- Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes
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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.
- Okutani, Kazuhiro,Nozaki, Koichi,Iwamura, Munetaka
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- 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
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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.
- Buenzli, Jean-Claude G.,Charbonniere, Loic J.,Ziessel, Raymond F.
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- Highly efficient G-quadruplex recognition by bisquinolinium compounds
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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
- De Cian, Anne,DeLemos, Elsa,Mergny, Jean-Louis,Teulade-Fichou, Marie-Paule,Monchaud, David
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- Models of molecular photocatalysts for water oxidation: Strategies for conjugating the Ru(bda) fragment (bda = 2,2′-bipyridine-6,6′-dicarboxylate) to porphyrin photosensitizers
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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 {
- Adamo, F.,Alessio, E.,Iengo, E.,Vidal, A.
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supporting information
(2020/12/09)
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- Self-assembled bilayers as an anchoring strategy: Catalysts, chromophores, and chromophore-catalyst assemblies
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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.
- Wang, Lei,Polyansky, Dmitry E.,Concepcion, Javier J.
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supporting information
p. 8020 - 8027
(2019/06/13)
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- Chromium(VI) oxide-mediated oxidation of polyalkyl-polypyridines to polypyridine-polycarboxylic acids with periodic acid
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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.
- Yamazaki, Shigekazu
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supporting information
p. 2210 - 2218
(2019/06/25)
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- 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)
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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.
- Yazdani, Sima,Silva, Braden E.,Cao, Thomas C.,Rheingold, Arnold L.,Grotjahn, Douglas B.
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- Spectroscopic and 1O2 Sensitization Characteristics of a Series of Isomeric Re(bpy)(CO)3Cl Complexes Bearing Pendant BODIPY Chromophores
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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.
- Potocny, Andrea M.,Teesdale, Justin J.,Marangoz, Alize,Yap, Glenn P. A.,Rosenthal, Joel
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supporting information
p. 5042 - 5050
(2019/04/25)
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- Uranyl Complexes with Aroylbis(N, N-dialkylthioureas)
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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.
- Noufele, Christelle Njiki,Pham, Chien Thang,Hagenbach, Adelheid,Abram, Ulrich
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p. 12255 - 12269
(2018/09/27)
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- Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts
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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.
- Forato, Florian,Belhboub, Anouar,Monot, Julien,Petit, Marc,Benoit, Roland,Sarou-Kanian, Vincent,Fayon, Franck,Jacquemin, Denis,Queffelec, Clémence,Bujoli, Bruno
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supporting information
p. 2457 - 2465
(2018/02/06)
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- Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution Using Aqueous H2O2 and Chiral Iron–Bis(oxazolinyl)bipyridine Catalysts
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An efficient method for the oxidation of aromatic sulfides has been developed by using aqueous H2O2, catalyzed by the in situ generated chiral Fe/6,6′-bis(4-isopropyloxazolin-2-yl)-2,2′-bipyridine (bipybox-iPr) complex. The corresponding sulfoxides were obtained with high enantioselectivities (up to 98.5:1.5 er) and in good yields (up to 61 %) when the mono-oxidation of the sulfides was performed in combination with the kinetic resolution of the sulfoxide into the sulfone.
- Jalba, Angela,Régnier, Noémie,Ollevier, Thierry
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p. 1628 - 1637
(2017/04/06)
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- Design and synthesis of new Ru-complexes as potential photo-sensitizers: Experimental and TD-DFT insights
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We report density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations on a novel organic ligand and a novel class of ruthenium complexes; cis-RuL2X2 with L = 2,2′-bipyridine-6,6′-bis ethyl ester phosphonate and phosphonic acid, X = Cl, CN or NCS. The calculations show that cis-configurations are more stable than the trans-counterparts. The DFT results have been used to help design such novel complexes for potential use as sensitizers. We demonstrate the opportunity to synthesize such complexes with high purity. The synthesis of these complexes relies on the preparation of the key intermediates cis-Ru(2,2′-bipyridine-6,6′-bisdiethyl ester phosphonate)Cl2. These complexes were characterized by 1H, 13C, and 31P NMR, elemental analysis and FTIR spectroscopy. The NCS complex shows the smallest optical band gap followed by the Cl and CN complexes, respectively, with the highest performance upon use as a sensitizer in dye-sensitized solar cells.
- Sharmoukh,Hassan, Walid M. I.,Gros, Philippe C.,Allam, Nageh K.
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p. 69647 - 69657
(2016/08/05)
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- Preparation method of 2,2'-bipyridine-6,6'-dicarboxylic acid
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The invention relates to a preparation method of 2,2'-bipyridine-6,6'-dicarboxylic acid. 2,2'-bipyridine-6,6'-dicarboxylic acid with higher yield is obtained by oxidizing a reactant 6,6'-dimethyl-2,2'-bipyridine with potassium permanganate in a mixed solvent of glacial acetic acid and water. Relative to the prior art, the method has the characteristics of mild reaction conditions, safety, simplicity and convenience in operation, easiness in product separation, higher yield, and the like.
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Paragraph 0011; 0012; 0013
(2018/02/04)
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- Synthesis, electrochemistry, and electrogenerated chemiluminescence of two BODIPY-appended bipyridine homologues
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Two new 2,2′-bipyridine (bpy) derivatives containing ancillary BODIPY chromophores attached at the 5- and 5′-positions (BB3) or 6- and 6′-positions (BB4) were prepared and characterized. In this work, the basic photophysics, electrochemistry, and electrog
- Qi, Honglan,Teesdale, Justin J.,Pupillo, Rachel C.,Rosenthal, Joel,Bard, Allen J.
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p. 13558 - 13566
(2013/09/24)
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- A simple and environmentally benign synthesis of polypyridine- polycarboxylic acids
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An oxidation method using dilute nitric acid solutions under solvothermal conditions has been developed to synthesise a series of polypyridine- polycarboxylic acids. It has been successfully applied to a range of methyl substituted polypyridines including symmetrical and asymmetrical 2,2′-bipyridines; 2,2′:6′,2″-terpyridines and; 2,2′:6′,2″:6″,2?-tetra-pyridines and yields crystalline polypyridine-polycarboxylic acids in a single step. Simple product recovery through filtration yields a recyclable filtrate. More forcing conditions led to demethylation of the polypyridine ligand most probably via decarboxylation. This simple approach avoids potentially harmful metal-based oxidants and negates any issues associated with the disposal of their resultant (hazardous) waste.
- Kelly, Niamh R.,Goetz, Sandrine,Hawes, Chris S.,Kruger, Paul E.
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scheme or table
p. 995 - 998
(2011/03/21)
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- Diastereoselective self-assembly of a homochiral europium triangle from a bipyoxazoline-carboxylate ligand
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(Figure Presented) A homochiral triangle: An enantiopure europium triangle selectively selfassembles from a new bipyoxazolinecarboxylate ligand in a concentrationdependent process (see scheme).
- Bozoklu, Guelay,Marchal, Claire,Gateau, Christelle,Pecaut, Jacques,Imbert, Daniel,Mazzanti, Marinella
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supporting information; experimental part
p. 6159 - 6163
(2010/07/07)
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- 2,2′-Dipyridyl-6,6′-dicarboxylic acid diamides: Synthesis, complexation and extraction properties
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New ligands for complexing of the post-transition metals - diamides of 2,2′-bipyridyl-6,6′-dicarboxylic acid were developed, synthesised and characterised. They were proposed to be effective extractants towards americium. The structures of the amides were studied in solid as well as in solution. The extraction of Am and lanthanides depending on diamide structure, chlorinated cobalt dicarbollide (CCD) - diamide ratio, type of diluent was studied. The optimal conditions for Am/REE separation were determined. The properties of new potentiometric sensors on the base of 2,2′-dipyridyl-6,6′-dicarboxylic acid diamides were studied. The correlation structure vs. properties of ionophores (i.e. extractants), their sensitivity and selectivity in sensor analysis and extraction are discussed.
- Alyapyshev,Babain,Borisova,Eliseev,Kirsanov,Kostin,Legin,Reshetova,Smirnova
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scheme or table
p. 1998 - 2005
(2010/08/21)
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- Remarkable tuning of the coordination and photophysical properties of lanthanide ions in a series of tetrazole-based complexes
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A series of seven new tetrazole-based ligands (Ll, L3-L8) containing terpyridine or bipyridine chromophores suited to the formation of luminescent complexes of lanthanides have been synthesized. All ligands were prepared from the respective carbonitriles by thermal cycloaddition of sodium azide. The crystal structures of the homoleptic terpyridine-tetrazolate complexes [Ln(Li)2]NHEt3 (Ln = Nd, Eu, Tb for i = 1, 2; Ln = Eu for i = 3, 4) and of the monoaquo bypyridine-tetrazolate complex [Eu(H 2O)(L7)2]NHEt3 were determined. The tetradentate bipyridine-tetrazolate ligand forms nonhelical complexes that can contain a water molecule coordinated to the metal. Conversely, the pentadentate terpyridine-tetrazolate ligands wrap around the metal, thereby preventing solvent coordination and forming chiral double-helical complexes similarly to the analogue terpyridine-carboxylate. Proton NMR spectroscopy studies show that the solid-state structures of these complexes are retained in solution and indicate the kinetic stability of the hydrophobic complexes of terpyridine-tetrazolates. UV spectroscopy results suggest that terpyridine-tetrazolate complexes have a similar stability to their carboxylate analogues, which is sufficient for their isolation in aerobic conditions. The replacement of the carboxylate group with tetrazolate extends the absorption window of the corresponding terpyridine- (≈ 20nm) and bipyridine-based (25 nm) complexes to-wards the visible region (up to 440 nm). Moreover, the substitution of the terpyridine-tetrazolate system with different groups in the ligand series L3-L6 has a very important effect on both absorption spectra and luminescence efficiency of their lanthanide complexes. The tetrazole-based ligands Ll and L3-L8 sensitize efficiently the luminescent emission of lanthanide ions in the visible and near-IR regions with quantum yields ranging from 5 to 53 % for Eu III complexes, 6 to 35 % for Tb1" complexes, and 0.1 to 0.3% for NdIII complexes, which is among the highest reported for a neodymium complex. The luminescence efficiency could be related to the energy of the ligand triplet states, which are strongly correlated to the ligand structures.
- Andreiadis, Eugen S.,Demadrille, Renaud,Imbert, Daniel,Pecaut, Jacques,Mazzanti, Marinella
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scheme or table
p. 9458 - 9476
(2010/04/05)
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- New systems based on 2,2'-dipyridyl-6,6'-dicarboxylic acid diamides for Am-Eu separation
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New synergistic extraction mixtures based on 2,2'-dipyridyl-6,6'-dicarboxylic acid diamides and chlorinated cobalt dicarbolide were proposed as highly effective for americium-europium separation in acidic media.
- Alyapyshev, Mikhail Yu.,Babain, Vasily A.,Borisova, Nataliya E.,Kiseleva, Rimma N.,Safronov, Dmitry V.,Reshetova, Marina D.
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experimental part
p. 336 - 337
(2009/05/27)
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- Asymmetric hetero-Diels-Alder reaction of glyoxylate esters and Danishefsky's diene catalyzed by chiral bis(oxazoline)-lanthanide complexes
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Asymmetric hetero-Diels-Alder reactions of glyoxylate esters and Danishefsky's diene catalyzed by various chiral bis(oxazoline)-lanthanide complexes afforded the corresponding aldol adducts, which upon treatment with trifluoroacetic acid, furnished the he
- Qian, Changtao,Wang, Longcheng
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p. 2203 - 2206
(2007/10/03)
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- Facile and efficient syntheses of 2,2'-bipyridine-based bis(phosphonic) acids
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The synthesis and characterization of new 2,2'-bipyridine ligands bearing two phosphonic acid groups either on the (4,4'), (5,5') or (6,6') positions are described.
- Penicaud, Virginie,Odobel, Fabrice,Bujoli, Bruno
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p. 3689 - 3692
(2007/10/03)
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- 52. Influence of Chelating Groups on the Luminescence Properties of Europium(III) and Terbium(III) Chelates in the 2,2'-Bipyridine Series
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Eight different 2,2'-bipyridine derivatives, i.e. 2, 5, 8, 10, 12, 13, 15, and 19 (Schemes 1 and 2), were prepared to study the influence of the chelating groups on the luminescence properties of their EuIII and TbIII chelates.According to our luminescence results, 2,2'-(methylenenitrilo)bis(acetic acid) as well as (methylenenitrilo)bis(methylphosphonic acid) in 6- and 6'-position of 2,2'-bipyridine is a suitable group when developing luminescent markers for bioaffinity assays based on time-resolved luminescence measurement.
- Mukkala, Veli-Matti,Kwiatkowski, Marek,Kankare, Jouko,Takalo, Harri
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p. 893 - 899
(2007/10/02)
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