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1,10-Phenanthroline-2,9-dicarboxylic acid

Pauraic McCarron, Malachy McCann, Michael Devereux, Kevin Kavanagh, Ciaran Skerry, Petros C Karakousis, Ana C Aor, Thaís P Mello, André L S Santos, Débora L Campos, Fernando R Pavan
Mycobacterium tuberculosis is the etiologic agent of tuberculosis. The demand for new chemotherapeutics with unique mechanisms of action to treat (multi)resistant strains is an urgent need. The objective of this work was to test the effect of manganese(II) and copper(II) phenanthroline/dicarboxylate complexes against M. tuberculosis . The water-soluble Mn(II) complexes, [Mn2 (oda)(phen)4 (H2 O)2 ][Mn2 (oda)(phen)4 (oda)2 ]·4H2 O ( 1 ) and {[Mn(3,6,9-tdda)(phen)2 ]·3H2 O·EtOH}n ( 3 ) (odaH2 = octanedioic acid, phen = 1,10-phenanthroline, tddaH2 = 3,6,9-trioxaundecanedioic acid), and water-insoluble complexes, [Mn(ph)(phen)(H2 O)2 ] ( 5 ), [Mn(ph)(phen)2 (H2 O)]·4H2 O ( 6 ), [Mn2 (isoph)2 (phen)3 ]·4H2 O ( 7 ), {[Mn(phen)2 (H2 O)2 ]}2 (isoph)2 (phen)·12H2 O ( 8 ) and [Mn(tereph)(phen)2 ]·5H2 O ( 9 ) (phH2 = phthalic acid, isophH2 = isophthalic acid, terephH2 = terephthalic acid), robustly inhibited the viability of M...
2018: Frontiers in Microbiology
Dan-Hong Zou, Peng Wang, Wen Luo, Jin-Le Hou, Qin-Yu Zhu, Jie Dai
Organic gelators and metal-coordination frameworks based on perylene derivatives as functional materials have attracted great attention because of their intense fluorescence emission as well as unique electronic and photonic properties. We report here the structures and properties of a luminescent titanium(IV) coordination compound of a perylene tetracarboxylate (PTC) derivative, [Ti2 (Oi Pr)6 (L1 )(phen)2 ] (1), along with its two naphthalene analogues, [Ti2 (Oi Pr)6 (L2 )(phen)2 ] (2) and [Ti2 (Oi Pr)6 (L2 )(bpy)2 ] (3), where L1 = 3,9-dicarboxylate-(4,10-diisopropanolcarboxylate)perylene, phen = 1,10-phenanthroline, L2 = 1,5-dicarboxylate-(2,6-diisopropanolcarboxylate)naphthalene, and bpy = 2,2'-bipyridine...
February 5, 2018: Inorganic Chemistry
Li He, Zhe Wei Peng, Zhong Wei Jiang, Xue Qian Tang, Cheng Zhi Huang, Yuan Fang Li
Novel metal-organic gels (MOGs) consisting of iron (Fe3+ ) as the central ion and 1,10-phenanthroline-2,9-dicarboxylic acid (PDA) as the ligand were synthesized by a mild facile strategy. The Fe(III)-containing metal-organic xerogels (Fe-MOXs), obtained after removing the solvents in MOGs, were found to exhibit outstanding performance in the catalysis of luminol chemiluminescence (CL) for the first time even in the absence of extra oxidants such as hydrogen peroxide. The possible CL mechanism was discussed according to the electro/optical measurements, including electron paramagnetic resonance (EPR), UV-vis absorption, and CL spectra, as well as the effects of radical scavengers on Fe-MOXs-catalyzed luminol CL system, suggesting that the CL emission of luminol might originate from the intrinsic oxidase-like catalytic activity of Fe-MOXs on the decomposition of dissolved oxygen...
September 20, 2017: ACS Applied Materials & Interfaces
Mark A Lashley, Alexander S Ivanov, Vyacheslav S Bryantsev, Sheng Dai, Robert D Hancock
Studies of the complexation of new promising ligands with uranyl (UO2 2+ ) and other seawater cations can aid the development of more efficient, selective, and robust sorbents for the recovery of uranium from seawater. In this work, we propose that the ligand design principles based on structural preorganization can be successfully applied to obtain a dramatic enhancement in UO2 2+ ion binding affinity and selectivity. This concept is exemplified through the investigation of the complexes of UO2 2+ , VO2 + , and VO2+ with the highly preorganized ligand 1,10-phenanthroline-2,9-dicarboxylic acid (PDA) using a combination of fluorescence and absorbance techniques, along with density functional theory (DFT) calculations...
October 17, 2016: Inorganic Chemistry
Taka-Aki Uchida, Koichi Nozaki, Munetaka Iwamura
Circularly polarized luminescence (CPL) was observed from [Eu(dppda)2 ](-) (dppda=4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid) and [Eu(pzpda)2 ](-) (pzpda=pyrazino[2,3-f][1,10]phenanthroline-7,10-dicarboxylic acid) in aqueous solutions containing various amino acids. The selectivity of these complexes towards amino acids enabled them to be used as chiral sensors and their behavior was compared with that of [Eu(pda)2 ](-) (pda=1,10-phenanthroline-2,9-dicarboxylic acid). As these Eu(III) complexes have achiral D2d structures under ordinary conditions, there were no CPL signals in the emission assigned to f-f transitions...
September 6, 2016: Chemistry, An Asian Journal
Samantha K Cary, Maryline G Ferrier, Ryan E Baumbach, Mark A Silver, Juan Lezama Pacheco, Stosh A Kozimor, Henry S La Pierre, Benjamin W Stein, Alexandra A Arico, Danielle L Gray, Thomas E Albrecht-Schmitt
The reaction of Ce(III) or Pu(III) with 1,10-phenanthroline-2,9-dicarboxylic acid (PDAH2) results in the formation of new f-element coordination complexes. In the case of cerium, Ce(PDA)(H2O)2Cl·H2O (1) or [Ce(PDAH)(PDA)]2[Ce(PDAH)(PDA)] (2) was isolated depending on the Ce/ligand ratio in the reaction. The structure of 2 is composed of two distinct substructures that are constructed from the same monomer. This monomer is composed of a Ce(III) cation bound by one PDA(2-) dianionic ligand and one PDAH(-) monoanionic ligand, both of which are tetradentate...
May 2, 2016: Inorganic Chemistry
Pierre Thuéry, Jack Harrowfield
Twelve new complexes were obtained from reaction of uranyl ions with the aliphatic dicarboxylic acids HOOC-(CH2)n-2-COOH (H2Cn; n = 7-10 and 12) under solvo-hydrothermal conditions, in the presence of 3d-block metal ions (Mn(2+), Fe(3+), Co(2+), Ni(2+), and Cu(2+)) and 2,2'-bipyridine (bipy) or 1,10-phenanthroline (phen). In contrast to previously reported triple-stranded helicates obtained with C9(2-) and C12(2-), all these complexes crystallize as polymeric one-dimensional (1D) or two-dimensional (2D) species...
March 7, 2016: Inorganic Chemistry
Bing Liu, Dongguang Yin, Kailin Song, Juan Ou Yang, Chengcheng Wang, Minghong Wu
In this study, a new europium complex of 4,4'-bis (1",1",1",2",2",3",3"-heptafluoro-4",6"- hexanedion-6"-yl)-o-terpheny-Eu(3+)-4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid-(3-aminopropyl) trimethoxysilane (BHHT-Eu(3+)-DPPDA-APTMS) was prepared first. Then novel core-shell Ag@SiO2 nanoparticles with BHHT-Eu(3+)-DPPDA-APTMS doped in shell were synthesized by a facile water-in-oil microemulsion method. The properties of the prepared complex and nanoparticles, and the effect of metal enhanced fluorescence for the nanoparticles were investigated...
January 2015: Journal of Nanoscience and Nanotechnology
Yu-Quan Feng, Yu-Long Hu, Hong-Wei Wang, Feng-Pu Cao
A new linear bismuth(III) coordination polymer, catena-poly[[chloridobismuth(III)]-μ3-1,10-phenanthroline-2,9-dicarboxylato-κ(6)O(2):O(2),N(1),N(10),O(9):O(9)], [Bi(C14H6N2O4)Cl]n, has been obtained by an ionothermal method and characterized by elemental analysis, energy-dispersive X-ray spectroscopy, IR spectroscopy, thermal stability studies and single-crystal X-ray diffraction. The structure is constructed by Bi(C14H6N2O4)Cl fragments in which each Bi(III) centre is seven-coordinated by one Cl atom, four O atoms and two N atoms...
August 2015: Acta Crystallographica. Section C, Structural Chemistry
Lele Duan, Lei Wang, Fusheng Li, Fei Li, Licheng Sun
The oxygen evolving complex (OEC) of the natural photosynthesis system II (PSII) oxidizes water to produce oxygen and reducing equivalents (protons and electrons). The oxygen released from PSII provides the oxygen source of our atmosphere; the reducing equivalents are used to reduce carbon dioxide to organic products, which support almost all organisms on the Earth planet. The first photosynthetic organisms able to split water were proposed to be cyanobacteria-like ones appearing ca. 2.5 billion years ago. Since then, nature has chosen a sustainable way by using solar energy to develop itself...
July 21, 2015: Accounts of Chemical Research
Kazuhiro Okutani, Koichi Nozaki, Munetaka Iwamura
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 Eu(III) 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...
June 2, 2014: Inorganic Chemistry
Guo-Dong Zou, Gui-Gang Zhang, Bing Hu, Jian-Rong Li, Mei-Ling Feng, Xin-Chen Wang, Xiao-Ying Huang
A 3D organic-inorganic hybrid compound, (2-MepyH)3[{Fe(1,10-phen)3}3][{Pr4Sb12O18(OH)Cl(11.5)}(TDC)(4.5)({Pr4Sb12O18(OH)Cl(9.5)} Cl)]·3(2-Mepy)·28H2O (1; 2-Mepy=2-methylpyridine, 1,10-phen=1,10-phenanthroline, H2TDC=thiophene-2,5-dicarboxylic acid), was hydrothermally synthesized and structurally characterized. Unusually, two kinds of high-nuclearity clusters, namely [(Pr4Sb12O18(OH)Cl11)(COO)5](5-) and [(Pr4Sb12O18(OH)Cl9)Cl(COO)5](4-), coexist in the structure of compound 1; two of the latter clusters are doubly bridged by two μ2-Cl(-) moieties to form a new centrosymmetric dimeric cluster...
November 4, 2013: Chemistry: a European Journal
Martina Sandroni, Megumi Kayanuma, Aurélien Planchat, Nadine Szuwarski, Errol Blart, Yann Pellegrin, Chantal Daniel, Mohammed Boujtita, Fabrice Odobel
We report here the synthesis and full chemical and physical characterizations of the first stable heteroleptic copper(I)-bis(diimine) complexes designed for implementation in dye sensitized solar cells (DSC). Thanks to the HETPHEN concept, pure and stable heteroleptic copper(I) complexes were isolated. Anchorage of the sensitizers was provided by 2,2'-biquinoline-4,4'-dicarboxylic acid (dcbqH2), while sterically challenged ligands 2,9-dimesityl-1,10-phenanthroline (L0) and N-hexyl-2,9-dimesityl-1,10-phenanthroline-[a:b]imidazo-(4'-dianisylaminophenyl) (L1) were used to complete the copper(I) coordination sphere...
August 14, 2013: Dalton Transactions: An International Journal of Inorganic Chemistry
Debashree Manna, Tapan K Ghanty
We have investigated the complexation behavior of preorganized 1,10-phenanthroline-2,9-dicarboxylic acid (PDA) based ligands with trivalent lanthanides and actinides using density functional theory with various GGA type exchange-correlation functionals and different basis sets. New ligands have been designed from PDA through functionalization with soft donor atoms such as sulfur, resulting in mono-thio-dicarboxylic acids (TCA/TCA1) and di-thio-dicarboxylic acid (THIO). It has been found that selectivity in terms of complexation energy of actinides over lanthanides is the maximum with TCA1 where the metal-ligand binding is through the O atoms...
August 21, 2012: Physical Chemistry Chemical Physics: PCCP
Shuang Jin, Mei-Feng Wen, Lu-Fang Liu, Ming-Juan Gao, Jian-Zhong Wu
5,6-Dioxo-1,10-phenanthroline-2,9-dicarboxylic acid dihydrate (H(2)pdda·2H(2)O), C(14)H(6)N(2)O(6)·2H(2)O, was obtained by carbonylation of 1,10-phenanthroline-2,9-dicarboxylic acid. Its first coordination compound, [MnCl(C(14)H(6)N(2)O(6))(H(2)O)(2)]Cl·2H(2)O, in which the H(2)pdda ligand remains protonated, was synthesized in aqueous acetic acid. H(2)pdda chelates one water molecule via hydrogen bonds in H(2)pdda·2H(2)O, whereas in the coordination compound it chelates one heptacoordinate Mn(II) atom via coordination bonds...
May 2012: Acta Crystallographica. Section C, Crystal Structure Communications
Yan-Li Miao, Jun-Liang Liu, Jin-Yan Li, Ji-Dong Leng, Yong-Cong Ou, Ming-Liang Tong
Two unique octa- and hendeca-nuclear dysprosium(III) clusters incorporating [Dy(4)(μ(3)-OH)(4)](8+) cubane units have been synthesized with the 1,10-phenanthroline-2,9-dicarbaldehyde dioxime (H(2)phendox) ligand and DyCl(3)·6H(2)O or Dy(OAc)(3)·4H(2)O. They are [Dy(8)(OH)(8)(phendox)(6)(H(2)O)(8)]Cl(2)(OH)(2)·18H(2)O·18MeOH (1) and [Dy(11)(OH)(11)(phendox)(6)(phenda)(3)(OAc)(3)](OH)·40H(2)O·7MeOH (2). Adjacent Dy(8) in 1 or Dy(11) in 2 motifs are packed by off-set π-π interactions of the aromatic rings on phendox(2-) to generate a 3D supramolecular architecture in the honeycomb topology and with 1D or 3D channels along the c-axis...
October 21, 2011: Dalton Transactions: An International Journal of Inorganic Chemistry
Anders Foller Larsen, Trond Ulven
A convenient and high-yielding multigram synthesis of the versatile intermediate 4,7-dichloro-1,10-phenanthroline-2,9-dicarboxylic acid is described. The intermediate is further efficiently derivatized to 4,7-diamino-1,10-phenanthroline-2,9-dicarboxamides with potential G-quadruplex stabilizing effects.
July 1, 2011: Organic Letters
Maryam Derakhshandeh, Zohreh Derikvand, Andya Nemati, Helen Stoeckli-Evans
The title proton-transfer compound, (C(14)H(13)N(2))[Ni(C(7)H(3)NO(5))(C(7)H(4)NO(5))]·2.35H(2)O, consists of an [Ni(hypydc)(hypydcH)](-) anion, a dmpH(+) cation and 2.35 uncoordinated water mol-ecules (where hypydcH(2) = 4-hy-droxy-pyridine-2,6-dicarb-oxy-lic acid and dmp = 2,9-dimethyl-1,10-phenanthroline). The Ni(II) atom is coordinated by two N atoms and four O atoms from the carboxyl-ate groups of the (hypydc)(2-) and (hypydcH)(-) ligands, forming a distorted octa-hedral environment. In the anion, the two pyridine rings are inclined to one another by 89...
2010: Acta Crystallographica. Section E, Structure Reports Online
Chongchen Wang
The title complex, C(12)H(9)N(2) (+)·C(14)H(9)O(4) (-) or (Hphen)(+)(Hbptc)(-) [H(2)btc = 2,2'-biphenyl-dicarboxylic acid and phen = 1,10-phenanthroline], has been synthesized under hydro-thermal conditions. The compound is composed of discrete cations (Hphen)(+) and anions (Hbptc)(-), which are linked by electrovalent bonding; the molecular and crystal structures are further strengthened by intra-molecular O-H⋯O and inter-molecular N-H⋯O hydrogen bonds.
2009: Acta Crystallographica. Section E, Structure Reports Online
Xiaoxia Zhu, Alison M Kriegel, Christopher A Boustany, Diane A Blake
Recombinant single-chain variable fragment antibodies (scFv) were specifically generated and selected for the measurement of environmental uranium with an antibody-based sensor. These sFvs, which recognized UO(2)(2+) complexed to 2,9-dicarboxyl-1,10-phenanthroline-acid (DCP), were produced using genetic material obtained from the spleen cells of rabbits immunized with UO(2)(2+)-DCP conjugated to keyhole limpet hemocyanin. Immunoglobulin light chain and heavy chain genes were amplified and cloned into the phagemid pSD3 for generation of a recombinant antibody library and phage-displayed antibodies...
May 15, 2011: Analytical Chemistry
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