74065-63-7

Usage

Uses

Used in Coordination Chemistry:
6,6′-bis(hydroxymethyl)-2,2′-bipyridine is used as a ligand for forming stable complexes with metal ions, which is crucial in coordination chemistry for studying metal ion properties and interactions.
Used in Catalysis:
In the field of catalysis, 6,6′-bis(hydroxymethyl)-2,2′-bipyridine is utilized as a component in catalysts, potentially enhancing the efficiency and selectivity of various chemical reactions.
Used in Fluorescence Sensing:
6,6′-bis(hydroxymethyl)-2,2′-bipyridine is employed as a component in fluorescence sensors, where its coordination with metal ions can lead to changes in fluorescence properties, allowing for the detection and measurement of specific analytes.
Used in Supramolecular Chemistry:
As a building block for supramolecular assemblies, 6,6′-bis(hydroxymethyl)-2,2′-bipyridine contributes to the construction of complex molecular structures with potential applications in various areas, including drug delivery and molecular recognition.
Used in the Synthesis of Coordination Polymers:
6,6′-bis(hydroxymethyl)-2,2′-bipyridine is used as a precursor in the synthesis of coordination polymers, which are materials with potential applications in gas storage, catalysis, and as functional materials in various industries.
Used in Material Science:
In material science, 6,6′-bis(hydroxymethyl)-2,2′-bipyridine is utilized in the development of new functional materials, taking advantage of its coordination chemistry properties to create materials with tailored properties for specific applications.

Upstream product

• 82740-67-8 6,6'-Bis(acetylhydroxymethyl)-2,2'-bipyridine 
• 49669-26-3 2,2'-bipyridine-6,6'-dicarbaldehyde 
• 33674-96-3 2-bromo-6-(hydroxymethyl)pyridine 
• 5315-25-3 2-bromo-6-methylpyridine 
• 366-18-7 [2,2]bipyridinyl 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 4411-83-0 2,2′-bipyridine-6,6′-dicarbonitrile 
• 65739-40-4 6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine 
• 4479-74-7 2,2'-bipyridine-6,6'-dicarboxylic acid 
• 150058-63-2 2-bromo-6-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)pyridine 
• 109-04-6 2-bromo-pyridine 
• 34160-40-2 6-bromo-2-pyridinecarbaldehyde 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 142593-07-5 dimethyl 2,2'-bipyridine-6,6'-dicarboxylate 

Downstream Products

• 96517-97-4 6,6'-bis-(bromomethyl)-2,2'-bipyridine 
• 123074-73-7 6-(hydroxymethyl)-6'-(bromomethyl)-2,2'-dipyridine 
• 74065-64-8 6,6'-di(chloromethyl)-2,2'-bipyridine 
• 49669-26-3 2,2'-bipyridine-6,6'-dicarbaldehyde 

Relevant academic research and scientific papers

A catalytic palladium active-metal template pathway to [2]rotaxanes

(Chemical Equation Presented) A multitasking template: [2]Rotaxanes have been synthesized with the help of a palladium active-metal template, which acts as both a template for threading and a catalyst for covalent-bond formation (see scheme). The synthesi

Step by Step Assembly of Polynuclear Lanthanide Complexes with a Phosphonated Bipyridine Ligand

The synthesis of the octadentate ligand L (LH8 = ((([2,2′-bipyridine]-6,6′-diylbis(methylene))bis(azanetriyl))tetrakis(methylene))tetrakis(phosphonic acid)) is reported. The coordination of L with various lanthanide cations was monitored by absorption and luminescence spectrophotometric titration experiments (Ln = Tb, Yb), potentiometry (Ln = La, Eu, Lu), and mass spectrometry (Ln = Tb). It was found that L forms very stable mononuclear (LnL) species in aqueous solutions (log K = 19.80(5), 19.5(2), and 19.56(5) for La, Eu, and Lu, respectively) with no particular trend along the series. Spectroscopic data showed the Ln cations to be enclosed in the cavity formed by the octadentate ligand, thereby shielding the metal from interactions with water molecules in the first coordination sphere. When more than one equivalent of cations is added, the formation of polynuclear [(LnL)2Lnx] complexes (x = 1-3) can be observed, the presence of which could be confirmed by electrospray and MALDI mass spectrometry experiments. DFT modeling of the mononuclear (LnL) complexes indicated that the coordination of the cation in the cavity of the ligand results in a very asymmetric charge distribution, with a region of small negative electrostatic potential on the hemisphere composed of the chromophoric bipyridyl moiety and an electron-rich domain at the opposite hemisphere around the four phosphonate functions. DFT further showed that this polarization is most likely at the origin of the strong interactions between the (LnL) complexes and the incoming additional cations, leading to the formation of the polynuclear species. 1H and 31P NMR were used to probe the possible exchange of the lanthanide complexed in the cavity of the ligand in D2O, revealing no detectable exchange after 4 weeks at 80 °C and neutral pD, therefore pointing out an excellent kinetic inertness.

Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts

RhL2 complexes of phosphonate-derivatized 2,2′-bipyridine (bpy) ligands L were immobilized on titanium oxide particles generated in situ. Depending on the structure of the bipy ligand—number of tethers (1 or 2) to which the phosphonate end groups are attached and their location on the 2,2′-bipyridine backbone (4,4′-, 5,5′-, or 6,6′-positions)—the resulting supported catalysts showed comparable chemoselectivity but different kinetics for the hydrogenation of 6-methyl-5-hepten-2-one under hydrogen pressure. Characterization of the six supported catalysts suggested that the intrinsic geometry of each of the phosphonate-derivatized 2,2′-bipyridines leads to supported catalysts with different microstructures and different arrangements of the RhL2 species at the surface of the solid, which thereby affect their reactivity.

Bipyridine ligand ruthenium complex is carried and its preparation method and application (by machine translation)

The invention relates to a novel bipyridine is carried ligand ruthenium complex and its preparation method and in the ester compound hydrogenation is the application of the alcohol compound in the reaction. The use of the bipyridine ligand ruthenium complex catalytic hydrogenation is carried ester compound alcohol compound method is characterized in that: in order to ester compound material in an amount of 0.001 - 0.3 μM % bipyridyl is carried ligand ruthenium complex as catalyst, adding esters compound material in an amount of 1 - 10mol % alkali, in the 25 - 100 °C and 1 - 10MPa hydrogen pressure catalytic hydrogenation under the conditions of ester compound corresponding alcohol compound. The invention of the bipyridine ligand ruthenium complex is carried is convenient to prepare, stable structure, in the ester compound in hydrogenation reaction exhibits excellent catalytic activity. This invention has overcome the ester compound or a non-homogeneous phase catalytic hydrogenation system requires high-temperature high-pressure reaction conditions and high defects of the catalyst amount, catalyst consumption is small, mild reaction conditions, the reaction selectivity is good, improves the economy and the safety of the production system. (by machine translation)

Csp2-Br bond activation of Br-pyridine by neophylpalladacycle: Formation of binuclear seven-membered palladacycle and bipyridine species

In this work, the synthesis and reactivity of seven-membered palladacycles are described, and a novel bi-pyridine synthesis in a catalytic pathway is reported. Neophyl-palladacycle(i) reacts with an excess of 2-Br-pyridine, giving the desired new binuclear seven-membered palladacycle (1) and unexpectedly, a bipyridine complex, [Pd(BiPy)Br2]. ESI-HRMS experiments show that fragmentation of the Pd-Br bond in 1 can take place producing unusual two coordinated Pd(ii) molecular ions, [Pd(NeoPyR)]+.

Correlation between the Structure and Catalytic Activity of [Cp*Rh(Substituted Bipyridine)] Complexes for NADH Regeneration

A series of water-soluble half-sandwich [Cp*RhIII(N^N)Cl]+ (Cp* = pentamethylcyclopentadiene, N^N-substituted 2,2′-bipyridine) complexes containing electron-donating substituents around the 2,2′-bipyridyl ligand were synthesized and fully characterized for the regioselective reduction of nicotinamide coenzyme (NAD+). The influence of the positional effect of the substituents on the structural, electrochemical, and catalytic properties of the catalyst was systematically studied in detail. The catalytic efficiency of the substituted bipyridine Cp*RhIII complexes are inversely correlated with their redox potentials. The 5,5′-substituted bipyridine Cp*RhIII complex, which had the lowest reduction potential, most effectively regenerated NADH with a turnover frequency of 1100 h-1. Detailed kinetic studies on the generation of intermediate(s) provide valuable mechanistic insight into this catalytic cycle and help to direct the future design strategy of corresponding catalysts.

Upconverted photosensitization of Tb visible emission by NIR Yb excitation in discrete supramolecular heteropolynuclear complexes

Addition of Tb3+ salts to a solution of a (YbLD) complex in D2O resulted in the formation of [(YbLD)2Tbx] (x = 1 to 3) complexes that, upon NIR excitation at 980 nm, showed an unprecedented Yb to Tb upconversion sensitization phenomenon resulting in the observation of the typical green emission of Tb.

Design and synthesis of new Ru-complexes as potential photo-sensitizers: Experimental and TD-DFT insights

We report density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations on a novel organic ligand and a novel class of ruthenium complexes; cis-RuL2X2 with L = 2,2′-bipyridine-6,6′-bis ethyl ester phosphonate and phosphonic acid, X = Cl, CN or NCS. The calculations show that cis-configurations are more stable than the trans-counterparts. The DFT results have been used to help design such novel complexes for potential use as sensitizers. We demonstrate the opportunity to synthesize such complexes with high purity. The synthesis of these complexes relies on the preparation of the key intermediates cis-Ru(2,2′-bipyridine-6,6′-bisdiethyl ester phosphonate)Cl2. These complexes were characterized by 1H, 13C, and 31P NMR, elemental analysis and FTIR spectroscopy. The NCS complex shows the smallest optical band gap followed by the Cl and CN complexes, respectively, with the highest performance upon use as a sensitizer in dye-sensitized solar cells.

Ruthenium complexes of tetradentate bipyridine ligands: Highly efficient catalysts for the hydrogenation of carboxylic esters and lactones

A new type of readily available, air-stable ruthenium complex of tetradentate bipyridine ligands has been developed. These complexes displayed exceptional efficiency for the hydrogenation of aromatic and aliphatic carboxylic esters and lactones at as low as 10 ppm catalyst loading under very mild conditions. the Partner Organisations 2014.

Na2(smbipy) - A bipyridine-derived ligand with chelating sulfonate tags and its 3d metal complexes

The sulfonated bipyridine derivative disodium 6,6′-bis(sulfonatomethyl)-2,2′-bipyridine [Na2(smbipy)] was synthesized, and its complexation behaviour towards divalent 3d metals in aqueous solution was explored. The complexes of late 3d metals [M(smbipy)(H2O)2]·H2O (M = Co, Ni, Zn) and [Cu(smbipy)(H2O)] are sparingly soluble in water, and their crystal structures show fourfold equatorial coordination (κ4N,N',O,O') of the smbipy ligand. Ammonia-rich solutions of the NiII and CuII aqua complexes yield the decomplexation products [Ni(NH3)6](smbipy), [Ni(NH3)5(H2O)](smbipy) and [Cu(NH3)4](smbipy)·2H2O. Buffered solutions with a reduced ammonia content lead to [Ni(smbipy)(NH3)2] and [Cu(smbipy)(NH3)3]·2H2O, and the latter shows twofold coordination of the smbipy ligand through the nitrogen atoms only (κ2N,N'). When nearly quantitative amounts of ammonia are applied, two closely related complexes with the core motif [(smbipy)Cu(μ-OH)2Cu] form. Crystal structures of all complexes were obtained, and their features are discussed.