1762-46-5

Usage

Uses

Used in Scientific Research:
Diethyl 2,2'-bipyridine-5,5'-dicarboxylate is used as a ligand in the synthesis of metal-organic frameworks (MOFs) for its ability to form multi-dimensional networks, which is crucial in creating structures with enhanced properties.
Used in Coordination Chemistry:
DEBPDC is employed as a bridging ligand in coordination chemistry, facilitating the formation of complexes with transition metals, which is essential for the development of new compounds with unique characteristics.
Used in Luminescent Materials:
Diethyl 2,2'-bipyridine-5,5'-dicarboxylate is used as a component in the creation of luminescent materials, where its ability to form complexes with metals contributes to the development of materials with specific light-emitting properties.
Used in the Creation of New Compounds:
DEBPDC is utilized as a ligand in the synthesis of new compounds with unique properties, which can be beneficial in various technological applications, such as in the fields of catalysis, sensing, and energy storage.

Upstream product

• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 1762-34-1 5,5'-dimethyl-2,2'-bipyridine 
• 64-17-5 ethanol 
• 151917-39-4 ethyl 6-iodonicotinate 
• 108-99-6 3-Methylpyridine 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 

Downstream Products

• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 63361-65-9 5,5’-bis(hydroxymethyl)-2,2’-bipyridine 
• 135822-72-9 2,2′-bipyridine-5,5′-dicarbaldehyde 
• 1802-29-5 2,2’-bipyridine-5,5’-dicarbonitrile 

Relevant academic research and scientific papers

The folding of a metallopeptide

We have applied solid-phase synthesis methods for the construction of tris(bipyridyl) peptidic ligands that coordinate Fe(ii) ions with high affinity and fold into stable mononuclear metallopeptides. The main factors influencing the folding pathway and ch

Discriminating octahedral transition metal ions: Highly selective tripodal tris-(2,2′-bipyridine) functionalized piperazine cyclophane receptor for Cu2+ ions

New tripodal transition metal ion receptors, tris(5-ethoxycarbonyl-2, 2′-bipyridine) and tris(5-carboxylate-2,2′-bipyridine) substituted 27-membered trimeric piperazine cyclophanes 5 and 7 as well as tetra(5-ethoxycarbonyl-2,2′-bipyridine) substituted 36-membered tetrameric piperazine cyclophane 6, have been prepared and their transition metal ion complexing properties studied in solution by UV-vis spectroscopy and in the solid state by single-crystal X-ray diffraction. The crystal structures of [H353+·Fe2+]·4(ClO 4-)·CF3COO- (V), [H 372+·Fe2+]·2(SO4 2-) (VII) and the reference complex [tris(5,5′- bis(ethoxycarbonyl)-2,2′-bipyridine)Fe(ii) perchlorate] (I) showed that the robust piperazine cyclophane is an optimal platform in preorganizing the 2,2′-bipy moieties to form a very fixed octahedral coordination site. In an acidic water solution, the highly preorganized structure of 5 gives a [5·Fe2+] complex, the stability of which is comparable with the classical tris(2,2′-bipy) Fe2+-complex but it is a significant 3.7 logK units more stable than the non-preorganized tetrameric analog [6·Fe2+]. Detailed studies with other similar divalent octahedral transition metal cations showed that the restricted octahedral coordination in complexes of 5 results in an unusual selectivity. The selectivity order [Zn2+2+2+≈ Fe2+2+] deviates significantly from that of typical tris(2,2′-bipy) complexes [Zn2+2+2+≈ Fe2+2+]. As a highlight, cyclophane 5 exhibits exceptionally high selectivity towards Cu2+ ions but very weak binding for Co2+. The Royal Society of Chemistry 2011.

Dynamic Stereoselection of Peptide Helicates and Their Selective Labeling of DNA Replication Foci in Cells**

Although largely overlooked in peptide engineering, coordination chemistry offers a new set of interactions that opens unexplored design opportunities for developing complex molecular structures. In this context, we report new artificial peptide ligands t

An Organometallic Isostere of an Amino Acid

An organometallic complex that mimics an amino acid, also known as an amino acid isostere, can be synthesized from a functionalized bipyridine ligand and a fac-[Re(CO)3]+ center. The reaction of an achiral ligand and metal results in a racemic mixture of

Remote control of bipyridine-metal coordination within a peptide dendrimer

The metal coordinating ability of a bipyridine ligand at the core of a peptide dendrimer was found to be controlled by the nature of amino acids placed at the dendrimer periphery, with coordination being promoted by anionic residues and inhibited by catio

Custom-fit ruthenium(II) metallopeptides: A new twist to DNA binding with coordination compounds

A new bipyridine building block has been used for the solid-phase synthesis of dinuclear DNA-binding ruthenium(II) metallopeptides. Detailed spectroscopic studies suggest that these compounds bind to the DNA by insertion into the DNA minor groove. Moreove

A Molecular Water-Oxidation Catalyst Derived from Ruthenium Diaqua Bis(2,2'-bipyridyl-5,5'-dicarboxylic acid)

Controlled-potential electrolysis of cis-RuIIL2(OH2)22+ (where L is 2,2'-bipyridyl-5,5'-dicarboxylic acid) in 0.5 M H2SO4 solutions leads to the formation of a relatively durable and active molecular water-oxidation catalyst.Detailed analyses by UV-visible absorption spectrophotometry, resonance Raman spectrophotometry, electrochemical measurements, HPLC, and elemental analysis indicate that the water-oxidation catalyst is an oxo-bridged dimer, L2(H2O)Ru-O-Ru(OH2)L2.The synthesis, spectrophotometric, and redox properties of the monomeric and dimeric ruthenium complexes have been characterized.The effectiveness of the oxo-bridged complex as a water-oxidation catalyst has been evaluated by electrochemical and spectrophotometric analyses and by determination of oxygen production.This newly discovered homogeneous catalyst is highly effective in mediating the thermal and visible-light-induced generation of oxygen from water.A comparison is made between the monomer and dimer and various analogues of the complexes.The presence of the COOH groups at the 5,5' positions of the bipyridyl ligands correlates with the unusual and favorable properties of cis-RuL2(OH2)2 and L2(OH2)Ru-O-Ru(OH2)L2.Dimeric ruthenium complexes of similar structure are also formed during the thermolysis and photolysis of Ru(II) tris(2,2'-bipyridyl-5,5'-dicarboxylic acid), RuL32+, in 0.5 M H2SO4 solutions containing peroxodisulfate.

Stereoselective formation of chiral metallopeptides

Playing into our hands: The achiral bipyridine amino acid fluorenylmethyloxycarbonyl 5-amino-3-oxapentanoic acid (Fmoc-O1PenBpy-OH) has been used for the solid-phase synthesis of metallopeptides. Circular dichroism, molecular modeling, and NMR spectroscop

A comparative study of Ru(ii) cyclometallated complexes versus thiocyanated heteroleptic complexes: Thermodynamic force for efficient dye regeneration in dye-sensitized solar cells and how low could it be?

Four novel Ru(ii) bipyridyl complexes MH12-15 were synthesized and characterized for dye-sensitized solar cells (DSSCs). Their photovoltaic performance including incident photon-to-current conversion efficiency (IPCE), total solar-to-power conversion efficiency (η%) and ground and excited state oxidation potentials and photoelectrochemical properties were evaluated on mesoporous nanocrystalline TiO2 and compared with the benchmark N719-dye under the same experimental conditions. MH12-15 showed stronger MLCT with significantly higher molar extinction coefficient for the lower energy absorption bands at 553 nm (27500 M-1 cm-1), 554 nm (34605 M-1 cm-1), 577 nm (23300 M-1 cm-1), and 582 nm (39000 M-1 cm-1), respectively, than that of N719 (14200 M-1 cm-1). The introduction of a cyclometallated ligand in dyes MH14 and 15 improved the optical properties and red-shifts of 24 nm and 28 nm, respectively, compared to the non-cyclometallated analogs MH12 and 13. The red shift in the UV-Vis spectra of MH14 and 15 can be attributed to the destabilization of the HOMO t2g of Ru(ii). However, the destabilization of the HOMO furnished an upward shift of the ground state oxidation potentials (GSOPs) of MH14 and 15 at -5.44 eV and -5.36 eV against vacuum, respectively, which resulted in a driving force of only 0.22 and 0.16 eV for regeneration of dyes MH14 and 15, respectively. In the case of NCS analogs, MH12 and 13, the GSOPs, however, were -5.56 and -5.51 eV, respectively, which produced a driving force of more than 0.25 eV for dye regeneration. The nanosecond transient absorbance measurements showed that the time needed for the oxidized forms of MH12-MH15 to regenerate the neutral dye is 6 μs, 4 μs, 13 μs and 18 μs, respectively, compared to N719 (2.3 μs). These kinetic data confirmed that the weak thermodynamic force, small negative free energy (-ΔG), for regeneration of MH14 and 15 neutral dyes makes the dye regeneration process kinetically sluggish, which contributed significantly to the loss of both photocurrent and photovoltage. This study clearly elucidated that although cyclometallation may produce significantly better light harvesting, the driving force of less than 0.25 eV is not sufficiently enough for effective dye regeneration. the Partner Organisations 2014.

Molecular Iridium Complexes in Metal-Organic Frameworks Catalyze CO2 Hydrogenation via Concerted Proton and Hydride Transfer

Molecular iridium catalysts immobilized in metal-organic frameworks (MOFs) were positioned in the condensing chamber of a Soxhlet extractor for efficient CO2 hydrogenation. Droplets of hot water seeped through the MOF catalyst to create dynamic gas/liquid interfaces which maximize the contact of CO2, H2, H2O, and the catalyst to achieve a high turnover frequency of 410 h-1 under atmospheric pressure and at 85 °C. H/D kinetic isotope effect measurements and density functional theory calculations revealed concerted proton-hydride transfer in the rate-determining step of CO2 hydrogenation, which was difficult to unravel in homogeneous reactions due to base-catalyzed H/D exchange.