Chemistry - A European Journal

Cover image for Vol. 16 Issue 48

December 27, 2010

Volume 16, Issue 48

Pages 14209–14587

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture: Oriented Free-Standing Ammonium Vanadium Oxide Nanobelt Membranes: Highly Selective Absorbent Materials (Chem. Eur. J. 48/2010) (page 14209)

      Rujia Zou, Zhenyu Zhang, Li Yu, Qiwei Tian, Jianghong Wu, Dr. Yangang Sun, Dr. Zhigang Chen and Prof. Dr. Junqing Hu

      Article first published online: 5 JAN 2011 | DOI: 10.1002/chem.201090238

      Thumbnail image of graphical abstract

      Highly selective, absorbent, free-standing, paper-like, highly oriented membranes composed of ammonium vanadium oxide (NH4V4O14) nanobelts have been created by taking advantage of the nanoscaled self-assembly of the architecture, and exhibit controllable wetting behavior ranging from superhydrophilic to superhydrophobic (when coated with silicone molecules). The as-obtained NH4V4O14 nanobelt membranes can selectively absorb a variety of both polar and nonpolar organic solvents; moreover, they can even separate two mixed solvents with very similar polarities and absorb solid contaminants in organic solvents. For more details see the Full Paper by J. Hu et al. on page 14307 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Inside Cover: Host–Guest-Driven Copolymerization of Tetraphosphonate Cavitands (Chem. Eur. J. 48/2010) (page 14210)

      Dr. Francesca Tancini, Dr. Roger M. Yebeutchou, Dr. Laura Pirondini, Dr. Rita De Zorzi, Prof. Dr. Silvano Geremia, Dr. Oren A. Scherman and Prof. Dr. Enrico Dalcanale

      Article first published online: 5 JAN 2011 | DOI: 10.1002/chem.201090239

      Thumbnail image of graphical abstract

      A temperature-induced cyclic-to-linear supramolecular ring-opening copolymerization driven by a reversible host–guest interaction between ditopic tetraphosphonate cavitands and N-methylpyridinium guests has been developed by E. Dalcanale et al. on page 14313 ff. The crystal structure of one copolymer shows the preference of the system for linear polymerization in the solid state.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Graphical Abstract: Chem. Eur. J. 48/2010 (pages 14213–14225)

      Article first published online: 5 JAN 2011 | DOI: 10.1002/chem.201090240

  4. Corrigenda

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
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  5. Retractions

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
    2. You have free access to this content
  6. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
  7. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Asymmetric Synthesis

      Asymmetric Hydrogenation of Minimally Functionalised Terminal Olefins: An Alternative Sustainable and Direct Strategy for Preparing Enantioenriched Hydrocarbons (pages 14232–14240)

      Dr. Oscar Pàmies, Prof. Pher G. Andersson and Dr. Montserrat Diéguez

      Article first published online: 7 DEC 2010 | DOI: 10.1002/chem.201001909

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      Chiral hydrocarbons through hydrogenation: This minireview highlights the progress made in the preparation of chiral hydrocarbons through asymmetric hydrogenation of minimally functionalised terminal olefins (see scheme).

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Supramolecular Dendrimers

      pH-Triggered Self-Assembly of Zwitterionic Polyglycerol Dendrons into Discrete and Highly Stable Supramolecular Dendrimers in Water (pages 14242–14246)

      Dipl.-Chem. Michael Merschky, Dr. Monika Wyszogrodzka, Prof. Dr. Rainer Haag and Prof. Dr. Carsten Schmuck

      Article first published online: 25 NOV 2010 | DOI: 10.1002/chem.201002658

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      pH-dependent dimerization: Zwitterionic polyglycerol dendrons self-assemble into discrete and well-defined dimers in water as shown by dynamic light scattering (DLS), gel permeability chromatography (GPC), and DOSY NMR spectroscopy. However, self-assembly occurs only at neutral pH as either protonation or deprotonation destroys the self-complementary zwitterionic binding motif in the core of the dendrimer. Hence, structure formation can be triggered back and forth by changing the pH of the solution.

    2. Cluster Compounds

      Polar 2D Sheet versus Nonpolar 1D Helix Metallosupramolecular Architectures Based on M6M′8 (M=PdII, NiII; M′=CuI, AgI) Cage Clusters with D-Penicillaminate (pages 14247–14251)

      Dr. Nobuto Yoshinari, Dr. Asako Igashira-Kamiyama and Prof. Takumi Konno

      Article first published online: 29 NOV 2010 | DOI: 10.1002/chem.201001886

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      To coil or not to coil: Chiral S-bridged 14-nuclear clusters with 12 free carboxylate groups, [M6M′8(D-pen)12Cl]5− (M=PdII, NiII; M′=CuI, AgI; D-pen=D-penicillaminate; see scheme), prepared from [M(D-pen)2]2− and M′Cl, were organized into heterotrimetallic supramolecular structures in combination with La3+.

    3. Redox-Mediated Self-Organization of Metallosupramolecular Architectures Composed of D-Penicillaminato CuI8CuII6 Clusters: Drastic Structural Change by Subtle pH Changes (pages 14252–14255)

      Dr. Nobuto Yoshinari, Kazuhiro Tatsumi, Dr. Asako Igashira-Kamiyama and Prof. Takumi Konno

      Article first published online: 29 NOV 2010 | DOI: 10.1002/chem.201002780

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      pH-dependent architecture: Cluster-based metallosupramolecular compounds, which are composed of [CuI6CuII8(D-pen)12Cl]5− (D-H2pen=D-penicillamine) cluster anions linked by Co2+ and/or K+ cations through D-pen carboxylate groups, were spontaneously synthesized by simple treatment of K[CoIII(D-pen)2] with CuICl in potassium acetate buffer solutions, accompanied by the redox between CoIII and CuI mediated by thiolate.

    4. Self-Assembly

      Photoswitching Vertically Oriented Azobenzene Self-Assembled Monolayers at the Solid–Liquid Interface (pages 14256–14260)

      Dr. David Bléger, Dr. Artur Ciesielski, Prof. Dr. Paolo Samorì and Prof. Dr. Stefan Hecht

      Article first published online: 24 NOV 2010 | DOI: 10.1002/chem.201002834

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      Up or down? Making use of self-assembly, the graphite surface is decorated with upright oriented photochromic units organized by a terfluorene platform. The azobenzenes within the monolayer could be converted from the trans to the cis form leading to substantial and reversible structural reorganization, as revealed by scanning tunneling microscopy (STM) studies.

    5. Bionanotechnology

      Aptamer/Nanoparticle-Based Sensitive, Multiplexed Electronic Coding of Proteins and Small Biomolecules through a Backfilling Strategy (pages 14261–14265)

      Xiaoqing Qian, Prof. Yun Xiang, Haixia Zhang, Ying Chen, Prof. Yaqin Chai and Prof. Ruo Yuan

      Article first published online: 24 NOV 2010 | DOI: 10.1002/chem.201002585

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      Sensing large and small simultaneously: Sensitive and multiplexed analysis of lysozyme and ATP analytes is achieved through target-induced release of aptamers from the DNA duplexes on a sensing surface, followed by backfilling hybridization of the resulting single-stranded DNAs with aptamers conjugated to the electrochemically encoded nanoparticles (see graphic).

    6. Homogeneous Catalysis

      Lewis Acid Assisted Stabilization of Side-On Bonded N2 in [Ru(NCN)]-Pincer Complexes—Computational Catalyst Design Directed at NH3 Synthesis from N2 and H2 (pages 14266–14271)

      Dr. Markus Hölscher and Prof. Dr. Walter Leitner

      Article first published online: 23 NOV 2010 | DOI: 10.1002/chem.201002010

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      With a little help of my boron: Ruthenium pincer complexes with Lewis acidic side arms help to stabilize side-on coordinated N2, which is necessary for catalytic reduction to NH3 with H2.

    7. Asymmetric Synthesis

      Gold-Catalyzed Direct Activation of Allylic Alcohols in the Stereoselective Synthesis of Functionalized 2-Vinyl-Morpholines (pages 14272–14277)

      Dr. Marco Bandini, Prof. Magda Monari, Alessandro Romaniello and Michele Tragni

      Article first published online: 18 NOV 2010 | DOI: 10.1002/chem.201002606

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      Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold-catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′-bis[di(3,5-di-tert-butyl-4-methyoxyphenyl)phosphine]-4,4′-bi-1,3-benzodioxole). The present methodology represents one of the few examples of enantioselective gold-catalyzed transformations involving unactivated alkenes.

    8. Lanthanide Structures

      Wheel-Shaped Lanthanide Iron Sulfide Clusters (pages 14278–14280)

      Prof. Dr. Sergey N. Konchenko, Dipl.-Chem. Tanja Sanden, Dr. Nikolay A. Pushkarevsky, Dr. Ralf Köppe and Prof. Dr. Peter W. Roesky

      Article first published online: 25 NOV 2010 | DOI: 10.1002/chem.201002510

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      Octanuclear lanthanide–iron clusters: The first lanthanide–carbonyl–sulfide–iron clusters were obtained by redox reactions of [(η5-C5Me5)2Ln(thf)2] (Ln=Sm, Yb) and [Fe2(μ-S2)(CO)6]. The resulting wheel-shaped clusters have 14-membered peripheral rings with [Fe63-S)6(CO)12]2− units in the center (see picture).

    9. Indoles

      Synthesis of Indoles by Conjugate Addition and Ligand-Free Copper-Catalyzed Intramolecular Arylation of Activated Acetylenes with o-Haloanilines (pages 14281–14284)

      Detian Gao, Dr. Masood Parvez and Prof. Dr. Thomas G. Back

      Article first published online: 8 DEC 2010 | DOI: 10.1002/chem.201002628

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      Air and water welcomeligands need not apply! A simple and efficient new synthesis of variously functionalized and substituted indoles was achieved by the addition and copper-catalyzed coupling of N-formyl-o-haloanilines with acetylenic sulfones, esters and ketones (see scheme; EWG=electron-withdrawing group). The reaction employs copper(II) acetate under ligand-free conditions without the need for exclusion of air and moisture.

    10. Supramolecular Chemistry

      Multivalency-Directed Magic-Ring [2](3)Catenane by Olefin Metathesis (pages 14285–14289)

      Yi Jiang, Xiao-Zhang Zhu and Prof. Chuan-Feng Chen

      Article first published online: 29 NOV 2010 | DOI: 10.1002/chem.201002111

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      As if by magic: On the basis of formation of a novel multivalency-directed complex between a trisdialkylammonium strand ion and a triptycene-derived homotritopic host, an interesting magic-ring [2](3)catenane was obtained by reversible olefin metathesis (see scheme).

    11. Organocatalysis

      Asymmetric Conjugate Addition of Oxindoles to 2-Chloroacrylonitrile: A Highly Effective Organocatalytic Strategy for Simultaneous Construction of 1,3-Nonadjacent Stereocenters Leading to Chiral Pyrroloindolines (pages 14290–14294)

      Dr. Xin Li, Prof. Dr. Sanzhong Luo and Prof. Dr. Jin-Pei Cheng

      Article first published online: 29 NOV 2010 | DOI: 10.1002/chem.201002563

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      Chiral pyrroloindoles: A highly enantioselective catalytic conjugate addition of 3-substituted oxindoles with 2-chloroacrylonitrile has been developed with a readily accessible alkyl bifunctional tertiary amine thiourea catalyst. Excellent stereoselectivity of up to >30:1 diastereomeric ratio and 99 % enantiomeric excess was achieved. The obtained Michael products could be easily converted to chiral pyrroloindole structures, which are widely distributed in natural indole alkaloids (see scheme).

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. Retractions
    7. News
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Structural Changes

      Flexibility and Sorption Selectivity in Rigid Metal–Organic Frameworks: The Impact of Ether-Functionalised Linkers (pages 14296–14306)

      Sebastian Henke, Dr. Rochus Schmid, Prof. Dr. Jan-Dierk Grunwaldt and Prof. Dr. Roland A. Fischer

      Article first published online: 7 DEC 2010 | DOI: 10.1002/chem.201002341

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      Just breathe! The implementation of linkers functionalised with flexible ether groups in known, but rigid metal–organic frameworks (MOFs), yields isoreticular frameworks that exhibit unexpected responsiveness towards small molecules and high sorption selectivity for CO2 (see figure).

    2. Nanostructures

      Oriented Free-Standing Ammonium Vanadium Oxide Nanobelt Membranes: Highly Selective Absorbent Materials (pages 14307–14312)

      Rujia Zou, Zhenyu Zhang, Li Yu, Qiwei Tian, Jianghong Wu, Dr. Yangang Sun, Dr. Zhigang Chen and Prof. Dr. Junqing Hu

      Article first published online: 24 NOV 2010 | DOI: 10.1002/chem.201002228

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      Tighten your belts! Highly selective, absorbent, free-standing, paper-like membranes made of ammonium vanadium oxide (NH4V4O14) nanobelts have been engineered by taking advantage of the nanoscaled self-assembly of this architecture. These selective, absorbent membrane materials are ideal candidates for separation and removal of pollution in industrial and environmental applications.

    3. Supramolecular Chemistry

      Host–Guest-Driven Copolymerization of Tetraphosphonate Cavitands (pages 14313–14321)

      Dr. Francesca Tancini, Dr. Roger M. Yebeutchou, Dr. Laura Pirondini, Dr. Rita De Zorzi, Prof. Dr. Silvano Geremia, Dr. Oren A. Scherman and Prof. Dr. Enrico Dalcanale

      Article first published online: 1 DEC 2010 | DOI: 10.1002/chem.201002237

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      Supramolecular alternating copolymers: Cyclic and linear AABB supramolecular copolymers were prepared by connecting complementary monomeric units through host–guest interactions. Thermodynamic and topological control of this process was achieved by controlling the flexibility of the ditopic guest spacer, solvent and concentration. The structure of the alternating copolymer formed by self-assembly of a bis(tetraphosphonate cavitand) and methyl viologen is shown.

    4. Sandwich Complexes

      Homoleptic Diphosphacyclobutadiene Complexes [M(η4-P2C2R2)2]x (M=Fe, Co; x=0, 1) (pages 14322–14334)

      Dr. Robert Wolf, Dr. Andreas W. Ehlers, Dr. Marat M. Khusniyarov, Prof. Dr. František Hartl, Dr. Bas de Bruin, Prof. Dr. Gary J. Long, Prof. Dr. Fernande Grandjean, Dr. Falko M. Schappacher, Prof. Dr. Rainer Pöttgen, Dr. J. Chris Slootweg, Dr. Martin Lutz, Prof. Dr. Anthony L. Spek and Prof. Dr. Koop Lammertsma

      Article first published online: 1 DEC 2010 | DOI: 10.1002/chem.201001913

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      Fancy a sandwich? Homoleptic sandwich anions that contain diphosphacyclobutadiene ligands result from the reaction of anthracene metalates [Fe(η4-C14H10)2] and [Co(η4-C14H10)2] with phosphaalkynes. Electrochemical and preparative investigations of [M(η4-P2C2tBu2)2] (M=Fe, Co) revealed that these anions are readily oxidized to neutral derivatives [M(η4-P2C2tBu2)2]. The electronic structures of the new sandwich complexes have been elucidated by using spectroscopic techniques and density functional theory calculations.

    5. Asymmetric Catalysis

      C2-Symmetric Chiral Disulfoxide Ligands in Rhodium-Catalyzed 1,4-Addition: From Ligand Synthesis to the Enantioselection Pathway (pages 14335–14347)

      Ronaldo Mariz, Dr. Albert Poater, Michele Gatti, Emma Drinkel, Justus J. Bürgi, Xinjun Luan, Sascha Blumentritt, Dr. Anthony Linden, Prof. Dr. Luigi Cavallo and Prof. Dr. Reto Dorta

      Article first published online: 12 NOV 2010 | DOI: 10.1002/chem.201001749

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      S[DOUBLE BOND]O selective! Chiral C2-symmetric disulfoxide ligands that possess biaryl atropisomeric backbones are synthesized by the Andersen methodology (see picture). Their synthesis, optical purity, electronic properties, and catalytic behavior in the prototypical rhodium-catalyzed 1,4-addition of phenylboronic acid to 2-cyclohexen-1-one are presented.

    6. Homogeneous Catalysis

      Comparing the Enantioselective Power of Steric and Electrostatic Effects in Transition-Metal-Catalyzed Asymmetric Synthesis (pages 14348–14353)

      Dr. Albert Poater, Dr. Francesco Ragone, Dr. Ronaldo Mariz, Prof. Dr. Reto Dorta and Prof. Dr. Luigi Cavallo

      Article first published online: 16 NOV 2010 | DOI: 10.1002/chem.201001938

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      Steric versus electronic: Analysis of two prototype Rh catalysts show that high enantioselectivity in asymmetric synthesis can be achieved using either steric or electrostatic effects. Topographic maps of the interaction surface between the catalyst and the substrate are proposed as a tool to quantify these effects.

    7. Reaction Mechanisms

      Mechanistic Insights into the cistrans Isomerization of Ruthenium Complexes Relevant to Catalysis of Olefin Metathesis (pages 14354–14364)

      Dr. Albert Poater, Dr. Francesco Ragone, Dr. Andrea Correa, Dr. Anna Szadkowska, Dr. Michał Barbasiewicz, Prof. Dr. Karol Grela and Prof. Dr. Luigi Cavallo

      Article first published online: 4 NOV 2010 | DOI: 10.1002/chem.201001849

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      All change! The mechanism of cis to trans isomerizations in Ru complexes (see figure) relevant to olefin metathesis is investigated with a combined experimental and theoretical approach.

    8. Cluster Compounds

      Cation–Cation Complexes of Pentavalent Uranyl: From Disproportionation Intermediates to Stable Clusters (pages 14365–14377)

      Victor Mougel, Dr. Pawel Horeglad, Dr. Grégory Nocton, Dr. Jacques Pécaut and Dr. Marinella Mazzanti

      Article first published online: 4 NOV 2010 | DOI: 10.1002/chem.201001929

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      Size matters: Large alkali ions promote the assembly of Schiff base complexes of pentavalent uranyl into three new stable polynuclear cation–cation clusters, while small cations assemble unstable intermediates, resulting in disproportionation (see figure). Protons also promote disproportionation.

    9. Nanoparticle Catalysis

      A Highly Efficient and Extensively Reusable “Dip Catalyst” Based on a Silver-Nanoparticle-Embedded Polymer Thin Film (pages 14378–14384)

      E. Hariprasad and Prof. T. P. Radhakrishnan

      Article first published online: 28 OCT 2010 | DOI: 10.1002/chem.201001679

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      A reusable silver nanoparticle catalyst: The high efficiency and extensive reusability of a nanocomposite polymer thin-film catalyst in the reduction of 4-nitrophenol by sodium borohydride demonstrates effective harnessing of the benefits of homogeneous and heterogeneous catalysis (see figure).

    10. Spin Labeling of DNA

      Site-Directed Spin-Labeling of DNA by the Azide–Alkyne ‘Click’ Reaction: Nanometer Distance Measurements on 7-Deaza-2′-deoxyadenosine and 2′-Deoxyuridine Nitroxide Conjugates Spatially Separated or Linked to a ‘dA-dT’ Base Pair (pages 14385–14396)

      Ping Ding, Dorith Wunnicke, Prof. Heinz-Jürgen Steinhoff and Prof. Frank Seela

      Article first published online: 29 NOV 2010 | DOI: 10.1002/chem.201001572

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      ‘Clicked’ DNA spin labels: Spin labels (spheres in the figure) have been incorporated by click chemistry into DNA duplexes at spatially separated positions or into a ‘dA-dT’ base pair with high efficiency. Very accurate distances between spin labels, within a range of 1–2 nm, were measured by continuous wave and pulse EPR spectroscopy.

    11. Superstructures

      T4 Virus-Based Toolkit for the Direct Synthesis and 3D Organization of Metal Quantum Particles (pages 14397–14403)

      Dr. Li Hou, Prof. Dr. Faming Gao and Dr. Na Li

      Article first published online: 18 NOV 2010 | DOI: 10.1002/chem.201000393

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      An ideal bioscaffold: The highly regular and symmetrical protein surface of a T4 capsid allows the site-directed adsorption and subsequent reduction of metal ions. Therefore, the growth of metal particles on a viral capsid in situ enables them to exist at a quantum size with a high degree of monodispersity (see scheme).

    12. Drug Delivery

      Magnetic, Luminescent Eu-Doped Mg–Al Layered Double Hydroxide and Its Intercalation for Ibuprofen (pages 14404–14411)

      Prof. Jun Wang, Jideng Zhou, Prof. Zhanshuang Li, Yanchao Song, Qi Liu, Prof. Zhaohua Jiang and Prof. Milin Zhang

      Article first published online: 29 OCT 2010 | DOI: 10.1002/chem.201000602

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      Illuminate your chemistry! Fe3O4 nanoparticles are coated on the ibuprofen intercalated Eu-doped Mg–Al layered double hydroxide (see figure). This composite exhibits superparamagnetic and luminescent properties as well as sustained release in simulated body fluid.

    13. β-Secretase Inhibition

      Structural Design, Solid-Phase Synthesis and Activity of Membrane-Anchored β-Secretase Inhibitors on Aβ Generation from Wild-Type and Swedish-Mutant APP (pages 14412–14423)

      Heinke Schieb, Dr. Sebastian Weidlich, Dr. Georg Schlechtingen, Philipp Linning, Dr. Gary Jennings, Dr. Margit Gruner, Prof. Dr. Jens Wiltfang, Dr. Hans-Wolfgang Klafki and Prof. Dr. Hans-Joachim Knölker

      Article first published online: 3 DEC 2010 | DOI: 10.1002/chem.201002878

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      Anchoring of β-secretase inhibitors to the lipid raft domains of the cell membrane by using a spacer-linked dihydrocholesterol leads to tripartite structures with substantially improved efficacy. The concept is applicable to different pharmacophores (ai; e shown in picture) and the best spacer lengths are in the range of 35–89 Å. Moreover, significant differences were demonstrated in the Aβ-peptide secretion from wild-type(wt) versus Swedish(sw)-mutant APP. The present results provide a basis for the development of potential new drugs for the treatment of Alzheimer's disease.

    14. Chemosensors

      Near-Infrared Cell-Permeable Hg2+-Selective Ratiometric Fluorescent Chemodosimeters and Fast Indicator Paper for MeHg+ Based on Tricarbocyanines (pages 14424–14432)

      Zhiqian Guo, Prof. Dr. Weihong Zhu, Mingming Zhu, Xumeng Wu and Prof. Dr. He Tian

      Article first published online: 29 OCT 2010 | DOI: 10.1002/chem.201001769

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      Mercury stops the blues: Near-infrared (NIR) ratiometric thiourea chemodosimeters exhibit several advantages, such as convenient synthesis, long wavelengths falling in the NIR region (650–900 nm), and clear color changes for use as indicator paper (see image). Their distinct response with Hg2+ ions is dependent on the electron-donating effect of the thiourea substituents.

    15. Organometallic Catalysts

      Preparation of Surface Organometallic Catalysts by Gas-Phase Ligand Stripping and Reactive Landing of Mass-Selected Ions (pages 14433–14438)

      Dr. Grant E. Johnson and Dr. Julia Laskin

      Article first published online: 4 NOV 2010 | DOI: 10.1002/chem.201002292

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      Surface immobilization: Highly active undercoordinated metal complexes may be prepared in the gas-phase through collision-induced dissociation and immobilized on surfaces through ion-reactive landing (see scheme). In situ TOF-SIMS analysis shows that the immobilized complexes exhibit behavior consistent with catalytic activity.

    16. Sensors

      A Photoelectrochemical Immunosensor Based on Au-Doped TiO2 Nanotube Arrays for the Detection of α-Synuclein (pages 14439–14446)

      Dr. Yarui An, Linlin Tang, Xiaoli Jiang, Hua Chen, Dr. Meicheng Yang, Prof. Litong Jin, Dr. Shengping Zhang, Prof. Chuangui Wang and Prof. Wen Zhang

      Article first published online: 29 OCT 2010 | DOI: 10.1002/chem.201001654

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      The straight dope: Highly ordered Au-doped TiO2 nanotubes were used to construct arrays that effectively immobilized primary antibodies with high stability and bioactivity to bind α-synuclein (see figure). Moreover, the Au-doped TiO2 nanotubes facilitated the improvement of the photocurrent response.

    17. Noncovalent Interactions

      Hydrogen Bonding Versus van der Waals Interactions: Competitive Influence of Noncovalent Interactions on 2D Self-Assembly at the Liquid–Solid Interface (pages 14447–14458)

      Dr. Kunal S. Mali, Kathleen Lava, Prof. Koen Binnemans and Prof. Steven De Feyter

      Article first published online: 9 NOV 2010 | DOI: 10.1002/chem.201001653

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      Discontinuous but ordered: Noncovalent interactions play an exceedingly decisive role in the process of self-assembly. To gain better insight into the role of noncovalent interactions, the competitive influence of hydrogen-bonding and van der Waals interactions was explored in the monolayers formed by simple 4-alkoxybenzoic acids at the liquid–solid interface (see image).

    18. Catalysis

      Bimetallic Catalysis Involving Dipalladium(I) and Diruthenium(I) Complexes (pages 14459–14468)

      Raj K. Das, Biswajit Saha, S. M. Wahidur Rahaman and Dr. Jitendra K. Bera

      Article first published online: 27 OCT 2010 | DOI: 10.1002/chem.201001960

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      Good couple: Metal–metal singly bonded [PdI[BOND]PdI] and [RuI[BOND]RuI] complexes exhibit bimetallic synergy in the catalytic C[BOND]C bond-coupling and aldehyde-olefination reactions, respectively (see figure).

    19. Synthetic Methods

      Probing the Influence of an Allylic Methyl Group in Zearalenone Analogues on Binding to Hsp90 (pages 14469–14478)

      Dipl.-Chem. Christian Rink, Dr. Florenz Sasse, Dr. Asta Zubrienė, Prof. Dr. Daumantas Matulis and Prof. Dr. Martin E. Maier

      Article first published online: 27 OCT 2010 | DOI: 10.1002/chem.201001752

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      Gimme five: The preparation and testing of zearalenone analogues in which acetate number five was replaced by a propionate is reported. The shown stereoisomer was slightly more active in binding to Hsp90; studies show that the position and stereochemistry of a methyl-bearing center can cause a significant difference in binding (see scheme).

    20. Antitumor Agents

      Characterization, Synthesis and Self-Aggregation of (−)-Alternarlactam: A New Fungal Cytotoxin with Cyclopentenone and Isoquinolinone Scaffolds (pages 14479–14485)

      Ai Hua Zhang, Dr. Nan Jiang, Dr. Wen Gu, Prof. Dr. Jing Ma, Yu Rong Wang, Dr. Yong Chun Song and Prof. Dr. Ren Xiang Tan

      Article first published online: 29 OCT 2010 | DOI: 10.1002/chem.201002205

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      Double the framework: The absolute configuration, chirality-activity relevance and self-aggregation of (−)-alternarlactam [(−)-1], a cytotoxin from Alternaria sp. HG1 culture with double antitumor pharmacophores in a new framework, were assigned by a combination of synthetic, spectroscopic and computational approaches.

    21. Metallocenes

      Double Friedel–Crafts Acylation Reactions on the Same Ring of a Metallocene: Synthesis of a 2,5-Diacetylphospharuthenocene (pages 14486–14497)

      Dr. Duncan Carmichael, Prof. Dr. Pascal Le Floch, Dr. Xavier F. Le Goff, Dr. Olivier Piechaczyk and Dr. Nicolas Seeboth

      Article first published online: 1 DEC 2010 | DOI: 10.1002/chem.200902409

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      Pathfinders: Double electrophilic acylation of the phospholyl ring occurs upon treatment of a phospharuthenocene with the classical Friedel–Crafts acylating agent MeCOCl/AlCl3 (see scheme). Theoretical calculations suggest that two pathways, mediated by either the ruthenium centre or the phosphorus atom, are available to the incoming acylium ion.

    22. Antitumor Agents

      Mitochondrial Mode of Action of a Thymidine-Based Cisplatin Analogue Breaks Resistance in Cancer Cells (pages 14498–14505)

      Liliane A. Onambele, Dr. Daniel Koth, Dr. Justyna A. Czaplewska, Prof. Ulrich S. Schubert, Dr. Helmar Görls, Prof. Shigenobu Yano, Dr. Makoto Obata, Dr. Michael Gottschaldt and Dr. Dr. Aram Prokop

      Article first published online: 27 OCT 2010 | DOI: 10.1002/chem.201000785

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      Prove your metal: Cisplatin analogues with platinum(II) and palladium(II) complexes based on 3′,5′-diamino thymidines were synthesized (see figure for an example) and one was found to induce apoptosis mediated by caspase-9 and -3 processing. Thymiplatin was proven to be active on cisplatin, vincristin and daunorubicin resistant leukemia cells, and was synergistic with cytarabin, vincristin, daunorubicin, and doxorubicin in lymphoma cells.

    23. Flow Chemistry

      Efficient Access to New Chemical Space Through Flow—Construction of Druglike Macrocycles Through Copper-Surface-Catalyzed Azide–Alkyne Cycloaddition Reactions (pages 14506–14512)

      Andrew R. Bogdan and Keith James

      Article first published online: 29 OCT 2010 | DOI: 10.1002/chem.201002215

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      Making macrocycles on the move! A series of 12- to 22-membered macrocycles with druglike functionality and properties have been generated by using the copper-catalyzed azide–acetylene cycloaddition reaction, conducted in flow in high-temperature copper tubing. The triazole-containing macrocycles have been generated in up to 90 % yield in a 5 min reaction, without resorting to high-dilution conditions.

    24. Porous Silica Materials

      Luminescent Porous Silica Fibers as Drug Carriers (pages 14513–14519)

      Dr. Zhiyao Hou, Dr. Cuimiao Zhang, Dr. Chunxia Li, Dr. Zhenhe Xu, Dr. Ziyong Cheng, Dr. Guogang Li, Dr. Wenxin Wang, Dr. Chong Peng and Prof. Jun Lin

      Article first published online: 12 NOV 2010 | DOI: 10.1002/chem.201000900

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      Multifunctional silica fibers, which possess a porous structure and display blue luminescence, can serve as a drug delivery host carrier, using ibuprofen (IBU) as a model drug, allowing the investigation of storage/release properties. The emission intensities of the silica fibers in the drug carrier system vary with the amount of IBU released, thus allowing easy monitoring.

    25. Donor–Acceptor Systems

      Anionic N-Heterocyclic Carbenes with N,N′-Bis(fluoroaryl) and N,N′-Bis(perfluoroaryl) Substituents (pages 14520–14533)

      Matthew G. Hobbs, Chrissy J. Knapp, Patrick T. Welsh, Javier Borau-Garcia, Dr. Tom Ziegler and Dr. Roland Roesler

      Article first published online: 27 OCT 2010 | DOI: 10.1002/chem.201001698

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      19F in carbenes: A series of anionic N-heterocyclic carbenes with six-membered ligand frameworks and varying degrees of fluorination have been incorporated into rhodium complexes (see scheme). Structural, spectroscopic and computational studies of these complexes revealed that the degree of fluorination can be used to efficiently tune their electronic properties over a broad range.

    26. Organocatalysis

      Indoline-3-Carboxylic Acid Derived Organocatalysts for the anti-Mannich Reaction (pages 14534–14544)

      Prof. Jörg Pietruszka and Dipl.-Ing. (FH) Robert Christian Simon

      Article first published online: 24 NOV 2010 | DOI: 10.1002/chem.201002130

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      Enzymatic kinetic resolution (E≫100) was applied in the synthesis of enantiopure indoline-3-carboxylic acid (1); the corresponding derivatives 24 were readily obtained after standard transformations. Compounds 14 were applied as organocatalysts in Mannich-type reactions (see scheme) to afford the products with high anti selectivity at low temperatures, in moderate to good yields

    27. Metallomesogens

      Silver Pyrazolates as Coordination-Polymer Luminescent Metallomesogens (pages 14545–14553)

      Dr. Joaquín Barberá, Ignacio Lantero, Sandra Moyano, Prof. José Luis Serrano , Dr. Anabel Elduque and Dr. Raquel Giménez

      Article first published online: 22 OCT 2010 | DOI: 10.1002/chem.201001766

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      Silver beats gold in promoting stable columnar liquid-crystalline self-organization. Whereas gold complexes of 3,5-diarylpyrazolate ligands are composed of discrete cyclic trinuclear molecules, the analogous silver complexes are 1D polymers that self-assemble in helical columns (see picture for a micrograph of a mesophase and a schematic of one helix).

    28. Cyclophane Receptors

      Tri- and Tetraurea Piperazine Cyclophanes: Synthesis and Complexation Studies of Preorganized and Folded Receptor Molecules (pages 14554–14564)

      M. Sc. Kari Raatikainen, Dr. N. Kodiah Beyeh and Prof. Kari Rissanen

      Article first published online: 12 NOV 2010 | DOI: 10.1002/chem.201001695

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      A fitting location: The rigid 27-membered triprotonated triurea cyclophane (n=1) binds an unprecedented anion pair, H2PO4⋅⋅⋅HPO42−, in the solid state. The tetra-N-ethylurea cyclophane (n=2) is less rigid and demonstrates an induced-fit recognition of diisopropyl ether in the solid state. The guest is encapsulated within the lipophilic interior of a quasicapsule formed through intramolecular hydrogen-bond-driven folding of the 36-membered cyclophane skeleton (see figure).

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      Article first published online: 5 JAN 2011 | DOI: 10.1002/chem.201090244

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