49669-26-3

Usage

Uses

Used in Coordination Chemistry:
2,2'-bipyridine-6,6'-dicarbaldehyde is used as a ligand for forming stable complexes with metal ions. Its ability to chelate metal ions makes it a valuable component in the synthesis of coordination polymers and metal-organic frameworks, which have potential applications in various fields such as catalysis, gas storage, and sensing.
Used in Catalysis:
In the field of catalysis, 2,2'-bipyridine-6,6'-dicarbaldehyde is used as a ligand to modify the properties of metal catalysts. Its coordination with metal ions can enhance the catalytic activity and selectivity of the catalysts, making it a useful component in the development of new catalytic systems.
Used in Luminescent Materials:
2,2'-bipyridine-6,6'-dicarbaldehyde is used as a building block in the synthesis of luminescent materials. Its ability to form complexes with metal ions can result in the development of materials with unique optical properties, which can be applied in areas such as light-emitting diodes (LEDs), sensors, and imaging.
Used in Molecular Electronics:
In molecular electronics, 2,2'-bipyridine-6,6'-dicarbaldehyde is used as a component in the design and synthesis of molecular devices. Its coordination with metal ions can lead to the formation of molecular wires and other electronic components, which can be integrated into molecular-scale electronic systems.
Used in Antitumor Applications:
2,2'-bipyridine-6,6'-dicarbaldehyde has been investigated for its potential antitumor properties. It can be used as a chemotherapeutic agent or in combination with other drugs to enhance the treatment of cancer. Its ability to form complexes with metal ions may also contribute to its antitumor activity by inducing apoptosis or inhibiting the growth of cancer cells.
Used in Antimicrobial Applications:
2,2'-bipyridine-6,6'-dicarbaldehyde has also been studied for its potential antimicrobial properties. It can be used as an antimicrobial agent to combat bacterial and fungal infections. Its ability to form complexes with metal ions may contribute to its antimicrobial activity by disrupting the cell membrane or inhibiting essential cellular processes.

Upstream product

• 49669-32-1 6,6'-di(1,3-dioxolan-2-yl)-2,2'-bipyridine 
• 4411-80-7 6,6'-dimethyl-2,2'-bipyridine 
• 49669-22-9 6,6'-Dibromo-2,2'-bipyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 74065-63-7 6,6′-bis(hydroxymethyl)-2,2′-bipyridine 
• 34160-40-2 6-bromo-2-pyridinecarbaldehyde 
• 49669-25-2 6,6'-dilithio-2,2'-bipyridine 
• 142593-07-5 dimethyl 2,2'-bipyridine-6,6'-dicarboxylate 
• 4479-74-7 2,2'-bipyridine-6,6'-dicarboxylic acid 
• 5315-25-3 2-bromo-6-methylpyridine 
• 1824-81-3 2-Amino-6-methylpyridine 
• 34199-87-6 6-bromo-2-(1,3-dioxolan-2-yl)pyridine 
• 626-05-1 2,6-Dibromopyridine 
• 96517-97-4 6,6'-bis-(bromomethyl)-2,2'-bipyridine 

Downstream Products

• 74065-63-7 6,6′-bis(hydroxymethyl)-2,2′-bipyridine 
• 74065-64-8 6,6'-di(chloromethyl)-2,2'-bipyridine 
• 1111635-90-5 6,6'-bis(aldimino)-2,2'-bipyridine (2,6-diisopropylanil) 

Relevant academic research and scientific papers

Dependence of the photophysical properties on the number of 2,2′-bipyridine units in a series of luminescent europium and terbium cryptates

The luminescence properties of a series of lanthanoid cryptates with an increasing number of 2,2′-bipyridine units have been investigated for the lanthanoids Eu and Tb in aqueous solution. The trends in important parameters that influence the photophysics in these complexes have been determined. With increasing bipyridine content, an increase is observed for the intersystem crossing efficiencies and the number of inner-sphere water molecules. In contrast, a decrease is found in the same direction for overall quantum yields, triplet energies, and sensitization efficiencies.

Dynamic covalent self-sorting and kinetic switching processes in two cyclic orders: Macrocycles and macrobicyclic cages

Dynamic covalent component self-sorting processes have been investigated for constituents of different cyclic orders, macrocycles and macrobicyclic cages based on multiple reversible imine formation. The progressive assembly of the final structures from dialdehyde and polyamine components involved the generation of kinetic products and mixtures of intermediates which underwent component selection and self-correction to generate the final thermodynamic constituents. Importantly, constitutional dynamic networks (CDNs) of macrocycles and macrobicyclic cages were set up either from separately prepared constituents or by in situ assembly from their components. Over time, these CDNs underwent conversion from a kinetically trapped out-of-equilibrium distribution of constituents to the thermodynamically self-sorted one through component exchange in different dimensional orders.

Concentration-dependent chemo- and regioselective metalation of 6,6′-dibromo-2,2′-bipyridine

A reliable and synthetically useful strategy for the selective single or double metalation of 6,6′-dibromo-2,2′-bipyridine via lithium-halogen exchange is discussed. Experimental conditions for the optimal formylation of the singly and doubly lithiated intermediates are outlined as well as unequivocal X-ray crystallographic evidence for the regiochemistry of a competing deprotonation pathway. Georg Thieme Verlag Stuttgart.

On the Chemistry of Pyrrole Pigments, XC: Pyridinologous Linear Tri- and Tetrapyrroles

One pyridinologous linear tripyrrole and two pyridinologous linear tetrapyrroles were prepared, and their structural aspects derived from spectroscopic measurements and force field calculations.The properties of these novel pyrrole pigments are compared with those of analogous linear tri- and tetrapyrroles. - Keywords.Pyridinologous linear tri- and tetrapyrroles; 1H-NMR spectra; UV-Vis spectra; Fluorescence; pKa-values; Configuration; Conformation.

2,2'-Bipyridyl 'Crown Ethers.' Synthesis and X-Ray Crystal Structure of a Cobalt(II) Complex

A newly-synthesized bipyridyl hexaethyleneglycol crown ether reacts with CoCl2 to form a pentacoordinate complex containing a novel CoII-O(ether) bond.

Electrochemical CO2 reduction by a cobalt bipyricorrole complex: Decrease of an overpotential value derived from monoanionic ligand character of the porphyrinoid species

A newly synthesized Co(ii) complex with a monoanionic bipyricorrole ligand is found to catalytically promote a selective CO2 electroreduction to CO with Faradaic efficiency of 75%. Catalytic Tafel plots show that the overpotential of Co(ii) bipyricorrole is 0.35 V lower than that of a Co(ii) complex with the dianionic tetraphenylporphyrin ligand.

Oligomeric pyridine derivative and organic electroluminescence element using the same

Provided are: a novel oligomeric pyridine derivative which has high electron transport characteristics and high thermal stability as a dark red organic EL material; an electron transport material which is produced from the derivative, and an organic EL element which uses the derivative. Specifically disclosed is an oligomeric pyridine derivative represented by general formula (1). In general formula (1), X and Y represent a carbon atom or a nitrogen atom, and R1 to R6 each independently represent a hydrogen atom, an alkyl group, or a heteroaryl group represented by general formula (2). In general formula (2), each of R7-R10 independently represents a hydrogen atom, an alkyl group, a 2-pyridyl group, a 3-pyridyl group or a 4-pyridyl group.

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.

A convenient alternative for the selective oxidation of alcohols by silica supported TEMPO using dioxygen as the final oxidant

Various primary and secondary alcohols were selectively oxidized to the corresponding aldehydes and ketones using silica supported TEMPO as a heterogeneous catalyst and nitrosonium tetrafluoroborate as a cocatalyst. No over-oxidation of aldehydes to acids, nitration processes or oxidation of double bonds was observed. The reported procedure is very convenient, and uses mild experimental conditions (room temperature and dioxygen as the terminal oxidant). Furthermore, the reactions proceeded cleanly and the isolation of the desired compounds required minimal work-up. A mechanistic pathway has been proposed, in which nitrogen oxides and oxoammonium ions act as an electron transfer double bridge.

Solid and solution state flexibility of sterically congested bis(imino)bipyridine complexes of zinc(II) and nickel(II)

Two new sterically demanding bis(imino)bipyridine ligands, 6,6′-{(2,6-i-Pr2C6H3)NCR} 2C10H6N2 (R = H (L1), Me (L2)), have been prepared in high yield by the condensation reaction of 2,6-diisopropylaniline with 6,6′-(OCR)2C10H 6N2 (R = H, Me). Palladium(0)-mediated cross coupling of 2-(Bu3Sn)-6-{C(Me)OCH2CH2O}C5H 3N with 2-Br-6-{C(Me)OCH2CH2O}C 5H3N, followed by an acid-mediated deprotection, has been employed as an efficient route to the precursor 6,6′-bis(acetyl)-2, 2′-bipyridine. Reaction of aldimino L1 with two equivalents of MX 2 [MX2 = ZnCl2, NiCl2 or (DME)NiBr2] in n-BuOH at elevated temperature gives the five-coordinate mononuclear complexes [(L1)MX2] (M = Zn, X = Cl 1; M = Ni, X = Cl 2a; M = Ni, X = Br 2b) as the sole products, in which one imine group is bound and the other uncoordinated (endo-exo). In the case of diamagnetic 1, VT 1H NMR spectroscopy reveals a fast exchange process operating between the two possible forms of the endo-exo isomer which is likely to proceed via an exo-exo intermediate (ΔH? interconversion = 35.6 ± 1.5 kJ mol-1, ΔG?298 = 47.4 ± 3.3 kJ mol -1). In contrast, treatment of ketimino L2 with MCl2 (MCl2 = ZnCl2 or NiCl2) affords bimetallic [(L2)Zn2Cl4] (4) and the six-coordinate monometallic species [(L2)NiCl2] (5), respectively; in 4, L2 adopts a bis(bidentate) bonding mode (endo-endo) while in 5 it acts as tetradentate ligand (endo-endo). Prolonged standing of 1 in chlorinated solvents results in partial hydrolysis and the formation of the 6-imino-6′-formyl-2,2′- bipyridine zinc complex, [(6-{(2,6-i-Pr2C6H 3)NCMe)-6′-(CHO)C10H6N 2)ZnCl2] (3) (endo-imine, exo-formyl). Single crystal X-ray structures are reported for L1, 1, 2a, 3, 4 and 5. The Royal Society of Chemistry 2009.