Chemistry - A European Journal

Cover image for Vol. 19 Issue 47

November 18, 2013

Volume 19, Issue 47

Pages 15773–16121

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    1. You have free access to this content
      Cover Picture: The Synthesis of Methylated, Phosphorylated, and Phosphonated 3′-Aminoacyl-tRNASec Mimics (Chem. Eur. J. 47/2013) (page 15773)

      Lukas Rigger, Rachel L. Schmidt, Kaitlyn M. Holman, Prof. Miljan Simonović and Prof. Dr. Ronald Micura

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/chem.201390186

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      Selenocysteine is the only amino acid that is synthesized on its cognate transfer RNA, in all domains of life. Its biosynthesis involves the enzyme O-phosphoseryl-tRNA: selenocysteinyl-tRNA synthase. To explore the enzyme mechanism, tRNASec substrates carrying aminoacyl moieties that mimic reaction intermediates are needed. The cover illustrates the synthetic path of phosphonated amino acid units to the 3′-amide linked adenosine conjugates, subsequent assembly of RNA strands and enzymatic ligation to full-length tRNASec derivatives. The cover also symbolizes the collaborative effort of the work from the two labs involved, R. Micura and co-workers in Innsbruck (Austria) and M. Simonović and co-workers in Chicago (USA). For more information see the Full Paper on page 15872 ff.

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      Inside Cover: Binding Cofactors with Triplex-Based DNA Motifs (Chem. Eur. J. 47/2013) (page 15774)

      Dipl.-Chem. Christoph Kröner, M. Sc. Anja Göckel, Wenjing Liu and Prof. Clemens Richert

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/chem.201390187

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      Glowing when reaching body temperature  The surface of a sepharose bead with immobilized triplex motifs releases bound NADH when approaching 37 °C. The NADH then induces bioluminescence. For more details, see the Full Paper by C. Richert et al. on page 15879 ff.

  2. Guest Editorial

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    1. Editorial

      You have free access to this content
      Guest Editorial: The 3rd Transatlantic Frontiers in Chemistry Symposium (pages 15777–15783)

      Dr. Anastassia N. Alexandrova, Dr. Stefan M. Huber and Dr. Ali Tavassoli

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/chem.201303417

      Truly international, truly multidisciplinary, truly inspirational… the 3rd Transatlantic Frontiers of Chemistry Symposium, held at Kloster Seeon in Germany on August 8–11, 2013 brought together 60 early-career chemistry academics from Germany, the UK, the USA, and Brazil. The Symposium exposed its participants to the breadth and diversity of current chemical research, an approach designed to forge new, sustainable transdisciplinary collaborations.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
  4. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    1. You have free access to this content
      Corrigendum: Recent Advances in Organocatalytic Methods for Asymmetric C[BOND]C Bond Formation (page 15794)

      Dr. Ulf Scheffler and Prof. Dr. Rainer Mahrwald

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/chem.201304141

      This article corrects:

      Recent Advances in Organocatalytic Methods for Asymmetric C[BOND]C Bond Formation

      Vol. 19, Issue 43, 14346–14396, Version of Record online: 20 SEP 2013

  5. News

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
  6. Minireview

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
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    9. Full Papers
    1. Cross-Coupling

      A Radical Process towards the Development of Transition-Metal-Free Aromatic Carbon[BOND]Carbon Bond-Forming Reactions (pages 15802–15814)

      Tek Long Chan, Dr. Yinuo Wu, Pui Ying Choy and Prof. Dr. Fuk Yee Kwong

      Version of Record online: 25 OCT 2013 | DOI: 10.1002/chem.201301583

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      No need for transition metals anymore: Joining two aromatic fragments by using an attractive transition-metal-free homolytic aromatic substitution pathway provides an efficient route to aromatic C[BOND]C bond formation, since transition metal catalysts and impurities can be avoided by using this reaction system (see scheme).

  7. Communications

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    1. Iron Catalysis

      X-ray Spectroscopic Verification of the Active Species in Iron-Catalyzed Cross-Coupling Reactions (pages 15816–15821)

      Roland Schoch, Willi Desens, Dr. Thomas Werner and Prof. Dr. Matthias Bauer

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/chem.201303340

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      X-ray absorption: The activation of the pre-catalyst as well as the catalytically active species and reaction mechanism of Fe-catalyzed cross-couplings were investigated by X-ray absorption spectroscopy. The active catalytic components are small iron clusters with three to four FeI centers. The reaction seems to proceed by an FeI/FeIII mechanism (see figure).

    2. DNA Binding

      Three-Pronged Probes: High-Affinity DNA Binding with Cap, β-Alanines and Oligopyrrolamides (pages 15822–15826)

      Dipl.-Chem. Rüdiger Haug, Dipl.-Chem. Markus Kramer and Prof. Clemens Richert

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/chem.201302972

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      TPP oligonucleotides: Hybridization probes that interrogate target sequences through base pairing, stacking on the terminus, and binding in the minor groove are presented (see figure). All subunits of the probes contribute to the target affinity, leading to melting point increases of up to 45 °C. (TPP=three-pronged probe)

    3. Microwave Chemistry

      Simulating Microwave Chemistry in a Resistance-Heated Autoclave Made of Semiconducting Silicon Carbide Ceramic (pages 15827–15830)

      Dr. David Obermayer, Dr. Markus Damm and Prof. Dr. C. Oliver Kappe

      Version of Record online: 15 OCT 2013 | DOI: 10.1002/chem.201303638

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      “Microwave chemistry” without microwaves: A resistance-heated SiC autoclave can effectively mimic the sealed-vessel capabilities, rapid heating and cooling profiles, and excellent process-control features that are inherent to modern microwave reactors. Applied to synthetic chemistry, the ready-to-assemble small device provides identical results as can be obtained in a (costly) microwave system (see figure).

    4. Responsive Gels

      Photoactive Hybrid Gelators Based on a Luminescent Inorganic [Cu4I4] Cluster Core (pages 15831–15835)

      Quentin Benito, Dr. Alexandre Fargues, Dr. Alain Garcia, Sébastien Maron, Dr. Thierry Gacoin, Prof. Jean-Pierre Boilot, Dr. Sandrine Perruchas and Dr. Franck Camerel

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/chem.201303567

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      Luminescent clustogelator: Hybrid gelators with a [Cu4I4] cluster core functionalized by cholesteryl derivatives allow solvent gelation through the formation of a globular network (see figure). The resulting gels display thermochromic and rigidochromic luminescence properties, the latter being used to probe the dynamics of the gelation phenomenon.

    5. Synthetic Methods

      General and Practical Carboxyl-Group-Directed Remote C[BOND]H Oxygenation Reactions of Arenes (pages 15836–15840)

      Yang Wang, Dr. Anton V. Gulevich and Prof. Dr. Vladimir Gevorgyan

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/chem.201303511

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      Two methods for remote aromatic C[BOND]H oxygenation reactions, have been developed. Method 1, the Cu-catalyzed oxygenation reaction, is highly efficient for cyclization of electron-neutral and electron-rich biaryl carboxylic acids into 3,4-benzocoumarins. Method 2, the K2S2O8-mediated oxygenation reaction, is more general and practical for cyclization of substrates with electron-donating and -withdrawing groups (see scheme).

    6. Photoresponsive Nanostructures

      Photocontrolled Self-Assembly of a Bis-Azobenzene-Containing α-Amino Acid (pages 15841–15846)

      Dr. Miriam Mba, Daniela Mazzier, Dr. Simone Silvestrini, Prof. Claudio Toniolo, Dr. Paola Fatás, Dr. Ana I. Jiménez, Prof. Carlos Cativiela and Dr. Alessandro Moretto

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/chem.201303015

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      Light-responsive vesicles: Derivatives of an α-amino acid with two azobenzene side chains self-assemble into vesicular structures that undergo morphological transitions upon light irradiation (see scheme). This is the first example of photoresponsive vesicle-like supramolecular structures formed exclusively by peptides or derivatized amino acids. The entrapment and subsequent light-induced release of functionalized gold nanoparticles are also shown.

    7. Nanoparticles

      Initial Stages in the Formation of Cu2ZnSn(S,Se)4 Nanoparticles (pages 15847–15851)

      Bo Hou, Dr. David Benito-Alifonso, Nessrin Kattan, Prof. David Cherns, Dr. M. Carmen Galan and Prof. David J. Fermín

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/chem.201302722

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      In the beginning: Intermediate species generated in the synthesis of Cu2ZnSn(S,Se)4 nanoparticles (see figure) in oleylamine have been identified. The solvent plays a central role in the reaction mechanism, determining the composition of the nanostructures.

    8. Organocatalysis

      Extending the Stetter Reaction with 1,6-Acceptors (pages 15852–15855)

      Katherine R. Law and Dr. Christopher S. P. McErlean

      Version of Record online: 22 OCT 2013 | DOI: 10.1002/chem.201303435

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      Pace Stetter: A new N-heterocyclic carbene (NHC)-catalysed transformation is described—the intramolecular vinylogous Stetter reaction. This transformation can be effected with both thiazolium and triazolium-based catalysts, using aromatic and aliphatic aldehydes, employing α,β,γ,δ-unsaturated esters, ketones, phosphonates and N-acylpyrroles, and can be conducted enantioselectively (see scheme).

    9. Asymmetric Synthesis

      Highly Enantioselective Decarboxylative Mannich Reaction of Malonic Acid Half Oxyesters with Cyclic Trifluoromethyl Ketimines: Synthesis of β-Amino Esters and Anti-HIV Drug DPC 083 (pages 15856–15860)

      Hai-Na Yuan, Dr. Shen Li, Dr. Jing Nie, Dr. Yan Zheng and Prof. Jun-An Ma

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/chem.201303307

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      An organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half oxyesters with cyclic ketimines was developed for the preparation of enantioenriched β-amino esters with a quaternary stereogenic center and the anti-HIV drug DPC 083 (see scheme).

  8. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Guest Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Communications
    9. Full Papers
    1. Gels

      Small-Peptide-Based Organogel Kit: Towards the Development of Multicomponent Self-Sorting Organogels (pages 15862–15871)

      Rouzbeh Afrasiabi and Prof. Dr. Heinz-Bernhard Kraatz

      Version of Record online: 29 OCT 2013 | DOI: 10.1002/chem.201303116

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      Smart self-sorting systems: A facile bottom-up strategy for the synthesis of a small library of organogelators has been proposed based on the predictive self-assembly of short peptides. The reported strategy was found to result in self-sorting systems that may prove important in the development of organogel-based multicomponent smart devices (see figure).

    2. RNA Mimics

      The Synthesis of Methylated, Phosphorylated, and Phosphonated 3′-Aminoacyl-tRNASec Mimics (pages 15872–15878)

      Lukas Rigger, Rachel L. Schmidt, Kaitlyn M. Holman, Prof. Miljan Simonović and Prof. Dr. Ronald Micura

      Version of Record online: 14 OCT 2013 | DOI: 10.1002/chem.201302188

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      The 21st amino acid: The biosynthesis of selenocysteine (Sec) involves the enzyme O-phosphoseryl-tRNA: selenocysteinyl-tRNA synthase (SepSecS). To explore the enzyme mechanism, tRNASec substrates carrying aminoacyl moieties that mimic particular reaction intermediates are needed. Here, we report on the solid-phase synthesis of methylated, phosphorylated, and phosphonated serinyl-derived RNA conjugates together with the corresponding tRNASec mimics, and validate their interaction with SepSecS (see figure).

    3. DNA Binding

      Binding Cofactors with Triplex-Based DNA Motifs (pages 15879–15887)

      Dipl.-Chem. Christoph Kröner, M. Sc. Anja Göckel, Wenjing Liu and Prof. Clemens Richert

      Version of Record online: 5 NOV 2013 | DOI: 10.1002/chem.201303098

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      Cofactor storage and release: DNA triplex motifs with a gap in the strand, such as the one depicted above (SAM=S-adenosyl-L-methionine, THF=tetrahydrofolate), were found to bind key biochemical cofactors with dissociation constants down to the submicromolar range. When NADH is released, bioluminescence can be induced upon warming to body temperature.

    4. Iron–Carbonyl Complexes

      Valence-to-Core X-Ray Emission Spectroscopy of Iron–Carbonyl Complexes: Implications for the Examination of Catalytic Intermediates (pages 15888–15897)

      Mario Ulises Delgado-Jaime, Prof. Serena DeBeer  and Prof. Matthias Bauer

      Version of Record online: 8 OCT 2013 | DOI: 10.1002/chem.201301913

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      Valence-to-core X-ray emission spectroscopy is applied to iron–carbonyl compounds. Analysis of the origins of the spectral features in terms of ligand and metal contributions is achieved by DFT calculations. The intensities of the observed features are explained through a quantization of the metal 3p and 4p contributions. This allows for the separation of carbonyl and hydrocarbon signals in catalytically relevant compounds and intermediates (see figure).

    5. Rotaxanes

      You have full text access to this OnlineOpen article
      Anion Sensing by Solution- and Surface-Assembled Osmium(II) Bipyridyl Rotaxanes (pages 15898–15906)

      Dr. Joshua Lehr, Dr. Thomas Lang, Dr. Octavia A. Blackburn, Timothy A. Barendt, Prof. Stephen Faulkner, Dr. Jason J. Davis and Prof. Paul D. Beer

      Version of Record online: 14 OCT 2013 | DOI: 10.1002/chem.201302886

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      Rotaxane reporters: The preparation of anion-templated [2]rotaxanes incorporating an optical- and electroactive osmium(II) bipyridyl reporter group is described. The subsequent selective anion recruitment by the generated interlocked cavity is analyzed by NMR spectroscopy, luminescence, and electrochemistry. Tethering to premodified gold electrode substrates by Huisgen cycloaddition enabled the generation of interlocked molecular films capable of selectively recruiting and reporting on the presence of chloride ions in solution (see figure).

    6. Electrochemiluminescence

      Facile Tuning of Luminescent Platinum(II) Schiff Base Complexes from Yellow to Near-Infrared: Photophysics, Electrochemistry, Electrochemiluminescence and Theoretical Calculations (pages 15907–15917)

      Dr. Ellen F. Reid, Dr. Vernon C. Cook, Dr. David J. D. Wilson and Dr. Conor F. Hogan

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/chem.201302339

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      Easy-tune platinum complexes: The emission colour and other properties of electrochemiluminescent platinum(II) salophen complexes may be readily and predictably tuned over a surprisingly wide range by small, easily implemented variations to the ligand structure. With an understanding of substituent mesomeric and inductive effects on frontier MOs, emission colour tuning from yellow to near-IR was achieved (see figure).

    7. Graphene Quantum Dots

      Preparation of Excitation-Independent Photoluminescent Graphene Quantum Dots with Visible-Light Excitation/Emission for Cell Imaging (pages 15918–15923)

      Dr. Shuai Chen, Xin Hai, Chang Xia, Prof. Dr. Xu-Wei Chen and Prof. Dr. Jian-Hua Wang

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/chem.201302207

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      Probing with p-GQDs: When excited by visible light at 490 nm, pyrrole-ring surface-functionalized graphene quantum dots (p-GQDs) are shown to have the longest emission wavelength reported thus far. The excitation-independent photoluminescence at a maximum of 550 nm facilitates live cell imaging in solutions with high ionic strength (see figure).

    8. Fluorescent Probes

      Cyclometalated Iridium(III) Complexes with Deoxyribose Substituents (pages 15924–15932)

      Ayan Maity, Dr. Jung-Suk Choi, Dr. Thomas S. Teets, Dr. Nihal Deligonul, Prof. Dr. Anthony J. Berdis and Prof. Dr. Thomas G. Gray

      Version of Record online: 8 OCT 2013 | DOI: 10.1002/chem.201301776

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      Glow and tell: The study of enzymatic nucleoside transport suffers for lack of optical probes that can be tracked noninvasively. Presented here are nucleoside analogues in which emissive, cyclometalated iridium(III) complexes are “clicked” to C-1 of deoxyribose in place of canonical nucleobases (see picture). The resulting complexes show visible luminescence at room temperature and 77 K with microsecond-length triplet lifetimes.

    9. Macroporous Materials

      Gold-Decorated Chiral Macroporous Films by the Self-Assembly of Functionalised Block Copolymers (pages 15933–15940)

      Silvia Suárez-Suárez, Prof. Gabino A. Carriedo and Dr. Alejandro Presa Soto

      Version of Record online: 9 OCT 2013 | DOI: 10.1002/chem.201303001

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      Decorated macroporous materials: A new method to support chemical functionalities at the surface of porous materials based on the synthesis and self-assembly of inorganic block copolymers with controlled quantities of randomly distributed functional groups is reported. The preparation and self-assembly of chiral polyphosphazene block copolymers functionalised with pyridine, morpholine and thiomorpholine groups is described (see figure, Au NPs=gold nanoparticles).

    10. Bonding Analysis

      Nearly Degenerate Isomers of C(BH)2: Cumulene, Carbene, or Carbone? (pages 15941–15954)

      Shiblee R. Barua, Prof. Wesley D. Allen, Prof. Elfi Kraka, Paul Jerabek, Rebecca Sure and Prof. Gernot Frenking

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/chem.201302181

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      Get bent: High-level quantum chemical calculations show that the molecule C(BH)2 has a linear and a bent form as energy minima that are energetically nearly degenerate (see figure).

    11. Molecular Switches

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      Theoretical Modelling of Photoswitching of Hyperpolarisabilities in Ruthenium Complexes (pages 15955–15963)

      Dr. Benjamin J. Coe, Dr. Aggelos Avramopoulos, Dr. Manthos G. Papadopoulos, Prof. Dr. Kristine Pierloot, Dr. Steven Vancoillie and Dr. Heribert Reis

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201301380

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      Switching excitedly: Excitation of dipolar ruthenium ammine complexes into metal-to-ligand charge-transfer (MLCT) states is predicted by density functional theory calculations to lead to substantial changes in molecular hyperpolarisabilities (see figure). Therefore, such complexes hold promise not only as redox-switchable species, but also for ultrafast photoswitching of nonlinear optical effects in appropriately organised materials.

    12. Sensors

      A Systematic Study of Fluorescence-Based Detection of Nitroexplosives and Other Aromatics in the Vapor Phase by Microporous Metal–Organic Frameworks (pages 15964–15971)

      Dr. Sanhita Pramanik, Zhichao Hu, Dr. Xiao Zhang, Chong Zheng, Sean Kelly and Prof. Dr. Jing Li

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201301194

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      Light up: The fluorescence quenching and enhancement of microporous metal–organic frameworks (MMOFs) by electron-deficient and electron-rich analytes, respectively, was studied (see figure). These effects could be explained by a donor–acceptor electron-transfer mechanism.

    13. Photochemistry

      A Noble-Metal-Free System for Photocatalytic Hydrogen Production from Water (pages 15972–15978)

      Dr. Esteban Mejía, Dr. Shu-Ping Luo, Dr. Michael Karnahl, Aleksej Friedrich, Dr. Stefanie Tschierlei, Dr. Annette-Enrica Surkus, Dr. Henrik Junge, Prof. Dr. Serafino Gladiali, Prof. Dr. Stefan Lochbrunner and Prof. Dr. Matthias Beller

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201302091

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      Not very noble: CuI complexes that contain bisphosphane and diimine ligands are active photosensitizers (PSs; see scheme) in the photocatalytic generation of hydrogen from water, by using [Fe3(CO)12] as a water-reduction catalyst (WRC) and triethylamine as a reductant (SR).

    14. Alcohol Oxidation

      A Convenient and Selective Palladium-Catalyzed Aerobic Oxidation of Alcohols (pages 15979–15984)

      Dr. Saravanan Gowrisankar, Dr. Helfried Neumann, Dirk Gördes, Kerstin Thurow, Dr. Haijun Jiao and Prof. Dr. Matthias Beller

      Version of Record online: 14 OCT 2013 | DOI: 10.1002/chem.201302526

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      Aerobic exercise: Catalytic amounts of Pd(OAc)2 in the presence of tertiary phosphine oxides (O[DOUBLE BOND]PR3) and molecular oxygen oxidize a variety of primary and secondary alcohols to aldehydes and ketones without formation of ester byproducts (see scheme). Spectroscopic investigations and DFT calculations suggest stabilization of the active palladium(II) catalyst by phosphine oxide ligands.

    15. Actinides

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      High-Pressure Synthesis and Characterization of New Actinide Borates, AnB4O8 (An=Th, U) (pages 15985–15992)

      Ernst Hinteregger, Dr. Thomas S. Hofer, Dr. Gunter Heymann, Lukas Perfler, Priv.-Doz. Dr. Florian Kraus and Prof. Dr. Hubert Huppertz

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201302378

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      Under pressure: New actinide borates ThB4O8 and UB4O8 were synthesized under high-pressure, high-temperature conditions in a Walker-type multianvil apparatus. The compounds were constructed from corner-sharing BO4 tetrahedra, which formed layers in the bc plane. The actinide cations were located between the boron–oxygen layers. Owing to their high stability and insolubility, these borates are of interest for the immobilization of nuclear waste (see figure).

    16. Total Synthesis

      Modular Total Synthesis of Rhizopodin: A Highly Potent G-Actin Dimerizing Macrolide (pages 15993–16018)

      Dr. Manuel Kretschmer , Dr. Michael Dieckmann , Prof. Dr. Pengfei Li , Dr. Sven Rudolph , Dipl.-Chem. Daniel Herkommer, Dr. Johannes Troendlin and Prof. Dr. Dirk Menche

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201302197

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      Actin on instinct: The total synthesis of the myxobacterial macrolide rhizopodin (see figure) has been accomplished in 29 steps. Exploiting its C2 symmetry, three main building blocks of similar complexity were synthesized, each from different routes. The construction of the macrocyclic core could be effected by either Heck or Suzuki macrocyclizations, as well as by Yamaguchi macrolactonization. Rhizopodin was obtained and fully characterized.

    17. Bimodal Dysprosium Complexes

      Dysprosium Complexes and Their Micelles as Potential Bimodal Agents for Magnetic Resonance and Optical Imaging (pages 16019–16028)

      Elke Debroye, Prof. Sophie Laurent, Prof. Luce Vander Elst, Prof. Robert N. Muller and Prof. Tatjana N. Parac-Vogt

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201302418

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      Seeing things clearly: Six diethylene triamine pentaacetic acid (DTPA) bisamide derivatives were prepared and the corresponding dysprosium complexes and their micelles were intensively screened for their use in bimodal (optical/magnetic resonance) imaging applications. High transverse relaxivities and notable quantum yields were achieved (see figure).

    18. Photophysics

      Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes (pages 16029–16035)

      Dr. Ehsan Ullah Mughal, Jens Eberhard and Prof. Dr. Dietmar Kuck

      Version of Record online: 14 OCT 2013 | DOI: 10.1002/chem.201303031

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      Extend your wings: Three tetracene chromophores were combined for the first time with the highly rigid and C3v-symmetrical core of triquinacene. Similar to other tribenzotriquinacene (TBTQ) derivatives, the linear arene units of 1 and 2 are oriented orthogonally to each other in space and are electronically independent (see figure). The highly concave molecular shape gives rise to an unusually high solubility of these tetracene derivatives in organic solvents.

    19. Click Chemistry

      Facet-Dependent Catalytic Activity of Cu2O Nanocrystals in the One-Pot Synthesis of 1,2,3-Triazoles by Multicomponent Click Reactions (pages 16036–16043)

      Dr. Kaushik Chanda, Sourav Rej and Prof. Dr. Michael H. Huang

      Version of Record online: 14 OCT 2013 | DOI: 10.1002/chem.201302065

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      Crystal facet matters: Rhombic dodecahedral Cu2O nanocrystals bounded by {110} facets are much more catalytically active than Cu2O octahedra and cubes for the multicomponent synthesis of a wide variety of 1,4-disubstituted 1,2,3-triazoles (see scheme). Rufinamide can also be prepared in high yield.

    20. Alkaloids

      Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis-Decahydroquinolines (pages 16044–16049)

      Prof. Dr. Mercedes Amat, Elena Ghirardi, Dr. Laura Navío, Dr. Rosa Griera, Dr. Núria Llor, Dr. Elies Molins and Prof. Dr. Joan Bosch

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/chem.201302894

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      Fantastic 4: Up to four stereocenters are generated in the reactions of (R)-phenylglycinol or (1S,2R)-1-amino-2-indanol with stereoisomeric mixtures of δ-keto-acid derivatives in stereoconvergent processes ultimately leading to cis-decahydroquinoline alkaloids (see scheme).

    21. Fluorescent Nanoprobes

      Reaction-Based and Single Fluorescent Emitter Decorated Ratiometric Nanoprobe to Detect Hydrogen Peroxide (pages 16050–16057)

      Chun-Yen Chen and Prof. Chao-Tsen Chen

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201302342

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      Dual-colored sensing: A novel reaction-based cross-linked polymeric nanoprobe with a self-calibrating ratiometric fluorescence readout to detect H2O2 is reported. Molecular polarity changes triggered by H2O2 lead to a hydrophobic–hydrophilic transition in the corresponding polymers. Covalently linked 3-hydroxyflavones fluorophores manifest this change in polarity as a ratiometric transition from green to blue, accompanied by a 500-fold increase in volume (see figure).

    22. Ionic Liquid Crystals

      Ionic Liquid Crystals Derived from Amino Acids (pages 16058–16065)

      Dipl.-Chem. Markus Mansueto, Dr. Wolfgang Frey and Prof. Dr. Sabine Laschat

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/chem.201302319

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      Ionic liquid crystals from amino acids: Novel chiral amino acid derived imidazolium salts with amine or amide units were prepared through the sulfamidate. Depending on the steric bulk of the R group, the chain lengths and the type of anion X, stable SmA phases were detected (see scheme; Bn=benzyl).

    23. Sensors

      A New Chiral Binaphthalene-Based Fluorescence Polymer Sensor for the Highly Enantioselective Recognition of Phenylalaninol (pages 16066–16071)

      Guo Wei, Shuwei Zhang, Chunhui Dai, Yiwu Quan, Prof. Dr. Yixiang Cheng and Prof. Dr. Chengjian Zhu

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201302726

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      That's why they call it the blues: A new chiral binaphthalene-based fluorescence polymer sensor showed a clear bright blue color change toward (D)-phenylalaninol with an enantiomeric fluorescence difference ratio ef of 8.99 (see scheme).

    24. Nanostructures

      Organogelation-Controlled Topochemical [2+2] Cycloaddition and Morphological Changes: From Nanofiber to Peculiar Coaxial Hollow Toruloid-Like Nanostructures (pages 16072–16079)

      Xiufeng Wang, Dr. Pengfei Duan and Prof. Dr. Minghua Liu

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/chem.201302200

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      Self-assembled toruloid-like nanostructures: An amphiphilic naphthylacryl-L-glutamide has been found to initially self-assemble into nanofibers, which then undergo a transformation to a family of coaxial hollow toruloid-like nanostructures in ethanol gel under irradiation (see images). A topochemical [2+2] cycloaddition in the organogels triggers this transformation. A reversible morphological transformation between the nanofibers and an unprecedented series of toruloid-like nanostructures can be induced by alternately heating and irradiating the gel.

    25. Gelators

      Solvent-Dependent Truxene-Based Nanostructures (pages 16080–16086)

      Sandra Gomez-Esteban, Marco Pezella, Angel Domingo, Dr. Gunther Hennrich and Dr. Berta Gómez-Lor

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/chem.201301069

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      Assembly line: Truxene derivatives self-assemble in solution and are able to gelate different solvent mixtures despite not having groups able to establish strong directional interactions (see figure). By taking advantage of the balance between molecule–molecule and molecule–solvent interactions, it is possible to control the final morphology of the resulting structures from fibrous superstructures to nanospheres.

    26. Electrocatalysis

      High-Efficiency Encapsulation of Pt Nanoparticles into the Channel of Carbon Nanotubes as an Enhanced Electrocatalyst for Methanol Oxidation (pages 16087–16092)

      Dr. Jianan Zhang, Dr. Shaojun Guo, Junyi Wei, Qun Xu, Prof. Wenfu Yan, Jianwei Fu, Shoupei Wang, Mingjing Cao and Zhimin Chen

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/chem.201302416

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      Capsule-like catalyst: A facile passway for enhancing the stability and activity of the methanol oxidation reaction (MOR) was realized by the use of Pt nanoparticles (NPs) confined inside the channel of carbon nanotubes (CNTs; Pt-in-CNTs, see figure) as a new enhanced electrocatalytic material.

    27. Cyclization

      Thermal Cyclization of Phenylallenes That Contain ortho-1,3-Dioxolan-2-yl Groups: New Cascade Reactions Initiated by 1,5-Hydride Shifts of Acetalic H Atoms (pages 16093–16103)

      Prof. Mateo Alajarin, Dr. Baltasar Bonillo, Marta Marin-Luna, Dr. Pilar Sanchez-Andrada and Prof. Angel Vidal

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/chem.201301608

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      Keeping the heat on: Heating solutions of 2-(1,3-dioxolan-2-yl)phenylallenes at reflux in toluene caused their conversion into 1-(2-hydroxy)ethoxynaphthalenes through cascade processes that were initiated by a hydride-like [1,5]-H shift (see scheme, ERC=electrocyclic ring-closure). DFT calculations disclosed an interesting balance between the two rotatory modes of the 6π-electrocyclization step, depending on the substituents at the two linking carbon atoms.

    28. Crystal Growth

      Antifreeze Protein-Induced Selective Crystallization of a New Thermodynamically and Kinetically Less Preferred Molecular Crystal (pages 16104–16112)

      Dr. Sen Wang, Prof. Xin Wen, Prof. James A. Golen, Josh F. Arifin and Prof. Arnold L. Rheingold

      Version of Record online: 9 OCT 2013 | DOI: 10.1002/chem.201302049

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      A powerful selection: A new, thermodynamically and kinetically less-preferred 5-methyluridine (m5U) dihydrate crystal was achieved by using a tiny amount of an antifreeze protein (DAFP-1). DAFP-1 efficiently inhibits the appearance of m5U hemihydrate, the only previously known crystalline form of m5U, and hence allows the growth of m5U dihydrate exclusively (see scheme).

    29. Drug Delivery

      Design and Synthesis of Lipidic Organoalkoxysilanes for the Self-Assembly of Liposomal Nanohybrid Cerasomes with Controlled Drug Release Properties (pages 16113–16121)

      Dr. Xiaolong Liang, Xiaoda Li, Lijia Jing, Peng Xue, Lingdong Jiang, Prof. Qiushi Ren and Prof. Dr. Zhifei Dai

      Version of Record online: 9 OCT 2013 | DOI: 10.1002/chem.201302518

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      Getting a head: A series of hybrid lipids with different numbers of triethoxysilane headgroups and hydrophobic alkyl chains linked by glycerol and pentaerythritol were synthesized for the construction of cerasomes (see figure). The number of triethoxysilane headgroups affected the properties of the cerasomes for encapsulation efficiency, drug loading, and release behavior.

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