Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 45

November 5, 2012

Volume 51, Issue 45

Pages 11173–11388

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. You have free access to this content
      Cover Picture: Precisely Tunable Photonic Crystals From Rapidly Self-Assembling Brush Block Copolymer Blends (Angew. Chem. Int. Ed. 45/2012) (page 11173)

      Dr. Garret M. Miyake, Dr. Victoria A. Piunova, Raymond A. Weitekamp and Prof. Dr. Robert H. Grubbs

      Article first published online: 15 OCT 2012 | DOI: 10.1002/anie.201208084

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      Molecular brush block copolymers rapidly self-assemble to photonic crystals that can reflect light from the UV, across the visible, and into the near-IR region of the spectrum. In their Communication on page 11246 ff., R. H. Grubbs et al. demonstrate that the blending of two different molecular weight brush block copolymers can predictably modulate the sizes of the polymer domains, enabling facile precision tuning of these photonic-band-gap materials.

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      Inside Cover: A Versatile, Ultralight, Nitrogen-Doped Graphene Framework (Angew. Chem. Int. Ed. 45/2012) (page 11174)

      Yang Zhao, Chuangang Hu, Yue Hu, Huhu Cheng, Prof. Gaoquan Shi and Prof. Liangti Qu

      Article first published online: 12 OCT 2012 | DOI: 10.1002/anie.201207760

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      A versatile, ultralight, N-doped, 3D graphene framework (GF) is prepared. In their Communication on page 11371 ff., L. Qu and co-workers show that this GF has an ultra-low density ((2.1±0.3) mg cm−3; a GF block can balance on a dandelion) and its adsorption capacity for oils is much higher than that of the best carbonaceous sorbents. The 3D open-pore structure and N doping make GF promising as an electrode material for supercapacitors and as a metal-free catalyst for the oxygen reduction reaction in fuel cells.

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      Inside Back Cover: Colloidal Analogues of Charged and Uncharged Polymer Chains with Tunable Stiffness (Angew. Chem. Int. Ed. 45/2012) (page 11389)

      Dr. Hanumantha Rao Vutukuri, Dr. Ahmet Faik Demirörs, Bo Peng, Dr. Peter D. J. van Oostrum, Dr. Arnout Imhof and Prof. Dr. Alfons van Blaaderen

      Article first published online: 16 OCT 2012 | DOI: 10.1002/anie.201208088

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      Colloidal analogues of (bio)polymer chains with tunable flexibility can be prepared from dielectric colloids by using a combination of electric fields and a simple bonding step, as described by H. R. Vutukuri, A. van Blaaderen, et al. in their Communication on page 11249 ff. These model systems can be used to study the classic bead-spring and bead-rod model systems for (semi)flexible and rigid polymers, respectively, in real space and in real time on the monomer level.

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      Back Cover: Mechanism of Formation of Palladium Nanoparticles: Lewis Base Assisted, Low-Temperature Preparation of Monodisperse Nanoparticles (Angew. Chem. Int. Ed. 45/2012) (page 11390)

      Renee W. Y. Man, Adam R. C. Brown and Prof. Michael O. Wolf

      Article first published online: 28 SEP 2012 | DOI: 10.1002/anie.201207400

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      Monodisperse palladium nanoparticles can be produced at lower temperature in the presence of a Lewis base via Pd amido and hydride intermediates. In their Communication on page 11350 ff., M. O. Wolf et al. use NMR studies to elucidate the mechanism of formation of amine-capped Pd nanoparticles from [Pd(acac)2]. Lewis bases increase the nucleophilicity of the amine to enhance the formation of a ketamine by-product, thus resulting in more facile formation of reactive intermediates and nanoparticles.

  2. Graphical Abstract

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    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 45/2012 (pages 11177–11190)

      Article first published online: 30 OCT 2012 | DOI: 10.1002/anie.201290074

  3. Flashback

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. News
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    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. 50 Years Ago... (page 11188)

      Article first published online: 30 OCT 2012 | DOI: 10.1002/anie.201206408

      Angewandte Chemie International Edition was first published in 1962, the mother journal first in 1888. In this monthly flashback, we feature some of the articles that appeared 50 years ago. This look back can open our eyes, stimulate discussion, or even raise a smile.

  4. News

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    3. Graphical Abstract
    4. Flashback
    5. News
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    7. News
    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
  5. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Flashback
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
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    11. Minireview
    12. Review
    13. Communications
    1. Ying-Chun Chen (page 11198)

      Article first published online: 11 JUL 2012 | DOI: 10.1002/anie.201203998

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      “My favorite name reaction is the Diels–Alder reaction. The secret of being a successful scientist is to keep reading and thinking …” This and more about Ying-Chun Chen can be found on page 11198.

  6. News

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    4. Flashback
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    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
  7. Book Review

    1. Top of page
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    7. News
    8. Book Review
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    10. Essay
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    13. Communications
    1. Modern Gold Catalyzed Synthesis. Edited by A. Stephen K. Hashmi and F. Dean Toste. (page 11200)

      Vincent Gandon

      Article first published online: 12 OCT 2012 | DOI: 10.1002/anie.201207733

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      Wiley-VCH, Weinheim, 2012. 402 pp., hardcover, € 139.00.—ISBN 978-3527319527

  8. Highlights

    1. Top of page
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    4. Flashback
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    6. Author Profile
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    8. Book Review
    9. Highlights
    10. Essay
    11. Minireview
    12. Review
    13. Communications
    1. Peptide Nanoparticles

      Nanoparticles and Peptides: A Fruitful Liaison for Biomimetic Catalysis (pages 11202–11204)

      Dr. Maciej Stodulski and Dr. Tanja Gulder

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201206373

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      Inspired by nature: Self-assembled peptide nanoparticles have been designed that accelerate ester hydrolysis (see picture; Cbz=carbobenzyloxy, NP=p-NO2-C6H4). The concerted interplay of the multivalent surface with the catalytically active peptide and the substrate at the same time combines several aspects decisive for the catalyst's efficiency, a property characteristic of enzymes.

    2. Nanorings

      A Dynamic Library of Porphyrinic True Nanorings (pages 11205–11207)

      Dr. Miłosz Pawlicki and Prof. Lechosław Latos-Grażyński

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201204858

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      Behind the wheel: A 10 nm diameter nanoring, containing 24 porphyrin units, has been created by a Vernier-templating self-organization of hexa- or octadentate templating units and linear covalently linked porphyrin oligomers. Coordination of a bidentate ligand triggers a conversion of the molecular nanocylinder into a molecular nanoannulus to afford the dimeric species, which can adopt a water wheel structure (see picture).

  9. Essay

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    10. Essay
    11. Minireview
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    13. Communications
    1. Microscopy

      The Invention of Immersion Ultramicroscopy in 1912—The Birth of Nanotechnology? (pages 11208–11212)

      Priv.-Doz. Dr.-Ing. Timo Mappes, Dipl.-Ing. Norbert Jahr, Dr. Andrea Csaki, Dr. Nadine Vogler, Prof. Dr. Jürgen Popp and Priv.-Doz. Dr. Wolfgang Fritzsche

      Article first published online: 12 OCT 2012 | DOI: 10.1002/anie.201204688

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      Dawn of nanotechnology: The immersion ultramicroscope was patented a century ago. When an analyte was examined with an antique instrument and with state-of-the-art technology, the historic assumptions were confirmed: the size and shape of the nanoparticles are in the same range as that described 100 years ago. The spectra of the Tyndall cones caused by the shape of the nanoparticles were also described correctly—long before electron microscopy was able to image single nanoparticles.

  10. Minireview

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    13. Communications
    1. Sensing Using SERS

      SERS Detection of Small Inorganic Molecules and Ions (pages 11214–11223)

      Prof. Ramón A. Alvarez-Puebla and Prof. Luis M. Liz-Marzán

      Article first published online: 16 OCT 2012 | DOI: 10.1002/anie.201204438

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      SERS you right: Surface-enhanced Raman scattering (SERS) can be used for the direct or indirect detection of inorganic molecules and even ions, in spite of their intrinsically low Raman scattering cross-sections. Recent advances even allow ion sensing and localization within living organisms (see picture).

  11. Review

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    13. Communications
    1. Microfluidics

      Microfluidics in the “Open Space” for Performing Localized Chemistry on Biological Interfaces (pages 11224–11240)

      Dr.  Govind V. Kaigala, Robert D. Lovchik and Dr.  Emmanuel Delamarche

      Article first published online: 30 OCT 2012 | DOI: 10.1002/anie.201201798

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      Space, the final frontier? Microfluidic technologies for controlling liquid dispensing and handling will become central for localizing (bio)chemical reactions/functions on biological interfaces. However, microfluidic systems must then operate in the “open space”, that is, without the sealed channels and chambers commonly used (see picture). The development of such open-space microfluidic technologies is reported.

  12. Communications

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    13. Communications
    1. Modified Nucleotides

      Structure-Based Design of a Highly Constrained Nucleic Acid Analogue: Improved Duplex Stabilization by Restricting Sugar Pucker and Torsion Angle γ (pages 11242–11245)

      Prof. Dr. Stephen Hanessian, Dr. Benjamin R. Schroeder, Robert D. Giacometti, Dr. Bradley L. Merner, Dr. Michael Østergaard, Dr. Eric E. Swayze and Dr. Punit P. Seth

      Article first published online: 22 AUG 2012 | DOI: 10.1002/anie.201203680

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      Dual conformational restriction: A new, highly constrained modification of the α-L-locked nucleic acid (α-L-LNA) scaffold that locks the sugar furanose ring in an N-type configuration and also restricts rotation around torsion angle γ was synthesized (see scheme). This new modification increases the thermostability of an oligonucleotide duplex compared to using a single mode of constraint alone.

    2. Block Copolymers

      Precisely Tunable Photonic Crystals From Rapidly Self-Assembling Brush Block Copolymer Blends (pages 11246–11248)

      Dr. Garret M. Miyake, Dr. Victoria A. Piunova, Raymond A. Weitekamp and Prof. Dr. Robert H. Grubbs

      Article first published online: 13 SEP 2012 | DOI: 10.1002/anie.201205743

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      Colorful: Enabled by their reduced capacity for chain entanglement, high-molecular-weight brush block copolymers can rapidly self-assemble to photonic crystals. The blending of two polymers of different molecular weight can predictably modulate the sizes of the polymer domains, giving rise to a facile means of precision tuning of these photonic-band-gap materials.

    3. Colloids

      You have full text access to this OnlineOpen article
      Colloidal Analogues of Charged and Uncharged Polymer Chains with Tunable Stiffness (pages 11249–11253)

      Dr. Hanumantha Rao Vutukuri, Dr. Ahmet Faik Demirörs, Bo Peng, Dr. Peter D. J. van Oostrum, Dr. Arnout Imhof and Prof. Dr. Alfons van Blaaderen

      Article first published online: 15 AUG 2012 | DOI: 10.1002/anie.201202592

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      Yanking the chain: A general method for the preparation of colloidal analogues of polymer chains was developed (see picture). The flexibility of these chains can be tuned by applying electric fields in combination with their subjection to simple linkage-forming procedures.

    4. Disarming Bacterial Resistance

      Potent Small-Molecule Suppression of Oxacillin Resistance in Methicillin-Resistant Staphylococcus aureus (pages 11254–11257)

      Tyler L. Harris, Dr. Roberta J. Worthington and Prof. Dr. Christian Melander

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201206911

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      Shields down! Adjuvant molecules that have the ability to restore the susceptibility of multi-drug-resistant bacteria, such as MRSA, to clinically available antibiotics are a promising alternative to the development of novel antimicrobials. Pictured is a potent small molecule (1) that, at sub-minimum inhibitory concentration (sub-MIC) levels, lowers the MIC of oxacillin (2) against a number of MRSA strains by up to 512-fold.

    5. Protein–Protein Interactions

      Sekikaic Acid and Lobaric Acid Target a Dynamic Interface of the Coactivator CBP/p300 (pages 11258–11262)

      Dr. Chinmay Y. Majmudar, Dr. Jonas W. Højfeldt, Carl J. Arevang, Dr. William C. Pomerantz, Jessica K. Gagnon, Pamela J. Schultz, Laura C. Cesa, Conor H. Doss, Dr. Steven P. Rowe, Victor Vásquez, Prof. Dr. Giselle Tamayo-Castillo, Prof. Dr. Tomasz Cierpicki, Prof. Dr. Charles L. Brooks III, Prof. Dr. David H. Sherman and Prof. Dr. Anna K. Mapp

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206815

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      Capturing a coactivator, naturally: The natural products sekikaic acid and lobaric acid, isolated after a high-throughput screen of a structurally diverse extract collection, effectively target the dynamic binding interfaces of the GACKIX domain of the coactivator CBP/p300 (see structure). These molecules are the most effective inhibitors of the GACKIX domain yet described and are uniquely selective for this domain.

    6. Platinum Chemistry

      Two-Photon-Activated Ligand Exchange in Platinum(II) Complexes (pages 11263–11266)

      Dr. Yao Zhao, Dr. Gareth M. Roberts, Simon E. Greenough, Dr. Nicola J. Farrer, Dr. Martin J. Paterson, William H. Powell, Prof. Dr. Vasilios G. Stavros and Prof. Dr. Peter J. Sadler

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201206283

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      Two photons are better than one: A square-planar PtII complex with derivatized pyridine ligands was synthesized (see scheme), which undergoes two-photon-induced ligand substitution with 600–740 nm light. Linear and quadratic density functional response theory allowed identification of the electronic transitions involved.

    7. Oligourea Foldamers

      Robust Helix Formation in a New Family of Oligoureas Based on a Constrained Bicyclic Building Block (pages 11267–11270)

      Dr. Baptiste Legrand, Christophe André, Emmanuel Wenger, Dr. Claude Didierjean, Dr. Marie Christine Averlant-Petit, Prof. Jean Martinez, Dr. Monique Calmes and Dr. Muriel Amblard

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201205842

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      BAC for more: A constrained bicyclic building block with urea linkages is an efficient combination for the formation of a highly rigid helical system. This type of bicyclic amino carbamoyl (BAC) foldamer was studied both in solution (see scheme) and in the solid state. A robust H-bond (dotted line) network was found between the carbonyl oxygen atoms (red) and the amino groups (dark blue) within the helix.

    8. DNA Nanostructures

      pH-Responsive Size-Tunable Self-Assembled DNA Dendrimers (pages 11271–11274)

      Tao Zhou, Ping Chen, Lin Niu, Juan Jin, Prof. Dr. Dehai Liang, Prof. Dr. Zhibo Li, Prof. Dr. Zhongqiang Yang and Prof. Dr. Dongsheng Liu

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201205862

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      Putting the DNA in dendrimers: A strategy to swiftly prepare DNA dendrimers based solely on DNA self-assembly is presented. This technique produces highly pure DNA dendrimers with an excellent yield of high generation dendrimers. The incorporation of molecular motors (i-motifs) into the DNA dendrimers allows for a change in size (up to 30%) in response to changing pH values (see scheme).

    9. Organic–Metal Particulate Catalysts

      Prominent Electronic and Geometric Modifications of Palladium Nanoparticles by Polymer Stabilizers for Hydrogen Production under Ambient Conditions (pages 11275–11278)

      Simon Jones, Jin Qu, Dr. Karaked Tedsree, Prof. Xue-Qing Gong and Prof. Shik Chi Edman Tsang

      Article first published online: 17 SEP 2012 | DOI: 10.1002/anie.201206035

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      A remarkable effect from the modification of electronic and geometric properties of Pd nanoparticles by the use of polymer pendant groups bound to the surface of palladium nanoparticles is reported. The degree of electron promotion to the Pd nanoparticles under ambient conditions was found to be dependent on the availability of the lone pair electrons of the pendant groups.

    10. Crystal Growth

      Is Dual Morphology of Rock-Salt Crystals Possible with a Single Additive? The Answer Is Yes, with Barbituric Acid (pages 11279–11283)

      Anik Sen and Dr. Bishwajit Ganguly

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201206170

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      Crystal face lift: Barbituric acid is shown to be a new crystal-habit modifier for sodium chloride crystals (see scheme). Two morphologies of salt crystals can be prepared separately with this new additive. It is of the few additives able to induce rhombic dodecahedron crystals for NaCl, and is required only a trace of amount, unlike other additives, such as glycine.

    11. Luminescent Motion

      Light-Emitting Electrochemical “Swimmers” (pages 11284–11288)

      Milica Sentic, Gabriel Loget, Prof. Dragan Manojlovic, Prof. Alexander Kuhn and Prof. Neso Sojic

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206227

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      Swimmer in the dark: Propulsion of a conducting object is intrinsically coupled with light emission using bipolar electrochemistry. Asymmetric redox activity on the surface of the swimmer (black bead; see picture) causes production of gas bubbles to propel the swimmer in a glass tube with simultaneous electrochemiluminescence (ECL) emission to monitor the progress of the swimmer.

    12. RNA Sequencing

      You have full text access to this OnlineOpen article
      Characterization of Modified RNA by Top-Down Mass Spectrometry (pages 11289–11292)

      Dipl.-Ing. Monika Taucher and Priv.-Doz. Dr. Kathrin Breuker

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206232

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      Characteristic mass differences between fragment ions from backbone cleavage of RNA by electron detachment (d, w) and fragment ions from collisionally activated dissociation (c, y) provide extensive sequence information (see picture). Structure analysis by this approach should be especially useful for the detailed characterization of synthetic or post-transcriptionally modified RNA.

    13. Living Materials

      Incorporation of Penicillin-Producing Fungi into Living Materials to Provide Chemically Active and Antibiotic-Releasing Surfaces (pages 11293–11296)

      Dr. Lukas C. Gerber, Dr. Fabian M. Koehler, Dr. Robert N. Grass and Prof. Dr. Wendelin J. Stark

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201204337

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      Living materials: Artificial biological niches are loaded with the penicillin-producing mold Penicillium chrysogenum. This living material consumes food through a nanoporous top layer and releases the antibiotic on-site. No reloading of the active compound is needed. Gram-positive bacteria were efficiently killed if nearby, whereas Gram-negative bacteria (control experiment, not sensitive to penicillin) were not affected.

    14. Chirality

      Symmetry Breaking in the Self-Assembly of Partially Fluorinated Benzene-1,3,5-tricarboxamides (pages 11297–11301)

      Patrick J. M. Stals, Peter A. Korevaar, Martijn A. J. Gillissen, Dr. Tom F. A. de Greef, Dr. Carel F. C. Fitié, Prof. Dr. Rint P. Sijbesma, Dr. Anja R. A. Palmans and Prof. Dr. E. W. Meijer

      Article first published online: 31 AUG 2012 | DOI: 10.1002/anie.201204727

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      The interplay of two subsequent aggregation processes results in a symmetry-breaking phenomenon in an achiral self-assembling system. Partially fluorinated benzene-1,3,5-tricarboxamide molecules self-assemble into a racemic mixture of one-dimensional P- and M-helical aggregates, followed by bundling into optically active higher-order aggregates or fibers (see picture).

    15. Energy Transfer

      Perfluorinated Aromatic Spacers for Sensitizing Europium(III) Centers in Dinuclear Oligomers: Better than the Best by Chemical Design? (pages 11302–11305)

      Dr. Jean-François Lemonnier, Lucille Babel, Dr. Laure Guénée, Dr. Prasun Mukherjee, Prof. Dr. David H. Waldeck, Dr. Svetlana V. Eliseeva, Prof. Dr. Stéphane Petoud and Prof. Dr. Claude Piguet

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201205082

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      Transfer news: The use of a simple method allows the various sensitization steps in EuIII-containing complexes to be deciphered. Incorporation of an increasing number of electron-withdrawing fluorine atoms on the rigid and electronically tunable phenyl spacer between two tridentate binding units (see picture, red O, dark blue N) affects the quantum yield, intersystem crossing, and energy-transfer processes in a rational way.

    16. CO2 Capture

      Equimolar CO2 Capture by N-Substituted Amino Acid Salts and Subsequent Conversion (pages 11306–11310)

      An-Hua Liu, Ran Ma, Chan Song, Zhen-Zhen Yang, Prof. Dr. Ao Yu, Yu Cai, Prof. Dr. Liang-Nian He, Ya-Nan Zhao, Bing Yu and Qing-Wen Song

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201205362

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      Steric bulk controls CO2 absorption: N-substituted amino acid salts in poly(ethylene glycol) reversibly absorb CO2 in nearly 1:1 stoichiometry. Carbamic acid is thought to be the absorbed form of CO2; this was supported by NMR and in situ IR spectroscopy, and DFT calculations. The captured CO2 could be converted directly into oxazolidinones and thus CO2 desorption could be sidestepped.

    17. Organic Light-Emitting Diodes

      Enhanced Electroluminescence Efficiency in a Spiro-Acridine Derivative through Thermally Activated Delayed Fluorescence (pages 11311–11315)

      Gábor Méhes, Hiroko Nomura, Dr. Qisheng Zhang, Dr. Tetsuya Nakagawa and Prof. Dr. Chihaya Adachi

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206289

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      Make your OLED fluorescent: An aromatic molecule based on a spiro-acridine derivative was designed (see picture), and its photoluminescence and electroluminescence were characterized. By combining the donor and acceptor moieties a small energy gap between the lowest singlet and triplet states was achieved. This design leads to an organic light-emitting diode (OLED) that rivals phosphorescent devices regarding exciton generation efficiency.

    18. Enediyne Biosynthese

      Environmental Control of the Calicheamicin Polyketide Synthase Leads to Detection of a Programmed Octaketide and a Proposal for Enediyne Biosynthesis (pages 11316–11319)

      Katherine Belecki and Prof. Dr. Craig A. Townsend

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206462

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      A light in the dark: The fermentation products of the polyketide synthase CalE8 (without its cognate thioesterase) were identified and gave some insight into the elusive early steps of calicheamicin biosynthesis. Fermentation in either the light or dark resulted in different proportions of a new octaketide (see scheme) and led to an updated mechanistic proposal.

    19. Solid-Phase Chemical Ligation

      Towards the Simplification of Protein Synthesis: Iterative Solid-Supported Ligations with Concomitant Purifications (pages 11320–11324)

      Dr. Vincent Aucagne, Dr. Ibai E. Valverde, Philippe Marceau, Dr. Mathieu Galibert, Dr. Nabil Dendane and Dr. Agnès F. Delmas

      Article first published online: 10 OCT 2012 | DOI: 10.1002/anie.201206428

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      Please release me: A new linker for the temporary tagging of peptides at their N-terminus after solid-phase elongation, and its potential for capture/release purification is demonstrated. This concept is extended to a remarkably efficient self-purifying N-to-C iterative triazole ligation strategy, which is applied to the synthesis of a polypeptide having 160 residues, in a high purity without the need for chromatographic purification (see picture; orange blocks: peptide segments).

    20. DNA Nanotechnology

      Assembly of Heterogeneous Functional Nanomaterials on DNA Origami Scaffolds (pages 11325–11327)

      Dr. Risheng Wang, Prof. Colin Nuckolls and Prof. Shalom J. Wind

      Article first published online: 10 OCT 2012 | DOI: 10.1002/anie.201206389

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      One on each side: Gold nanoparticles (AuNPs) and semiconducting quantum dots (QDs) are integrated on a single DNA origami scaffold. Streptavidin-functionalized QDs bind to biotin anchors on one side of the DNA origami, while DNA-coated AuNPs bind through DNA hybridization to single-stranded DNA on the other side of the scaffold. This approach offers a new path toward the organization of complex systems consisting of disparate materials.

    21. Asymmetric Organocatalysis

      Enantioselective Synthesis of Highly Functionalized Phosphonate-Substituted Pyrans or Dihydropyrans Through Asymmetric [4+2] Cycloaddition of β,γ-Unsaturated α-Ketophosphonates with Allenic Esters (pages 11328–11332)

      Dr. Cheng-Kui Pei, Yu Jiang, Yin Wei and Prof. Dr. Min Shi

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206958

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      Tell me which you want: Catalytic asymmetric [4+2] cycloadditions of β,γ-unsaturated α-ketophosphonates with allenic esters catalyzed by organocatalysts derived from different cinchona alkaloids have been developed, affording phosphonate-substituted functionalized pyran and dihydropyran derivatives in excellent yields with high enantioselectivities under mild conditions. The choice of product is controlled by the hydrogen bonding characteristics of the chosen catalyst.

    22. Synthetic Methods

      Palladium-Catalyzed Dehydrogenation/Oxidative Cross-Coupling Sequence of β-Heteroatom-Substituted Ketones (pages 11333–11336)

      Youngtaek Moon, Daeil Kwon and Prof. Dr. Sungwoo Hong

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201206610

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      Concise and selective: The title one-pot sequence allows formation of the enone functionality and subsequent cross-coupling. The process provides access to highly functionalized cyclic enolones and enaminones from readily accessible β-heteroatom-substituted cyclic ketones.

    23. π Complexes

      Cyclopentadienylruthenium π Complexes of Subphthalocyanines: A “Drop-Pin” Approach To Modifying the Electronic Features of Aromatic Macrocycles (pages 11337–11342)

      Dr. Esmeralda Caballero, Javier Fernández-Ariza, Prof. Vincent M. Lynch, Dr. Carlos Romero-Nieto, Dr. M. Salomé Rodríguez-Morgade, Prof. Jonathan L. Sessler, Prof. Dirk M. Guldi and Prof. Tomás Torres

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201206111

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      Facing facts: Coordination of Cp*Ru (Cp*=C5Me5) to the concave and convex π surfaces of subphthalocyanines constitutes a new approach to the functionalization of subazaporphyrins. While the convex face shows higher reactivity, coordination to the concave side produces a stronger diatropic influence on the Cp* ligand and a greater perturbation of the macrocyclic π-electronic features.

    24. CO2 Reduction

      Frustrated Lewis Pair Inspired Carbon Dioxide Reduction by a Ruthenium Tris(aminophosphine) Complex (pages 11343–11345)

      Michael J. Sgro and Prof. Dr. Douglas W. Stephan

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201205741

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      Frustrating ruthenium: The ruthenium complex 1 is shown to bind carbon dioxide or aldehyde in a manner similar to a frustrated Lewis pair. Compound 2 catalyzes the reduction of CO2 in the presence of pinacolborane (HBpin), yielding MeOBpin and O(Bpin)2 (see picture; Ru red, P orange, N green, O light red, C black).

    25. Gold Catalysis

      Highly Enantioselective Transfer Hydrogenation of Quinolines Catalyzed by Gold Phosphates: Achiral Ligand Tuning and Chiral-Anion Control of Stereoselectivity (pages 11346–11349)

      Xi-Feng Tu and Prof. Liu-Zhu Gong

      Article first published online: 17 SEP 2012 | DOI: 10.1002/anie.201204179

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      A little gold goes a long way: As little as 0.01 mol % of chiral gold phosphate is sufficient to afford the asymmetric transfer hydrogenation of quinolines with high stereoselectivity (up to 98 % ee). The achiral ligands on gold were found to have considerable effect on the catalytic efficiency.

    26. Nanoparticle Formation

      Mechanism of Formation of Palladium Nanoparticles: Lewis Base Assisted, Low-Temperature Preparation of Monodisperse Nanoparticles (pages 11350–11353)

      Renee W. Y. Man, Adam R. C. Brown and Prof. Michael O. Wolf

      Article first published online: 26 SEP 2012 | DOI: 10.1002/anie.201205057

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      Small and cool: The mechanism of formation of amine-capped Pd nanoparticles from [Pd(acac)2] (acac=acetylacetonate) is elucidated, and shown to involve Pd–amido and Pd–hydride intermediates. The addition of a Lewis base results in a significant reduction in the temperature at which highly monodisperse nanoparticles are isolated.

    27. Homogeneous Catalysis

      Pd-PEPPSI-IPentCl: A Highly Effective Catalyst for the Selective Cross-Coupling of Secondary Organozinc Reagents (pages 11354–11357)

      Matthew Pompeo, Dr. Robert D. J. Froese, Dr. Niloufar Hadei and Prof. Michael G. Organ

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201205747

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      No migration? No problem! A series of new N-heterocyclic carbene based Pd complexes has been created and evaluated in the Negishi cross-coupling of aryl and heteroaryl chlorides, bromides, and triflates with a variety of secondary alkylzinc reagents (see scheme). The direct elimination product is nearly exclusively formed; in most examples there is no migratory insertion at all.

    28. Host–Guest Chemistry

      Acyclic Cucurbit[n]uril-Type Molecular Containers Bind Neuromuscular Blocking Agents In Vitro and Reverse Neuromuscular Block In Vivo (pages 11358–11362)

      Dr. Da Ma, Ben Zhang, Dr. Ulrike Hoffmann, Dr. Martina Grosse Sundrup, Prof. Dr. Matthias Eikermann and Prof. Lyle Isaacs

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201206031

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      Be My Guest: Two acyclic cucurbit[n]uril-type receptors that carry SO3-groups bind tightly to several commonly used neuromuscular blocking agents, such as rocuronium, in aqueous solution as revealed by direct and competitive UV/Vis binding assays. One of these containers functions as a potent reversal agent for rocuronium-induced neuromuscular block in rats.

    29. Heterocycle Synthesis

      Modular Synthesis of Phenanthridine Derivatives by Oxidative Cyclization of 2-Isocyanobiphenyls with Organoboron Reagents (pages 11363–11366)

      Dr. Mamoru Tobisu, Keika Koh, Takayuki Furukawa and Prof. Dr. Naoto Chatani

      Article first published online: 10 OCT 2012 | DOI: 10.1002/anie.201206115

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      Where HAS you been? A manganese-mediated annulation of 2-isocyanobiaryls with organoboronic acids is developed for the synthesis of a broad range of phenanthridine derivatives (see scheme). Mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution (HAS) of an imidoyl radical intermediate.

    30. Oxygenation

      Synthesis of Oxazoles through Copper-Mediated Aerobic Oxidative Dehydrogenative Annulation and Oxygenation of Aldehydes and Amines (pages 11367–11370)

      Zejun Xu, Chun Zhang and Prof. Dr. Ning Jiao

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201206382

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      A fragment-assembling strategy is used to form oxazoles from aryl acetaldehydes, amines, and molecular oxygen under mild conditions (see scheme). The transformation is highly efficient with the removal of six hydrogen atoms, including the cleavage of four C(sp3)[BOND]H bonds.

    31. Ultralight Graphene

      A Versatile, Ultralight, Nitrogen-Doped Graphene Framework (pages 11371–11375)

      Yang Zhao, Chuangang Hu, Yue Hu, Huhu Cheng, Prof. Gaoquan Shi and Prof. Liangti Qu

      Article first published online: 4 OCT 2012 | DOI: 10.1002/anie.201206554

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      Graphene lite: A density of (2.1±0.3) mg cm−3, the lowest to date for a graphene framework architecture, is achieved by preparing an ultralight, N-doped, 3D graphene framework (see photo of a block of the material balancing on a dandelion). Its adsorption capacity for oils and organic solvents is much higher than that of the best carbonaceous sorbents, and it is a promising electrode material for supercapacitors (484 F g−1) and as a metal-free catalyst for the oxygen reduction reaction.

    32. Asymmetric Catalysis

      Dirhodium Carboxylates Catalyzed Enantioselective Coupling Reactions of α-Diazophosphonates, Anilines, and Electron-Deficient Aldehydes (pages 11376–11380)

      Cong-Ying Zhou, Jing-Cui Wang, Jinhu Wei, Zhen-Jiang Xu, Zhen Guo, Kam-Hung Low and Prof. Dr. Chi-Ming Che

      Article first published online: 16 OCT 2012 | DOI: 10.1002/anie.201206551

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      Chiral dirhodium carboxylate complexes ([Rh2(S-PTAD)4] or [Rh2(S-PTTL)4], see scheme) efficiently catalyze asymmetric three-component coupling reactions of α-diazophosphonates, anilines, and electron-deficient aldehydes to give α-amino-β-hydroxyphosphonates. The high level of enantiocontrol provides evidence for the intermediacy of metal-bound ammonium ylide in the product-forming step.

    33. Natural Products

      The Total Synthesis of Corallopyronin A and Myxopyronin B (pages 11381–11384)

      Dr. Andreas Rentsch and Prof. Dr. Markus Kalesse

      Article first published online: 8 OCT 2012 | DOI: 10.1002/anie.201206560

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      Leading the way: The synthesis of natural products with new biological targets is one of the driving forces for the development of new antibiotics. The synthesis of the two secondary metabolites corallopyronin and myxopyronin (see picture) have been achieved, which are prominent leads for the inhibition of bacterial RNA polymerase.

    34. Nanostructures

      Electronic Properties of Trifluoromethylated Corannulenes (pages 11385–11388)

      Bernd M. Schmidt, Prof. Dr. Shu Seki, Berit Topolinski, Dr. Kei Ohkubo, Prof. Dr. Shunichi Fukuzumi, Hidehiro Sakurai and Prof. Dr. Dieter Lentz

      Article first published online: 9 OCT 2012 | DOI: 10.1002/anie.201205757

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      With great stacking comes great conductivity: Trifluoromethylated corannulenes are unexpectedly strong electron acceptors in solution. Even a polycrystalline film of 1,2-(F3C)2-corannulene (top structure and curve in the plot) exhibits conductivity three orders of magnitude higher than that of pristine corannulene!

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