51595-55-2

Usage

Uses

Used in Coordination Chemistry:
4,4-dinitro-2,2-bipyridine N,N-dioxide is used as a ligand for forming coordination complexes with transition metals, which is crucial in various chemical processes. Its ability to bind with metals enhances the reactivity and selectivity of these complexes, making it a valuable component in the synthesis of new compounds and materials.
Used in the Design of Organic Materials:
As a potential building block, 4,4-dinitro-2,2-bipyridine N,N-dioxide is utilized in the design and synthesis of new organic materials. Its unique properties contribute to the development of materials with specific characteristics, such as improved stability or reactivity, which can be tailored for various applications.
Used in Catalyst Design:
4,4-dinitro-2,2-bipyridine N,N-dioxide is also used as a component in the design of catalysts. Its structural and electronic features allow for the creation of catalysts with enhanced performance, which can be applied in various chemical reactions to improve efficiency and selectivity.
Used in Research and Development:
In the field of research and development, 4,4-dinitro-2,2-bipyridine N,N-dioxide serves as a key compound for exploring new chemical reactions and mechanisms. Its interaction with transition metals and its role in complex formation provide insights into the development of novel chemical processes and applications.
Used in Chemical Synthesis:
In the chemical synthesis industry, 4,4-dinitro-2,2-bipyridine N,N-dioxide is employed as a reagent or intermediate in the production of various compounds. Its ability to form coordination complexes with metals can facilitate the synthesis of new molecules with specific properties, contributing to the advancement of the chemical synthesis field.

Upstream product

• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 366-18-7 [2,2]bipyridinyl 

Downstream Products

• 84175-09-7 4,4'-dibromo-2,2'-bipyridine N,N'-dioxide 
• 254450-33-4 4,4'-([2,2'-bipyridine]-4,4'-diyl)diphenol 
• 85698-56-2 N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine 
• 1309659-71-9 C₂₂H₁₄N₄O₄ 
• 6153-92-0 4,4'-diphenyl-2,2'-bipyridine 
• 854049-33-5 4,4'-bis(p-dimethylaminophenyl)-2,2'-bipyridine 
• 254450-32-3 4,4'-bis(p-methoxyphenyl)-2,2'-bipyridine 
• 854049-20-0 4,4'-bis(p-fluorophenyl)-2,2'-bipyridine 
• 854049-27-7 4,4'-bis(p-cyanophenyl)-2,2'-bipyridine 
• 133810-44-3 4,4’-diethynyl-2,2’-bipyridine 
• 1297609-44-9 4,4'-bis(1-benzyl-1H-[1,2,3]triazol-4-yl)-[2,2']bipyridinyl 
• 1297609-43-8 4,4'-bis(4-phenyl-[1,2,3]triazol-1-yl)-[2,2']bipyridinyl 1,1'-dioxide 
• 5470-22-4 4-chloropicolinic acid 
• 479417-36-2 4,4'-bis(diphenyl ether)-2,2'-bipyridine 

Relevant academic research and scientific papers

'Wiring' of glucose oxidase and lactate oxidase within a hydrogel made with poly(vinyl pyridine) complexed with [Os(4,4′-dimethoxy-2,2′-bipyridine)2Cl]+/2+

Glucose and lactate electrodes based on hydrogels made by crosslinking glucose oxidase and the redox polymer formed upon complexing poly(vinyl pyridine) (PVP) with [Os(dmo-bpy)2Cl]+/2+ (dmo-bpy = 4,4′-dimethoxy-2,2′-bipyridine) on vitreous carbon electrode surfaces have been investigated. The redox potential of the hydrogels was +35 mV vs. SCE and their glucose electrooxidation current reached a plateau at +150 mV vs. SCE. Urate and acetaminophen were not electrooxidized at this potential at rates that would interfere with the glucose and lactate assays. At a glucose concentration of 1 mM, the addition of 0.1 mM ascorbate increased the current by 17%. At 5 mM glucose, switching the atmosphere from argon to oxygen reduced the currents by 11%.

Exchange of pyridine and bipyridine ligands in trimethylplatinum(iv) iodide complexes: Substituent and solvent effects

A series of mononuclear trimethylplatinum(iv) complexes of bipyridine ligands, [PtMe3(L-L)I] (L-L = bipy, 4-Mebipy, 4-MeObipy and 4-Me2Nbipy) has been synthesized by the reaction of trimethylplatinum(iv) iodide with bipyridine ligands L-L in an equimolar ratio. Also, treatment of mononuclear trimethylplatinum(iv) iodide complexes of pyridine ligands, [PtMe3L2I] (L = py, 4-Mepy, 4-MeOpy and 4-Me2Npy) with the corresponding bipyridine ligands leads to the exchange of the pyridines by the bipyridine ligands, thereby resulting in the formation of the more stable chelate bipyridine complexes. The ligand-exchange reactions have been studied by 1H NMR spectroscopy. The 1H NMR spectra of a 1: 1 mixture of mononuclear pyridine complexes [PtMe3L2I] and corresponding bipyridine ligands L-L reveal the formation of two chelate bipyridine complexes, [PtMe3(L-L)I] and [PtMe3(L-L)L]I, in solution. Speciation of the pyridine and bipyridine complexes in solution was found to be dependent on the substituent as well as on the nature of the solvent. Furthermore, crystal structures of three bipyridine complexes [PtMe3(L-L)I] (L-L = 4-Mebipy, 4-MeObipy and 4-Me2Nbipy) have also been investigated here.

Electrochemistry and spectroscopy of substituted [Ru(phen)3]2+ and [Ru(bpy)3]2+ complexes

The metal-to-ligand charge transfer property of nitrogen-based ruthenium complexes earns it a central place in dye-sensitized solar cell and photo-catalytic H2O and CO2 reduction research and applications. Electronic and spectral tuning are conveniently done by altering substituents and ligands. Cyclic voltammograms and UV–visible spectra of a synthesized series of electronically altered phenanthroline and bipyridyl ruthenium complexes (ΔE°' > 1.4 V for RuII-III) were obtained and, amongst others, correlated with DFT computed HOMO energies and ionization potentials. A good linear relationship with R2 = 0.97 were found for the combined bipyridyl and phenanthrolinato ruthenium series, thereby providing a convenient computational tool for the theoretical prediction of associated redox potentials. TDDFT closely simulates spectral properties of these complexes, where λmax varies from 420 to 520 nm. The former wavelength is representative of the dione-phenanthroline and the latter of the dinitro-bipyridyl ruthenium complex.

The synthesis of diethyl 2-(2,2 ′ -bipyridin-4-ylmethylene)malonate and diethyl 3,3 ′ -(2,2 ′ -bipyridine-4,4 ′ -diyl)diacrylate

Abstract: The new acrylic acid derivatives diethyl 2-(2,2′-bipyridin-4-ylmethylene)malonate and diethyl 3,3′-(2,2′-bipyridine-4,4′-diyl)diacrylate which may be used for the introduction of metal coordination sites in polyacrylates were synthesized and characterized. Intermediates of the syntheses were prepared by improved synthetic protocols working under microwave conditions whenever it was advantageous for the resulting product in terms of reaction time and/or chemical yield. In addition, the crystal structure of one of the intermediates, 4,4′-dibromo-2,2′-bipyridine (6), is reported, in which molecules are arranged into infinite chains by C-H—Br interactions. Graphical Abstract: SYNOPSIS Synthesis and characterization of new 2,2’-bipyridine ligands with substituents related to acrylic acid esters are reported. These compounds offer the possibility to incorporate 2,2’-bipyridine ligands or coordination compounds derived from them into polyacrylate materials. [Figure not available: see fulltext.].

Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A

Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.

Electronic effects on reactivity and anticancer activity by half-sandwich N,N-chelated iridium(iii) complexes

The synthesis and characterization of a series of organometallic half-sandwich N,N-chelated iridium(iii) complexes bearing a range of electron-donating and withdrawing substituents were described. The X-ray crystal structures of complexes 1, 3 and 5 have been determined. This work demonstrated how the aqueous chemistry, catalytic activity in converting coenzyme NADH to NAD+ and anticancer activity can be controlled and fine-tuned by the modification of the ligand electronic perturbations. In general, the introduction of an electron-withdrawing group (-Cl and-NO2) on the bipyridine ring resulted in increased anticancer activity, whereas an electron-donating group (-NH2,-OH and-OCH3) decreased the anticancer activity. Complex 6 bearing a strongly electron-withdrawing NO2 group displayed the highest anticancer activity (7.3 ± 1.2 μM), ca. three times as active as cisplatin in the A549 cell line. Notably, selective cytotoxicity for cancer cells over normal cells was observed for complexes 1 and 6. DNA binding does not seem to be the primary mechanism for cancer fighting. However, the aqueous chemistry, cell apoptosis and cell cycle, which show similar dependence on the ligand electronic perturbations as the anticancer activity, appear to together contribute to the anticancer potency of theses complexes. This work may provide an alternative strategy to enhance anticancer activity for these N,N-chelated organometallic half-sandwich iridium(iii) complexes.

Ruthenium(II)–Pyridylimidazole Complexes as Photoreductants and PCET Reagents

Complexes of the type [Ru(bpy)2pyimH]2+[bpy = 2,2′-bipyridine; pyimH = 2-(2-pyridyl)imidazole] with various substituents on the bpy ligands can act as photoreductants. Their reducing power in the ground state and in the long-lived3MLCT excited state is increased significantly upon deprotonation, and they can undergo proton-coupled electron transfer (PCET) in the ground and excited state. PCET with both the proton and electron originating from a single donor resembles hydrogen atom transfer (HAT) and can be described thermodynamically by formal bond dissociation free energies (BDFEs). Whereas the class of complexes studied herein has long been known, their N–H BDFEs have not been determined even though this is important in view of assessing their reactivity. Our study demonstrates that the N–H BDFEs in the3MLCT excited states are between 34 and 52 kcal mol–1depending on the chemical substituents at the bpy spectator ligands. Specifically, we report on the electrochemistry and PCET thermochemistry of three heteroleptic complexes in 1:1 (v/v) CH3CN/H2O with CF3, tBu, and NMe2substituents on the bpy ligands.

In order to BipySi for preparation of the prismatic body cage oligomeric silsesquioxane and its rare earth luminescent material

The invention relates to a cage type oligomeric silsesquioxane prepared by taking BipySi as supplement bodies and a rare earth luminescent material prepared from cage type oligomeric silsesquioxane. By taking 1,3,5,7,9,11,14-heptaisobutyl tricyclic[7,3.3.15,11] heptatrisiloxane-intra-3,7,14-triol as a matrix, alpha-thenoyl trifluoroacetone silanized derivative, a dipyridine silanized derivative and a terpyridyl silanized derivative as supplement bodies, the supplement bodies react with the matrix in form of supplements to form integrated novel cage type oligomeric silsesquioxane. The cage type oligomeric silsesquioxane is combined with rare earth elements to form a POSS/rare earth ion luminescent material. The obtained rare earth ion luminescent material/POSS is rich in luminescent color, high in color purity, long in fluorescent lifetime (0.5-1.5ms), high in quantum efficiency (20) and strong in thermal stability (350 DEG C) and light stability, is a valuable optical material and can be applied to the field of display and development, light source, X-ray intensifying screen and the like.

Long-Lived, Emissive Excited States in Direct and Amide-Linked Thienyl-Substituted RuII Complexes

The excited state behavior of a new series of homoleptic and heteroleptic RuII complexes bearing thienyl groups appended to a 2,2′-bipyridine chelating ligand via direct, secondary and tertiary amide linkages is examined. The results of nanosecond transient absorption spectroscopy, emission lifetime measurements and bimolecular quenching experiments are correlated to determine that although the amide linkage does not act as a conjugated bridge to the peripheral substituents, it does not preclude possible electron transfer processes. Complexes bearing directly bound thienyl and bithienyl substituents exhibit long excited state and emission lifetimes (τem = 2 and 15 μs), with high emission quantum yields in solution (Φ = 0.35) and slow rates of non-radiative decay.

Hydroxyl and amino functionalized cyclometalated Ir(III) complexes: Synthesis, characterization and cytotoxicity studies

A series of Ir(III) complexes (?N)2Ir(N N) (N N are 4,4′-dihydroxy-2,2′-bipyridine and 4,4′-diamino-2,2′-bipyridine, and ?N are phenylpyridine, benzo[h]quinolone, and 2-phenylquinoline) were synthesized and characterized. Two of the complexes were structurally characterized via X-ray crystallography. The photophysical and photochemical properties of these complexes were studied. Preliminary studies of their applications on pH sensing, and cell imaging were also performed.