4479-74-7

Usage

Uses

Used in Coordination Chemistry:
2,2'-Bipyridine-6,6'-dicarboxylic acid is used as a chelating ligand for [forming stable metal complexes] due to [its ability to bind to metal ions through bipyridine and dicarboxylic acid functional groups].
Used in the Synthesis of Luminescent Materials:
2,2'-Bipyridine-6,6'-dicarboxylic acid is used as a building block for [creating luminescent materials] because of [its unique coordination properties that allow for the formation of metal complexes with specific optical characteristics].
Used in Catalyst Development:
2,2'-Bipyridine-6,6'-dicarboxylic acid is used as a component in [catalyst synthesis] for [its role in enhancing the catalytic activity of metal complexes].
Used in Sensor Technology:
2,2'-Bipyridine-6,6'-dicarboxylic acid is used as a sensing element for [developing sensors] because of [its capacity to form complexes with metal ions that can respond to specific stimuli or analytes].

Upstream product

• 4411-80-7 6,6'-dimethyl-2,2'-bipyridine 
• 4411-83-0 2,2′-bipyridine-6,6′-dicarbonitrile 
• 49669-22-9 6,6'-Dibromo-2,2'-bipyridine 
• 124-38-9 carbon dioxide 
• 109-04-6 2-bromo-pyridine 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 65739-40-4 6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine 
• 366-18-7 [2,2]bipyridinyl 
• 109-06-8 α-picoline 
• 626-05-1 2,6-Dibromopyridine 

Downstream Products

• 65739-40-4 6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine 
• 74065-63-7 6,6′-bis(hydroxymethyl)-2,2′-bipyridine 
• 49669-26-3 2,2'-bipyridine-6,6'-dicarbaldehyde 
• 142593-07-5 dimethyl 2,2'-bipyridine-6,6'-dicarboxylate 
• 2093382-71-7 6,6′-bis[(S)-4-tert-butyloxazolin-2-y1]-2,2′-bipyridine 
• 273216-89-0 6,6′-bis[4-phenyloxazolin-2-y1]-2,2′-bipyridine 

Relevant academic research and scientific papers

Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes

The circularly polarized luminescence (CPL) from [Eu(pda)2] - (pda = 1,10-phenanthroline-2,9-dicarboxylic acid) and [Eu(bda) 2]- (bda = 2,2-bipyridine-6,6-dicarboxylic acid) in aqueous solutions containing various amino acids was investigated. The europium(III) complexes exhibited bright-red luminescence assignable to the f-f transition of the EuIII ion when irradiated with UV light. Although the luminescence was not circularly polarized in the solid state or in aqueous solutions, in accordance with the achiral crystal structure, the complexes exhibited detectable induced CPL (iCPL) in aqueous solutions containing chiral amino acids. In the presence of l-pyrrolidonecarboxylic acid, both [Eu(pda) 2]- and [Eu(bda)2]- showed similar iCPL intensity (glum ～ 0.03 for the 5D0 → 7F1 transition at 1 mol·dm-3 of the amino acid). On the other hand, in the presence of l-histidine or l-arginine, [Eu(pda)2]- exhibited intense CPL (g lum ～ 0.08 for the 5D0 → 7F1 transition at 0.10 mol·dm-3 of the amino acid), whereas quite weak CPL was observed for [Eu(bda)2] - under the same conditions (glum 2]- was found to be a good chiral CPL probe with high sensitivity (about 10-2 mol·dm-3) and high selectivity for l-histidine at pH 3 and for l-arginine at pH 7. The mechanism of iCPL was evaluated by analysis of the fine structures in the luminescence spectra and the amino acid concentration dependence of glum. For the [Eu(pda)2]--histidine/arginine systems, the europium(III) complexes possess coordination structures similar to that in the crystal with slight distortion to form a chiral structure due to specific interaction with two zwitterionic amino acids. This mechanism was in stark contrast to that of the europium(III) complex-pyrrolidonecarboxylic acid system in which one amino acid coordinates to the EuIII ion to yield an achiral coordination structure.

Structural and photophysical properties of Lnin complexes with 2,2'-bipyridine-6,6'-dicarboxylic acid: Surprising formation of a H-bonded network of bimetallic entitiesf

The ligand H2L = 2,2'-bipyridine-6,6'-dicarboxylic acid reacts with Ln(NOj)j-.vH2O (.v = 6, Ln = Eu, Tb; x = 5, Ln = Gd) in MeOH/Et3N to give complexes with 1:2 and 2:3 metal : ligand stoichiometry, (Et3NH)[LnL2] and [LnjlHjOl-A'HjO (x = 1, Ln = Eu, Tb; .v = 0, Ln = Gd) which have been isolated and characterised. A sizeable quantum yield is obtained for the 1:2 Eu : Ligand complex in aqueous solution (Euabs = 11.5 ±2.3% at pH = 6.6), pointing to an efficient ligand-to-metal energy transfer. The presence of some inner-sphere interaction with water was deduced from Eu(5D0) lifetime measurements in water (0.86 ±0.01 ms vs. 1.55 ±0.02 ms in the solid state between 10 and 295 K, 7es[ = 0.3-0.4 water molecule). For [TbL2]-, sensitisation of Tbm also occurs ( = 6.3 ± 1.3% at pH = 6.6) but the Tb(5D4) excited level is de-populated at room temperature by a back-transfer process to the ligand. The crystal structure obtained for the 2:3 Tb : ligand complex evidences two distinct terbium sites, one Tb1" being complexed to two ligands affording a mono-anionic complex, itself linked to the second terbium ion with a u-carboxylate bridge; the generic formulation of the crystallised complex is [TbLj-u-TbL(H2O)3]'2H2O ' 2MeOH. Consecutive dimers are linked by an elaborate network of H-bonds involving interstitial solvent molecules. A photophysical study of the 2:3 Eu: Ligand complex in the solid state points to the same structural features, revealing two metal ion sites with essentially no bonded water (q = 0.3, site I) and with 3 co-ordinated water molecules (q = 2.8, site II), respectively. The H2L synthon is therefore an interesting building block for the design of elaborate compartmental ligands and/or of supramolecular functional assemblies. The Royal Society of Chemistry 2000.

Highly efficient G-quadruplex recognition by bisquinolinium compounds

Syntheses and telomeric G-quadruplex-DNA binding properties of novel bisquinolinium compounds are reported. This series exhibits remarkable efficiency both in terms of stabilization and selectivity, thus combining the performances of the most potent quadruplex binders reported so far. These bisquinolinium compounds then represent an ideal tradeoff between rapid synthetic access and efficient target recognition. The study also highlights important structural parameters that lead to the design of highly selective G-quadruplex binders. Copyright

Models of molecular photocatalysts for water oxidation: Strategies for conjugating the Ru(bda) fragment (bda = 2,2′-bipyridine-6,6′-dicarboxylate) to porphyrin photosensitizers

Model dyads, in which the Ru(bda) water oxidation catalyst (WOC) is connected to a porphyrin, were prepared following two different modular strategies: i) the direct linkage approach, in which porphyrins bearing peripheral pyridyl rings are bound to the {

Self-assembled bilayers as an anchoring strategy: Catalysts, chromophores, and chromophore-catalyst assemblies

Anchoring strategies for immobilization of molecular catalysts, chromophores, and chromophorecatalyst assemblies on electrode surfaces play an important role in solar energy conversion devices such as dyesensitized solar cells and dye-sensitized photoelectrosynthesis cells. They are also important in interfacial studies with surface-bound molecules including electron-transfer dynamics and mechanistic studies related to small molecule activation catalysis. Significant progress has been made in this area, but many challenges remain in terms of stability, synthetic complexity, and versatility. We report here a new anchoring strategy based on selfassembled bilayers. This strategy takes advantage of noncovalent interactions between long alkyl chains chemically bound to a metal-oxide electrode surface and long alkyl chains on the molecule being anchored. The new methodology is applicable to the heterogenization of both catalysts and chromophores as well as to the in situ "synthesis" of chromophore-catalyst assemblies on the electrode surface.

Chromium(VI) oxide-mediated oxidation of polyalkyl-polypyridines to polypyridine-polycarboxylic acids with periodic acid

4,4′-Dicarboxy-2,2′-bipyridine was synthesized quantitatively by chromium(VI) oxide-mediated oxidation of 4,4′-dimethyl-2,2′-bipyridine or 4,4′-diethyl-2,2′-bipyridine with periodic acid as the terminal oxidant in sulfuric acid. 5,5′-Dicarboxy-2,2′-bipyridine and 6,6’-dicarboxy-2,2′-bipyridine were also synthesized by the method from the corresponding dimethyl bipyridines in excellent yields. 4,4′,4″-Tricarboxy-2,2′:6′,2″-terpyridine was obtained in 80% yield from 4,4′,4″-triethyl-2,2′:6′,2″-terpyridine, and 4,4′,4″,4′″-tetracarboxy-2,2′:6′,2″:6″,2′″-quaterpyridine was obtained in 72% yield from 4,4′,4″,4′″-tetraethyl-2,2′:6′,2″:6″,2′″-quaterpyridine by the same procedure.

X-ray crystallography and electrochemistry reveal electronic and steric effects of phosphine and phosphite ligands in complexes RuII(κ4-bda)(PR3)2 and RuII(κ3-bda)(PR3)3 (bda?=?2,2′-bipyridine-6,6′-dicarboxylato)

We have examined coordination of PR3 = triphenylphosphine, triethylphosphine, triisopropyl phosphite, trimethyl phosphite, and 1,3,5-triaza-7-phosphaadamantane (PTA) to the fragment RuII(bda) to better understand how different phosphine and phosphite ligands influence the electronic and structural properties of the RuII complexes. PTA and P(OMe)3 afforded complexes with three phosphorus ligands bound to Ru, with the bda being tridentate (κ3-N,N,O) in complexes 4 and 5; for the other three phosphorus ligands, even in the presence of >2 equiv, only RuII(κ4-bda)(PR3)2 species 1–3 were seen. Both experimental and computational methods were used to study the complexes. Steric effects are the main factor determining whether bis- or tris(PR3) complexes are formed. Cyclic voltammetry studies of the complexes revealed an increase in RuIII/II potential upon having another phosphorus ligand in the equatorial position. Computational studies predict that the additional phosphine ligand in the equatorial plane of 4 engages in significant orbital mixing with the ruthenium center that results in lower energy bonding as compared to the axial phosphine ligands. This work provides the first evaluation of phosphorus ligand steric and electronic effects on the RuII(bda) fragment.

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.

Uranyl Complexes with Aroylbis(N, N-dialkylthioureas)

The reaction of isophthaloylbis(N,N-diethylthiourea), H2L1, with UO2(CH3COO)2·2H2O and NEt3 as a supporting base gives a tetranuclear, anionic complex of the composition [{UO2(L1)}4(OAc)2]2-, in which the uranyl ions are S,O-chelate bonded. Each two of them are additionally linked by an acetato ligand. Similar reactions of various uranyl starting materials (uranyl acetate, uranyl nitrate, (NBu4)2[UO2Cl4]) with corresponding pyridine-centered ligands (pyridine-2,6-dicarbonylbis(N,N-dialkylthioureas), H2L2) yield mononuclear, neutral compounds, in which the thiourea derivatives are coordinated as S,N,N,N,S-five-dentate chelators. The equatorial coordination spheres of the formed hexagonal bipyramidal complexes [UO2(L2)(solv)] are completed by solvent ligands (H2O, MeOH, or DMF). Attempted reactions without a supporting base result in decomposition of the organic ligands and the formation of hexanuclear uranyl complexes with pyridine-2,6-dicarboxylato ligands, while the use of an excess of base results in condensation and the formation of dinuclear [{UO2(L2)(μ-OMe)}2]2- complexes. A stable complex of the composition [UO2(L3)] results from reactions of common uranyl starting materials with 2,2′-bipyridine-6,6′-dicarbonylbis(N,N-diethylthiourea) (H2L3). The equatorial coordination sphere of the neutral, hexagonal bipyramidal complex is occupied by an SN4S donor atom set, which is provided by the hexadentate organic ligand. While the uranium complexes with {L1}2- and {L2}2- are labile and rapidly decompose in acidic solutions, [UO2(L3)] is stable over a wide pH range, and the ligand readily extracts uranyl ions from aqueous solutions into organic solvents.

Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts

RhL2 complexes of phosphonate-derivatized 2,2′-bipyridine (bpy) ligands L were immobilized on titanium oxide particles generated in situ. Depending on the structure of the bipy ligand—number of tethers (1 or 2) to which the phosphonate end groups are attached and their location on the 2,2′-bipyridine backbone (4,4′-, 5,5′-, or 6,6′-positions)—the resulting supported catalysts showed comparable chemoselectivity but different kinetics for the hydrogenation of 6-methyl-5-hepten-2-one under hydrogen pressure. Characterization of the six supported catalysts suggested that the intrinsic geometry of each of the phosphonate-derivatized 2,2′-bipyridines leads to supported catalysts with different microstructures and different arrangements of the RhL2 species at the surface of the solid, which thereby affect their reactivity.