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Usage

Uses

Used in Organic Synthesis:
5,5'-(2,2'-bipyridine)diacid chloride is used as a building block for the preparation of various functional molecules, contributing to the development of new compounds with potential applications in different fields.
Used in Coordination Chemistry:
5,5'-(2,2'-bipyridine)diacid chloride is used as a ligand in the coordination chemistry of transition metal ions, enabling the formation of new and potentially useful metal complexes.
Used in Catalyst Development:
As a key intermediate in the preparation of metal-containing coordination complexes, 5,5'-(2,2'-bipyridine)diacid chloride is used in the development of catalysts for various chemical reactions, contributing to advancements in catalysis.
Used in Materials Science:
5,5'-(2,2'-bipyridine)diacid chloride is utilized in the synthesis of metal complexes that have potential applications in materials science, such as in the development of new materials with unique properties.
Used in Pharmaceutical Industry:
5,5'-(2,2'-bipyridine)diacid chloride is used in the preparation of metal complexes that have potential applications in medicine, including as therapeutic agents or in drug delivery systems.

Upstream product

• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 1762-34-1 5,5'-dimethyl-2,2'-bipyridine 
• 108-99-6 3-Methylpyridine 
• 3510-66-5 2-Bromo-5-methylpyridine 

Downstream Products

• 184421-52-1 [2,2']Bipyridinyl-5,5'-dicarboxylic acid bis-[4-(4-butoxy-benzoyloxy)-phenyl] ester 
• 1135140-63-4 5,5'-bis(benzylamido)-2,2'-bipyridine 
• 1064684-97-4 C₄₄H₃₆N₁₀ 
• 1802-29-5 2,2’-bipyridine-5,5’-dicarbonitrile 

Relevant academic research and scientific papers

Copper(II) complexes of two TEMPO-functionalized polypyridyl ligands: structure and catalytic activity in alcohol oxidation

The reaction of copper(II) salts with Bpy-TEMPO and Tpy-TEMPO (Bpy-TEMPO?=?[2,2′]Bipyridinyl-5,5′-dicarboxylic acid bis-[(2,2,6,6-tetramethyl-1-oxy-piperidin-4-yl)-amide]; Tpy-TEMPO?=?2,2,6,6-tetramethyl-4-(2,2′:6′,2″-terpyridin-4′-yloxy)piperidin-1-oxyl) gave dinuclear Bpy-TEMPO-Cu2 (1) and mononuclear Tpy-TEMPO-Cu (2), respectively. The Cu(II) complexes were characterized by single crystal X-ray analysis. In 1, Cu(II) has a distorted square pyramidal coordination geometry, with a bridging chloride as the axial ligand. The Cu(II) core in 2 also exhibited a distorted square pyramidal coordination geometry, with one chloride as an axial ligand. Weak interactions such as π-interactions and hydrogen bonds are observed in both complexes. When applied as catalysts for the oxidation of benzyl alcohol to benzaldehyde in air, 1 exhibited higher activity than 2 for reactions in o-xylene at 60°C with DBU as a base. High yield (67%) of benzaldehyde was observed when using 1 as a catalyst in a solution of o-xylene with DBU at 60°C.

Stretchable self-healing polymeric dielectrics cross-linked through metal-ligand coordination

A self-healing dielectric elastomer is achieved by the incorporation of metal-ligand coordination as cross-linking sites in nonpolar polydimethylsiloxane (PDMS) polymers. The ligand is 2,2′-bipyridine-5,5′-dicarboxylic amide, while the metal salts investigated here are Fe2+ and Zn2+ with various counteranions. The kinetically labile coordination between Zn2+ and bipyridine endows the polymer fast self-healing ability at ambient condition. When integrated into organic field-effect transistors (OFETs) as gate dielectrics, transistors with FeCl2 and ZnCl2 salts cross-linked PDMS exhibited increased dielectric constants compared to PDMS and demonstrated hysteresis-free transfer characteristics, owing to the low ion conductivity in PDMS and the strong columbic interaction between metal cations and the small Cl- anions which can prevent mobile anions drifting under gate bias. Fully stretchable transistors with FeCl2-PDMS dielectrics were fabricated and exhibited ideal transfer characteristics. The gate leakage current remained low even after 1000 cycles at 100% strain. The mechanical robustness and stable electrical performance proved its suitability for applications in stretchable electronics. On the other hand, transistors with gate dielectrics containing large-sized anions (BF4-, ClO4-, CF3SO3-) displayed prominent hysteresis due to mobile anions drifting under gate bias voltage. This work provides insights on future design of self-healing stretchable dielectric materials based on metal-ligand cross-linked polymers.

Induction of diastereoselectivity in fe(II) Tris(amino acid-bipyridine) complexes

A group of iron(II) tris-bipyridine complexes bearing L-amino acids (L-Lys, L-Phe, L-Ser, L-Val) was prepared to investigate the predetermination of chirality of metal complexes by the chiral amino acid subunits. Noncovalent interactions and solvent polarity seemed to be important factors in inducing diastereoselectivity of the metal complexes. These phenomena were explained by 1H NMR and CD spectroscopic studies and molecular mechanics calculations.

The first asymmetric synthesis of chiral ruthenium tris(bipyridine) from racemic ruthenium bis(bipyridine) complexes

The first 'one-pot' asymmetric synthesis of ruthenium tris(bipyridine) derivatives starting from corresponding racemic ruthenium bis(bipyridine) complexes is described. This is achieved through the stereocontrolled formation of reactive intermediates derived from (R)-(+)- or (S)-(-)-methyl p-tolyl sulfoxide, which can be easily converted to the products with a retention of configuration at the metal center. (C) 2000 Elsevier Science Ltd.

Pigment-acceptor-catalyst triads for photochemical hydrogen evolution

In order to solve the problems of global warming and shortage of fossil fuels, researchers have been endeavoring to achieve artificial photosynthesis: splitting water into H2 and O2 under solar light illumination. Our group has recently invented a unique system that drives photoinduced water reduction through "Z-scheme" photosynthetic pathways. Nevertheless, that system still suffered from a low turnover number (TON) of the photocatalytic cycle (TON=4.1). We have now found and describe herein a new methodology to make significant improvements in the TON, up to around TON=14-27. For the new model systems reported herein, the quantum efficiency of the second photoinduced step in the Z-scheme photosynthesis is dramatically improved by introducing multiviologen tethers to temporarily collect the high-energy electron generated in the first photoinduced step. These are unique examples of "pigment-acceptor-catalyst triads", which demonstrate a new effective type of artificial photosynthesis. Electron harvesting: Photo-hydrogen-evolving molecular devices showing substantially improved turnover numbers have been developed by introducing multiviologen tethers into a [PtCl2(2,2′-bipyridine)]-based moiety serving as a light-harvesting and H2-evolving center (see scheme). The improved photocatalytic performance is attributed to the rapidly regenerating character of the pigment due to intramolecular electron transfer from the pigment to the electron reservoirs.

Effect of ligand derivatization at different positions on photochemical properties of hybrid Re(I) photocatalysts

Hybrid CO2-reduction photocatalysts based on Re(bpy)(CO)3Cl, where bpy is 2,2′-bipyridine, were synthesized in order to investigate the effect of different ligand derivatization strategies on photochemical properties of the hybrid Re(I) systems. Derivatization of the bpy ligand was carried out at the 4,4′- and 5,5′-positions with electron-withdrawing amide groups. The derivatized ligands were grafted on mesoporous silica via a dipodal silane coupling agent and were further coordinated with Re(I). The synthesized hybrid photocatalysts were studied using spectroscopic techniques, including UV-visible, in situ infrared and electron paramagnetic resonance (EPR) spectroscopy, and tested in photochemical CO2 reduction. An interesting light-induced color change was observed for the hybrid photocatalyst involving derivatization of the bpy ligand at the 5,5′-positions. Combined UV-visible and EPR studies indicated that in the reduced form of this hybrid photocatalyst electron density was more localized on the bpy ligand than on the Re(I) center. Further studies with in situ infrared spectroscopy demonstrated possible formation of a carbonate-bridged binuclear Re(I) species on this hybrid photocatalyst. Our results are particularly relevant to developing new molecular and hybrid photocatalytic systems which involve extensive derivatization of coordinating ligands with functional groups for improved solar energy conversion.

Spectroscopic and 1O2 Sensitization Characteristics of a Series of Isomeric Re(bpy)(CO)3Cl Complexes Bearing Pendant BODIPY Chromophores

Two new Re(I)bipyridyltricarbonyl chloride complexes, Re(BB3)(CO)3Cl and Re(BB4)(CO)3Cl, featuring BODIPY groups appended to the 5,5′- or 6,6′-positions of the bipyridine ligand, respectively, were synthesized as structurally isomeric compliments to a previously reported 4,4′-substituted homologue, Re(BB2)(CO)3Cl. X-ray crystal structures of the compounds show that the 4,4′-, 5,5′-, and 6,6′-substitution patterns place the BODIPY groups at progressively shorter distances of 9.43, 8.39, and 5.56 ?, respectively, from the complexes' Re centers. The photophysical properties of the isomeric complexes were investigated to ascertain the manner in which the heavy rhenium atom might induce intersystem crossing of the pendant BODIPY moieties positioned at progressively shorter through-space distances. Electronic absorption spectroscopy revealed that the three metal complexes retain the strong visible absorption features characteristic of the bpyBODIPY (BB2-BB4) ligands; however, the fluorescence of the parent borondipyrromethane appended ligands is attenuated by more than an order of magnitude in Re(BB2)(CO)3Cl and Re(BB3)(CO)3Cl and by more than two orders of magnitude in Re(BB4)(CO)3Cl. Furthermore, phosphorescence from Re(BB4)(CO)3Cl is observed under a nitrogen atmosphere, consistent with highly efficient ISC to the triplet-excited state. Singlet oxygen sensitization studies confirm that all three complexes produce singlet oxygen with quantum yields that increase as the distance of the BODIPY groups to the heavy rhenium center is decreased. The trends observed across the series of rhenium complexes with respect to emission and 1O2 sensitization properties can be rationalized in terms of the varied distal separation between the metal center and BODIPY groups in each system.

Glycosylated tris-bipyridine ferrous complexes as molecular mimics of densely packed glycoclusters on cell surfaces: spatial carbohydrate packing of glycoclusters changes on additions of salts

Tris-bipyridine ferrous complexes having β-lactosides, β-maltosides or α-mannosides with serinol spacers were prepared as molecular mimics of densely packed carbohydrate clusters on cell surfaces. Conformational analysis on these glycosylated complexes we

Platinum(II)-glutamic acid dendrimer conjugates: Synthesis, characterization, DFT calculation, conformational analysis and catalytic properties

A series of platinum(II)-L-glutamic acid dendrimer conjugates having the formula PtCl2(5,5′-Gn(OR)-2,2′-bipyridine); Gn (n = 0, 1, 2), have been synthesized by various amide bond formation methods. The dendrimer complexes were terminated as car

Glycosylated tris-bipyridine ferrous complexes for probing a mechanism behind carbohydrate-carbohydrate interactions: Spatial carbohydrate packing of glycoclusters changes on additions of salts in carbohydrate- and anion-dependent manners

2,2′-Bipyridines containing two β-maltoside, β-lactoside, or β-isomaltoside appendages were prepared and successively complexed with ferrous ion to afford hexavalent glycoclusters having tris-bipyridine ferrous complex cores. Each of these metalloglycoclu