Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 18

Early View (Online Version of Record published before inclusion in an issue)

Editor: Peter Gölitz, Deputy Editors: Neville Compton, Haymo Ross

Online ISSN: 1521-3773

Associated Title(s): Angewandte Chemie, Chemistry - A European Journal, Chemistry – An Asian Journal, ChemistryOpen, ChemPlusChem, Zeitschrift für Chemie

  1. Communications

    1. Light-Emitting Diodes | Hot Paper

      Organic Light-Emitting Diodes Using a Neutral π Radical as Emitter: The Emission from a Doublet

      Qiming Peng, Ablikim Obolda, Prof. Dr. Ming Zhang and Prof. Dr. Feng Li

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201500242

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      Organic electronics: An organic open-shell molecule (TTM-1Cz) was used as an emitter in organic light-emitting diodes (OLEDs). There is only one electron at the highest occupied molecular orbital (see picture), leading to the excited state of TTM-1Cz to be a doublet. The key issue of how to harvest the triplet energy in an OLED is thus circumvented, because the radiative decay of the doublet is totally spin-allowed.

  2. Editorials

    1. You have free access to this content
      Sustainable Chemistry for Energizing the Planet

      Marc Fontecave

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502134

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      “… There is an unprecedented global consensus that an energetic transition, not to say a revolution, is urgently required. The transition can be defined as the process by which all fossil fuels (and nuclear energy) are replaced by renewable energies. How can we achieve this transition in the shortest time? …” Read more in the Editorial by Marc Fontecave.

  3. Communications

    1. Photosystem II

      Resolving the Differences Between the 1.9 Å and 1.95 Å Crystal Structures of Photosystem II: A Single Proton Relocation Defines Two Tautomeric Forms of the Water-Oxidizing Complex

      Dr. Simon Petrie, Prof. Ron J. Pace and Prof. Rob Stranger

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502463

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      Double act: Assuming the ‘low’ Mn oxidation state paradigm, DFT calculations show that the structures of the water-oxidizing complex (WOC) of photosystem II in the recent XFEL study at 1.95 Å and the earlier XRD study at 1.9 Å are simply tautomers that are related by a single proton relocation involving W2, O5, and the His337 residue.

    2. Colloidosomes | Hot Paper

      Electrostatic Assembly/Disassembly of Nanoscaled Colloidosomes for Light-Triggered Cargo Release

      Song Li, Basem A. Moosa, Jonas G. Croissant and Prof. Niveen M. Khashab

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501615

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      Nanocapsules for large cargos: Nanoscaled colloidosomes were designed by electrostatic assembly of organosilica nanoparticles (NPs) with oppositely charged surfaces, arising from different contents of a bridged nitrophenylene-alkoxysilane derivative in the silica. The positive charge was reversed by light irradiation because of the photoreaction of nitrophenylene moieties.

    3. Metallacycles

      Five-Membered Cyclic Metal Carbyne: Synthesis of Osmapentalynes by the Reactions of Osmapentalene with Allene, Alkyne, and Alkene

      Dr. Congqing Zhu, Yuhui Yang, Jingjing Wu, Ming Luo, Jinglan Fan, Dr. Jun Zhu and Prof. Dr. Haiping Xia

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502412

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      General and efficient: Various osmapentalynes were synthesized by a general route via an osmapentalene derivative. The experimental data together with DFT calculations confirm the aromaticity of these fused five-membered rings. Development of this synthetic approach will facilitate the exploration of the reactivities and applications of osmapentalynes, a brand-new aromatic system.

    4. Synthetic Methods

      Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System

      Alexander Köpfer and Prof. Dr. Bernhard Breit

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502086

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      β,γ-Unsaturated aldehydes are obtained by a rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes. For unsymmetrically 1,1-disubstituted allenes the Z-configured product is formed in up to >95 % selectivity. This is the first time that these building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products.

    5. C[BOND]H Activation

      Rhodium(III)-Catalyzed ortho C[BOND]H Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to π-Conjugated Poly-heterocycles

      Dr. Xurong Qin, Xiaoyu Li, Quan Huang, Hu Liu, Prof. Dr. Di Wu, Qiang Guo, Prof. Dr. Jingbo Lan, Prof. Dr. Ruilin Wang and Prof. Dr. Jingsong You

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501982

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      Under construction: The highly regioselective title reaction directly furnishes ortho-carboxy bi(hetero)aryls. The method has the potential to lead to the rapid construction of a library of appealing poly-heterocycles, given the complete regiocontrol, readily available substrates, and functional-group tolerance.

    6. Electrochemistry | Very Important Paper

      Oxygen Reduction Mediated by Single Nanodroplets Containing Attomoles of Vitamin B12: Electrocatalytic Nano-Impacts Method

      Dr. Wei Cheng and Prof. Dr. Richard G. Compton

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501820

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      Single Vitamin B12 (VB12) nanodroplets are used to mediate the reduction of oxygen in neutral buffer (see picture). The mechanism of oxygen reduction mediated by single VB12 droplets is revealed as via both CoII and CoI reduced from CoIII in VB12 through one- or two-electron transfer followed by the four-electron reduction of oxygen.

    7. Cumulated Double Bonds

      Cumulene Rotaxanes: Stabilization and Study of [9]Cumulenes

      Michael Franz, Dr. Johanna A. Januszewski, Dominik Wendinger, Dr. Christian Neiss, Dr. Levon D. Movsisyan, Dr. Frank Hampel, Prof. Dr. Harry L. Anderson, Prof. Dr. Andreas Görling and Prof. Dr. Rik R. Tykwinski

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501810

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      Loaded and locked: An approach to stabilizing [n]cumulenes was developed based on locking the cumulene within a rotaxane. The result is a stabilized [9]cumulene that enables the study of properties as a function of cumulene length in unprecedented detail, including by quantitative UV/Vis spectroscopy, cyclic voltammetry, and differential scanning calorimetry. The experimental results are supported by DFT calculations.

    8. Lithium-Ion Batteries

      Non-Invasive In Situ Dynamic Monitoring of Elastic Properties of Composite Battery Electrodes by EQCM-D

      Netanel Shpigel, Mikhael D. Levi, Sergey Sigalov, Olga Girshevitz, Doron Aurbach, Leonid Daikhin, Nicolas Jäckel and Volker Presser

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501787

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      Intercalation-induced frequency (ΔF) and resonance width (ΔW) changes of composite Li-ion battery electrodes during their charge/discharge processes can be measured by electrochemical quartz-crystal microbalance with dissipation monitoring (EQCM-D). This visualizes in situ the dynamic character of the viscoelastic properties of the polymeric binders. PVdF=polyvinylidene fluoride, CMC=carboxymethylcellulose.

    9. Cross-Coupling

      Trifluoromethylthiolation of Aryl Iodides and Bromides Enabled by a Bench-Stable and Easy-To-Recover Dinuclear Palladium(I) Catalyst

      Dr. Guoyin Yin, Indrek Kalvet and Prof. Dr. Franziska Schoenebeck

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501617

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      Pd double team: The cross-coupling enabled by an air-, moisture-, and thermally-stable dinuclear PdI complex was explored. Highly efficient C[BOND]SCF3 coupling of a range of aryl iodides and bromides was achieved and the catalyst was recovered by simple column chromatography, thus highlighting its robustness and the possibility for catalyst recycling. Kinetic and computational data support the feasibility of dinuclear PdI catalysis.

    10. Carbon Dioxide Reduction

      An Air- and Water-Tolerant Zinc Hydride Cluster That Reacts Selectively With CO2

      David M. Ermert, Dr. Ion Ghiviriga, Prof. Dr. Vincent J. Catalano, Prof. Dr. Jason Shearer and Prof. Dr. Leslie J. Murray

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501539

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      Playing favorites: The reaction of [Zn3Cl3L], in which L3− is a tris(β-diketiminate) cyclophane, with K(sBu)3BH afforded [Zn3(μ-H)3L] (see picture). This air-stable complex was unreactive towards water, methanol, and other substrates at room temperature but reduced CO2 to generate [Zn3(μ-H)2(μ-1,1-O2CH)]. In contrast, [Zn3(OH)3L] was found to be unreactive towards CO2 at 90 °C.

    11. Natural Products

      The Synthesis and Biological Evaluation of Desepoxyisotedanolide and a Comparison with Desepoxytedanolide

      Arun Naini, Dr. Yazh Muthukumar, Dr. Aruna Raja, Dr. Raimo Franke, Ian Harrier, Prof. Dr. Amos B. Smith III, Prof. Dr. Dongjoo Lee, Prof. Dr. Richard E. Taylor, Dr. Florenz Sasse and Prof. Dr. Markus Kalesse

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501526

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      A step in the right direction: Desepoxyisotedanolide, a hypothetical biosynthetic precursor of the tedanolide desepoxytedanolide, was synthesized. Biological studies of the two macrolactones revealed an additional cellular target for desepoxytedanolide, as well as evidence that the proposed isomerization of the precursor provides a survival advantage for the producing microorganism.

    12. Dihydroxylation

      Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols

      Dr. Peter K. Dornan, Zachary K. Wickens and Prof. Robert H. Grubbs

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501505

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      Two steps with one cat.: 1,2-anti-Diols are accessible through a tandem Z-selective cross-metathesis/dihydroxylation using an assisted tandem catalysis protocol. Both steps are catalyzed by the Ru complex, and the stereocontrol of the cross-metathesis is translated through high stereospecificity in the dihydroxylation step to diastereoselectivity for the 1,2-anti-diol.

    13. Lithium-Ion Batteries

      Controllable Synthesis of Mesoporous Peapod-like Co3O4@Carbon Nanotube Arrays for High-Performance Lithium-Ion Batteries

      Dr. Dong Gu, Dr. Wei Li, Fei Wang, Hans Bongard, Bernd Spliethoff, Dr. Wolfgang Schmidt, Dr. Claudia Weidenthaler, Prof. Dr. Yongyao Xia, Prof. Dr. Dongyuan Zhao and Prof. Dr. Ferdi Schüth

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501475

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      Trapped in carbon nanotubes: Size-controllable Co3O4 nanoparticles exclusively confined in the intratubular pores of the carbon nanotube arrays (CMK-5) have been prepared by a nanocasting method with a Co3O4 loading amount of up to 70 wt %. The resultant nanocomposites show excellent performance when used as anode materials for lithium ion batteries.

    14. Bioluminescence

      Novel Mechanism of Bioluminescence: Oxidative Decarboxylation of a Moiety Adjacent to the Light Emitter of Fridericia Luciferin

      Maxim A. Dubinnyi, Zinaida M. Kaskova, Natalja S. Rodionova, Mikhail S. Baranov, Andrey Yu. Gorokhovatsky, Alexey Kotlobay, Kyril M. Solntsev, Aleksandra S. Tsarkova, Valentin N. Petushkov and Ilia V. Yampolsky

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501668

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      Let there be light: The oxyluciferin from the bioluminescent worm Fridericia heliota was isolated and its structure elucidated. The results provide insight into a novel bioluminescence mechanism. Oxidative decarboxylation of a lysine fragment of the luciferin supplies energy for light generation, while a fluorescent CompX moiety remains intact and serves as the light emitter.

    15. Ionic Liquids | Hot Paper

      Potential-Dependent Adlayer Structure and Dynamics at the Ionic Liquid/Au(111) Interface: A Molecular-Scale In Situ Video-STM Study

      Dr. Rui Wen, Björn Rahn and Prof. Dr. Olaf M. Magnussen

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501715

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      Potentially structured: Au (111) electrodes were studied in the room-temperature ionic liquid 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide by high-speed scanning tunneling microscopy. Two distinct transitions in the molecular arrangement of cations at the interface and their sub-second dynamic behavior are observed with decreasing potential.

    16. Cyclo-P5 Complexes

      An Inverted-Sandwich Diuranium μ-η55-Cyclo-P5 Complex Supported by U-P5 δ-Bonding

      Dr. Benedict M. Gardner, Dr. Floriana Tuna, Prof. Eric J. L. McInnes, Dr. Jonathan McMaster, Dr. William Lewis, Prof. Alexander J. Blake and Prof. Stephen T. Liddle

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501728

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      Not your everyday sandwich: Reaction of 1 with P4 affords the unprecedented actinide inverted-sandwich cyclo-P5 complex 2. Theoretical calculations suggest the principal bonding in the U(P5)U unit is two polarized δ-bonds, and combined characterization data suggest charge transfer from uranium to the cyclo-P5 unit to give a cyclo-P5 charge state that approximates to a dianion.

  4. News

  5. Editorials

    1. You have free access to this content
      Chemistry and the Max Planck Society: A Stable Bond Resonating into the Future

      Dr. Christoph Ettl and Prof. Dr. Martin Stratmann

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502721

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      “… The challenge for chemistry is no longer just the synthesis of increasingly complex molecular structures, but to tailor functionalities. Chemistry is at the core of the molecular sciences, reaching out into many other areas. The Max Planck Society is committed to fostering progress in chemistry as one of the key fields of the future …” Read more in the Editorial by Martin Stratmann and Christoph Ettl.

  6. Cover Pictures

    1. Enzymatically Active Ultrathin Pepsin Membranes

      Michiel J. T. Raaijmakers, Thomas Schmidt, Monika Barth, Murat Tutus, Nieck E. Benes and Matthias Wessling

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201503395

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      Ultrathin films of cross-linked enzymes that allow simultaneous enzymatic conversion and selective removal of digestion products are described in the Communication by N. E. Benes, M. Wessling et al. (DOI: 10.1002/anie.201411263). Covalent bonds are formed in an interfacial reaction between the cross-linker and pepsin, thereby producing thin supported membrane films of potentially unlimited surface area. The high water flux through the membranes transports large proteins to the surface, where they are retained and digested.

    2. Potential-Dependent Adlayer Structure and Dynamics at the Ionic Liquid/Au(111) Interface: A Molecular-Scale In Situ Video-STM Study

      Dr. Rui Wen, Björn Rahn and Prof. Dr. Olaf M. Magnussen

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502798

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      Shrouded in mystery, the interface structure of ionic liquids is unclear despite their popularity for electrochemical applications. In their Communication (DOI: 10.1002/anie.201501715), O. M. Magnussen et al. address the molecular arrangement and sub-second dynamics of these iconic compounds on gold electrodes by high-speed tunneling microscopy. With decreasing potential, distinct transitions in the structure and surface mobility of the innermost layer of 1-butyl-1-methylpyrrolidinium cations are found.

  7. Communications

    1. Corannulenes

      Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom

      Dr. Shingo Ito, Yuki Tokimaru and Prof. Kyoko Nozaki

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502599

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      Bowled over: A novel benzene-fused azacorannulene (left) was synthesized by the 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a heteroatom-doped corannulene derivative and in the solid state bowl-in-bowl columnar π-stacking is observed (right).

    2. Homogeneous Catalysis | Hot Paper

      Cobalt-Catalyzed Hydrogenation of Esters to Alcohols: Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy

      Dr. Dipankar Srimani, Dr. Arup Mukherjee, Dr. Alexander F. G. Goldberg, Dr. Gregory Leitus, Dr. Yael Diskin-Posner, Dr. Linda J. W. Shimon, Yehoshoa Ben David and Prof. Dr. David Milstein

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502418

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      Getting involved: The atom-efficient and environmentally benign catalytic hydrogenation of carboxylic acid esters to alcohols has been accomplished in recent years mainly with precious-metal-based catalysts. Presented here is the first cobalt-catalyzed hydrogenation of esters to alcohols. Unexpectedly, the evidence indicates the unprecedented involvement of ester enolate intermediates.

    3. Photonic Crystals

      The Mechanism of Color Change in the Neon Tetra Fish: a Light-Induced Tunable Photonic Crystal Array

      Dvir Gur, Dr. Benjamin A. Palmer, Ben Leshem, Prof. Dan Oron, Prof. Peter Fratzl, Prof. Steve Weiner and Prof. Lia Addadi

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502268

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      Color switch: The physical mechanism of the light-triggered color change in the lateral stripe of the neon tetra is controlled by changing the tilt angle of the guanine crystal arrays. It is shown that the color change can be described by the “Venetian blinds” model.

    4. Electron Microscopy

      Direct Imaging of Octahedral Distortion in a Complex Molybdenum Vanadium Mixed Oxide

      Dr. Thomas Lunkenbein, Dr. Frank Girgsdies, Anna Wernbacher, Dr. Johannes Noack, Dr. Gudrun Auffermann, Akira Yasuhara, Achim Klein-Hoffmann, Prof. Wataru Ueda, Dr. Maik Eichelbaum, Dr. Annette Trunschke, Prof. Robert Schlögl and Dr. Marc G. Willinger

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502236

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      ABF-STEM (annular bright field scanning transmission electron microscopy) was used to study a beam-sensitive (Mo,V) mixed oxide. The recorded micrographs show the oxygen sublattice and directly reveal the local distortion in the metal–oxygen octahedra. From the observed distortion, conclusions on the oxidation state of each metal site can be drawn just by looking at the atomic arrangement.

    5. Asymmetric Synthesis

      Enzymatic Chemoselective Aldehyde–Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin

      Dr. Giovanni Bernacchia, Prof. Olga Bortolini, Dr. Morena De Bastiani, Dr. Lindomar Alberto Lerin, Dr. Sabrina Loschonsky, Prof. Alessandro Massi, Prof. Dr. Michael Müller and Dr. Pier Paolo Giovannini

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502102

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      Enzyme catalysis: The substrate scope of the thiamine diphosphase (ThDP)-dependent acetoin:dichlorophenolindophenol oxidoreductase (Ao:DCPIP OR) has been extended to the aldehyde–ketone carboligation reaction. The use of methylacetoin as the acetyl anion donor allows a complete control of the chemoselectivity. Some of the resulting tertiary alcohols displayed stereochemistry opposite to that obtained with other ThDP-dependent enzymes.

    6. Cooperative Catalysis

      Enantioselective Syntheses of Heteroyohimbine Natural Products: A Unified Approach through Cooperative Catalysis

      Ashkaan Younai, Bi-Shun Zeng, Herbert Y. Meltzer and Karl A. Scheidt

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502011

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      The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

    7. Enzyme Catalysis

      Unprecedented Mechanism Employed by the Salmonella enterica EutT ATP:CoIrrinoid Adenosyltransferase Precludes Adenosylation of Incomplete CoIIrrinoids

      Dr. Kiyoung Park, Dr. Paola E. Mera, Theodore C. Moore, Dr. Jorge C. Escalante-Semerena and Dr. Thomas C. Brunold

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501930

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      Being specific: Compelling evidence has been found that EutT catalyzes the thermodynamically challenging reduction of CoIIrrinoids to form “supernucleophilic” CoI intermediates by a different mechanism to other ATP:corrinoid adenosyltransferases. Spectroscopic, kinetics, and bioassay results suggest that EutT converts cob(II)alamin into an effectively four-coordinate CoII species to facilitate CoII[RIGHTWARDS ARROW]CoI reduction (DMB=5,6-dimethylbenzimidazole).

  8. Author Profiles

    1. Jianwei Sun

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201502973

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      If I were not a scientist, I would be a peasant leading a carefree life. My favorite food is Chinese chives stir-fried with egg.

  9. Communications

    1. Coatings

      Graft-Copolymer-Based Approach to Clear, Durable, and Anti-Smudge Polyurethane Coatings

      Dr. Muhammad Rabnawaz and Prof. Guojun Liu

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501360

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      No more smudges: A graft-copolymer-based approach was used to prepare clear polyurethane coatings that repel water, diiodomethane, hexadecane, ink, and an artificial fingerprint liquid. Different coating methods can be used to apply the coatings to different surfaces, which can thus be protected from fingerprints, stains, and graffiti.

    2. Cancer Immunotherapy

      Multiformat T-Cell-Engaging Bispecific Antibodies Targeting Human Breast Cancers

      Dr. Yu Cao, Dr. Jun Y. Axup, Dr. Jennifer S. Y. Ma, Dr. Rongsheng E. Wang, Dr. Seihyun Choi, Dr. Virginie Tardif, Dr. Reyna K. V. Lim, Holly M. Pugh, Dr. Brian R. Lawson, Gus Welzel, Dr. Stephanie A. Kazane, Dr. Ying Sun, Dr. Feng Tian, Shailaja Srinagesh, Dr. Tsotne Javahishvili, Prof. Peter G. Schultz and Dr. Chan Hyuk Kim

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201500799

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      Bispecific antibodies are highly effective for targeting breast cancer cells with antigens of low abundance. It is suggested that the monovalent BiFab in the absence of an Fc domain may be the best bispecific antibody format to trigger antigen-dependent T-cell activation and target tumor eradication for low or heterogeneous Her2-expressing cancers.

    3. Nanotechnology

      An Organic Microlaser Array Based on a Lateral Microcavity of a Single J-aggregation Microbelt

      Dr. Qing Liao, Xue Jin, Haihua Zhang, Dr. Zhenzhen Xu, Prof. Jiannian Yao and Prof. Hongbing Fu

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501060

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      Array of light: A low-threshold lateral-cavity organic microlaser based on a single-crystalline organic microbelt has been developed. By cutting a single microbelt into six pieces by a top-down two-photon processing technique, a compact and uniform 1×6 microlaser array with excellent reproducibility and addressable high precision was also successfully fabricated, which could be used in future miniaturized coherent light sources and nanophotonics.

    4. Donor–Acceptor Systems

      Polyimide Dendrimers Containing Multiple Electron Donor–Acceptor Units and Their Unique Photophysical Properties

      Dr. Francesca M. Toma, Dr. Fausto Puntoriero, Dr. Toan V. Pho, Marcello La Rosa, Dr. Young-Si Jun, Dr. Bertrand J. Tremolet de Villers, James Pavlovich, Prof. Galen D. Stucky, Prof. Sebastiano Campagna and Prof. Fred Wudl

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501298

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      Quick as a flash: New polyimide dendrimers exhibiting rich photophysical properties have been synthesized. For example, in one of the new species, two different charge-separated states can be obtained on the femtosecond timescale. Such charge-separated states independently decay on the picosecond timescale.

    5. Water Reduction with Cobalt Oximes

      Distinct Proton and Water Reduction Behavior with a Cobalt(III) Electrocatalyst Based on Pentadentate Oximes

      Debashis Basu, Dr. Shivnath Mazumder, Xuetao Shi, Dr. Richard J. Staples, Prof. H. Bernhard Schlegel and Prof. Cláudio N. Verani

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501410

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      A pentadentate oxime is used for the construction of a new cobalt catalyst, which drives the preferential coordination favored by CoI catalysts in proton/water reduction. This species evolves H2 in the presence of weak acids in MeCN. Superior catalysis is also observed in water, however, the molecular catalyst yields Co-based nanoparticles.

    6. Polymer Assembly

      Crystalline Hetero-Stereocomplexed Polycarbonates Produced from Amorphous Opposite Enantiomers Having Different Chemical Structures

      Dr. Ye Liu, Meng Wang, Wei-Min Ren, Yue-Chao Xu and Prof. Dr. Xiao-Bing Lu

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201501417

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      Mixed enantiomers: A unique strategy for polymer assembly was demonstrated through the formation of crystalline hetero-stereocomplexed polymeric materials by the cocrystallization of amorphous isotactic polycarbonates with opposite configurations and different chemical structures. This study is expected to open up a new way to prepare various semicrystalline materials with a wide variety of physical properties and degradability.

    7. Ammine Borates

      High-Pressure Synthesis of Cd(NH3)2[B3O5(NH3)]2: Pioneering the Way to the Substance Class of Ammine Borates

      M. Sc. Gerhard Sohr, Mag. Nina Ciaghi, M. Sc. Michael Schauperl, Dr. Klaus Wurst, Prof. Dr. Klaus R. Liedl and Prof. Dr. Hubert Huppertz

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201500706

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      Ammonize me! The first compound in the class of ammine borates has been synthesized by a multi-anvil high-pressure/high-temperature experiment. The previously unknown adduct of ammonia to an inorganic BO3 group of a borate can be stabilized with this method, resulting in a BO3(NH3) tetrahedron as a new structural element.

    8. DNA Nanostructures

      Assembly and Purification of Enzyme-Functionalized DNA Origami Structures

      Christopher Timm and Prof. Dr. Christof M. Niemeyer

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201500175

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      A functional art form: The efficient separation of enzyme-decorated DNA origami structures from unbound proteins by free-flow electrophoresis (FFE; see picture) enabled a differentiated assessment of the activity of origami-tethered and non-DNA-bound enzymes. It was found that enzyme arranged on origami structures were more active than the free enzymes.

  10. Reviews

    1. Patient Diagnostics

      From the Bench to the Field in Low-Cost Diagnostics: Two Case Studies

      Dr. Ashok A. Kumar, Dr. Jonathan W. Hennek, Dr. Barbara S. Smith, Dr. Shailendra Kumar, Patrick Beattie, Sidhartha Jain, Dr. Jason P. Rolland, Dr. Thomas P. Stossel, Dr. Catherine Chunda-Liyoka and Prof. George M. Whitesides

      Article first published online: 27 APR 2015 | DOI: 10.1002/anie.201411741

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      Fielding questions: This Review shares lessons from two case studies in the development of point-of-care tests: a colorimetric, paper-based liver function test using serum transaminases (left), and a test for sickle cell disease using aqueous multiphase systems and differences in the density of red blood cells characteristic of sickle cell disease (right).

  11. Communications

    1. Hydrosilylation

      Chemoselective Silylative Reduction of Conjugated Nitriles under Metal-Free Catalytic Conditions: β-Silyl Amines and Enamines

      Dr. Narasimhulu Gandhamsetty, Juhyeon Park, Jinseong Jeong, Dr. Sung-Woo Park, Dr. Sehoon Park and Prof. Dr. Sukbok Chang

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502366

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      Triple whammy: The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. Based on the mechanistic understanding, a preparative route to enamines was also established using bulky silanes. The reaction is chemoselective, has a broad scope, and proceeds under mild reaction conditions. The mechanism of the triple hydrosilylation is discussed.

    2. Lewis Pairs

      Elusive Silane⋅Alane Complex [Si[BOND]H⋅⋅⋅Al]: Isolation, Characterization, and Multifaceted Frustrated-Lewis-Pair-Type Catalysis

      Dr. Jiawei Chen and Prof. Dr. Eugene Y.-X. Chen

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502400

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      Al does it all: The elusive silane–alane complex [Si[BOND]H⋅⋅⋅Al] was isolated and structurally characterized by spectroscopic and X-ray diffraction methods. The Janus-like nature of this adduct, coupled with strong silane activation, effects multifaceted frustrated-Lewis-pair-type catalysis. Its use in four different reactions is described.

    3. Helical Structures | Very Important Paper

      One-Step Synthesis of [16]Helicene

      Kazuyuki Mori, Dr. Takashi Murase and Prof. Dr. Makoto Fujita

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502436

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      An aromatic spiral layer: A [16]helicene core was prepared in a single step by sextuple photocyclization from a single-strand arylene–vinylene precursor containing four phenylene and three naphthylene units linked by six vinylene spacers. X-ray crystallographic analysis revealed the triple-layered structure. A new guideline for the design of precursor olefins resulted in the longest helicene synthesized to date.

    4. C[BOND]H Activation

      Rhodium-Catalyzed Enantioselective Intramolecular C[BOND]H Silylation for the Syntheses of Planar-Chiral Metallocene Siloles

      Dr. Qing-Wei Zhang, Kun An, Li-Chuan Liu, Yuan Yue and Prof. Dr. Wei He

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502548

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      New on the (metallo)cene: The title reaction of cyclopentadiene (Cp) rings in Fe and Ru metallocenes is reported. Fine-tuning the steric hindrance of diphosphine ligands led to the identification of (S)-TMS-Segphos [(S)-L], which enabled efficient, enantioselective C[BOND]H silylation of the Cp rings in metallocenes under mild reaction conditions. cod=1,5-cyclooctadiene, TMS=trimethylsilyl.

    5. Liquid Crystals | Very Important Paper

      A Planarized Triphenylborane Mesogen: Discotic Liquid Crystals with Ambipolar Charge-Carrier Transport Properties

      Dr. Tomokatsu Kushida, Ayumi Shuto, Prof. Dr. Masafumi Yoshio, Prof. Dr. Takashi Kato and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502678

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      B planar, B aligned: A planarized triphenylborane, bearing three 3,4,5-tridodecyloxyphenyl groups, forms a hexagonal columnar liquid-crystalline phase at ambient temperature. It has a columnar π-stacked structure and ambipolar carrier-transport properties with hole- and electron-mobility values of 3×10−5 cm2 V−1 s−1 and approximately 10−3 cm2 V−1 s−1, respectively.

    6. Porous Materials

      Porous Carbon Fibers Containing Pores with Sizes Controlled at the Ångstrom Level by the Cavity Size of Pillar[6]arene

      Dr. Tomoki Ogoshi, Kumiko Yoshikoshi, Ryuta Sueto, Dr. Hirotomo Nishihara and Prof. Tada-aki Yamagishi

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501854

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      The hole story: Two dimensional (2D) supramolecular polymerization of pillar[6]arenes afforded hexagonal 2D porous sheets. Carbonization of these sheets gives a carbon material containing pores with a size that is precisely controlled at the Ångstrom level by the cavity size of the precursor pillar[6]arene.

    7. Reaction Mechanisms

      You have full text access to this OnlineOpen article
      Rate and Equilibrium Constants for the Addition of N-Heterocyclic Carbenes into Benzaldehydes: A Remarkable 2-Substituent Effect

      Dr. Christopher J. Collett, Dr. Richard S. Massey, Dr. James E. Taylor, Oliver R. Maguire, Dr. AnnMarie C. O'Donoghue and Prof. Andrew D. Smith

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501840

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      It takes 2-: Measurement of rate and equilibrium constants for the reaction between N-aryl triazolium NHC precatalysts and substituted benzaldehydes under catalytic and stoichiometric conditions demonstrate the remarkable kinetic and thermodynamic effect of the benzaldehyde 2-substituent in these reactions, potentially providing insight into the chemoselectivity of cross-benzoin reactions.

    8. Hydrogen Production | Hot Paper

      Micromotor-Based Energy Generation

      Dr. Virendra V. Singh, Fernando Soto, Kevin Kaufmann and Prof. Joseph Wang

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501971

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      Fuel metal jacket: Micromotors give enhanced energy generation by the movement of Pt-black/Ti Janus microparticles in liquid-phase chemical fuel. The autonomous motion of these micromotors leads to enhanced mixing and transport of NaBH4 fuel compared to static microparticles or films, and hence to a substantially faster hydrogen-generation rate. The practical utility is illustrated by powering a hydrogen–oxygen fuel cell car.

    9. Interfacial Chemistry

      Tuning the Metal–Support Interaction by Structural Recognition of Cobalt-Based Catalyst Precursors

      Kim Larmier, Dr. Céline Chizallet and Dr. Pascal Raybaud

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502069

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      The interaction of cobalt-based catalyst precursors with γ-alumina and amorphous silica-alumina surfaces was investigated by means of DFT calculations. A structural recognition between the surface and the precursor could be evidenced. A model for the growth of the experimentally observed β-Co(OH)2 on the surface could be proposed from those calculations.

    10. Ceric Ammonium Nitrate (CAN)

      Revisiting the Solution Structure of Ceric Ammonium Nitrate

      Dr. Thomas J. Demars, Dr. Mrinal K. Bera, Dr. Soenke Seifert, Dr. Mark R. Antonio and Dr. Ross J. Ellis

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201502336

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      What CAN it be? The solution structure of ceric ammonium nitrate (CAN)—a vital chemical feedstock in organic synthesis—is revisited, challenging a half-century-old assertion with a radically different model. In nitric acid solutions a dinuclear oxo bridged structure is found, suggesting CAN is able to act as a two-electron transfer reagent, and not as generally assumed a one-electron transfer reagent.

    11. Biological Activity

      Neuritogenic Militarinone-Inspired 4-Hydroxypyridones Target the Stress Pathway Kinase MAP4K4

      Dr. Peter Schröder, Dipl.-Biol. Tim Förster, M. Sc. Stefan Kleine, M. Sc. Christian Becker, Dr. André Richters, Dr. Slava Ziegler, Prof. Dr. Daniel Rauh, Dr. Kamal Kumar and Prof. Dr. Herbert Waldmann

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501515

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      No stress: Reported herein is the synthesis of a militarinone-inspired 4-hydroxy-2-pyridone collection, its investigation for enhancement of neurite outgrowth, and the discovery of the stress pathway kinase MAP4K4 as a target of the discovered neuritogenic pyridones. The findings support the notion that MAP4K4 may be a new target for the treatment of neurodegenerative diseases.

    12. Gold Complexes

      Synthesis and Characterization of a Gold Vinylidene Complex Lacking π-Conjugated Heteroatoms

      Robert J. Harris and Prof. Ross A. Widenhoefer

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501474

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      Good as gold: Cationic gold (β,β-disilyl)vinylidene complex 1 was generated by addition of a pendant silylium ion to the C[TRIPLE BOND]C bond of a gold acetylide complex (see scheme, P=PtBu2(o-biphenyl)). The vinylidene C1 and C2 atoms of 1 undergo facile interconversion, presumably via a π-disilacyclohexyne intermediate. 29Si NMR analysis of 1 indicates delocalization of positive charge onto both the β-silyl groups and the (P)Au fragment.

    13. Asymmetric Catalysis

      Catalytic Enantioselective Synthesis of N,Cα,Cα-Trisubstituted α-Amino Acid Derivatives Using 1H-Imidazol-4(5H)-ones as Key Templates

      Julen Etxabe, Joseba Izquierdo, Dr. Aitor Landa, Prof. Mikel Oiarbide and Prof. Claudio Palomo

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501275

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      A BB method: 1H-imidazol-4(5H)-ones serve as effective and easily available α-amino acid surrogates for the catalytic and highly diastereo- and enantioselective direct construction of N-substituted quaternary α-amino acid derivatives. The reaction is catalyzed by a Brønsted base (BB) and proceeds with different Michael acceptors. EWG=electron-withdrawing group.

    14. Natural Product Synthesis

      Asymmetric Total Synthesis of Mycoleptodiscin A

      Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Prof. Dr. Ang Li

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501021

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      The first and enantioselective total synthesis of mycoleptodiscin A (see picture), a structurally unusual indolosesquiterpenoid, is accomplished by using iridium-catalyzed polyene cyclization and copper-mediated C[BOND]N bond forming reactions as key steps.

    15. Organocatalysis

      Design, Synthesis, and Application of a Chiral Sulfinamide Phosphine Catalyst for the Enantioselective Intramolecular Rauhut–Currier Reaction

      Xiao Su, Wei Zhou, Yangyan Li and Prof. Dr. Junliang Zhang

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201500907

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      Xiao-Phos: A new class of chiral sulfinamide phosphine catalyst was developed. These Xiao-Phos catalysts can be prepared from inexpensive commercially available starting materials and show good performance in the enantioselective intramolecular Rauhut–Currier reaction under mild conditions. Moreover, kinetic resolution was also observed with the use of two different substituted racemic precursors.

    16. Radical Frameworks

      Radical Covalent Organic Frameworks: A General Strategy to Immobilize Open-Accessible Polyradicals for High-Performance Capacitive Energy Storage

      Fei Xu, Hong Xu, Xiong Chen, Prof. Dr. Dingcai Wu, Yang Wu, Hao Liu, Dr. Cheng Gu, Prof. Dr. Ruowen Fu and Prof. Dr. Donglin Jiang

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201501706

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      Efficient energy storage: A facile strategy for converting a conventional covalent organic framework into outstanding energy storage materials is described. The channel walls are provided with organic radicals in a controlled manner to achieve immobilized openly accessible polyradicals, leading to the development of a new facile and general way to design COFs for high-performance electrochemical energy storage.

    17. RNA Structures | Hot Paper

      Targeted Detection of G-Quadruplexes in Cellular RNAs

      Dr. Chun Kit Kwok and Prof. Shankar Balasubramanian

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201500891

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      Hunting G4s: This study describes a new approach for detecting and mapping RNA G-quadruplexes (G4) in low-abundance cellular transcripts by coupling reverse transcriptase stalling (RTS) and an amplification strategy (HBLMPCR). Rational control of RNA G4-mediated RTS can be achieved by exploiting RNA G4–cation and RNA G4–ligand interactions, as well as use a selective reverse transcriptase for monitoring purposes.

    18. C[BOND]H Activation

      Isomerization of Olefins Triggered by Rhodium-Catalyzed C[BOND]H Bond Activation: Control of Endocyclic β-Hydrogen Elimination

      Stephanie Y. Y. Yip and Dr. Christophe Aïssa

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201500596

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      Control of endocyclic β-H elimination of a pivotal five-membered metallacycle enables the rhodium-catalyzed isomerization of 4-pentenals into 3-pentenals without decarbonylation and leads to trans olefins with exquisite selectivity. Other sensitive olefins, even if prone to isomerization, remain intact. Endocyclic β-H elimination can also be prevented, in which case an enantiodivergent reaction on the racemic substrate was observed.

    19. Energy Conversion

      Dye-Controlled Interfacial Electron Transfer for High-Current Indium Tin Oxide Photocathodes

      Zhongjie Huang, Mingfu He, Mingzhe Yu, Kevin Click, Damian Beauchamp and Prof. Yiying Wu

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201500274

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      ITO as a photocathode: The scarcity of optimal p-type semiconductors has hindered the development of efficient photocathodes for dye-sensitized solar cells and photoelectrosynthesis cells. Mesoporous indium tin oxide (ITO), an n-type degenerated semiconductor, can generate remarkably high cathodic currents after sensitization by energy-aligned cyclometalated RuII complexes. Studies into the mechanism indicate hole injection from the excited dye.

    20. Heterocycles

      Organocatalyzed CO2 Trapping Using Alkynyl Indoles

      Dr. Zhuo Xin, Dr. Camille Lescot, Dr. Stig D. Friis, Prof. Dr. Kim Daasbjerg and Prof. Dr. Troels Skrydstrup

      Article first published online: 23 APR 2015 | DOI: 10.1002/anie.201500233

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      Caught in a trap: The first trapping of CO2 through organocatalyzed C[BOND]C and C[BOND]O bond formation is reported. By using alkynyl indoles, this method generates novel indole lactone derivatives by using as little as 5 mol % of the simple organic base 1,5,7-triazabicyclo-[4.4.0]dec-5-ene as an organocatalyst. The transformation shows excellent atom economy and a broad substrate scope, including aromatic, heteroaromatic, and aliphatic 2-alkynyl indoles.

    21. Bolaamphiphiles

      Hydrogen-Bond-Regulated Distinct Functional-Group Display at the Inner and Outer Wall of Vesicles

      Amrita Sikder, Dr. Anindita Das and Dr. Suhrit Ghosh

      Article first published online: 21 APR 2015 | DOI: 10.1002/anie.201500971

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      The unidirectional assembly of two bola-shaped unsymmetric π-amphiphiles that feature a naphthalene–diimide chromophore connected to nonionic and anionic head groups on opposite arms is enabled by the formation of hydrogen bonds. These interactions fully compensate for electrostatic repulsion and induce the curvature of the bolaamphiphiles, which leads to monolayer vesicles with different surface functionalities and enzyme inhibition abilities.

    22. Donor–Acceptor Systems

      Revealing the Charge-Transfer Interactions in Self-Assembled Organic Cocrystals: Two-Dimensional Photonic Applications

      Weigang Zhu, Dr. Renhui Zheng, Xiaolong Fu, Prof. Hongbing Fu, Prof. Qiang Shi, Dr. Yonggang Zhen, Dr. Huanli Dong and Prof. Wenping Hu

      Article first published online: 20 APR 2015 | DOI: 10.1002/anie.201501414

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      Crystal clear: A new crystal of a donor–acceptor (D–A) complex was prepared and it has a two-dimensional morphology. The charge-transfer interactions were fully investigated. This organic cocrystal has unique two-dimensional optical waveguide properties, and has potential applications in next-generation optoelectronic communications.

    23. Synthetic Methods

      Hydroxy-Directed, Fluoride-Catalyzed Epoxide Hydrosilylation for the Synthesis of 1,4-Diols

      Dr. Yong-Qiang Zhang, Nico Funken, Peter Winterscheid and Prof. Dr. Andreas Gansäuer

      Article first published online: 20 APR 2015 | DOI: 10.1002/anie.201501729

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      A modular, convergent, and stereoselective synthesis of 1,4-diols by epoxide hydrosilylation has been developed (see scheme). The reaction occurs under fluoride catalysis, is high yielding, highly regioselective, and can be carried out on a large scale.

    24. Hybrid Materials | Hot Paper

      Polyoxometalate Complexes of Anatase-Titanium Dioxide Cores in Water

      Dr. Manoj Raula, Gal Gan Or, Marina Saganovich, Dr. Offer Zeiri, Prof. Yifeng Wang, Dr. Michele R. Chierotti, Prof. Roberto Gobetto and Prof. Ira A. Weinstock

      Article first published online: 20 APR 2015 | DOI: 10.1002/anie.201501941

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      Redox-active ligands for TiO2: Polyoxometalate (POM) electron acceptors serve as covalently coordinated inorganic ligands for anatase-TiO2 nanocrystals, giving assemblies positioned between molecular macroanions and traditional colloidal nanoparticles. The POM ligands have tunable redox potentials, providing options for controlling reactions of soluble metal oxide semiconductor nanocrystals.

    25. Water Splitting

      Electrodeposited Cobalt-Phosphorous-Derived Films as Competent Bifunctional Catalysts for Overall Water Splitting

      Nan Jiang, Dr. Bo You, Meili Sheng and Dr. Yujie Sun

      Article first published online: 20 APR 2015 | DOI: 10.1002/anie.201501616

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      Split and polished: Electrodeposited cobalt-phosphorous-derived films (Co-P) can act as superior bifunctional catalysts for overall water splitting. When employed as catalysts on both the anode and cathode for water electrolysis, the Co-P/Co-P catalyst couple can rival the integrated performance of IrO2 and Pt in alkaline media. Such a bifunctional Co-P film is a promising catalyst candidate for overall water-splitting electrolysis.

    26. DNA Nanotechnology

      Folding and Imaging of DNA Nanostructures in Anhydrous and Hydrated Deep-Eutectic Solvents

      Dr. Isaac Gállego, Prof. Martha A. Grover and Prof. Nicholas V. Hud

      Article first published online: 20 APR 2015 | DOI: 10.1002/anie.201412354

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      Who needs water? DNA structures, such as a two-dimensional DNA origami, can be folded in an anhydrous deep-eutectic solvent composed of glycerol and choline chloride (“glycholine”). In hydrated glycholine, folding is accelerated, and more complex nanostructures can be isothermally folded, demonstrating that DNA self-assembly kinetics can be tuned by changing solvent viscosity.

    27. Enzyme Catalysis

      Reshaping an Enzyme Binding Pocket for Enhanced and Inverted Stereoselectivity: Use of Smallest Amino Acid Alphabets in Directed Evolution

      Dr. Zhoutong Sun, Dr. Richard Lonsdale, Xu-Dong Kong, Prof. Jian-He Xu, Prof. Jiahai Zhou and Prof. Dr. Manfred T. Reetz

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201501809

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      Emil Fischer’s lock-and-key hypothesis has been revisited in experiments to reshape the binding pocket of limonene epoxide hydrolase (see picture) by using a single amino acid building block in the saturation mutagenesis of a 10-residue site. Catalytic variants selective for the formation of both (R,R)- and (S,S)-1,2-cyclohexanediol in the hydrolytic desymmetrization of cyclohexene oxide were identified in one and the same mutant library.

    28. Natural Products

      Total Synthesis of Diterpenoid Steenkrotin A

      Saiyong Pan, Jun Xuan, Beiling Gao, An Zhu and Prof. Dr. Hanfeng Ding

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502034

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      Work of steen: A concise and diastereoselective total synthesis of the diterpenoid (±)-steenkrotin A is reported for the first time. The key features of the strategy are based on a rhodium-catalyzed O[BOND]H bond insertion, an intramolecular carbonyl-ene reaction, sequential SmI2-mediated Ueno–Stork and ketyl–olefin cyclizations, and a cascade intramolecular aldol condensation/vinylogous retro-aldol/aldol process.

    29. Photocatalysis

      Controlling the Selectivity of the Surface Plasmon Resonance Mediated Oxidation of p-Aminothiophenol on Au Nanoparticles by Charge Transfer from UV-excited TiO2

      Dr. Jiale Wang, Prof. Dr. Romulo A. Ando and Prof. Dr. Pedro H. C. Camargo

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502077

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      Controlling selectivity: The selectivity of the surface plasmon resonance (SPR) mediated oxidation of p-aminothiophenol was controlled by the choice of catalysts (Au or TiO2-Au nanoparticles; NPs) and by the modulation of the charge transfer from UV-excited TiO2 to Au. While p,p-dimercaptobenzene was obtained using Au NPs as catalyst, the use of TiO2-Au NPs under both UV illumination and SPR excitation led to the formation of p-nitrophenol.

    30. Electrochemistry

      High-Yield Electrosynthesis of Hydrogen Peroxide from Oxygen Reduction by Hierarchically Porous Carbon

      Yanming Liu, Prof. Xie Quan, Xinfei Fan, Dr. Hua Wang and Dr. Shuo Chen

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502396

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      The electroreduction of O2 is achieved with hierarchically porous carbon (HPC) to give H2O2. It exhibits good selectivity, high production rate and current efficiency for the electrosynthesis of H2O2 at a wide range of pH values. The correlation between H2O2 production rate and sp3-C atoms and defects was explored. This provides an effective method for tuning the activity of carbon materials for the selective electrosynthesis of H2O2. RE=reference electrode.

  12. Cover Pictures

    1. You have free access to this content
      Designed Enclosure Enables Guest Binding Within the 4200 Å3 Cavity of a Self-Assembled Cube

      William J. Ramsay, Filip T. Szczypiński, Dr. Haim Weissman, Dr. Tanya K. Ronson, Maarten M. J. Smulders, Dr. Boris Rybtchinski and Prof. Jonathan R. Nitschke

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502796

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      Designing large metal–organic hosts whose cavities are sufficiently differentiated from the solvent environment to enable guest binding is a challenge. In their Communication (DOI: 10.1002/anie.201501892), J. R. Nitschke et al. report a rational strategy that allows the size of a self-assembled cube to be increased whilst maintaining an enclosed cavity capable of binding a variety of mono- and dianionic guests. The degree of cavity occupancy appears less important than cavity enclosure and Coulombic effects.

    2. You have free access to this content
      How a Zigzag Carbon Nanotube Grows

      Dr. Qinghong Yuan and Prof. Dr. Feng Ding

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201503234

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      The ultra-slow growth of zigzag (ZZ) carbon nanotubes (CNTs) on nanoparticle catalysts can be explained by studying the unique kinetics of ZZ CNT growth. The underlying growth mechanism is revealed by Q. Yuan and F. Ding in their Communication (10.1002/anie.201500477). Understanding the mechanism enables an experimental route to maximize the synthesis of the very rare ZZ CNTs to be identified.

  13. Highlights

    1. RNA Interference

      Tumor-targeted Delivery of Anti-microRNA for Cancer Therapy: pHLIP is Key

      Prof. Dr. Ernst Wagner

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502146

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      pHLIP opens the door to the cell: An improved cytosolic transfer of anti-microRNAs (anti-miRs) against onco-miRs paves the way for future cancer therapies. The employed anti-miR–peptide conjugates are based on peptide nucleic acids (PNAs), which are connected with the membrane translocation peptide pHLIP through a disulfide bond. The PNAs are thus transferred into the cell and released by the cleavage of the S[BOND]S bond (see scheme).

  14. Communications

    1. Electrochemistry

      Radical Compatibility with Nonaqueous Electrolytes and Its Impact on an All-Organic Redox Flow Battery

      Dr. Xiaoliang Wei, Dr. Wu Xu, Dr. Jinhua Huang, Dr. Lu Zhang, Dr. Eric Walter, Dr. Chad Lawrence , Dr. M. Vijayakumar, Dr. Wesley A. Henderson, Dr. Tianbiao Liu, Dr. Lelia Cosimbescu, Dr. Bin Li, Dr. Vincent Sprenkle and Dr. Wei Wang

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201501443

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      Picky radical redox species: The choice of both solvent and salt used in the supporting electrolyte is found to greatly affect the cycling stability of nonaqueous all-organic flow chemistry because of substantial variations in the chemical stability of the charged radical redox species. This mechanistic understanding articulates the significance of electrolyte optimization for achieving performance improvements for nonaqueous redox flow batteries.

  15. Book Reviews

    1. N-Heterocyclic Carbenes. Effective Tools for Organometallic Synthesis. Edited by Steven P. Nolan

      Martin Albrecht

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502195

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      , Wiley-VCH, Weinheim 2014. 568 pp., € 149.00.—ISBN 978-3527334902

  16. Author Profiles

    1. Shao Q. Yao

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201502764

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      My favorite author (fiction) is Dan Brown. My favorite motto is “Do your best”.

  17. Communications

    1. Mass Spectrometry

      On-demand Ambient Ionization of Picoliter Samples using Charge Pulses

      Dr. Anyin Li, Adam Hollerbach, Qingjie Luo and Prof. R. Graham Cooks

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201501895

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      Relay electrospray ionization (rESI) from a capillary containing a sample solution (or from an array of such capillaries) is triggered by charge deposition onto the capillary. With no requirement for physical contact, high-throughput sample screening is enabled by rapidly addressing individual secondary (sample) capillaries. Subpicoliter sample volumes can be loaded and sprayed.

    2. Supramolecular Chemistry | Very Important Paper

      High-Fidelity Noncovalent Synthesis of Hydrogen-Bonded Macrocyclic Assemblies

      Carlos Montoro-García, Jorge Camacho-García, Dr. Ana M. López-Pérez, Nerea Bilbao, Sonia Romero-Pérez, Dr. María J. Mayoral and Dr. David González-Rodríguez

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201501321

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      Fine design of a dinucleoside monomer leads to hydrogen-bonded macrocyclic tetramer assemblies with high effective molarities and remarkable thermodynamic and kinetic stability. The behavior of these assemblies in various solvents is discussed.

    3. Topology Transformation

      Star/Linear Polymer Topology Transformation Facilitated by Mechanical Linking of Polymer Chains

      Dr. Daisuke Aoki, Dr. Satoshi Uchida and Prof. Dr. Toshikazu Takata

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201500578

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      From star to linear: A rotaxane-linked arm-containing star polymer, formed by the attractive interaction of ammonium and crown ether groups, was transformed to a linear polymer by the removal of the attractive interaction by the N-acetylation of the ammonium moiety. The polymer component linked to the wheel component of the rotaxane linkage moves to the urethane terminal, thereby changing its shape.

    4. Colloidal Crystals

      Non-Brownian Particle-Based Materials with Microscale and Nanoscale Hierarchy

      Melissa H. Lash, Jahnelle C. Jordan, Laura C. Blevins, Dr. Morgan V. Fedorchak, Dr. Steven R. Little and Dr. Joseph J. McCarthy

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201500273

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      Non-Brownian microparticle mixtures are assembled into unique multicomponent colloidal crystals and their inverse structures. By mimicking the effects of Brownian motion through agitation and tuning of the particle sizes and volume ratios, unique stoichiometric patterns are created and can serve as an analogue to autonomously formed nanostructures.

    5. Dendrimeric siRNA

      Dendrimeric siRNA for Efficient Gene Silencing

      Dr. Cheol Am Hong, Dr. Ahmed A. Eltoukhy, Prof. Hyukjin Lee, Prof. Robert Langer, Prof. Daniel G. Anderson and Prof. Yoon Sung Nam

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201412493

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      Self-assembly of siRNA molecules provides precisely controlled generation of dendrimeric siRNA nanostructures. The second-generation dendrimers can be complexed with a low-molecular-weight cationic polymer (PBAE) to generate stable nanostructures (ca. 160 nm diameter) by electrostatic interactions. Condensation and gene silencing efficiencies increase with increased generations of siRNA dendrimers owing to high charge density and structural flexibility.

    6. Heterometallic Cages

      [CrIII8MII6]12+ Coordination Cubes (MII=Cu, Co)

      Dr. Sergio Sanz, Helen M. O'Connor, Eufemio Moreno Pineda, Dr. Kasper S. Pedersen, Dr. Gary S. Nichol, Dr. Ole Mønsted, Dr. Høgni Weihe, Dr. Stergios Piligkos, Prof. Eric J. L. McInnes, Dr. Paul J. Lusby and Prof. Euan K. Brechin

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201501041

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      All about cubes: [CrIII8MII6]12+ (M=Cu, Co) cubes were constructed from a simple [CrIIIL3] metalloligand and a “naked” MII salt. The flexibility in the design proffers the potential to tune the physical properties, as all the constituent parts of the cage can be changed without structural alteration. Statistical and EPR spectroscopy were used to interpret the magnetic behavior.

    7. Energy-Storage Devices

      Aqueous Manganese Dioxide Ink for Paper-Based Capacitive Energy Storage Devices

      Jiasheng Qian, Huanyu Jin, Dr. Bolei Chen, Mei Lin, Dr. Wei Lu, Dr. Wing Man Tang, Dr. Wei Xiong, Prof. Lai Wa Helen Chan, Prof. Shu Ping Lau and Dr. Jikang Yuan

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201501261

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      Printing the future: A simple chemical reduction method has been used to synthesize aqueous MnO2 ink that exhibits long-term stability and can form continuous thin films on various substrates without the need for any binder. The as-prepared MnO2 ink can also be coated onto conductive A4 paper to form capacitive energy storage devices.

    8. Phosphorus Ring Systems

      Low-Temperature Isolation of the Bicyclic Phosphinophosphonium Salt [Mes*2P4Cl][GaCl4]

      Jonas Bresien, Kirill Faust, Prof. Dr. Axel Schulz and Dr. Alexander Villinger

      Article first published online: 17 APR 2015 | DOI: 10.1002/anie.201500892

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      Bicycle ride: The first bicyclic triphosphinophosphonium cation was synthesized from dichlorocyclotetraphosphane [ClP(μ-PMes*)]2 and Lewis acid GaCl3 at low temperatures (see scheme). The reaction proceeds via a highly reactive tetraphosphenium intermediate, which was trapped by reaction with dimethylbutadiene (dmb).

  18. Author Profiles

    1. Ross A. Widenhoefer

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201502598

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      I advise my students to to work hard and not to accept mediocrity. Chemistry is fun because you can make a career out of your favorite hobby.

  19. Book Reviews

    1. The Lithium Air Battery: Fundamentals. Edited by Nobiyuki Imanishi, Alan C. Luntz, and Peter G. Bruce

      Bruno Scrosati

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201502703

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      , Springer, New York 2014, hardcover, 332 pp., € 135.19.— ISBN 978-1489980618

  20. Communications

    1. Mass Spectrometry

      Development of Experiment and Theory to Detect and Predict Ligand Phase Separation on Silver Nanoparticles

      Zachary Farrell, Steve Merz, Jon Seager, Caroline Dunn, Dr. Sergei Egorov and Dr. David L. Green

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201500906

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      Two different mixtures: MALDI mass spectrometry and self-consistent mean-field calculations are combined to detect and predict ligand phase separation on Ag nanoparticles after synthesis. The progression of the monolayer morphology from a well-mixed random ligand distribution (see picture, left) to an intermediate degree of phase separation (right) with changes in ligand length is determined.

    2. Lipid Membranes

      Amphipathic DNA Origami Nanoparticles to Scaffold and Deform Lipid Membrane Vesicles

      Dr. Aleksander Czogalla, Dominik J. Kauert, Dr. Henri G. Franquelim, Dr. Veselina Uzunova, Dr. Yixin Zhang, Prof. Ralf Seidel and Prof. Petra Schwille

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201501173

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      Amphipathic DNA origami structures were engineered, which have a flat membrane-binding interface decorated with cholesterol-derived anchors and sticky oligonucleotide overhangs enabling formation of ordered arrays on a membrane. Such DNA origami structures are capable of deforming free-standing lipid membranes (see picture), mimicking the biological activity of coat-forming proteins.

    3. Electron Correlation

      A Practicable Real-Space Measure and Visualization of Static Electron-Correlation Effects

      Prof. Dr. Stefan Grimme and Dr. Andreas Hansen

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201501887

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      Hot FOD: The inclusion of static electron correlation (SEC) is mandatory for accurate quantum chemistry yet is particularly difficult to calculate. An analysis tool is developed based on a fractional occupation number weighted electron density (ρFOD) that is plotted as an isosurface and shows the “hot” (strongly correlated) electrons. Spatial integration of ρFOD yields a single number which can be used to globally quantify SEC.

    4. Epitope Mapping

      A Phosphorylation-Induced Turn Defines the Alzheimer’s Disease AT8 Antibody Epitope on the Tau Protein

      Dr. Neha S. Gandhi, Dr. Isabelle Landrieu, Dr. Cillian Byrne, Dr. Predrag Kukic, Dr. Laziza Amniai, Dr. François-Xavier Cantrelle, Dr. Jean-Michel Wieruszeski, Dr. Ricardo L. Mancera, Dr. Yves Jacquot and Dr. Guy Lippens

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201501898

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      The AT8 epitope of the phosphorylated tau protein was mapped by NMR spectroscopy, and its defining structural features were derived by a combination of NMR analyses and molecular dynamics. A particular turn conformation is stabilized by a hydrogen bond of the phosphorylated Thr205 residue (pThr205) to the amide proton of Gly207.

    5. Carbon Dots

      Cu–N Dopants Boost Electron Transfer and Photooxidation Reactions of Carbon Dots

      Wenting Wu, Liying Zhan, Weiyu Fan, Jizhong Song, Xiaoming Li, Zhongtao Li, Ruiqin Wang, Jinqiang Zhang, Jingtang Zheng, Mingbo Wu and Prof. Dr. Haibo Zeng

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201501912

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      Doped dots: Cu–N-doped carbon dots (Cu-CDs) were fabricated by a one-step pyrolytic synthesis using Na2[Cu(EDTA)] as the precursor. Cu–N dopants concomitantly boost the conductivity and the electron-accepting and -donating abilities of the CDs, enhancing the electron-transfer process in the photooxidation of 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (see picture; H yellow, N blue, C light blue, O red).

    6. Agostic Interactions

      Characterizing Pressure-Induced Uranium C[BOND]H Agostic Bonds

      Prof. Polly L. Arnold, Dr. Alessandro Prescimone, Dr. Joy H. Farnaby, Dr. Stephen M. Mansell, Prof. Simon Parsons and Prof. Nikolas Kaltsoyannis

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201411250

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      Under pressure: Computational analyses and high-pressure X-ray crystallography are combined to study the UIII compound [UN′′2]2(μ-η66-C6H6) (N′′=N(SiMe3)2). With increasing pressure, the U[BOND]U distances decrease and close contacts between the U and ligand C[BOND]H groups become significantly shorter. Calculations suggest that the greater U⋅⋅⋅H interaction at high pressure can be classified as agostic.

    7. Synthetic Methods

      Benzannulation of Triynes to Generate Functionalized Arenes by Spontaneous Incorporation of Nucleophiles

      Rajdip Karmakar, Dr. Sang Young Yun, Jiajia Chen, Prof. Yuanzhi Xia and Prof. Daesung Lee

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201412468

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      Small but profound: In the benzannulation reaction of 1,3,8-triynes, a small structural difference has a profound impact on the structure of the products. When R is a silyl group, a nucleophile is incorporated into the newly formed benzene core, whereas when R is an aryl group, nucleophile trapping occurs at the benzylic carbon atom connected to the aryl group.

    8. Responsive Materials | Very Important Paper

      Responsive Inverse Opal Hydrogels for the Sensing of Macromolecules

      Ing. Jean-Philippe Couturier, Dr. Martin Sütterlin, Prof. Dr. André Laschewsky, Dr. Cornelia Hettrich and Dr. Erik Wischerhoff

      Article first published online: 16 APR 2015 | DOI: 10.1002/anie.201500674

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      A successful marriage: The combination of smart hydrogels and inverse opal structures unites simplicity with efficacy for sensing macromolecules. While the inverse opal structure provides structural color and a large accessible interface for binding, the induced phase transition of the analyte-responsive hydrogel produces strong optical effects. The resulting spectral shifts can surpass 100 nm and are easily detected.

  21. News

  22. Communications

    1. Terpene Biosynthesis

      Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy

      Lena Barra, Dr. Kerstin Ibrom and Prof. Dr. Jeroen S. Dickschat

      Article first published online: 15 APR 2015 | DOI: 10.1002/anie.201501765

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      Feeding of (2,3,4,5,6-13C5)mevalonolactone to Hypomyces odoratus resulted in a completely 13C-labeled sesquiterpene ether. Its structure was elucidated by 13C,13C COSY and classic NMR experiments, resulting in a structural revision of hypodoratoxide. The absolute configuration was inferred from one of its co-metabolites. Feeding of other 13C-labeled mevalonolactone isotopologues confirmed skeletal rearrangements during terpene cyclization.

    2. Medicinal Chemistry

      A Combination of Spin Diffusion Methods for the Determination of Protein–Ligand Complex Structural Ensembles

      Dr. Jens Pilger, Dr. Adam Mazur, Dr. Peter Monecke, Dr. Herman Schreuder, Dr. Bettina Elshorst, Dr. Stefan Bartoschek, Dr. Thomas Langer, Dr. Alexander Schiffer, Dr. Isabelle Krimm, Melanie Wegstroth, Dr. Donghan Lee, Dr. Gerhard Hessler, Dr. K.-Ulrich Wendt, Dr. Stefan Becker and Prof. Dr. Christian Griesinger

      Article first published online: 15 APR 2015 | DOI: 10.1002/anie.201500671

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      Protein–ligand complexes: A combination of the spin-diffusion-based NMR methods INPHARMA, trNOE, and STD (STI; see picture) results in an accurate scoring function for docking modes and therefore determination of protein–ligand complex structures. Applications are shown on the model system protein kinase A and the drug targets glycogen phosphorylase and soluble epoxide hydrolase.

  23. Reviews

    1. Water–Air Interfaces

      Molecular Structure and Dynamics of Water at the Water–Air Interface Studied with Surface-Specific Vibrational Spectroscopy

      Mischa Bonn, Yuki Nagata and Ellen H. G. Backus

      Article first published online: 15 APR 2015 | DOI: 10.1002/anie.201411188

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      Lightly scratching the surface: A central question regarding the water–air interface is to what extent the structure and dynamics of water molecules is influenced by the breaking of hydrogen bonds, and thus how they differ from those in the bulk water? One method to study the water–air interface is the laser-based surface-specific vibrational spectroscopy. The advances made by these investigations are presented and discussed.

  24. Communications

    1. Boron Cluster Anions

      Functionalization of closo-Borates via Iodonium Zwitterions

      Prof. Dr. Piotr Kaszyński and Dr. Bryan Ringstrand

      Article first published online: 15 APR 2015 | DOI: 10.1002/anie.201411858

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      Openo­ to change: The simple preparation of iodonium zwitterions of closo-borates and their reactions with nucleophiles (see scheme) provided access to a broad spectrum of cluster derivatives with potential as new classes of pharmaceuticals and materials with tailored properties. The presented reactions demonstrate the synthetic versatility of closo-borate aryliodonium zwitterions.

    2. Metal–Organic Clusters | Hot Paper

      Controllable Scission and Seamless Stitching of Metal–Organic Clusters by STM Manipulation

      Huihui Kong, Likun Wang, Qiang Sun, Chi Zhang, Dr. Qinggang Tan and Prof. Dr. Wei Xu

      Article first published online: 15 APR 2015 | DOI: 10.1002/anie.201501701

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      Lateral STM manipulations enable the controllable scission of a complicated metal–organic cluster consisting of nickel atoms and uracil molecules (see Scheme, left) into its elementary structural motifs (right). Furthermore, the elementary units can be seamlessly stitched back together into the original cluster. STM=scanning tunneling microscopy.

    3. Protein Dynamics

      Sampling of Glycan-Bound Conformers by the Anti-HIV Lectin Oscillatoria agardhii agglutinin in the Absence of Sugar

      Marta G. Carneiro, Leonardus M. I. Koharudin, David Ban, T. Michael Sabo, Pablo Trigo-Mourino, Adam Mazur, Christian Griesinger, Angela M. Gronenborn and Donghan Lee

      Article first published online: 14 APR 2015 | DOI: 10.1002/anie.201500213

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      Nothing to get excited about: NMR spectroscopic studies revealed that a lectin with activity against the human immunodeficiency virus recognizes high-mannose sugars by conformational selection within the ground state, in contrast to the popular “excited-state” model. In the absence of sugars, both the sugar-free and sugar-bound protein conformations observed by X-ray crystallography (see picture) exist as conformational substates in solution.