1024-94-8

Upstream product

• 5470-18-8 2-Chloro-3-nitropyridine 
• 23056-40-8 2-chloro-5-methyl-3-nitro-pyridine 
• 577-19-5 2-nitrophenyl bromide 
• 13091-23-1 4-chloro-3-nitropyridine 

Downstream Products

• 132034-28-7 6-phenyl-5H-dipyrido<3,2-d:2',3'-f><1,3>diazepine 
• 1407543-92-3 dibenzyl ((2S,2'S)-([2,2'-bipyridine]-3,3'-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl))dicarbamate 
• 1407543-93-4 (S)-benzyl 2-((3'-amino-[2,2'-bipyridin]-3-yl)carbamoyl)pyrrolidine-1-carboxylate 
• 1628224-62-3 (2S,2'S)-N,N'-([2,2'-bipyridine]-3,3'-diyl)bis(2-amino-3-phenylpropanamide) 
• 1628224-61-2 C₄₄H₄₀N₆O₆ 
• 949084-46-2 N₃,N₃'-bis(diphenylphosphino)-2,2'-bipyridine-3,3'-diamine 
• 1407482-92-1 [C₁₀H₆N₂{PPh₂NHRh(cod)Cl}₂] 
• 475666-93-4 thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester 
• 638205-25-1 3,3'-dinitro-5'-phenylethynyl-5-trimethylsilanylethynyl-[2,2']bipyridinyl 
• 857256-62-3 3,3'-dinitro-5,5'-bis-phenylethynyl-[2,2']bipyridinyl 
• 638205-20-6 5'-ethynyl-3,3'-dinitro-5-phenylethynyl-[2,2']bipyridinyl 

Relevant academic research and scientific papers

On the electronic structure of nitro-substituted bipyridines and their platinum complexes

We report the preparation and electrochemical studies of a systematic series of mono- and di-nitro-substituted 2,2′-bipyridine (bipy) compounds [x-NO2-bipy (x = 3,4) and x,x′-(NO2) 2-bipy (x,x′ = 3, 4, 5)] and their complexes with platinum(ii), [Pt(x-NO2-bipy)Cl2] and [Pt(x,x′-(NO 2)2-bipy)Cl2]. The effect of the number and substitution pattern of the nitro groups on the low-lying acceptor molecular orbitals (involved in charge transfer transitions) is probed by in situ UV/Vis/NIR and EPR spectroelectrochemical methods, supported by DFT calculations. The LUMOs of x-NO2-bipy (x = 3-5) are largely localised on the NO2-pyridyl moiety; this is also true of their {PtCl 2} complexes but with a small but significant shift of electron density from the nitro groups. The LUMOs of x,x′-(NO2) 2-bipy with x = 3 and 5 are delocalised over both NO 2-pyridyl rings, but for 4,4′-(NO2)2-bipy is localised on a single NO2-pyridyl ring. In all cases the LUMO of the [Pt(x,x′-(NO2)2-bipy)Cl2] complexes is delocalised over both nitro-pyridyl rings. For all complexes, the 4(4′) derivatives allows greatest overlap with metal valence orbitals in the LUMO. The Royal Society of Chemistry.

Halogen Bond-Catalyzed Friedel?Crafts Reactions of Furans Using a 2,2’-Bipyridine-Based Catalyst

A halogen bond donor based on a 2,2’-bipyridine framework has been synthesized, and used to catalyze Friedel?Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so that if it indeed proved to be an efficient halogen bond donor organocatalyst, an enantioenriched version of it could potentially serve as a stereoselective catalyst. (Figure presented.).

The coordination chemistry of 3,3′-diamino-2,2′-bipyridine and its dication: Exploring the role of the amino groups by x-ray crystallography

The synthesis and structural chemistry of a series of new divalent transition metal complexes of the bis-bidentate ligand 3,3′-diamino-2,2′-bipyridine (L1) and its dication L1H2 are described. Ligand L1 reacts with salts of divalent transition metals to afford the (1:1) metal-ligand complexes (2a-2d) as well as the tris complexes (3a-3f). All complexes were fully characterised by spectroscopic methods and the following compounds [Cu(L1)Cl2]2 (2a), [Cu(L1)(OAc)2] (2b), [Zn(L1)3][OTf]2 (3a), and [Zn(L1)3][ZnCl4] (3e and 3f) were structurally characterised. Results from single crystal X-ray diffraction measurements indicate that formation of an intra-molecular hydrogen bond between the two amino groups allows the ligand to coordinate divalent metal ions through their diimine binding sites. Furthermore, the structure of compound 2a reveals that it crystallises as a dimer in which each copper ion is bound to two pyridine nitrogen atoms and two chloride ions in a distorted square planar arrangement, with a long axial contact from a neighbouring amino group completing the approximately square-pyramidal geometry at CuII. Complexation of this ligand in acidic conditions afforded the compound [Cu(L1H2)Cl4] (4), as well as the two salts [L1H2][CuCl4] (5a) and [L1H2][ZnCl4] (5b). All three compounds have been structurally characterised and results indicate that the dication (L1H2) displays a different coordination preference for the chelation of metal ions. In all three cases, both of the heterocyclic N atoms of the ligand are protonated, thus preventing chelation to the metal ion, although for compound 4 crystallographic studies reveal that the two amino functionalities coordinate the copper(II) ion. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Asymmetric synthesis of novel axially chiral 2,2′-bipyridine n,n′-dioxides bearing α-amino acid residues and their applications in enantioselective allylation of aromatic aldehydes with allyltrichlorosilane

A series of novel axially chiral 2,2′-bipyridine N,N′-dioxides bearing C1 or C2-symmetry have been synthesized by the use of enantiopure α-amino acids as chiral sources. The absolute stereochemistry of the axial chirality of these or

Design, synthesis and use of novel 3,3-disubstituted 2,2-bipyridine-based chiral ligands: Asymmetric catalysis in direct aldol reactions

A wide range of chiral ligands based on the 2,2-bipyridine scaffold were designed and synthesized. In complexation with metal Lewis acids, the reactivity and stereoselectivity of the prepared chiral ligands were examined in asymmetric catalytic direct ald

Applications of transition metal complexes containing 3,3′- bis(diphenylphosphinoamine)-2,2′-bipyridine ligand to transfer hydrogenation of ketones

Hydrogen transfer reduction processes are attracting increasing interest from synthetic chemists in view of their operational simplicity. 3,3′-bis(diphenylphosphinoamine)-2,2′-bipyridine, (Ph 2PNH)2C10H6N2, was prepared through a single step reaction of 3,3′-diamino-2,2′- bipyridine with diphenylchlorophosphine. Reaction of (Ph2PNH) 2C10H6N2 with [Ru(η6- benzene)(μ-Cl)Cl]2, [Rh(μ-Cl)(cod)]2 or [Ir(η5-C5Me5)(μ-Cl)Cl]2 gave a range of new bridged dinuclear complexes [C10H6N 2{NHPPh2Ru(η6-benzene)Cl2} 2], 1, [C10H6N2{PPh 2NHRh(cod)Cl}2], 2 and [C10H6N 2{NHPPh2Ir(η5-C5Me 5)Cl2}2], 3, respectively. All new complexes have been fully characterized by analytical and spectroscopic methods. 1H31P-{1H} NMR, 1H13C HETCOR or 1H1H COSY correlation experiments were used to confirm the spectral assignments. 1, 2 and 3 are suitable catalyst precursors for the transfer hydrogenation of acetophenone derivatives. Notably [Ru((Ph 2PNH)2C10H6N2) (η6-benzene)Cl2], 1 acts as an excellent catalyst, giving the corresponding alcohols in 98-99% yields in 10 min at 82 °C (TOF ≤600 h-1) for the transfer hydrogenation reaction in comparison to analogous rhodium or iridium complexes. This transfer hydrogenation is characterized by low reversibility under these conditions.

Synthesis and testing of new end-functionalized oligomers for molecular electronics

Several new classes of oligomers have been synthesized with functionalities designed to aid in the understanding of molecular device behavior, specifically when molecules are interfaced between proximal electronic probes. The compounds synthesized are series of azobenzenes, bipyridines and oligo(phenylene vinylene)s that bear acetyl-protected thiols for ultimate attachment to metallic surfaces. Some initial electrochemical and solid-state test results are also reported.

Synthesis and preliminary testing of molecular wires and devices

Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.

Alternative synthesis of dibenzo-and dipyrido-[1,3]diazepines from thioamides and o,o'-diaminobiaryls

Thioamides were treated with iodomethane, and then o,o'-diaminobiphenyl or bipyridyl to afford 6-substituted-5H-dibenzo- or dipyrido [1,3]diazepines in good yields.

Intramolecular hydrogen bonding in acylated 2,2'-bipyridine-3,3'-diamines

Various di- and monoacylated 2,2'-bipyridine-3,3'-diamines (amides 1a-f, 8, 9, ureas 1g-h, 8b and acylureas 1i-j) have been synthesized and characterized.All molecules show strong intramolecular hydrogen bonding between the acyl NH of one ring and the pyr