 (23.4mg, 10mol%) and t-BuOK (50.5mg, 1.5equiv). The tube was sealed, purged three times with argon and 1mL of anhydrous dioxane was added. The reaction mixture was stirred at 110C for 18h. After cooling to room temperature, 10mL of H2O were added and the aqueous layer was extracted three times with ethyl acetate (3¡Á10 mL). The combined organic layers were dried with MgSO4 and the solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (50/50: CH2Cl2/cyclohexane) affording 51.2 mg of L1 (0.145 mmol, 48%) as an amorphous pale yellow solid.

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Reference£º
Article; Tabey, Alexis; Mendy, Jonathan; Hermange, Philippe; Fouquet, Eric; Tetrahedron Letters; vol. 58; 32; (2017); p. 3096 – 3100;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI