581-46-4

Usage

Uses

Used in Coordination Chemistry:
[3,3']BIPYRIDINYL is used as a ligand for the formation of metal complexes, leveraging its ability to bind with a variety of metal ions to create stable and well-defined structures. This application is crucial in various chemical processes and the development of new materials.
Used in Catalysis:
As a component in catalytic systems, [3,3']BIPYRIDINYL enhances the efficiency of chemical reactions, often improving the selectivity and speed of these processes. Its role in catalysis is significant in both academic research and industrial applications.
Used in Material Science:
[3,3']BIPYRIDINYL contributes to the development of new materials with unique properties, such as those with enhanced conductivity or light-emitting capabilities. Its structural characteristics make it a key component in the advancement of material technologies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [3,3']BIPYRIDINYL is utilized in the design and synthesis of pharmaceutical compounds, potentially leading to the creation of new drugs with improved therapeutic properties.
Used in Optoelectronics:
[3,3']BIPYRIDINYL is used in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices, capitalizing on its fluorescence properties to enhance the performance and efficiency of these technologies.
Used in Research and Development:
[3,3']BIPYRIDINYL serves as a valuable tool in research and development settings, where its properties are explored for potential new applications and to gain a deeper understanding of its interactions with other chemical entities.

Upstream product

• 625-92-3 3,5-dibromopyridine 
• 636-73-7 3-pyridinesulfonic acid 
• 3723-32-8 3,3'-bipyridine-2,2'-dicarboxylic acid 
• 56-81-5 glycerol 
• 110-86-1 pyridine 
• 30435-62-2 C₁₉H₁₄N₂O₂ 
• 60573-68-4 3-pyridyllithium 
• 626-55-1 3-Bromopyridine 
• 626-60-8 3-Chloropyridine 
• 59020-09-6 3-(trimethylstannyl)pyridine 
• 89878-14-8 3-Diethylboranylpyridine 
• 1120-90-7 3-iodopyridine 
• 5326-34-1 4-Bromo-3-nitrotoluene 
• 577-19-5 2-nitrophenyl bromide 

Downstream Products

• 31251-28-2 1,2,3,4,5,6-hexahydro[3,3']bipyridinyl 
• 59-67-6 nicotinic acid 
• 101001-97-2 6-chloro-3,3'-bipyridine 

Relevant academic research and scientific papers

Boronic acid-based bipyridinium salts as tunable receptors for monosaccharides and α-hydroxycarboxylates

Several novel diboronic acid-substituted bipyridinium salts were prepared and, using a fluorescent reporter dye, were tested for their ability to selectively bind various monosaccharides and α-hydroxycarboxylates in an aqueous medium. The fluorescence sensing mechanism relies on the formation of a ground-state charge-transfer complex between the dye and bipyridinium. An X-ray crystal structure of this complex is described herein. Glucose selectivity over fructose and galactose was achieved by designing the bipyridinium-based receptors to be capable of attaining a 1:1 receptor/substrate stoichiometry via cooperative diboronic acid binding.

Iron(ii) thio- and selenocyanate coordination networks containing 3,3′-bipyridine

A number of different compounds have been synthesised by reaction of solutions containing Fe(NCE)2 (E = S, Se) with solutions containing 3,3′-bipyridine. When the solvent used is methanol, the products are the monomeric compounds trans-{Fe(NCS)2(3,3′-bipy) 2(MeOH)2} 1 or trans-{Fe(NCSe)2(3,3′- bipy)2(MeOH)2} 2, but when acetonitrile is used the layered coordination network {Fe(NCS)2(3,3′-bipy)2} 3 or doubly interpenetrated coordination network {Fe(NCSe)2(3, 3′-bipy)2} 4 is formed instead. Using methanol to dissolve the Fe(NCE)2 and CHX3 (X = Cl, Br) to dissolve the 3,3′-bipyridine yields solvated coordination networks of stoichiometry {Fe(NCE)2(3,3′-bipy)2}·2CHX3. The crystal structures of all of these compounds except 4 are presented.

Photon-Induced Reactions of Aromatics Adsorbed on Rough and Smooth Silver Surfaces

We have investigated the thermal and photon-induced chemistry of several aromatics adsorbed on smooth and roughtened Ag(111) surfaces at low temperatures (110 K).Pyrazine, pyridine, 3-chloropyridine, and chlorobenzene quantitatively desorb from Ag(111) near 200 K.After roughtening the surface with 2 kV Ar ion bombardment, the breadth of the molecular desorption curves increases, and there is a high-temperature tail due to desorption from defecty sites produced by the roughening process.Upon UV photolysis of 1 monolayer, chlorobenzene and 3-chloropyridine photodissociate on smooth and rough Ag surfaces, whereas no detectable photoreaction were observed for pyrazine or pyridine absorbed on either surface.For the molecules that did not undergo photodissociation, a shift to lower energy in the photodissociation threshold was observed on the rough surface relative to the smooth: 3.3 eV versus 3.5 eV for chlorobenzene and 3.5 eV versus 3.9 eV for 3-chloropyridine.We postulate that the decrease in the photodissociation threshold is due to defect sites produced by surface roughening, through either excitation of the surface plasmon resonance, which is allowed on the rough but not the smooth surface, or a more localized excitation near defect sites.Excitation in the molecular absorption band shows that the photodissociation yield is enhanced for 3-chloropyridine and quenched for chlorobenzene on the rough surface relative to the smooth.Theoretical calculations suggest that there is a decrease in the decay rate for 3-chloropyridine and an increase in the decay rate for chlorobenzene on the rough surface compared to smooth.Differences between the quenching rates for 3-chloropyridine and chlorobenzene may be related to the different molecular orientations of these two molecules on the surface.

Effect of Surface Roughness on the Photodissociation Threshold of Chlorobenzene and 3-Chloropyridine Adsorbed on Silver

We have investigated the photodissociation of chlorobenzene and 3-chloropyridine adsorbed on smooth and rough Ag surfaces.Photolysis of adsorbed chlorobenzene and 3-chloropyridine with UV radiation results in C-Cl bond dissociation.Biphenyl and bipyridyl desorb from the surface near 400 K, and AgCl desorbs near 800 K in postirradiation temperature-programmed desorption.Compared to a smooth surface, there is a red shift in the photodissociation threshold for both molecules when adsorbed on a rough surface.Possible mechanisms for the red shift are discussed.This study demonstrates the importance of substrate morphology on surface photochemistry.

Fluorinated Boronic Acid-Appended Bipyridinium Salts for Diol Recognition and Discrimination via 19F NMR Barcodes

Fluorinated boronic acid-appended benzyl bipyridinium salts, derived from 4,4′-, 3,4′-, and 3,3′-bipyridines, were synthesized and used to detect and differentiate diol-containing analytes at physiological conditions via 19F NMR spectroscopy. An array of three water-soluble boronic acid receptors in combination with 19F NMR spectroscopy discriminates nine diol-containing bioanalytescatechol, dopamine, fructose, glucose, glucose-1-phosphate, glucose-6-phosphate, galactose, lactose, and sucroseat low mM concentrations. Characteristic 19F NMR fingerprints are interpreted as two-dimensional barcodes without the need of multivariate analysis techniques.

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates

Despite their importance to medicine and materials science, the synthesis of biheteroaryls by cross-coupling remains challenging. We describe here a new, general approach to biheteroaryls: the Ni-and Pd-catalyzed multimetallic cross-Ullmann coupling of he

Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air

Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.

Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions

Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.

Tandem Mn–I Exchange and Homocoupling Processes Mediated by a Synergistically Operative Lithium Manganate

Pairing lithium and manganese(II) to form lithium manganate [Li2Mn(CH2SiMe3)4] enables the efficient direct Mn–I exchange of aryliodides, affording transient (aryl)lithium manganate intermediates which in turn undergo spontaneous C?C homocoupling at room temperature to furnish symmetrical (bis)aryls in good yields under mild reaction conditions. The combination of EPR with X-ray crystallographic studies has revealed the mixed Li/Mn constitution of the organometallic intermediates involved in these reactions, including the homocoupling step which had previously been thought to occur via a single-metal Mn aryl species. These studies show Li and Mn working together in a synergistic manner to facilitate both the Mn–I exchange and the C?C bond-forming steps. Both steps are carefully synchronized, with the concomitant generation of the alkyliodide ICH2SiMe3 during the Mn–I exchange being essential to the aryl homocoupling process, wherein it serves as an in situ generated oxidant.