Chemistry - A European Journal

Cover image for Vol. 17 Issue 19

May 2, 2011

Volume 17, Issue 19

Pages 5209–5447

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Communications
    8. Full Papers
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    1. Cover Picture: Generation of Carbanions through Stibine–Metal and Bismuthine–Metal Exchange Reactions and Its Applications to Precision Synthesis of ω-End-Functionalized Polymers (Chem. Eur. J. 19/2011) (page 5209)

      Eiichi Kayahara, Hiroto Yamada and Prof. Dr. Shigeru Yamago

      Article first published online: 20 APR 2011 | DOI: 10.1002/chem.201190092

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      Organostibine and organobismuthine groups at the living polymer ends are selectively transformed to the corresponding carbanions by a heteroatom–metal exchange reaction (transmetallation). Due to the high reactivity of these heteroatom species, the exchange reaction takes place even in the presence of various polar functional groups, which potentially react with organometallic reagents. For more details see the Full Paper on page 5272 ff., by S. Yamago et al.

  2. Inside Cover

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    1. Inside Cover: Molecular Aspects of Glucose Dehydration by Chromium Chlorides in Ionic Liquids (Chem. Eur. J. 19/2011) (page 5210)

      Dr. Yanmei Zhang, Dr. Evgeny A. Pidko and Prof. Dr. Emiel J. M. Hensen

      Article first published online: 20 APR 2011 | DOI: 10.1002/chem.201190093

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      Transient self-organization of Cr complexes into binuclear structures is the key to the selective dehydration of glucose to 5-hydroxymethylfurfural by chromium chlorides in ionic liquids. In their Full Paper on page 5281 ff., E. J. M. Hensen et al. demonstrate that the mechanism of the selective glucose transformations does not depend on the oxidation state of the chromium catalyst. Because of its enhanced Lewis acidity, CrCl3x H2O (x=0 or 6) shows higher activity and selectivity to HMF compared to CrCl2.

  3. Back Cover

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    1. Back Cover: A Facile Route to Water-Soluble Coronenes and Benzo[ghi]perylenes (Chem. Eur. J. 19/2011) (page 5210)

      Cordula D. Schmidt, Dr. Nina Lang, Dr. Norbert Jux and Prof. Dr. Andreas Hirsch

      Article first published online: 20 APR 2011 | DOI: 10.1002/chem.201190097

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      The synthesis of benzoperylene and coronene compounds usually requires time consuming, thermally activated reactions that involve co-reactants and/or catalysts. In their Full Paper on page 5289 ff., A. Hirsch et al. describe a new synthetic approach to benzoperylenes and coronenes by a photo-induced electrocyclic reaction. The transformation of the corresponding dendronized bay-functionalized perylene diimides into benzoperylene and coronene compounds, as well as the aggregation behavior of each derivative, are investigated by absorption and fluorescence spectroscopy.

  4. Graphical Abstract

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    1. Graphical Abstract: Chem. Eur. J. 19/2011 (pages 5213–5220)

      Article first published online: 20 APR 2011 | DOI: 10.1002/chem.201190094

  5. News

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  6. Communications

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    1. Asymmetric Catalysis

      Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Nitrones to Alkylidene Malonates: Highly Enantioselective Synthesis of Multisubstituted Isoxazolidines (pages 5226–5229)

      Donghui Chen, Zhen Wang, Jiangting Li, Zhigang Yang, Dr. Lili Lin, Dr. Xiaohua Liu and Prof. Dr. Xiaoming Feng

      Article first published online: 5 APR 2011 | DOI: 10.1002/chem.201100053

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      All under control! A catalytic asymmetric 1,3-dipolar cycloaddition reaction of nitrones to alkylidene malonates, catalyzed by chiral N,N′-dioxide–Ni(ClO4)26 H2O complexes, has been developed with excellent yields, diastereo-, and enantioselectivities (see scheme, R1=aryl, R2=alkyl, R3, R4=Ph). In addition, a possible transition state has also been proposed to elucidate the high level of enantio- and diastereocontrol.

    2. [4]Diboradicarbametalloarenophanes

      Unexpected Generation of Diastereomers by Double Diboration of a Dialkyne (pages 5230–5233)

      Florian Bauer, Prof. Dr. Holger Braunschweig, Katrin Gruß, Prof. Dr. Christoph Lambert, Prof. Dr. Krishna K. Pandey, Dr. Krzysztof Radacki and Dr. Dörte Reitzenstein

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201002614

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      Diastereomeric and interconvertable [4]diboradicarbaferrocenophanes were obtained by platinum-catalyzed diboration of a dialkyne. They were fully characterized and their electrochemistry was studied by cyclic voltammetry. DFT calculations were carried out to examine the interconversion reaction.

    3. Nucleophilic Addition

      Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl or Vinyl Chlorides to α-Ketoamides Through C[BOND]Cl Bond Activation (pages 5234–5237)

      Jin-Xiu Hu, Hao Wu, Prof. Dr. Chuan-Ying Li, Wei-Jian Sheng, Prof. Dr. Yi-Xia Jia and Prof. Dr. Jian-Rong Gao

      Article first published online: 1 APR 2011 | DOI: 10.1002/chem.201100256

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      Nickeleophilic addition! The first example of a nickel-catalyzed direct intramolecular nucleophilic addition of aryl or vinyl chlorides to α-ketoamides through C[BOND]Cl bond activation is reported, which takes place under mild reaction conditions (see scheme).

    4. Glycoconjugates

      Straightforward Preparation of Functionalized α-CF2-Galactosides through an Oxygen to Carbon Acyl Migration (pages 5238–5241)

      Sophie Colombel, Morgane Sanselme, Dr. Eric Leclerc, Prof. Dr. Jean-Charles Quirion and Prof. Dr. Xavier Pannecoucke

      Article first published online: 11 APR 2011 | DOI: 10.1002/chem.201100183

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      A privileged Glycon! A radical-addition Meerwein–Ponndorf–Verley (MPV) reduction sequence provides access to functionalized α-CF2-galactosides (see scheme). Introduction of a CF2Br group in the pseudo-anomeric position aided the transfer of an aglycon chain from O-2 to C-1′ through an intramolecular addition–reduction sequence, which involved a Br–Li exchange. This methodology gives access to a wide range of fluorinated C-glycosidic analogues of glycoconjugates.

    5. Asymmetric Catalysis

      Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to 2-Nitrostyrenes by tert-Butanesulfinylphosphine Ligand (pages 5242–5245)

      Feng Lang, Guihua Chen, Dr. Liangchun Li, Junwei Xing, Fuzhong Han, Linfeng Cun and Prof. Dr. Jian Liao

      Article first published online: 6 APR 2011 | DOI: 10.1002/chem.201100135

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      Particularly picky ligands! An efficient (S/C, substrate/catalyst, up to 500) Rh-catalyzed enantioselective addition of arylboronic acids to 2-nitrostyrenes under mild conditions was developed, which gave excellent yields (up to 99 %) and enantioselectivities (up to 98 % ee) by using tert-butanesulfinylphosphine as a ligand (see scheme). Based on this method, (R)-cherylline was synthesized in 70 % overall yield.

    6. Cycloaddition Reactions

      Visualizing the Product of a Formal Cycloaddition of 7,7,8,8-Tetracyano-p-quinodimethane (TCNQ) to an Acetylene-Appended Porphyrin by Scanning Tunneling Microscopy on Au(111) (pages 5246–5250)

      Petra Fesser, Dr. Cristian Iacovita, Christian Wäckerlin, Saranyan Vijayaraghavan, Dr. Nirmalya Ballav, Dr. Kara Howes, Dr. Jean-Paul Gisselbrecht, Maura Crobu, Prof. Corinne Boudon, Prof. Meike Stöhr, Prof. Thomas A. Jung and Prof. François Diederich

      Article first published online: 11 APR 2011 | DOI: 10.1002/chem.201100733

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      Click it: The applicability of a formal [2+2] cycloaddition between electron-rich alkynes and electron-deficient TCNQ on an atomically clean Au(111) surface was demonstrated by scanning tunneling microscopy (STM) and X-ray photoelectron spectroscopy (XPS). At low coverage, monomeric and self-assembled dimeric species of the initial compounds as well as of the reaction product, a TCNQ-conjugated porphyrin, could be visualized.

    7. Host–Guest Systems

      Photoresponsive Soft Nanotubes for Controlled Guest Release (pages 5251–5255)

      Dr. Naohiro Kameta, Asuka Tanaka, Dr. Haruhisa Akiyama, Dr. Hiroyuki Minamikawa, Dr. Mitsutoshi Masuda and Dr. Toshimi Shimizu

      Article first published online: 6 APR 2011 | DOI: 10.1002/chem.201100179

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      Light, transformation, release! Self-assembly of a simple amphiphile with an azobenzene unit produced an organic nanotube with 20 nm inner diameter. The trans-to-cis photoisomerization of the azobenzene unit within the solid bilayer membranes of the nanotube induced the transformation to cylindrical nanofibers (see graphic). This way, the nanotube was able to precisely release encapsulated guest molecules as a response to photostimulus.

    8. Protease Inhibitors

      New Cathepsin Inhibitors to Explore the Fluorophilic Properties of the S2 Pocket of Cathepsin B: Design, Synthesis, and Biological Evaluation (pages 5256–5260)

      Prof. Dr. Santos Fustero, Dr. Vanessa Rodrigo, Dr. María Sánchez-Roselló, Dr. Carlos del Pozo, Prof. Dr. Joaquín Timoneda, Maxim Frizler, Dr. Mihiret T. Sisay, Prof. Dr. Jürgen Bajorath, Dr. Luis P. Calle, Dr. F. Javier Cañada, Prof. Dr. Jesús Jiménez-Barbero and Prof. Dr. Michael Gütschow

      Article first published online: 30 MAR 2011 | DOI: 10.1002/chem.201100113

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      Fluor-in or out? Based on β,β-difluorinated cycloaliphatic amino acids, a library of new dipeptide nitriles was evaluated as human cathepsin inhibitors. The orientation of the fluorinated face relative to the protein structure of cathepsin B was elucidated by molecular modeling and NMR studies (see figure). For (R)-configured eutomers, the fluorine atoms are directed to the S2 pocket, whereas in (S)-configured distomers, the fluorinated face is solvent-exposed.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Back Cover
    5. Graphical Abstract
    6. News
    7. Communications
    8. Full Papers
    9. Preview
    1. Fluorescent Imaging

      Coenzyme Q Functionalized CdTe/ZnS Quantum Dots for Reactive Oxygen Species (ROS) Imaging (pages 5262–5271)

      Li-Xia Qin, Wei Ma, Dr. Da-Wei Li, Dr. Yang Li, Prof. Xiaoyuan Chen, Prof. Heinz-Bernhard Kraatz, Prof. Tony D. James and Prof. Yi-Tao Long

      Article first published online: 18 APR 2011 | DOI: 10.1002/chem.201003749

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      Biomimetic electron transfer: An in situ fluorescence spectroelectrochemical study demonstrates that the reduced state of [CoQCnS]2 significantly enhanced the FL intensity of CdTe/ZnS QDs, while the oxidized state of the coenzyme Q conjugates quench the fluorescence to varying degrees. The system is supremely sensitive to NADH and superoxide radical (O2.), and represents a biomimetic electron-transfer system modeling part of the mitochondrial respiratory chain.

    2. Exchange Reactions

      Generation of Carbanions through Stibine–Metal and Bismuthine–Metal Exchange Reactions and Its Applications to Precision Synthesis of ω-End-Functionalized Polymers (pages 5272–5280)

      Eiichi Kayahara, Hiroto Yamada and Prof. Dr. Shigeru Yamago

      Article first published online: 8 APR 2011 | DOI: 10.1002/chem.201100265

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      All's well that ends well: The generation of carbanions from organostibine and -bismuthine compounds was achieved thorough a heteroatom–metal exchange reaction (see scheme). The highly chemoselective exchange reaction could be applied to precision synthesis of varieties of ω-end-functionalized polymers that possess a polar functional group.

    3. Homogeneous Catalysis

      Molecular Aspects of Glucose Dehydration by Chromium Chlorides in Ionic Liquids (pages 5281–5288)

      Dr. Yanmei Zhang, Dr. Evgeny A. Pidko and Prof. Dr. Emiel J. M. Hensen

      Article first published online: 12 APR 2011 | DOI: 10.1002/chem.201003645

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      Active sites organize: The catalytic reactivity of different Cr salts for the selective dehydration of glucose to 5-hydroxymethylfurfural has been investigated. The unique reactivity of chromium chlorides in ionic liquid relates to the transient self-organization of catalytic Cr complexes, which promotes the initial glucose to fructose isomerization step (see graphic). The reaction mechanism does not depend on the formal oxidation state of the metal center.

    4. Click Chemistry

      A Facile Route to Water-Soluble Coronenes and Benzo[ghi]perylenes (pages 5289–5299)

      Cordula D. Schmidt, Dr. Nina Lang, Dr. Norbert Jux and Prof. Dr. Andreas Hirsch

      Article first published online: 11 APR 2011 | DOI: 10.1002/chem.201003232

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      Given the green light: Click reactions at the bay-positions of perylene diimides were carried out for the first time. The newly formed triazole units undergo electrocyclisation reactions with the neighbouring perylene bay-position to form benzoperylenes or coronenes (see scheme). The reactions occur in solution in 55–87 % yield by irradiation with light, providing a simple, new and environmentally friendly route to coronenes and benzoperylenes.

    5. Organic Electronics

      Columnar Mesophases Based on Zinc Chlorophyll Derivatives Functionalized with Peripheral Dendron Wedges (pages 5300–5310)

      Sanchita Sengupta, Dr. Shinobu Uemura, Sameer Patwardhan, Dr. Valerie Huber, Dr. Ferdinand C. Grozema, Prof. Dr. Laurens D. A. Siebbeles, Dr. Ute Baumeister and Prof. Dr. Frank Würthner

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201002659

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      Chlorophyll liquid crystal: Semisynthetic zinc chlorins derived from chlorophyll a and functionalized with peripheral dendron wedges (see figure) self-assemble into tubular columnar liquid crystalline phases, forming a bio-inspired functional material for charge transport.

    6. Nucleotide Receptors

      Nucleotide Recognition in Water by a Guanidinium-Based Artificial Tweezer Receptor (pages 5311–5318)

      Dipl.-Chem. Hannes Y. Kuchelmeister and Prof. Carsten Schmuck

      Article first published online: 1 APR 2011 | DOI: 10.1002/chem.201003393

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      Nucleotides preferred: The symmetric peptide-based tweezer receptor 1 forms stable 1:1 complexes with nucleotides in water (pH 7). The host prefers nucleotides over phosphate and mononucleotides over di- or trinucleotides (see scheme). Hence, complex formation is due also to π-stacking interactions with the nucleobase.

    7. Drug Delivery

      Degradable Dual pH- and Temperature-Responsive Photoluminescent Dendrimers (pages 5319–5326)

      Prof. Youqing Shen, Xinpeng Ma, Bo Zhang, Zhuxian Zhou, Qihang Sun, Erlei Jin, Prof. Meihua Sui, Prof. Jianbin Tang, Jinqiang Wang and Prof. Maohong Fan

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201003495

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      Dendrimers for drug delivery: Poly(β-aminoester) dendrimers have been developed as the first such degradable dendrimers to be both pH and temperature responsive as well as photoluminescent. These dendrimers constitute ideal drug carriers because their thermal sensitivity allows the loading of drugs without the use of organic solvents, their pH sensitivity facilitates fast intracellular drug release (see graphic), and their photoluminescence provides a means of monitoring drug loading and release.

    8. Fullerene Dyads

      Solvent-Polarity-Tunable Dimeric Association of a Fullerene (C60)–N,N-Dimethylaminoazobenzene Dyad: Modulated Electronic Coupling of the Azo Chromophore with a Substituted 3D Fullerene (pages 5327–5343)

      K. Senthil Kumar and Prof. Archita Patnaik

      Article first published online: 14 MAR 2011 | DOI: 10.1002/chem.201002981

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      The 3D effect: Substitution of fullerene C60 with a J-aggregate-forming azobenzene-based chromophore yields an antiparallel H-type dimer, as evidenced from XRD and electronic structure calculations (see picture). The results reveal a novel C60–azobenzene chromophoric system for the construction of supramolecular assemblies with optoelectronically active constituents.

    9. Biosensors

      Fluorometric Sensing of Biogenic Amines with Aggregation-Induced Emission-Active Tetraphenylethenes (pages 5344–5349)

      Mitsutaka Nakamura, Dr. Takanobu Sanji and Prof. Masato Tanaka

      Article first published online: 24 MAR 2011 | DOI: 10.1002/chem.201003285

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      Sensitize your chemistry! A fluorometric sensor for detection and identification of biogenic amines with carboxylic acid modified tetraphenylethenes based on aggregation-induced emission (AIE) is reported (see scheme).

    10. Electron Transfer

      Phototriggering Electron Flow through ReI-modified Pseudomonas aeruginosa Azurins (pages 5350–5361)

      Dr. Ana María Blanco-Rodríguez, Dr. Angel J. Di Bilio, Dr. Crystal Shih, Dr. Anna Katrine Museth, Dr. Ian P. Clark, Dr. Michael Towrie, Dr. Andrea Cannizzo, Dr. Jawahar Sudhamsu, Prof. Dr. Brian R. Crane, Dr. Jan Sýkora, Dr. Jay R. Winkler, Prof. Dr. Harry B. Gray, Dr. Stanislav Záliš and Prof. Dr. Antonín Vlček Jr.

      Article first published online: 5 APR 2011 | DOI: 10.1002/chem.201002162

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      Time to accelerate! IR spectroscopic and DFT/time-dependent (TD)DFT analysis reveals factors underlying the dramatic acceleration of long-range electron transfer (ET) in mutants of Pseudomonas aeruginosa azurin labeled with a [ReI(CO)3(α-diimine)] chromophore next to a tryptophan (see scheme). The Re–tryptophan pair operates as a single photoactive unit that triggers several ET pathways (ET1, ET2), in fs–ns timescales and efficient hole-injection into the peptide.

    11. Heterocycles

      Difunctionalisation of Arenes and Heteroarenes by Directed Metallation and Sulfoxide–Magnesium Exchange (pages 5362–5372)

      Dr. Laurin Melzig, Dr. Christian B. Rauhut, Dipl.-Chem. Nikolaus Naredi-Rainer and Prof. Dr. Paul Knochel

      Article first published online: 1 APR 2011 | DOI: 10.1002/chem.201003657

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      Successful exchange: Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes were prepared in a two-step sequence, triggered by an aryl sulfoxide group. The chemoselective reagents used, TMPMgClLiCl (TMP=tetramethylpiperidine) and iPrMgClLiCl, are compatible with a broad range of functional groups (see scheme; E=electrophile.)

    12. Cyclodextrins

      Hydrogenated and Fluorinated Host–Guest Surfactants: Complexes of Cyclodextrins with Alkanes and Fluoroalkyl-Grafted Alkanes (pages 5373–5380)

      Zeng-Pei Dou, Dr. Hang Xing and Dr. Jin-Xin Xiao

      Article first published online: 24 MAR 2011 | DOI: 10.1002/chem.201003443

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      Surfactants based on host–guest interactions that are the inclusion complexes of substituted cyclodextrins (CD*) and alkanes/fluoroalkyl-grafted alkanes have been designed. CD* played the role of headgroup and the exposed part of the guests acted as the hydrophobic tail. Compared with the shuttle structure of hydrogenated host–guest surfactants, the structure of the fluorinated ones was locked by subtle intermolecular recognition (see scheme).

    13. Main Group Chemistry

      Tuning Main Group Redox Chemistry through Steric Loading: Subvalent Group 13 Metal Complexes of Carbazolyl Ligands (pages 5381–5386)

      Hassanatu B. Mansaray, Michael Kelly, Dr. Dragoslav Vidovic and Dr. Simon Aldridge

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201003440

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      Carbazoles and indiums: The ability of substituted carbazol-9-yl systems to ligate in σ-fashion through the amido N-donor, or to adopt alternative coordination modes through the π system of the central five-membered ring, can be tuned by systematic variation in the steric demands of substituents in the 1- and 8-positions. The differing affinities of the two modes of coordination for hard and soft metal centres can be shown to influence not only cation selectivity, but also the redox properties of the metal centre (see figure).

    14. DNA–Protein Conjugate

      Transglutaminase-Mediated Synthesis of a DNA–(Enzyme)n Probe for Highly Sensitive DNA Detection (pages 5387–5392)

      Dr. Momoko Kitaoka, Yukito Tsuruda, Yukari Tanaka, Prof. Masahiro Goto, Dr. Masayuki Mitsumori, Kounosuke Hayashi, Dr. Yoshiyuki Hiraishi, Dr. Katsuyuki Miyawaki, Prof. Sumihare Noji and Prof. Noriho Kamiya

      Article first published online: 5 APR 2011 | DOI: 10.1002/chem.201003744

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      DNA detector: A glutamine-modified DNA probe was synthesized by the polymerase chain reaction by using a glutamine-modified 2′-deoxyuridine 5′-triphosphate analogue as a substrate of DNA polymerase. The DNA–(alkaline phosphatase)n conjugate probe was highly sensitive and could directly visualize the target DNA bound on a membrane immediately after hybridization (see graphic).

    15. Metal Ion Complexes

      Stability and Structure of Mixed-Ligand Metal Ion Complexes That Contain Ni2+, Cu2+, or Zn2+, and Histamine, as well as Adenosine 5′-Triphosphate (ATP4−) or Uridine 5′-Triphosphate (UTP4−): An Intricate Network of Equilibria (pages 5393–5403)

      Dr. Bernd Knobloch, Dr. Ariel Mucha, Dipl.-Ing. Bert P. Operschall, Prof. Dr. Helmut Sigel, Prof. Dr. Małgorzata Jeżowska-Bojczuk, Prof. Dr. Henryk Kozłowski and Prof. Dr. Roland K. O. Sigel

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201001931

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      An impressive structural variability: The stability differences between the ternary complexes M(UTP)(Ha)2− and M(ATP)(Ha)2− reflect the formation of macrochelates in the binary M(ATP)2− species, where the phosphate-bound M2+ also interacts with N7. This interaction is inhibited upon formation of M(ATP)(Ha)2− suggesting that, when bound to an enzyme, M(ATP)2− complexes may exist in a closed macrochelated form only, if no enzyme group coordinates directly to M2+. Ha=histamine.

    16. Templated Synthesis

      Transition-Metal-Complexed Cyclic [3]- and [4]Pseudorotaxanes Containing Rigid Ring-and-Filament Conjugates: Synthesis and Solution Studies (pages 5404–5414)

      Dr. Julie Voignier, Dr. Julien Frey, Dr. Tomáš Kraus, Dr. Miloš Buděšínský, Dr. Josef Cvačka, Prof. Valérie Heitz and Dr. Jean-Pierre Sauvage

      Article first published online: 25 MAR 2011 | DOI: 10.1002/chem.201003592

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      Squares versus triangles: Cyclic daisy-chain-type [3]- and [4]pseudorotaxanes are formed upon the addition of copper(I) or silver(I) ions to a rigid ligand consisting of a ring containing a chelating unit to which a rigid string with another chelating unit is appended (see picture). The equilibrium between tri- and tetrameric species depends on concentration, temperature, and the templating cation.

    17. O2 Formation

      Calcium Manganese Oxides as Oxygen Evolution Catalysts: O2 Formation Pathways Indicated by 18O-Labelling Studies (pages 5415–5423)

      Dr. Dmitriy Shevela, Sergey Koroidov, Dr. M. Mahdi Najafpour, Prof. Dr. Johannes Messinger and Dr. Philipp Kurz

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201002548

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      Clearly labelled: Oxygen formed in reactions catalysed by (calcium) manganese oxides showed distinct 18O-labelling patterns depending on the oxidation agent used. The results allow parallels to be drawn to manganese metalloenzymes involved in O[BOND]O bond formation in vivo.

    18. Host–Guest Systems

      Triptycene-Derived Oxacalixarenes as New Wheels for the Synthesis of [2]Rotaxanes: Acid–Base- and Metal-Ion-Switchable Complexation Processes (pages 5424–5431)

      Shu-Zhen Hu and Prof. Chuan-Feng Chen

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201003545

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      Making the wheels go round: Triptycene-derived oxacalixarenes were shown to be new useful wheels for the formation of stable [2]pseudorotaxanes (see scheme) and for the further synthesis of novel [2]rotaxanes. Moreover, switchable complexation processes of the [2]pseudorotaxanes were also achieved by acid–base stimuli or Hg2+ association/dissociation.

    19. Fullerene Dumbbells

      Synthesis and Photoinduced Energy- and Electron-Transfer Processes of C60–Oligothienylenevinylene–C70 Dumbbell Compounds (pages 5432–5444)

      Dr. Maxence Urbani, Beatriz Pelado, Dr. Pilar de la Cruz, Ken-ichi Yamanaka, Prof. Osamu Ito and Fernando Langa

      Article first published online: 4 APR 2011 | DOI: 10.1002/chem.201002318

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      Lopsided dumbbells: Two unsymmetrical dumbbell molecules based on N-methylpyrrolidinefullerene and oligothienylenevinylenes (nTV; n=2, 4) have been synthesized. An 1H NMR spectroscopic study allowed the identification of four different isomers formed due to the presence of C70. Photoinduced charge-separation processes in polar solvents gave charge-separated radical-ion pairs (see figure) with a lifetime of 50 ns for n=4.

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      Preview: Chem. Eur. J. 20/2011 (page 5447)

      Article first published online: 20 APR 2011 | DOI: 10.1002/chem.201190096

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