Chemistry - A European Journal

Cover image for Vol. 16 Issue 17

May 3, 2010

Volume 16, Issue 17

Pages 4951–5225

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Communications
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    1. Cover Picture: Intensely Fluorescent Azobenzenes: Synthesis, Crystal Structures, Effects of Substituents, and Application to Fluorescent Vital Stain (Chem. Eur. J. 17/2010) (page 4951)

      Junro Yoshino, Akiko Furuta, Tetsuya Kambe, Hiroaki Itoi, Naokazu Kano, Takayuki Kawashima, Yuzuru Ito and Makoto Asashima

      Version of Record online: 23 APR 2010 | DOI: 10.1002/chem.201090078

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      Intensely fluorescent azobenzene derivatives, featuring an intramolecular N–B interaction that was confirmed by X-ray crystallographic analyses, emit intense green, yellow and orange fluorescence. Their application to fluorescent vital stain visualization of living tissues was investigated by microinjection into Xenopus embryos, suggesting they are nontoxic towards the embryos. For more details see the Full Paper on page 5026 ff.

  2. Inside Cover

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    4. Graphical Abstract
    5. News
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    1. Inside Cover: Solvent-Dependent Self-Discrimination of Bis(2-hydroxyphenyl)diamides (Chem. Eur. J. 17/2010) (page 4952)

      Akinobu Matsuzawa, Akihiro Nojiri, Naoya Kumagai and Masakatsu Shibasaki

      Version of Record online: 23 APR 2010 | DOI: 10.1002/chem.201090079

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      Self-discrimination ofS- and R-valine-derived bis(2-hydroxyphenyl)diamides in an ensemble of eight structurally related molecules showcase their specific aggregation through the hydrogen-bonding network of the bis(2-hydroxyphenyl)diamide framework. For more details, see the Full Paper by M. Shibasaki, N. Kumagai et al. on page 5036 ff.

  3. Graphical Abstract

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  4. News

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    5. News
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  5. Review

    1. Top of page
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    1. Biomass

      Useful Products from Complex Starting Materials: Common Chemicals from Biomass Feedstocks (pages 4970–4980)

      Amanda-Lynn Marshall and Peter J. Alaimo

      Version of Record online: 14 APR 2010 | DOI: 10.1002/chem.200903028

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      Edible chemicals? A rapidly expanding area of chemical research is the use of plant biomass for the industrial production of useful organic compounds, for which there is high demand. Among the most challenging targets are simple halocarbons, alkenes, and arenes. This article highlights those targets that have been accessed recently by using biomass-derived materials as the source.

  6. Communications

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    1. Nanostructures

      Three-Dimensional Conductive Nanowire Networks for Maximizing Anode Performance in Microbial Fuel Cells (pages 4982–4985)

      Yong Zhao, Kazuya Watanabe, Ryuhei Nakamura, Shigeki Mori, Huan Liu, Kazuyuki Ishii and Kazuhito Hashimoto

      Version of Record online: 25 MAR 2010 | DOI: 10.1002/chem.200903486

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      Pore genius: A nanoporous composite of graphite felt and polyaniline was developed and used as the anode of a microbial fuel cell, resulting in an order of magnitude increase in power output. The hierarchical conductive anode is a promising strategy for constructing highly efficient microbial fuel cells (see figure).

    2. Asymmetric Catalysis

      Chiral Bis(oxazolinyl)phenyl RuII Catalysts for Highly Enantioselective Cyclopropanation (pages 4986–4990)

      Jun-ichi Ito, Satoshi Ujiie and Hisao Nishiyama

      Version of Record online: 25 MAR 2010 | DOI: 10.1002/chem.200903514

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      Good to excellent enantioselectivities (up to 99 % ee) of trans-cyclopropane derivatives were achieved in the cyclopropanation of alkenes with tert-butyl α-diazoacetate by using 0.5 mol % of a mononuclear chiral ruthenium aqua complex containing the chiral bis(oxazolinyl)phenyl ligand, which was obtained via C[BOND]H activation by RuCl3⋅3 H2O in the presence of Mg and cyclooctadiene (cod). Intramolecular cyclopropanation reactions using the new Ru complex also proceed with high yields and excellent enantioselectivities.

    3. Biaryl Formation

      Aryl Phosphoramides: Useful Electrophiles for Suzuki–Miyaura Coupling Catalyzed by a NiCl2/dppp System (dppp=1,3-Bis(diphenylphosphino)propane) (pages 4991–4994)

      Yu-Long Zhao, You Li, Yu Li, Lian-Xun Gao and Fu-She Han

      Version of Record online: 31 MAR 2010 | DOI: 10.1002/chem.201000420

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      Suzuki–Miyaura coupling: We disclose a new strategy for phenol activation in the first Suzuki–Miyaura coupling of phenol derivatives activated by forming aryl bis(2-oxo-3-oxazolidinyl)phosphines as a highly efficient and broadly applicable methodology for the diverse synthesis of biaryls and heterobiaryls (see scheme). The use of readily available, stable NiCl2/dppp as the catalyst system also provides an important advance.

    4. Reaction Mechanisms

      Mechanistic Exploration of the Intramolecular Hydroalkoxylation of Allenyl Alcohols Mediated by Organolanthanide Complexes: A DFT Study (pages 4995–4998)

      Sven Tobisch

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.201000275

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      An efficient route toward functionalised cyclic ethers: Computational mechanistic analysis indicates an operative Ln[BOND]O σ-bond insertion mechanism with a turnover-limiting cyclisation for the intramolecular hydroalkoxylation of allenyl alcohols (see scheme).

    5. Cluster Compounds

      Gold Sulfide Nanoclusters: A Unique Core-In-Cage Structure (pages 4999–5003)

      De-en Jiang, Michael Walter and Sheng Dai

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.201000327

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      Core in cage: By using a DFT-based basin-hopping method, we found putative global minima for three gold sulfide nanoclusters, observed in mass spectrometry, that all show a symmetric core-in-cage structure: a metallic Au core inside a cage with S as vertices and Au at the edges (see figure). This core-in-cage structure is distinct from bulk gold sulfide. This work fills the knowledge gap regarding the structure of gold sulfide nanoclusters of ≈1 nm.

    6. Chiral Recognition

      Three Point Chiral Recognition and Resolution of Amino Alcohols Through Well-Defined Interaction Inside a Metallocavity (pages 5004–5007)

      Subash C. Sahoo and Manabendra Ray

      Version of Record online: 25 MAR 2010 | DOI: 10.1002/chem.201000078

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      A perfect fit! The cavity of a chiral binuclear NiII complex recognises enantiomers of amino alcohols by recognising three different groups around the chiral carbon through non-covalent interactions (see scheme). The recognised enantiomer is recoverable from the cavity by metathesis with KNO3. Optical rotation of the isolated amino alcohol shows the enantiomer separation (ee) is 87 % in the first step and 100 % after metathesis.

    7. Self-Assembly

      A Scanning Probe Microscopy Study of Annulated Redox-Active Molecules at a Liquid/Solid Interface: The Overruling of the Alkyl Chain Paradigm (pages 5008–5012)

      Bo Liu, Ying-Fen Ran, Zhihai Li, Shi-Xia Liu, Chunyang Jia, Silvio Decurtins and Thomas Wandlowski

      Version of Record online: 31 MAR 2010 | DOI: 10.1002/chem.201000017

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      Overruled! The self-assembly of a novel group of fused donor–acceptor molecules (1) comprising hexaazatriphenylene and tetrathiafulvalene branches was studied by STM at the liquid/solid interface. A 2D assembled chiral porous network with C3 symmetry was found, which is dictated by strong interactions of the extended π-conjugated cores of the fused units with the HOPG substrate overruling the directional forces of alkyl chains.

    8. Sensors

      A Simple Assay for the Fluorometric Detection of Lithium Ions in Aqueous Solution (pages 5013–5017)

      Jie Gao, Sébastien Rochat, Xuhong Qian and Kay Severin

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903119

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      Lithium sensing made easy: A turn-on fluorescence sensor for Li+ can be generated by dissolving readily accessible starting materials in a buffered aqueous solution. The sensor allows the detection of Li+ in the sub-millimolar concentration range.

  7. Full Papers

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

      Binuclear Terbium(III) Complex as a Probe for Tyrosine Phosphorylation (pages 5018–5025)

      Hiroki Akiba, Jun Sumaoka and Makoto Komiyama

      Version of Record online: 13 APR 2010 | DOI: 10.1002/chem.200903379

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      Phosphotyrosine sensing: By using the luminescence from binuclear complexes of TbIII, phosphorylated Tyr residues in peptides (see picture) were selectively detected in neutral aqueous solutions. These binuclear complexes were successfully used for real-time monitoring of enzymatic phosphorylation of a peptide by a tyrosine kinase.

    2. Boron-Based Fluorophores

      Intensely Fluorescent Azobenzenes: Synthesis, Crystal Structures, Effects of Substituents, and Application to Fluorescent Vital Stain (pages 5026–5035)

      Junro Yoshino, Akiko Furuta, Tetsuya Kambe, Hiroaki Itoi, Naokazu Kano, Takayuki Kawashima, Yuzuru Ito and Makoto Asashima

      Version of Record online: 14 APR 2010 | DOI: 10.1002/chem.201000258

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      What intense fluorescence! Several 2-borylazobenzenes have been synthesized. They emit intense green, yellow, and orange fluorescence (see picture). The 4′-siloxy derivative shows the highest fluorescence quantum yield ever reported for an azobenzene.

    3. Self-Discrimination

      Solvent-Dependent Self-Discrimination of Bis(2-hydroxyphenyl)diamides (pages 5036–5042)

      Akinobu Matsuzawa, Akihiro Nojiri, Naoya Kumagai and Masakatsu Shibasaki

      Version of Record online: 6 APR 2010 | DOI: 10.1002/chem.201000321

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      Self-help: Specific self-discrimination of valine-derived bis(2-hydroxyphenyl)diamides (S)- and (R)-1 a in an ensemble of eight structurally related molecules showcases the specific aggregation through the hydrogen-bonding network of the bis(2-hydroxyphenyl)diamide framework.

      Corrected by:

      Corrigendum: Corrigendum: Solvent-Dependent Self-Discrimination of Bis(2-hydroxyphenyl)diamides

      Vol. 17, Issue 46, 12846, Version of Record online: 4 NOV 2011

    4. Molecular Memories

      Organosilyl/-germyl Polyoxotungstate Hybrids for Covalent Grafting onto Silicon Surfaces: Towards Molecular Memories (pages 5043–5051)

      Nicoleta Joo, Séverine Renaudineau, Guillaume Delapierre, Gérard Bidan, Lise-Marie Chamoreau, René Thouvenot, Pierre Gouzerh and Anna Proust

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903336

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      Update your memory! A hybrid organosilyl/-germyl Keggin polyoxotungstate was covalently grafted to an n-type silicon wafer (see figure) and the electrochemical behavior of the thus modified electrode was investigated.

    5. Porphyrin Arrays

      Large Porphyrin Squares from the Self-Assembly of meso-Triazole-Appended L-Shaped mesomeso-Linked ZnII–Triporphyrins: Synthesis and Efficient Energy Transfer (pages 5052–5061)

      Chihiro Maeda, Pyosang Kim, Sung Cho, Jong Kang Park, Jong Min Lim, Dongho Kim, Josh Vura-Weis, Michael R. Wasielewski, Hiroshi Shinokubo and Atsuhiro Osuka

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903195

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      Getting it together: In a noncoordinating solvent, spontaneous assembly occurs to form a tetrameric array from mesomeso-linked diporphyrins, and a dodecameric porphyrin square from L-shaped mesomeso-linked triporphyrins (see graphic). Efficient excited-energy transfer (EET) between the mesomeso-linked ZnII–porphyrin units was revealed.

    6. Anion–π Interactions

      CH-Directed Anion–π Interactions in the Crystals of Pentafluorobenzyl-Substituted Ammonium and Pyridinium Salts (pages 5062–5069)

      Markus Albrecht, Michael Müller, Olga Mergel, Kari Rissanen and Arto Valkonen

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903016

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      Weak, but strong enough: Weak CH hydrogen-bond donors are strong enough to control the position of anions on top of electron-deficient aromatic systems, which leads to the observation of asymmetric (η1–η3) and symmetric (η6) anion–π complexes (see picture).

    7. Metal–Organic Frameworks

      Effect of Bulkiness on Reversible Substitution Reaction at MnII Center with Concomitant Movement of the Lattice DMF: Observation through Single-Crystal to Single-Crystal Fashion (pages 5070–5077)

      Madhab C. Das and Parimal K. Bharadwaj

      Version of Record online: 22 MAR 2010 | DOI: 10.1002/chem.200903129

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      A reversible movement (5.672 Å) of a lattice DMF molecule from the channel of a 3D porous coordination polymer to the MnII center to substitute the bound aqua ligand has been observed in a single-crystal to single-crystal fashion (see figure). Depending upon bulkiness of guest molecules, either full or partial substitution takes place at the MnII center and the 3D channel.

    8. Molecular Aggregation

      Controlled Aggregation of Multiple Guanidinium Ions through a Hydrogen-Bonded Network Assembly with Deprotonated Forms of Kemp’s Triacid (pages 5078–5088)

      Jie Han, Shuang-Quan Zang and Thomas C. W. Mak

      Version of Record online: 25 MAR 2010 | DOI: 10.1002/chem.200903134

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      It's a trap! By using deprotonated forms of Kemp's triacid as anionic building blocks that provide a system of carboxylate groups converging toward a tetrahedral or octahedral void in a crystalline environment, four or eight proximal guanidinium ions have been entrapped within it, respectively (see figure).

    9. Oligonucleotides

      Electron Attachment to Hydrated Oligonucleotide Dimers: Guanylyl-3′,5′-Cytidine and Cytidylyl-3′,5′-Guanosine (pages 5089–5096)

      Jiande Gu, Yaoming Xie and Henry F. Schaefer III

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200902977

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      Electrons favor cytosines: Dinucleoside phosphate deoxycytidylyl-3′,5′-deoxyguanosine and deoxyguanylyl-3′,5′-deoxycytidine systems are investigated, and the exploration of electron attachment to these ssDNA subunits (see figure) brings us closer to reliably predicting the electron affinities of ssDNA. The results suggest that forming base-centered radical anions in ssDNA might be a pathway to either N[BOND]C glycosidic bond rupture or C[BOND]O σ bond breakage.

    10. Reaction Mechanisms

      Disulfide Bond Cleavage: A Redox Reaction Without Electron Transfer (pages 5097–5101)

      Florian Hofbauer and Irmgard Frank

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200902831

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      Mechanically induced chemistry: The mechanically induced reduction of a disulfide bond consists of the motion of electron pairs and a series of proton transfers. Car–Parrinello molecular dynamics simulations (see figure) reveal the elementary reaction steps of such a condensed-phase reaction.

      Corrected by:

      Corrigendum: Corrigendum: Disulfide Bond Cleavage: A Redox Reaction Without Electron Transfer

      Vol. 17, Issue 48, 13380, Version of Record online: 18 NOV 2011

    11. Deprotection–Cyclization Mechanism

      A Time-Resolved Spectroscopic Study of the Bichromophoric Phototrigger 3′,5′-Dimethoxybenzoin Diethyl Phosphate: Interaction Between the Two Chromophores Determines the Reaction Pathway (pages 5102–5118)

      Chensheng Ma, Wai Ming Kwok, Hui-Ying An, Xiangguo Guan, Michael Yunyi Fu, Patrick H. Toy and David Lee Phillips

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200902891

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      Bichromophore photochemistry: A comparative femtosecond transient absorption study on the dichromophoric phototrigger 3′,5′-dimethoxybenzoin diethyl phosphate (DMBDP) and two reference compounds shows the governing role of inter-chromophore electronic interactions in determining the photophysics and photodeprotection pathway of DMBDP in acetonitrile (see figure; DMBF=dimethoxybenzofuran). This reveals a novel concerted deprotection–cyclization mechanism.

    12. Organic Electronics

      Heteroheptacenes with Fused Thiophene and Pyrrole Rings (pages 5119–5128)

      Peng Gao, Don Cho, Xiaoyin Yang, Volker Enkelmann, Martin Baumgarten and Klaus Müllen

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903562

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      A versatile core: Heteroheptacenes containing thiophene and/or pyrrole rings (see picture) are shown to have structural, optical, and electrochemical properties that vary considerably depending upon the substitution of the alkyl and heterole components.

    13. Sensors

      Rational Design of Fluorescent Bioimaging Probes by Controlling the Aggregation Behavior of Squaraines: A Special Effect of Ionic Liquid Pendants (pages 5129–5137)

      Wenhai Wang, Afu Fu, Jingbo Lan, Ge Gao, Jingsong You and Lijuan Chen

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903492

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      Explore your chemical senses! Water-soluble imidazolium-based squaraines have been successfully employed as fluorescent bioimaging reagents by controlling their aggregation tendencies in aqueous media (see figure). This type of squaraine can further serve as an Fe2+-selective sensor based on the reaction between squaraine and a hydroxyl radical.

    14. Solid-State Chemistry

      Structural Characterisation of the Li Argyrodites Li7PS6 and Li7PSe6 and their Solid Solutions: Quantification of Site Preferences by MAS-NMR Spectroscopy (pages 5138–5147)

      Shiao Tong Kong, Özgül Gün, Barbara Koch, Hans Jörg Deiseroth, Hellmut Eckert and Christof Reiner

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903023

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      Cool structures: The Li argyrodites Li7PS6 and Li7PSe6 and their solid solutions undergo temperature-dependent phase transitions. The respective high- (HT) and low-temperature (LT) modifications were analysed by means of X-ray and MAS-NMR methods. Special emphasis was put on the site preferences of the S/Se distribution in the solid solutions and the disorder/order of Li atoms in the HT and LT modifications.

    15. Heterogeneous Catalysis

      Lanthanide-Catalyst-Mediated Tandem Double Intramolecular Hydroalkoxylation/Cyclization of Dialkynyl Dialcohols: Scope and Mechanism (pages 5148–5162)

      SungYong Seo and Tobin J. Marks

      Version of Record online: 26 MAR 2010 | DOI: 10.1002/chem.200903027

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      Tandem double intramolecular hydroalkoxylation/cyclization processes for dialkynyl dialcohol substrates mediated by homoleptic [Ln{N(SiMe3)2}3] lanthanide amido precatalysts exhibit a broad reaction scope in substrate type, including both alkyl and aryl primary and secondary terminal dialkynyl dialcohols and internal dialkynyl dialcohols (see scheme).

    16. Aryl Migration

      BF3⋅OEt2-Catalyzed Intermolecular Reactions of Vinylidenecyclopropanes with Bis(p-alkoxyphenyl)methanols: A Novel Cationic 1,4-Aryl-Migration Process (pages 5163–5172)

      Lei Wu, Min Shi and Yuxue Li

      Version of Record online: 22 MAR 2010 | DOI: 10.1002/chem.200903131

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      From allene to indene: Catalyzed by BF3⋅OEt2, the reactions of vinylidenecyclopropanes with bis(p-alkoxyphenyl)methanols lead to indene derivatives as diastereomeric rotamers by a novel cationic 1,4-aryl migration (see scheme). Mechanistic insights could be gained by means of DFT calculations.

    17. Cycloisomerization

      Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloadditions and Cycloisomerizations of Bis(sulfonylallene)s (pages 5173–5183)

      Takamasa Kawamura, Fuyuhiko Inagaki, Syu Narita, Yasuhito Takahashi, Shuichi Hirata, Shinji Kitagaki and Chisato Mukai

      Version of Record online: 25 MAR 2010 | DOI: 10.1002/chem.200903568

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      Favoring medium-sized rings: RhI-catalyzed carbonylative [2+2+1] cycloadditions and cycloisomerizations of 1,n-bis(sulfonylallene)s (n=4–6) easily afford bicyclo[n.3.0]alkadienones and monocyclic compounds containing two vicinal exo-methylene moieties, respectively (see scheme; m=0–2). These reactions are characterized by [1,3]- or [1,5]-H shifts and are suitable for medium-sized ring construction.

    18. Nanowires

      Molecular Template Assisted Growth of Ultrathin Silicon Carbide Nanowires with Strong Green Light Emission and Excellent Field-Emission Properties (pages 5184–5190)

      Guangcheng Xi, Yanting He and Chao Wang

      Version of Record online: 22 MAR 2010 | DOI: 10.1002/chem.200902490

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      Fine threading: A novel ultrathin β-SiC nanowire structure (see figure) has been prepared through a 1,10-phenanthroline-assisted molecule template route. Stable and strong green light emission at 500 nm and superior field emission with a low turn-on field and large current density are observed.

    19. Synthetic Methods

      Room-Temperature, Ligand- and Base-Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives (pages 5191–5204)

      François-Xavier Felpin, Karinne Miqueu, Jean-Marc Sotiropoulos, Eric Fouquet, Oier Ibarguren and Julia Laudien

      Version of Record online: 1 APR 2010 | DOI: 10.1002/chem.200903050

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      Simplicity does not mean inefficiency! The Pd(OAc)2-catalyzed Heck reaction of aryl diazonium salts with 2-arylacrylates led to cis-stilbenes with good to excellent stereoselectivity. This sustainable protocol features low palladium loading in methanol at room temperature under ligand- and base-free conditions. The stereoselectivity experimentally observed for the synthesis of cis-stilbenes has been rationalized by DFT calculations.

    20. Methane Storage

      Metal–Organic Frameworks with Exceptionally High Methane Uptake: Where and How is Methane Stored? (pages 5205–5214)

      Hui Wu, Jason M. Simmons, Yun Liu, Craig M. Brown, Xi-Sen Wang, Shengqian Ma, Vanessa K. Peterson, Peter D. Southon, Cameron J. Kepert, Hong-Cai Zhou, Taner Yildirim and Wei Zhou

      Version of Record online: 31 MAR 2010 | DOI: 10.1002/chem.200902719

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      Totally adsorbing! Detailed experimental neutron diffraction studies combined with computational investigations reveal where and how methane is adsorbed in MOFs with exceptionally high methane uptake. In addition to the open metal coordination sites, accessible small cages/channels in these MOFs are found to play a big role in storing methane (see figure).

    21. Polymer Nanowires

      Synthesis of Cobalt Ion-Based Coordination Polymer Nanowires and Their Conversion into Porous Co3O4 Nanowires with Good Lithium Storage Properties (pages 5215–5221)

      Chengchao Li, Xiaoming Yin, Libao Chen, Qiuhong Li and Taihong Wang

      Version of Record online: 16 MAR 2010 | DOI: 10.1002/chem.200901632

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      Good storage: Cobalt ion-based coordination polymer nanowires (see figure) were synthesized by using nitrilotriacetic acid (NA) as a chelating agent by a one-step hydrothermal approach, which can be converted into porous Co3O4 nanowires with good lithium storage properties.

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      Preview: Chem. Eur. J. 18/2010 (page 5225)

      Version of Record online: 23 APR 2010 | DOI: 10.1002/chem.201090082

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