- Color responses of novel receptors for AcO- and a test paper for AcO- in pure aqueous solution
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An efficient AcO- sensor L which contains 1,10-phenanthroline-based and nitrophenylhydrazine-based groups, and its water-soluble Ru(II) complex were synthesized, characterized and studied in this Letter. Via UV-vis experiments and 1H NMR titration in DMSO solution, it was found that there were potential hydrogen bonds between the N{double bond, long}CH and AcO- after the deprotanation of two -NH during the reaction of L or its Ru complex with anions. Furthermore, an easy-to-prepare test paper was developed to detect AcO- at 10 mg/L in pure aqueous solution.
- Yu, Xudong,Lin, Hai,Cai, Zunsheng,Lin, Huakuan
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- A new efficient photosensitizer for nanocrystalline solar cells: Synthesis and characterization of m-bis(4,7-dicarboxy-l,10phenanthroline)dithiocyanato ruthenium(n)
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The complexes [NBu4]2-n[a.y-Ru(H2-xdcphen)2X 2 (n = 0 or 1; H2dcphen; =4,7-dicarboxy-l,10-phenanthroline; X = Cl, CN or SCN) were synthesized and spectroscopically characterized as a new class of photosensitizers. The energy levels of the LUMO and HOMO of ra-[Ru(H2dcphen)2(NCS)2] were estimated to be -1.02 and 0.89 V (vs. SCE), respectively, slightly more positive than those of [NBu4]2n[m-Ru(H2-xdcbpy)2(NCS) 2] (x = 0 or 1 ; H2dcbpy = 4,4'-dicarboxy-2,2'-bipyridine). A more intense and broader MLCT absorption of [NBu4]2[raeRu(H2-xdcphen)2(NCS)2] (;; = 0 or 1 ) than that of [NBu4]2-x[rae-Ru(H1-xdcbpy) 2(NCS)2] (;; = 0 or 1) was observed in ethanol solution at around 525 nm in the visible region. It is demonstrated that the new complexes act as efficient light harvesting antennae for dye-sensitized solar cells. A [NBu4]2-x[cw-Ru(Hdcphen)2(NCS)2] sensitized nanocrystalline TiO2 film shows a remarkable solar light to electrical power conversion efficiency of 6.1% at 100mWcm-2of AM 1.5. The Royal Society of Chemistry 2000.
- Yanagida, Masatoshi
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- BODIPY-functionalized 1,10-phenanthroline as a long wavelength sensitizer for near-infrared emission of the ytterbium(iii) ion
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Two BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) moieties were chemically appended to the 4,7-positions of 1,10-phenanhtroline resulting in two new ligands (BODIPY-Phen and 4I-BODIPY-Phen) with strong absorption at 507 nm and 540 nm, respectively. BODIPY-Phen emits fluorescence strongly centered at 507 nm, whereas the fluorescence of 4I-BODIPY-Phen was completely quenched due to the introduction of four I atoms at its 2,6 positions. The two ligands reacted readily with tris(1,1,1,5,5,5-hexafluoro-2,4-pentanedionate) ytterbium(iii) dihydrate through substitution reactions forming eight-coordinate complexes that emit strongly at 976 nm upon excitation at their absorption maximal positions. Both complexes exhibited a lifetime of ~11 μs in dichloromethane at room temperature.
- Kukoyi, Adedayo,Micheli, Eric A.,Liu, Beibei,He, Hongshan,Stanley May
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- Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors
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Among 18 human chemokine receptors, CCR1, CCR4, CCR5, and CCR8 were activated by metal ion Zn(II) or Cu(II) in complex with 2,2′-bipyridine or 1,10-phenanthroline with similar potencies (EC50 from 3.9 to 172 μM). Besides being agonists, they acted as selective allosteric enhancers of CCL3. These actions were dependent on a conserved glutamic acid at TM-7 (VII:06/7.39). A screening of 20 chelator analogues in complex with Zn(II) identified compounds with increased potencies, with 7 reaching highest potency at CCR1 (EC50 of 0.85 μM), 20 at CCR8 (0.39 μM), and 8 at CCR5 (1.0 μM). Altered selectivity for CCR1 and CCR8 over CCR5 (11, 12) and a receptor-dependent separation of allosteric from intrinsic properties were achieved (20). The pocket similarities of CCR1 and CCR8, contrary to CCR5 as proposed by the ligand screen, were elaborated by computational modeling. These studies facilitate exploration of chemokine receptors as possible targets for therapeutic intervention.
- Thiele, Stefanie,Malmgaard-Clausen, Mikkel,Steen, Anne,Rummel, Pia C.,Rosenkilde, Mette M.,Engel-Andreasen, Jens,Nielsen, Mads C.,Ulven, Trond,Gloriam, David E.,Frimurer, Thomas M.
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- A BODIPY-functionalized PdII photoredox catalyst for Sonogashira C-C cross-coupling reactions
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We report for the first time a BODIPY-functionalized dichloro(1,10-phenanthroline)palladium(ii) complex as an efficient photoredox catalyst for the Sonogashira C-C cross-coupling between phenylacetylene derivatives and iodobenzene derivatives with yields
- Dissanayake, Komadhie C.,Ebukuyo, Peters O.,Dhahir, Yasser J.,Wheeler, Kraig,He, Hongshan
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- Surface immobilized copper(i) diimine photosensitizers as molecular probes for elucidating the effects of confinement at interfaces for solar energy conversion
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Heteroleptic copper(i) bis(phenanthroline) complexes with surface anchoring carboxylate groups have been synthesized and immobilized on nanoporous metal oxide substrates. The species investigated are responsive to the external environment and this work provides a new strategy to control charge transfer processes for efficient solar energy conversion.
- Eberhart, Michael S.,Phelan, Brian T.,Niklas, Jens,Sprague-Klein, Emily A.,Kaphan, David M.,Gosztola, David J.,Chen, Lin X.,Tiede, David M.,Poluektov, Oleg G.,Mulfort, Karen L.
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- A Simple and Selective Fluorescent Sensor for Zn2+ and H+ Ions in Aqueous Solution with OR Logic Gate Function
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The synthesis and properties of a new compound, viz., (N,N′-[1,10-phenanthroline-4,7-diyldi((E)methylylidene)]bis(1,10-phenanthrolin-5-amine) (1), is described. Compound 1 can be used as a selective fluorescent Zn2+ sensor in buffered solution. Furthermore, 1 induces turn on fluorogenic response to H+ ions. Finally, it is shown that an OR logic gate can be constructed with 1 by using Zn2+ and H+ as two-inputs. [Figure not available: see fulltext.]
- Algi, Melek Pamuk
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- Synthesis and DNA-binding properties of 1,10-phenanthroline analogues as intercalating-crosslinkers
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(Chemical Equation Presented) We synthesized a series of bis(bromomethyl)4 ,10-phenanthrolines as novel anticancer lead compounds and examined their DNA-binding properties. 5,6-Bis(bromomethyl)-1,10-phenanthroline showed DNA intercalating activity and DNA crosslinking activity, furthermore it is stable in aqueous solution.
- Higashi, Toshinori,Inami, Keiko,Mochizuki, Masataka
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- A Fluorescent Hypochlorite Probe Built on 1,10-Phenanthroline Scaffold and its Ion Recognition Features
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In this study, the synthesis of 7-((Hydroxyimino)methyl)-1,10-phenanthroline-4-carbaldehyde oxime (1) in two steps starting from 4,7-dimethyl-1,10-phenanthroline (2) is reported. It is found that compound 1 can be used as a fluorogenic probe for the detection of hypochlorite ion in aqueous solution. NMR and mass spectral analysis indicate that probe 1 undergoes a chemical transformation through its oxime units upon treatment with hypochlorite, which results in a remarkable enhancement of the emission intensity. Also, metal ion recognition properties of probe 1 is investigated. It is noted that compound 1 is responsive to Zn2+, Cd2+, Ni2+ and Cu2+ metal ions, which reduced the emission intensity under identical conditions.
- Algi, Melek Pamuk
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- Rapid and highly sensitive dual-channel detection of cyanide by bis-heteroleptic ruthenium(II) complexes
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Two new ruthenium complexes [Ru(bipy)2(PDA)]2+ (1) and [Ru(phen)2(PDA)]2+ (2) (PDA = 1,10-phenanthroline-4,7- dicarboxaldehyde) have been synthesized to detect cyanide based on the well-known formation of cyanohydrins. Both 1[PF6]2 and 2[PF6]2 were fully characterized by various spectroscopic techniques and their solid state structures determined by single-crystal X-ray diffraction. Their anion binding properties in pure and aqueous acetonitrile were thoroughly examined using two different channels, i.e., UV-vis absorption and photoluminescence (PL). After addition of only 2 equiv of CN-, the PL intensity of 1[PF6]2 and 2[PF6] 2 was enhanced ~55-fold within 15 s along with a diagnostic blue shift of the emission by more than 100 nm. PL titrations of 1[PF 6]2 and 2[PF6]2 with CN- in CH3CN furnished the very high overall cyanohydrin formation constants log β[CN-] = 15.36 ± 0.44 (β[CN-] = 2.3 × - 1015 M-2) and log β[CN-] = 16.37 ± 0.53 (β[CN-] = 2.3 × 1016 M-2), respectively. For both probes, the second constant, K2, is about 57-84 times less than K1, suggesting that the cyanohydrin reaction is stepwise. The stepwise mechanism is further supported by results of a 1H NMR titration of 2[PF 6]2 with CN-. The high selectivity of 2[PF 6]2 for CN- was established by PL in the presence of other competing anions. Furthermore, the color change from orange-red to yellow and the appearance of a orange luminescence, which can be observed by the naked eye, provides a simple real-time method for cyanide detection. Finally, theoretical calculations were carried out to elucidate the details of the electronic structure and transitions involved in the ruthenium probes and their cyanide adducts.
- Khatua, Snehadrinarayan,Samanta, Debabrata,Bats, Jan W.,Schmittel, Michael
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- A highly selective dual channel hypochlorite probe based on fluorescein and 1,10-phenanthroline
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In this study, a highly selective dual channel (UV-vis and fluorescence) responsive hypochlorite probe based on fluorescein and 1,10-phenanthroline is described. It is found that this compound can be used as both a fluorogenic and chromogenic probe for the detection of the hypochlorite ion in aqueous solution. NMR and mass spectral analysis show that the probe reacts with the hypochlorite ion, which triggers both a remarkable enhancement of the emission intensity (turn on), and a color change from a colorless state to yellow. More importantly, the probe displays extremely high selectivity to hypochlorite among other common ROS and many ions in aqueous solution.
- Algi, Melek Pamuk
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- Selenous Acid in an Aromatic Framework: Insights Into a Temperature-Sensitive Internal Redox System from the Solid State
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We report on a new compound composed of a phenanthroline network in which emerging channels are alternately occupied by selenous acid (H2SeO3) and dioxane molecules. The material undergoes a variety of structural changes due to both its redox activity as well as its thermal decomposition. We investigate an internal redox system of the incorporated selenous acid and the aldehyde groups of the phenanthroline framework. The reduction process of the selenium species was further elucidated by cyclic voltammetry, while the oxidation process was also monitored by1H NMR spectra. The thermal behavior reveals that the material can undergo a reversible, topotactic transition due to dioxane and water (de)intercalation.
- Straub, Laura C.,Wickleder, Mathias S.,Rasche, Bertold
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p. 3641 - 3648
(2022/03/03)
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- Synthesis and photophysical properties of new ruthenium(II) charge-transfer sensitizers containing a 4,7-bis(E-carboxyvinyl)-1,10-phenanthroline ligand
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A series of ruthenium(II) complexes containing carboxyvinyl-conjugated phenanthroline and another auxiliary ligand have been designed, synthesized, and characterized. Starting from [RuCl2(p-cymene)]2, two types of Ru(II) complexes, [Ru(dcvphen)(4,7-R2-phenanthroline)(NCS) 2] and [Ru(dcvphen)(4,4′-R2-bipyridine)(NCS) 2] (dcvphen = 4,7-bis(E-carboxyvinyl)-1,10-phenanthroline, R = -CH = CHCOOH, -COOH, H), were synthesized by a one-pot reaction in DMF. Final products were obtained as a tetrabutylammonium salt form of Ru(II) complexes with reasonable yields. UV-Vis absorption studies on the newly synthesized Ru(II) complexes were carried out. Furthermore, it was shown that a dye-sensitized solar cell fabricated with representative [Ru(dcvphen)2(NCS) 2][TBA]2 complex dye exhibited a reasonable power conversion efficiency of 1.0 %.
- Tak, Jungae,Kim, Minki,Park, Sejoo,Yun, Soo Hong,Kim, Jihye,Park, Byoungchoo,Kim, Byeong Hyo
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p. 1101 - 1108
(2014/06/24)
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- Europium(III) and terbium(III) luminescent lanthanidomesogens
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Liquid-crystalline columnar phenanthroline-based ligand, for the first time substituted in 4,7-positions, is synthesized and used to induce low temperature mesomorphism in his corresponding lanthanide complexes. Stable liquid crystalline Eu(III) and Tb(II
- Szerb, Elisabeta I.,Crispini, Alessandra,La Deda, Massimo,Pucci, Daniela,Liguori, Paola F.,Pettinari, Claudio
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experimental part
p. 86 - 99
(2012/01/04)
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