Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 5

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. Traceless Directing Groups

      Carboxylic Acids as Traceless Directing Groups for the Rhodium(III)-Catalyzed Decarboxylative C[BOND]H Arylation of Thiophenes

      Yuanfei Zhang, Huaiqing Zhao, Min Zhang and Prof. Weiping Su

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411701

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      Who was in control? A rhodium(III)-catalyzed carboxylic acid directed decarboxylative C[BOND]H/C[BOND]H cross-coupling of benzoic acids with thiophenes has been developed. This method provides straightforward access to biaryl scaffolds with diverse substitution patterns, many of which previously required lengthy synthetic sequences.

    2. Asymmetric Cyclization | Hot Paper

      Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids

      Kang Du, Pan Guo, Yuan Chen, Zhen Cao, Dr. Zheng Wang and Prof. Dr. Wenjun Tang

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411817

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      One, two, three: An enantioselective palladium-catalyzed dearomative cyclization was developed for the efficient construction of a series of chiral tricyclic phenanthrenone derivatives bearing all-carbon quaternary centers. This method was applied in highly efficient syntheses of a kaurene intermediate, the skeleton of the anabolic steroid boldenone, and the antimicrobial diterpene (−)-totaradiol.

    3. Nanocrystalline Silicon | Hot Paper

      Preparation of Nanocrystalline Silicon from SiCl4 at 200 °C in Molten Salt for High-Performance Anodes for Lithium Ion Batteries

      Ning Lin, Ying Han, Liangbiao Wang, Jianbin Zhou, Jie Zhou, Dr. Yongchun Zhu and Prof. Yitai Qian

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411830

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      Reduction of SiCl4 with metallic Mg is realized in molten AlCl3 at the low temperature of 200 °C in a stainless steel autoclave. AlCl3 not only acts as a molten salt, but also participates in the reaction. The as-prepared Si nanoparticles are highly crystalline, which is highly desirable for high-performance Li-ion batteries.

    4. NMR Spectroscopy

      A Nuclear Singlet Lifetime of More than One Hour in Room-Temperature Solution

      Gabriele Stevanato, Dr. Joseph T. Hill-Cousins, Dr. Pär Håkansson, Dr. Soumya Singha Roy, Dr. Lynda J. Brown, Prof. Dr. Richard C. D. Brown, Dr. Giuseppe Pileio and Prof. Dr. Malcolm H. Levitt

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411978

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      A long-lived nuclear singlet: A molecular system based on a 13C2-labelled naphthalene core has been designed to support long-lived nuclear singlet order in solution. A nuclear singlet lifetime exceeding one hour has been achieved in room-temperature solution.

    5. Host–Guest Systems

      Easy Access to Modified Cyclodextrins by an Intramolecular Radical Approach

      Dr. Dimitri Alvarez-Dorta, Dr. Elisa I. León, Dr. Alan R. Kennedy, Dr. Angeles Martín, Dr. Inés Pérez-Martín and Prof. Dr. Ernesto Suárez

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201412300

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      The successful match of cyclodextrins (CDs) with radical chemistry is reported. The di-alkoxyl radical generated from 6I,IV-diol-α-CD under oxidative conditions led to a stable crystalline bis(1,3,5-trioxocane) with a guest n-hexane molecule. The primary face of the bis(1,3,5-trioxocane) is severely distorted toward a narrower elliptical shape.

    6. Metal-Mediated Base Pairs

      A Highly Stabilizing Silver(I)-Mediated Base Pair in Parallel-Stranded DNA

      Indranil Sinha, Dr. Célia Fonseca Guerra and Prof. Dr. Jens Müller

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411931

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      I′m stranded: An artificial nucleoside forms Ag+-mediated base pairs both in antiparallel-stranded duplexes with Watson–Crick-type geometry and in parallel-stranded duplexes with Hoogsteen-type geometry. The base pair within the parallel-stranded duplex is significantly more stabilizing and is the most strongly stabilizing Ag+-mediated base pair reported for any type of nucleic acid.

  2. Author Profiles

    1. Knut Rurack

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201412102

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      I lose track of time when I listen to music (especially live). My favorite saying is “Starting is easy, but perseverance is an art”.

  3. Communications

    1. Second-Harmonic Generation Materials

      A Facile Synthetic Route to a New SHG Material with Two Types of Parallel π-Conjugated Planar Triangular Units

      Dr. Jun-Ling Song, Dr. Chun-Li Hu, Dr. Xiang Xu, Dr. Fang Kong and Prof. Jiang-Gao Mao

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201412344

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      Pb2(BO3)(NO3) is a new second-harmonic generation (SHG) material that contains parallel π-conjugated nitrate and borate anions. It was obtained through a facile hydrothermal reaction, shows a remarkable strong SHG response of about 9.0 times that of potassium dihydrogen phosphate (KDP), and is phase-matchable.

  4. Cover Pictures

    1. You have free access to this content
      Controlling Internal Pore Sizes in Bicontinuous Polymeric Nanospheres

      Dr. Beulah E. McKenzie, Dr. Heiner Friedrich, Dr. Maarten J. M. Wirix, Joël F. de Visser, Olivia R. Monaghan, Paul H. H. Bomans, Dr. Fabio Nudelman, Dr. Simon J. Holder and Prof. Dr. Nico A. J. M. Sommerdijk

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201500264

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      In their Communication (DOI: 10.1002/anie.201408811), S. J. Holder, N. A. J. M. Sommerdijk et al. resolved the internal morphology of complex polymeric nanospheres and demonstrated that the internal structure can be controlled by changing the overall molecular weight and relative hydrophilic content of the composite polymer. This opens the way for using these bicontinuous polymer nanospheres in a variety of applications, such as controlled release vectors and as templates for the synthesis of inorganic and hybrid materials.

    2. You have free access to this content
      Intermolecular Enantioselective Dearomatization Reaction of β-Naphthol Using meso-Aziridine: A Bifunctional In Situ Generated Magnesium Catalyst

      Dongxu Yang, Linqing Wang, Fengxia Han, Dan Li, Dr. Depeng Zhao and Prof. Dr. Rui Wang

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201500289

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      A chiral ligand with a long arm has led to the in situ formation of a magnesium catalyst that effects a highly diastereo- and enantioselective dearomatization reaction. R. Wang and co-workers describe in their Communication (DOI: 10.1002/anie.201410257) how the complex is highly efficient for the dearomatization of β-naphthol derivatives with aziridines and how the dearomatized products can be easily transformed into a polycyclic core skeleton and a polyhydroxylated compound.

    3. You have free access to this content
      A Complex Perovskite-Type Oxynitride: The First Photocatalyst for Water Splitting Operable at up to 600 nm

      Dr. Chengsi Pan, Dr. Tsuyoshi Takata, Mamiko Nakabayashi, Dr. Takao Matsumoto, Prof. Naoya Shibata, Prof. Yuichi Ikuhara and Prof. Kazunari Domen

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201500325

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      Water splitting on a particulate-type photocatalyst using solar energy is expected to be a scalable and cost-effective route for hydrogen production. However, most of the photocatalysts developed to date can only utilize a small part of the sunlight spectrum. In their Communication (DOI: 10.1002/anie.201410961), K. Domen et al. describe the development of a novel water-splitting photocatalyst operable over a wide range of the visible-light spectrum.

    4. You have free access to this content
      A D-Peptide Ligand of Nicotine Acetylcholine Receptors for Brain-Targeted Drug Delivery

      Xiaoli Wei, Dr. Changyou Zhan, Qing Shen, Prof. Wei Fu, Cao Xie, Jie Gao, Chunmei Peng, Prof. Ping Zheng and Prof. Weiyue Lu

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201500512

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      Peptide ligands efficiently aid brain-targeted drug delivery by hijacking cognate receptors expressed on brain capillary endothelial cells. However, enzymatic barriers inactivate L-peptides and undermine the transport efficiency. In their Communication (DOI: 10.1002/anie.201411226), W. Lu, C. Zhan, et al. have identified a D-peptide ligand of nicotine acetylcholine receptors that is resistant to proteolysis and verified its superiority for brain-targeted drug delivery in comparison to the L-peptide ligand.

  5. Communications

    1. Porphyrinoids

      Sunlight-Driven Formation and Dissociation of a Dynamic Mixed-Valence Thallium(III)/Thallium(I) Porphyrin Complex

      Victoria Ndoyom, Luca Fusaro, Vincent Dorcet, Bernard Boitrel and Stéphane Le Gac

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411616

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      Newton’s cradle: A mixed-valence thallium(III)/thallium(I) bis-strap porphyrin complex, with TlIII bound to the N core and TlI attached to a strap, was generated by the addition of TlOAc to the free base and exposure to indirect sunlight. Exposure of the complex to direct sunlight leads to thallium dissociation and to the recovery of the free porphyrin.

    2. Small Molecule Activation

      Addition of Ethylene or Hydrogen to a Main-Group Metal Cluster under Mild Conditions

      Petra Vasko, Shuai Wang, Heikki M. Tuononen and Prof. Philip P. Power

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411595

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      Tinned small molecules: Reactions of the tin cluster Sn8(Arinline image)4 under mild conditions yields two new insertion compounds from incorporation of ethylene (see picture; left) or H2 (right; Sn blue, C gray). To our knowledge, these are the first reactions between a stable main-group cluster and small molecules.

    3. Helical Superstructures

      Design of Aromatic Helical Polymers for STM Visualization: Imaging of Single and Double Helices with a Pattern of π–π Stacking

      Dr. Junyan Zhu, Prof. Zeyuan Dong, Prof. Shengbin Lei, Dr. Lili Cao, Prof. Bing Yang, Dr. Wenfang Li, Yuanchao Zhang, Prof. Junqiu Liu and Prof. Jiacong Shen

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410975

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      Seeing is believing: STM imaging of rationally designed helical polymers with a pattern of π–π stacking of the helical structures revealed single- and double-helical superstructures (see picture), including the smallest helical architecture observed to date, with a diameter of approximately 1.3 nm. The interconversion of single and double helices was further underpinned by experimental analyses.

    4. Lead Structure Optimization

      Tracing Binding Modes in Hit-to-Lead Optimization: Chameleon-Like Poses of Aspartic Protease Inhibitors

      Maren Kuhnert, Dr. Helene Köster, Dr. Ruben Bartholomäus, Dr. Ah Young Park, Amir Shahim, Prof. Dr. Andreas Heine, Dr. Holger Steuber, Prof. Dr. Gerhard Klebe and Prof. Dr. Wibke E. Diederich

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411206

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      Changing poses: The optimization of lead structures relies on the systematic variation of the substituents decorating a given hit scaffold which is based on one binding pose that is supposed to be invariable. For a given core scaffold, only minor chemical variations were found to result in four different binding modes. An indicative metrics is suggested to assess candidates that qualify for structural revalidation.

    5. Imaging Agents | Hot Paper

      Highly Fluorescent and Water-Soluble Diketopyrrolopyrrole Dyes for Bioconjugation

      Dr. Elodie Heyer, Pauline Lory, Dr. Jérôme Leprince, Dr. Mathieu Moreau, Prof. Anthony Romieu, Prof. Massimo Guardigli, Prof. Aldo Roda and Dr. Raymond Ziessel

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411274

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      All-in-one solution! A simple but very effective synthetic strategy to make diketopyrrolopyrrole (DPP) dyes water-soluble and highly fluorescent in aqueous media for bioconjugation to proteins is presented. Bovine serum albumin-DPP conjugates with unprecedentedly high quantum yields were obtained, thus enabling detection of minute amounts of fluorescent proteins through epifluorescence microscopy.

    6. Supramolecular Chemistry

      C3-Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as Motif of Porous Molecular Crystals

      Dr. Ichiro Hisaki, Shoichi Nakagawa, Dr. Norimitsu Tohnai and Prof. Mikiji Miyata

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411438

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      Construction of porous crystalline two-dimensional frameworks is achieved through non-interpenetrated stacking of a multiporous hexagonal network possessing three kinds of voids with different sizes and shapes. A cavity volume of up to 58 % is obtained.

    7. Cross-Coupling

      Efficient Synthesis of Sterically Hindered Arenes Bearing Acyclic Secondary Alkyl Groups by Suzuki–Miyaura Cross-Couplings

      Chengxi Li, Tianyu Chen, Bowen Li, Guolan Xiao and Prof. Dr. Wenjun Tang

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411518

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      No side reaction: The shown bulky P,P[DOUBLE BOND]O ligands (right) successfully inhibit isomerization and reduction side reactions of the cross-coupling of sterically hindered substrates such as di-ortho-substituted aryl bromides with acyclic secondary alkylboronic acids. The method also allows the preparation of ortho-alkoxy di-ortho-substituted isopropyl arenes in excellent yields.

    8. Smart Drug Delivery System

      Antitumor Drug Delivery Modulated by A Polymeric Micelle Having Upper Critical Solution Temperature

      Dr. Weishuo Li, Dr. Liwen Huang, Xiaoying Ying, Prof. Dr. You Jian, Prof. Dr. Yuan Hong, Prof. Dr. Fuqiang Hu and Prof. Dr. Yongzhong Du

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411524

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      Smart device: Poly(AAm-co-AN)-g-PEG micelles were used as a temperature-triggered drug delivery system based on their upper critical solution temperature. The polymeric micelles displayed a good drug release profile both in vitro and in vivo. Additionally, an excellent antitumor efficiency was achieved. DOX=doxorubicin.

    9. Electrochemistry

      One-Pot Synthesis of Pt–Co Alloy Nanowire Assemblies with Tunable Composition and Enhanced Electrocatalytic Properties

      Dr. Bao Yu Xia, Hao Bin Wu, Nan Li, Ya Yan, Prof. Xiong Wen (David) Lou and Prof. Xin Wang

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411544

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      Three-dimensional (3D) Pt–Co alloy nanostructures with tunable composition are synthesized by an effective solvothermal method. The interconnected 3D Pt3Co nanowire assembly exhibits significantly enhanced electrocatalytic activity and durability compared with commercial Pt based catalysts and a 3D Pt nanowire assembly. This is mainly attributed to the synergetic effects from composition and structural advantages.

  6. Book Reviews

    1. Ligand Design in Medicinal Inorganic Chemistry. Edited by Tim Storr.

      Christian Hartinger

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201412260

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      John Wiley & Sons, Hoboken, 2014. 472 pp., hardcover, € 149.00.—ISBN 978-1118488522

  7. Communications

    1. Radical Complexes

      Enhanced Luminescent Properties of an Open-Shell (3,5-Dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl Radical by Coordination to Gold

      Yohei Hattori, Dr. Tetsuro Kusamoto and Prof. Dr. Hiroshi Nishihara

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411572

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      A gold(I) complex containing an open-shell luminescent (3,5-dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl (PyBTM) radical was prepared. The complex has fluorescence that is centered mainly on the coordinated PyBTM ligand. The photoluminescence quantum yield, fluorescence wavelength, and the stability in the photoexcited state all increased upon coordination to AuI.

    2. Heterogeneous Catalysis

      The Electronic Factor in Alkane Oxidation Catalysis

      Dr. Maik Eichelbaum, Dr. Michael Hävecker, Dr. Christian Heine, Anna Maria Wernbacher, Dr. Frank Rosowski, Dr. Annette Trunschke and Prof. Robert Schlögl

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410632

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      Decades-old concepts in semiconductor physics such as gas-phase-dependent band bending (see figure) could be proven in heterogeneous oxidation catalysis for selective alkane oxidation reactions on vanadium oxide based catalysts by near-ambient-pressure X-ray photoelectron spectroscopy. These “electronic factors” are discussed as descriptors for selective catalyst materials.

    3. NMR Spectroscopy

      You have full text access to this OnlineOpen article
      Anomalous Nuclear Overhauser Effects in Carbon-Substituted Aziridines: Scalar Cross-Relaxation of the First Kind

      Dr. Ilya Kuprov, Prof. David M. Hodgson, Johannes Kloesges, Christopher I. Pearson, Dr. Barbara Odell and Prof. Timothy D. W. Claridge

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410271

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      Scalar relaxation: Apparently anomalous cross-peaks in 2D 1H NOESY spectra of carbon-substituted aziridines are shown to arise from scalar cross-relaxation of the first kind (SRFK; see picture), due to modulation of scalar coupling constants between protons. Such effects will likely be seen in NOESY spectra of other small molecules experiencing dynamic exchange modulation of scalar 1H-1H coupling constants.

    4. Macrocycles

      Zethrene and Dibenzozethrene: Masked Biradical Molecules?

      Ya-Chu Hsieh, Hau-Yu Fang, Yi-Ting Chen, Rong Yang, Prof. Chen-I Yang, Prof. Pi-Tai Chou, Prof. Ming-Yu Kuo and Prof. Yao-Ting Wu

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410316

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      Shelling out: Substituents and π-conjugation remarkably affect structures and properties of zethrene series. The parent dibenzozethrene and zethrene are both singlet open-shell biradicals, but the former has stronger biradical characteristics than the latter, as verified experimentally and theoretically, whereas all substituted derivatives have a closed-shell ground state.

    5. Superatoms

      [Ag21{S2P(OiPr)2}12]+: An Eight-Electron Superatom

      Dr. Rajendra S. Dhayal, Jian-Hong Liao, Dr. Yu-Chiao Liu, Dr. Ming-His Chiang, Dr. Samia Kahlal, Prof. Jean-Yves Saillard and Prof. C. W. Liu

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410332

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      Silver super skeleton: A single-crystal X-ray diffraction study of a novel [Ag21{S2P(OiPr)2}12](PF6) nanocluster shows an unprecedented silver-centered icosahedron with additional eight capping silver atoms to generate an Ag21 metal skeleton. DFT calculations indicate that this stable monocationic nanocluster is an eight-electron superatom.

    6. Electrocatalysis

      Palladium–Cobalt Nanotube Arrays Supported on Carbon Fiber Cloth as High-Performance Flexible Electrocatalysts for Ethanol Oxidation

      An-Liang Wang, Xu-Jun He, Xue-Feng Lu, Han Xu, Ye-Xiang Tong and Prof. Gao-Ren Li

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410792

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      PdCo nanotube arrays supported on carbon fiber cloth for use as high-performance electrocatalysts were synthesized for ethanol electrooxidation. The system of nanotube arrays on carbon fiber cloth is highly flexible, and its high electrocatalytic performance is almost constant regardless of the distorted state, such as normal, bent, and twisted.

    7. Solar Cells

      Application of the Tris(acetylacetonato)iron(III)/(II) Redox Couple in p-Type Dye-Sensitized Solar Cells

      Ishanie Rangeeka Perera, Dr. Torben Daeneke, Satoshi Makuta, Dr. Ze Yu, Prof. Dr. Yasuhiro Tachibana, Dr. Amaresh Mishra, Prof. Dr. Peter Bäuerle, Dr. C. André Ohlin, Prof. Dr. Udo Bach and Prof. Dr. Leone Spiccia

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201409877

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      Here comes the sun: The use of an electrolyte based on the tris(acetylacetonato)iron(III)/(II) redox couple (green spheres) in p-type dye-sensitized solar cells resulted in rapid dye regeneration and an energy conversion efficiency of 2.51 %. Devices were constructed using a porous NiO layer (brown spheres) on the working electrode sensitized with PMI–6T–TPA, a perylene–thiophene–triphenylamine dye (red spheres).

    8. Nanostructures

      Oligomeric Hydrogels Self-Assembled from Reduction-Controlled Condensation

      Shuang Liu, Anming Tang, Maolin Xie, Yundan Zhao, Prof. Dr. Jun Jiang and Prof. Dr. Gaolin Liang

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201409952

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      Bowl full of gel: A biocompatible condensation reaction was employed to synthesize amphiphilic macrocyclized oligomers, which instantly self-assembled into nanofibers through parallel stacking and formed oligomeric hydrogels.

    9. Zintl Clusters

      Linking Deltahedral Zintl Clusters with Conjugated Organic Building Blocks: Synthesis and Characterization of the Zintl Triad [R-Ge9-CH[DOUBLE BOND]CH[BOND]CH[DOUBLE BOND]CH-Ge9-R]4−

      Manuel M. Bentlohner, Dr. Wilhelm Klein, Dr. Zohreh H. Fard, Laura-Alice Jantke and Prof. Dr. Thomas F. Fässler

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410199

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      Zintl triads: The general possibility to synthesize electronically coupled Zintl clusters using conjugated electron π-systems as linkers in analogy to fullerene–linker–fullerene triads opens a new area of applications for Zintl clusters.

    10. Fluorescent Probes

      You have full text access to this OnlineOpen article
      Fluorescence Microscopy Visualization of Contacts Between Objects

      Tomislav Suhina, Bart Weber, Dr. Chantal E. Carpentier, Dr. Kinga Lorincz, Prof. Dr. Peter Schall, Prof. Dr. Daniel Bonn and Prof. Dr. Albert M. Brouwer

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410240

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      All the fun of the surface: By using rigidochromic fluorescent probe molecules attached to a surface, the contact area between the surface and an object can be visualized. Confinement of the molecules suppresses nonradiative decay and turns on the fluorescence.

    11. Biological Charge Resonance

      Probing Bis-FeIV MauG: Experimental Evidence for the Long-Range Charge-Resonance Model

      Dr. Jiafeng Geng, Ian Davis and Prof. Dr. Aimin Liu

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410247

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      Small molecules were used to experimentally investigate the biological long-range charge-resonance (CR) model proposed in the high-valence bis-FeIV intermediate of MauG. The chemical nature of the bis-FeIV species was demonstrated to be an equilibrium of different resonance structures as predicted by the CR model. This study provides supporting evidence for the first CR phenomenon in a biological catalytic intermediate.

    12. DNA Nanotechnology | Hot Paper

      Reversible Reconfiguration of DNA Origami Nanochambers Monitored by Single-Molecule FRET

      Dr. Barbara Saccà, Dr. Yuji Ishitsuka, Dr. Rebecca Meyer, Andreas Sprengel, Elisa-Charlott Schöneweiß, Prof. G. Ulrich Nienhaus and Prof. Christof M. Niemeyer

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201408941

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      Inspired by their natural counterparts, dynamic compartmentalization systems were realized, in which the switchable mechanical movement of small DNA motifs was integrated into a DNA origami scaffold. The kinetics of the movement was determined by distance-dependent energy transfer between two fluorophores.

    13. Protein Modification

      You have full text access to this OnlineOpen article
      Structure and Mechanism of an Aspartimide-Dependent Peptide Ligase in Human Legumain

      Dr. Elfriede Dall, M. Sc. Julia C. Fegg, Prof. Dr. Peter Briza and Prof. Dr. Hans Brandstetter

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201409135

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      Peptide bond (bio-)synthesis requires ATP as a coupling reagent. By contrast, human legumain ligase exploits an endogenous energy reservoir that results from the conversion of a conserved aspartate to a metastable succinimide. Legumain’s protease activity recharges the succinimide. This functional duality may account for the generation of three-dimensional epitopes for MHC presentation through the cleavage and splicing of sequentially distant epitopes.

    14. Protein Structure

      Structure and Mechanism of the Caseinolytic Protease ClpP1/2 Heterocomplex from Listeria monocytogenes

      Maria Dahmen, Marie-Theres Vielberg, Prof. Dr. Michael Groll and Prof. Dr. Stephan A. Sieber

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201409325

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      All together now: The crystal structure of the heterooligomeric ClpP1 and ClpP2 complex from Listeria monocytogenes was solved. Taken together with biochemical data, the structure provides insights into the catalysis and transient stability of the complex, as well as its interaction with the associated ClpX chaperone. Subtle differences in the S1 pockets could be predicted and are the basis for the development of specific inhibitors.

  8. Reviews

    1. Ligand Design

      Molecular Recognition in Chemical and Biological Systems

      Dipl.-Chem. Elke Persch, Dipl.-Chem. Oliver Dumele and Prof. Dr. François Diederich

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201408487

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      Both are required: Chemical model systems and the study of biological receptors are both required to understand molecular recognition processes. The identification and quantification of noncovalent interactions and deciphering the role of water are key elements for structure-based drug design. Several case studies are presented in which weak intermolecular interactions were applied to innovative ligand design and optimization.

  9. Communications

    1. Fuel-Cell Membranes

      Nanometer-Scale Water- and Proton-Diffusion Heterogeneities across Water Channels in Polymer Electrolyte Membranes

      Dr. Jinsuk Song, Prof. Dr. Oc Hee Han and Prof. Dr. Songi Han

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201408318

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      On the surface of it… The water/proton diffusivity in Nafion within 1 nm of spin probes located in specific heterogeneous regions of the polymer electrolyte membrane (PEM) was significantly faster near the fluorocarbon and the acidic groups lining the water channels than within the water channels (see picture). Thus, surface chemistry at the (sub-)nanometer scale dictates key transport properties and offers new design principles for PEMs.

    2. Polymer Photoreactions

      λ-Orthogonal Pericyclic Macromolecular Photoligation

      Kai Hiltebrandt, Dr. Thomas Pauloehrl, Dr. James P. Blinco, Katharina Linkert, Prof. Dr. Hans G. Börner and Prof. Dr. Christopher Barner-Kowollik

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410789

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      It’s up to the wavelength: The concept of λ-orthogonal photochemistry is presented using light-induced pericyclic photoreactions. A functionalized electron-poor alkene is reacted with various selectively photoactive groups on a polymer; the selectivity depends on the wavelength of the light used.

    3. Fuel Cells | Very Important Paper

      A Carbon–Air Battery for High Power Generation

      Binbin Yang, Prof. Ran Ran, Yijun Zhong, Dr. Chao Su, Prof. Moses O. Tadé and Prof. Zongping Shao

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201411039

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      Midair refueling: A carbon–air battery based on a anode-supported tubular solid-oxide fuel cell integrated with a CO2 separation membrane (see picture) composed of a CO32− mixture and an O2− conducting phase showed both high energy density and power output. A small stack composed of two batteries can be operated continuously for 200 min, which is promising for use as a portable power device.

  10. Obituaries

    1. Paul von Ragué Schleyer (19302014)

      Prof. George A. Olah and Prof. G. K. Surya Prakash

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201411952

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      Paul von Ragué Schleyer, Graham Perdue Professor at the University of Georgia passed away on November 21, 2014. Schleyer was an eminent and prolific physical organic chemist, whose pioneering contributions included the application of computational chemistry to broad fields of physical organic, inorganic, organometallic, and mechanistic chemistry concepts.

  11. Communications

    1. Multicomponent Reactions | Hot Paper

      Base-Promoted Coupling of Carbon Dioxide, Amines, and N-Tosylhydrazones: A Novel and Versatile Approach to Carbamates

      Wenfang Xiong, Dr. Chaorong Qi, Haitao He, Lu Ouyang, Prof. Dr. Min Zhang and Prof. Dr. Huanfeng Jiang

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410605

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      Carbene intermediate? No! An unprecedented strategy for the synthesis of a range of organic carbamates through the coupling of carbon dioxide, amines, and N-tosylhydrazones is reported. The base-promoted reaction is proposed to proceed via a carbocation intermediate and is characterized by excellent functional group tolerance and a wide substrate scope.

    2. Gold Clusters

      The Structure and Optical Properties of the [Au18(SR)14] Nanocluster

      Shuang Chen, Shuxin Wang, Juan Zhong, Yongbo Song, Dr. Jun Zhang, Prof. Hongting Sheng, Prof. Yong Pei and Prof. Manzhou Zhu

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410295

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      Gold mine: The X-ray crystallographic structure of cyclohexylthiolate-protected [Au18(SR)14] nanocluster shows it has a Au9 bi-octahedral kernel (Au gold, S pink, C gray). This Au9 core is formed by two octahedral Au6 units sharing one triangular face. A gold atom in the Au9 core, which can also be considered as part of the Au4(SR)5 staple motif offering new insight into the evolution from AuI complexes to larger Au nanoclusters.

    3. Structure of Boron

      Determination of Phase Stability of Elemental Boron

      Prof. Mary Anne White, Anthony B. Cerqueira, Dr. Catherine A. Whitman, Michel B. Johnson and Dr. Tadashi Ogitsu

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201409169

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      Elementary information: Through experimental thermodynamics, the fundamental question of which structure of elemental boron is most stable has been answered: it is the unique disordered β-form.

    4. Asymmetric Catalysis

      Ferrocene-Based Planar Chiral Imidazopyridinium Salts for Catalysis

      Dr. Christopher T. Check, Dr. Ki Po Jang, C. Benjamin Schwamb, Alexander S. Wong, Michael H. Wang and Prof. Dr. Karl A. Scheidt

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410118

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      Planar chiral azolium salts that incorporate a sterically demanding iron sandwich complex are synthesized. These new N-heterocyclic carbenes can be employed both as organocatalysts and as ligands for transition-metal catalysis, which demonstrates their unprecedented versatility and potential broad utility in asymmetric catalysis.

    5. Gold Clusters

      Structure Determination of [Au18(SR)14]

      Anindita Das, Chong Liu, Hee Young Byun, Prof. Katsuyuki Nobusada, Shuo Zhao, Prof. Nathaniel Rosi and Prof. Rongchao Jin

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410161

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      Heart of gold: A decade after the first report of the [Au18(SR)14] cluster, its structure is finally obtained (see picture, gold pink, sulfur yellow, cyclohexyl groups as wire frame). It has a bi-octahedral (or hexagonal closing packing) Au9 kernel protected by staple-like surface motifs.

    6. Ionic Liquids

      Polymeric Ionic Liquid and Carbon Black Composite as a Reusable Supporting Electrolyte: Modification of the Electrode Surface

      Seung Joon Yoo, Long-Ji Li, Prof. Dr. Cheng-Chu Zeng and Prof. Dr. R. Daniel Little

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410207

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      A composite electrolyte that combines the features of a polymeric ionic liquid with the properties of carbon nanoparticles enables electrochemical oxidations without an additional supporting electrolyte. The composite can be reused in subsequent electrolyses. In addition, the composite electrolyte can improve the kinetics through modification of the electrode surface.

  12. Reviews

    1. Super-Wettability

      Bioinspired Super-Wettability from Fundamental Research to Practical Applications

      Dr. Liping Wen, Dr. Ye Tian and Prof. Lei Jiang

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201409911

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      Wet, wet, wet: Surfaces with super-wettability, including three-dimensional, two-dimensional, and one-dimensional materials surfaces can be prepared. By combining different super-wettability properties, novel functional solid/liquid interfacial systems can be generated and integrated into devices for tackling many different problems.

  13. Author Profiles

    1. James A. Dumesic

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411477

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      My favorite composer is Richard Wagner. I really enjoy the orchestrations in his operas. If I could be any age I would be my current age. I always feel that we are doing our best work at the present time.

  14. Communications

    1. Heteroarenes

      Sulfur-Annulated Hexa-peri-hexabenzocoronene Decorated with Phenylthio Groups at the Periphery

      Dr. Yuan-Zhi Tan, Dr. Silvio Osella, Yi Liu, Bo Yang, Prof. Dr. David Beljonne, Prof. Dr. Xinliang Feng and Prof. Dr. Klaus Müllen

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201409932

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      Sulfur annulation: The unprecedented sulfur-annulated hexa-peri-hexabenzocoronenes were synthesized and unambiguously characterized by X-ray diffraction, revealing the distinct sulfur-annulated peripheral structure. Associated with DFT calculations, the strain minimization of the aromatic carbon skeleton should be responsible for the regioselective sulfur annulation at the bay positions.

    2. Carbohydrates

      Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions

      Dr. Angie Garcia, Douglas A. L. Otte, Dr. Walter A. Salamant, Jillian R. Sanzone and Prof. K. A. Woerpel

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410043

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      Making an approach: In contrast to observations with carbohydrates, alkoxy groups can accelerate acetal hydrolysis even though they are inductively electron withdrawing. The alkoxy group must be able to approach the acetal carbon atom without developing too much strain. The data are most consistent with the alkoxy group stabilizing the developing positive charge by electrostatic stabilization, not formation of a new covalent bond.

    3. Reaction Intermediates

      Dinuclear Copper Intermediates in Copper(I)-Catalyzed Azide–Alkyne Cycloaddition Directly Observed by Electrospray Ionization Mass Spectrometry

      Dr. Claudio Iacobucci, Dr. Samantha Reale, Prof. Jean-François Gal and Prof. Francesco De Angelis

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410301

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      Mechanistic aspects of the CuAAC reaction have been clarified by electrospray ionization mass spectrometry (ESI-MS). Dinuclear copper intermediates have been detected for the first time and characterized. Neutral and ion-tagged reactants provided complementary evidence for the reaction catalytic cycle.

    4. Gene Delivery

      A Tailor-Made Specific Anion-Binding Motif in the Side Chain Transforms a Tetrapeptide into an Efficient Vector for Gene Delivery

      Mao Li, Stefanie Schlesiger, Prof. Shirley K. Knauer and Prof. Carsten Schmuck

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410429

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      Cell-penetrating peptides are widely utilized as vectors for gene delivery. Guanidinocarbonylpyrrole groups, which are tailor-made anion binding sites, were introduced into the side chains of tetralysine to obtain 1. This enormously enhances the cellular uptake of the corresponding peptide/DNA polyplexes relative to peptides with natural amino acids. Tetrapeptide analogue 1 is a highly efficient transfection vector and also shows negligible cytotoxicity.

    5. Perfluorinated Alkoxides

      A Convenient Route to Tetraalkylammonium Perfluoroalkoxides from Hydrofluoroethers

      Benson J. Jelier, Dr. Jon L. Howell, Prof. Craig D. Montgomery, Prof. Daniel B. Leznoff and Prof. Chadron M. Friesen

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410639

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      Fluoride free! The preparation of a series of tetraalkylammonium perfluoroalkoxides under mild, fluoride-free conditions is achieved by the methylation of tertiary amines with commercially available, partially fluorinated ethers. This practical synthesis paves a new way to an underrepresented class of thermally stable compounds bearing α-fluorines.

    6. DNA Nanotechnology

      Gold-Nanoparticle-Mediated Jigsaw-Puzzle-like Assembly of Supersized Plasmonic DNA Origami

      Guangbao Yao, Dr. Jiang Li, Dr. Jie Chao, Dr. Hao Pei, Dr. Huajie Liu, Prof. Yun Zhao, Dr. Jiye Shi, Dr. Qing Huang, Prof. Lianhui Wang, Prof. Wei Huang and Prof. Chunhai Fan

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410895

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      Over the limit: A jigsaw-puzzle-like assembly strategy mediated by gold nanoparticles (AuNPs) is used to break the size limit of classic DNA origami. DNA-functionalized AuNPs are used as universal joints to assemble triangular DNA origami (see picture; red arrow denotes AuNP binding site) to form higher-order super-origami plasmonic nanostructures.

    7. Heterocycle Synthesis

      Palladium(0)-Catalyzed Iminohalogenation of Alkenes: Synthesis of 2-Halomethyl Dihydropyrroles and Mechanistic Insights into the Alkyl Halide Bond Formation

      Chen Chen, Longlei Hou, Mian Cheng, Prof. Jianhua Su and Dr. Xiaofeng Tong

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410996

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      Eliminated: The use of electron-poor phosphine ligands proved to be crucial to promoting alkyl bromide and chloride reductive elimination in the title reaction with γ,δ-unsaturated oxime esters. Furthermore, SN2-type alkyl bromide and chloride reductive elimination has also been established.

    8. Gas Adsorption

      You have full text access to this OnlineOpen article
      Two-Dimensional Covalent Organic Frameworks for Carbon Dioxide Capture through Channel-Wall Functionalization

      Ning Huang, Dr. Xiong Chen, Prof. Dr. Rajamani Krishna and Prof. Dr. Donglin Jiang

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411262

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      Efficient CO2 capture is achieved by converting a conventional two-dimensional covalent organic framework (COF) to an outstanding CO2 capture materials with large capacity and high selectively. The nanopore walls are chemically engineered with functional groups in a controlled manner to enhance interactions with CO2, leading to the development of a new general way to design COFs for gas storage and separation.

    9. DNA Intercalators

      Tuning the Excited State of Water-Soluble IrIII-Based DNA Intercalators that are Isostructural with [RuII(NN)2(dppz)] Light-Switch Complexes

      Sasha Stimpson, Dan R. Jenkinson, Andrew Sadler, Dr. Mark Latham, Dr Ashley Wragg, Dr. Anthony J. H. M. Meijer and Dr. Jim A. Thomas

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411346

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      The same but different: Two new IrIII complexes, with IrIII(NN)2 moieties coordinated to either the DNA-intercalating ligand dipyridophenazine (dppz) or its cyclometalating analogue benzopyridophenazine (bppz), are reported. Experimental and computational studies show that the systems have very different excited states (see picture; dppz complex (top), bppz (bottom)) and both bind to DNA with affinities comparable to their RuII analogues.

    10. Polymer Gels

      Photoreversible Gelation of a Triblock Copolymer in an Ionic Liquid

      Dr. Takeshi Ueki, Yutaro Nakamura, Ryoji Usui, Yuzo Kitazawa, Soonyong So, Prof. Dr. Timothy P. Lodge and Prof. Dr. Masayoshi Watanabe

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411526

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      Make or break: The reversible micellization and gel-to-sol transition of an ionic liquid/ABA block copolymer solution triggered by a photostimulus is described. Photorheology is employed to monitor the light-induced viscoelastic property changes of the functional liquid resulting from hierarchical changes in the microscopic substructure of the macromolecular building blocks.

    11. Natural Product Synthesis | Hot Paper

      Total Synthesis of (−)-Caprazamycin A

      Hugh Nakamura, Dr. Chihiro Tsukano, Motohiro Yasui, Shinsuke Yokouchi, Dr. Masayuki Igarashi and Prof. Dr. Yoshiji Takemoto

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411954

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      Abra‘capraza’: Caprazamycin A has significant antibacterial activity against Mycobacterium tuberculosis (TB). The first total synthesis is herein reported and features the scalable preparation of the syn-β-hydroxy amino acid with a thiourea-catalyzed diastereoselective aldol reaction, construction of a diazepanone with an unstable fatty-acid side chain, and global deprotection with hydrogenation.

  15. Cover Pictures

    1. You have free access to this content
      Excluded-Volume Effects in Living Cells

      David Gnutt, Mimi Gao, Oliver Brylski, Dr. Matthias Heyden and Prof. Dr. Simon Ebbinghaus

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201500265

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      The interior of cells is highly crowded and has unique physicochemical properties. In their Communication (DOI: 10.1002/anie.201409847), S. Ebbinghaus and co-workers utilize a polymer-based sensor to study the effects of the excluded volume in living cells. They show that the cellular environment causes a significant compression of the sensor only under osmotic stress conditions. Thus the balance of compressive forces and nonspecific interactions can be used to fine-tune the properties within the cell.

  16. Reviews

    1. Water Purification

      Synthetic Membranes for Water Purification: Status and Future

      Prof. Anthony G. Fane, Prof. Rong Wang and Prof. Matthew X. Hu

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201409783

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      Membrane technology offers the best options to “drought proof” mankind on an increasingly thirsty planet by purifying seawater or used water. The driving forces for development of membranes for water production are described in this Review. An update is provided for developments in the various preparation techniques for the range of membrane types.

  17. Communications

    1. G-Quadruplexes

      Formation of DNA:RNA Hybrid G-Quadruplex in Bacterial Cells and Its Dominance over the Intramolecular DNA G-Quadruplex in Mediating Transcription Termination

      Ren-yi Wu, Dr. Ke-wei Zheng, Jia-yu Zhang, Yu-hua Hao and Prof. Dr. Zheng Tan

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201408719

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      A transcription check-point: Transcription through guanine-rich regions produces DNA:RNA hybrid G-quadruplexes. In turn, these regulate transcription by mediating premature termination of transcription.

    2. Photocatalytic H2 Production | Hot Paper

      Palladium versus Platinum: The Metal in the Catalytic Center of a Molecular Photocatalyst Determines the Mechanism of the Hydrogen Production with Visible Light

      Michael G. Pfeffer, Dr. Bernhard Schäfer, Dr. Grigory Smolentsev, Dr. Jens Uhlig, Dr. Elena Nazarenko, Dr. Julien Guthmuller, Dr. Christian Kuhnt, Dr. Maria Wächtler, Prof. Dr. Benjamin Dietzek, Prof. Dr. Villy Sundström and Prof. Dr. Sven Rau

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201409438

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      Show your metal: The mechanism of the visible light-driven hydrogen production with an intramolecular photocatalyst depends on the nature of the catalytically active metal center. In Ru–M systems, where M=Pt or Pd, palladium forms metal colloids as initial step, whereas platinum shows a high stability and there is no change in the (N^N)PtCl2 coordination sphere.

    3. Mechanophores

      Pinpointing Mechanochemical Bond Rupture by Embedding the Mechanophore into a Macrocycle

      Dipl.-Chem. Doreen Schütze, M. Sc. Katharina Holz, M. Sc. Julian Müller, Prof. Dr. Martin K. Beyer, Prof. Dr. Ulrich Lüning and Prof. Dr. Bernd Hartke

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201409691

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      Caught in the act: A 1,4-diaryl-1,2,3-triazole was embedded in a poly(ethylene glycol) chain and additionally bridged by an aliphatic chain. Single polymer molecules were then stretched in an atomic force microscope. Mechanochemical bond rupture in the macrocycle leads to a defined length increase of the polymer of more than 1 nm, which is large enough to be measured directly for a single molecule.

    4. Electrochemistry

      Oxide-Supported IrNiOx Core–Shell Particles as Efficient, Cost-Effective, and Stable Catalysts for Electrochemical Water Splitting

      Hong Nhan Nong, Dr. Hyung-Suk Oh, Tobias Reier, Dr. Elena Willinger, Dr. Marc-Georg Willinger, Prof. Dr. Valeri Petkov, Dr. Detre Teschner and Prof. Dr. Peter Strasser

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411072

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      Water splitting: IrNiOx core–shell nanoparticles consisting of a thin IrOx shell and an Ir-low/Ir-free core supported on mesoporous antimony doped tin oxide are demonstrated to provide substantial advances toward more efficient, stable, and less expensive electrolytic water splitting catalysts.

    5. Biocatalysis

      Engineered L-Serine Hydroxymethyltransferase from Streptococcus thermophilus for the Synthesis of α,α-Dialkyl-α-Amino Acids

      Karel Hernandez, Igor Zelen, Giovanna Petrillo, Prof. Dr. Isabel Usón, Claudia M. Wandtke, Dr. Jordi Bujons, Dr. Jesús Joglar, Dr. Teodor Parella and Prof. Dr. Pere Clapés

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411484

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      Quaternary stereocenters are obtained with a stereoselective biocatalyst. Chirally pure α,α-dialkyl-α-amino acid derivatives were synthetized through aldol addition of D-Ala and D-Ser to a variety of acceptor aldehydes. This reaction is catalyzed by the engineered pyridoxal-5′-phosphate dependent biocatalyst SHMTSth Y55T. (SHMTSth is the L-serine hydroxymethyltransferase from Streptococcus thermophilus).

    6. Gas Separation | Very Important Paper

      Remarkably Enhanced Gas Separation by Partial Self-Conversion of a Laminated Membrane to Metal–Organic Frameworks

      Dr. Yi Liu, Dr. Jia Hong Pan, Nanyi Wang, Frank Steinbach, Dr. Xinlei Liu and Prof. Jürgen Caro

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411550

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      From LDH to MOF: The partial transformation of a ZnAl-NO3 layered double hydroxide (LDH) membrane to a ZIF-8 metal–organic framework (MOF) top layer led to the formation of the composite membrane ZIF-8-ZnAl-NO3 LDH. This membrane is characterized by remarkably enhanced H2/CH4 gas separation and H2 permeance.

    7. Morphology Transformation

      Reversible Morphological Transformation between Polymer Nanocapsules and Thin Films through Dynamic Covalent Self-Assembly

      Jeehong Kim, Dr. Kangkyun Baek, Dr. Dinesh Shetty, Dr. Narayanan Selvapalam, Gyeongwon Yun, Dr. Nam Hoon Kim, Dr. Young Ho Ko, Dr. Kyeng Min Park, Dr. Ilha Hwang and Prof. Dr. Kimoon Kim

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411842

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      Nano-transformers: A facile synthesis of polymer nanocapsules and thin films by multiple in-plane cross-linking of mercaptopropylcucurbit[6]uril through disulfide bonds was achieved. The reversible nature of disulfide linkages allows reversible morphological transformations by simple solvent exchanges.

  18. Obituaries

    1. Rudolf Hoppe (19222014)

      Prof. Dr. Martin Jansen

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411646

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      Rudolf Hoppe, emeritus professor at the University of Gießen, passed away on November 24, 2014. Hoppe was one of the biggest names in the field of inorganic solid-state chemistry, and was among the first to report the noble-gas compound XeF2. His other achievements included the preparation of compounds with transition metals in uncommonly high or low oxidation states.

  19. Communications

    1. Sustainable Polymers

      Alternating Copolymerization of Propylene Oxide with Biorenewable Terpene-Based Cyclic Anhydrides: A Sustainable Route to Aliphatic Polyesters with High Glass Transition Temperatures

      Nathan J. Van Zee and Prof. Geoffrey W. Coates

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410641

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      Terpene-based cyclic anhydrides are copolymerized with propylene oxide using metal salen catalysts to provide amorphous aliphatic polyesters with exceptionally high glass transition temperatures (Tg up to 109 °C). The polymerization conditions and choice of catalyst have a dramatic impact on the microstructure and ultimately the Tg value of the resulting polymer.

    2. Black Phosphorus

      Identifying the Crystalline Orientation of Black Phosphorus Using Angle-Resolved Polarized Raman Spectroscopy

      Juanxia Wu, Nannan Mao, Prof. Liming Xie, Prof. Hua Xu and Prof. Jin Zhang

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410108

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      A compass to precisely identify the zigzag and armchair directions of black phosporus (BP) sheets is provided by angle-resolved polarized Raman spectroscopy. The Raman modes of BP show periodic variation (90° or 180°) with the sample rotation angle. Under parallel polarization, the Ag2 mode intensity achieves the larger (or smaller) local maximum when the armchair (or zigzag) direction is along the polarization direction of scattered light.

    3. Organocatalysis

      Catalytic Enantioselective [5+2] Cycloaddition between Oxidopyrylium Ylides and Enals under Dienamine Activation

      Ane Orue, Dr. Uxue Uria, Prof. Efraim Reyes, Prof. Luisa Carrillo and Prof. Jose L. Vicario

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410723

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      By using all its powers of persuasion, a bifunctional secondary-amine/squaramide catalyst encouraged 1-acetoxyisochroman-4-ones to react as benzopyrylium ylides with α,β-unsaturated aldehydes in efficient [5+2] cycloaddition reactions with high diastereo- and enantioselectivity. The transformation proceeds by dienamine activation and involves β,γ-functionalization of the enal (see scheme).

    4. Photocatalysis

      Interface Engineering of CoOx/Ta3N5 Photocatalyst for Unprecedented Water Oxidation Performance under Visible Light Irradiation

      Shanshan Chen, Dr. Shuai Shen, Guiji Liu, Yu Qi, Prof. Fuxiang Zhang and Prof. Can Li

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409906

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      Hydrophilic interface modification of a CoOx-modified Ta3N5 photocatalyst with a magnesia nanolayer significantly improves its water oxidation efficiency under visible light irradiation. The essential roles of the interface modification are proposed to enhance the interfacial coverage of the CoOx/Ta3N5 photocatalyst and to decrease the defect density of Ta3N5 semiconductor. AQE=apparent quantum efficiency.

    5. Aromaticity

      Carbo-Quinoids: Stability and Reversible Redox-Proaromatic Character towards Carbo-Benzenes

      Kévin Cocq, Valérie Maraval, Nathalie Saffon-Merceron, Alix Saquet, Corentin Poidevin, Christine Lepetit and Remi Chauvin

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201407889

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      Back and forth: The carbo-mer of the para-quinodimethane core is stable within a bis(9-fluorenylidene) derivative. Oxidation of the carbo-quinoid with MnO2 in the presence of SnCl2 and ethanol affords p-bis(9-ethoxy-fluoren-9-yl)-carbo-benzene, which is converted back into the carbo-quinoid by reduction with SnCl2, thus evidencing a chemical reversibility of the interconversion between a pro-aromatic carbo-quinoid and an aromatic carbo-benzene.

    6. 2D Materials

      Functionalization of Liquid-Exfoliated Two-Dimensional 2H-MoS2

      Dr. Claudia Backes, Dr. Nina C. Berner, Xin Chen, Paul Lafargue, Pierre LaPlace, Mark Freeley, Prof. Georg S. Duesberg, Prof. Jonathan N. Coleman and Dr. Aidan R. McDonald

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409412

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      Surface modification: Functionalization of liquid-exfoliated, defect-free, layered 2H-MoS2 was achieved through coordination of metal carboxylate salts by basal-plane sulfur atoms. The surface-coordinated metal center acts as an anchor for ligating organic functionalities. X-ray photoelectron spectroscopy (XPS) provides strong evidence for the coordination of MoS2 surface sulfur atoms to the M(OAc)2 salt (see picture).

    7. Gallium Selenide

      Revealing the Preferred Interlayer Orientations and Stackings of Two-Dimensional Bilayer Gallium Selenide Crystals

      Dr. Xufan Li, Dr. Leonardo Basile, Dr. Mina Yoon, Dr. Cheng Ma, Dr. Alexander A. Puretzky, Dr. Jaekwang Lee, Dr. Juan C. Idrobo, Dr. Miaofang Chi, Dr. Christopher M. Rouleau, Dr. David B. Geohegan and Dr. Kai Xiao

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409743

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      Bilayer GaSe 2D crystals with different twist angles were grown through a controllable vapor-phase deposition method. The commensurate stacking configurations (AA′ and AB stacking) and Ga-terminated edge structure in as-synthesized bilayer crystals are clearly observed at the atomic scale for the first time. Theoretical analysis reveals that the energies of the interlayer coupling are responsible for the preferred orientations.

    8. Synthetic Methods

      Intramolecular C[BOND]H Activation through Gold(I)-Catalyzed Reaction of Iodoalkynes

      Pablo Morán-Poladura, Dr. Eduardo Rubio and Prof. Dr. José M. González

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409970

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      Golden dance: The cycloisomerization reaction of 1-(iodoethynyl)-2-(1-methoxyalkyl)arenes gives the corresponding 3-iodo-1-substituted-1H-indene. Gold(I) catalysis triggers a selective intramolecular carbon–carbon bond-forming event, which involves the insertion of benzylic C[BOND]H bonds in the catalytically assembled gold(I) iodovinylidene intermediate.

  20. News

  21. Communications

    1. Bioinorganic Drugs

      The Biological Activity of Zeise’s Salt and its Derivatives

      Dr. Sandra Meieranz, Dr. Maria Stefanopoulou, Dr. Gerhard Rubner, Dr. Kerstin Bensdorf, Dominic Kubutat, Prof. Dr. William S. Sheldrick and Prof. Dr. Ronald Gust

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410357

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      Zeise screen: Organometallic compounds with aspirin substructure have interesting biological effects. Investigations into aspirin-derivatives of Zeise’s salt, demonstrate that Zeise’s salt itself is pharmacologically active and represents a potent inhibitor of cyclooxygenase enzymes, which suggest its use as pharmacophor in medicinal chemistry for the design of new metal-based drugs.

    2. Heterogeneous Catalysis

      Nanoscale Magnetic Stirring Bars for Heterogeneous Catalysis in Microscopic Systems

      Shuliang Yang, Dr. Changyan Cao, Yongbin Sun, Peipei Huang, Fangfang Wei and Prof. Weiguo Song

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410360

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      Nanostirrers: Nanometer-sized magnetic stirring bars containing Pd nanoparticles for heterogeneous catalysis in microscopic system were prepared. They displayed far better catalytic activity than the commercial Pd/C for the hydrogenation of methylene blue in an array of microdroplets.

    3. Boron Compounds

      Fine-Tuning the Nucleophilic Reactivities of Boron Ate Complexes Derived from Aryl and Heteroaryl Boronic Esters

      Dr. Guillaume Berionni, Dipl.-Chem. Artem I. Leonov, Dr. Peter Mayer, Dr. Armin R. Ofial and Prof. Dr. Herbert Mayr

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410562

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      Tailor-made nucleophiles: Kinetic studies reveal that the nucleophilic reactivities of boron ate complexes depend mainly on the nature of the covalently bound ligands at boron. Thus ethylene glycol -B(gly) and neopentyl glycol -B(neo) derivatives are 104 times more reactive than analogous pinacol -B(pin) and catechol -B(cat) derivatives. These insights can be used to tailor the reactivities of boron ate complexes.

    4. Battery Electrodes

      Wet-Chemical Synthesis of Phase-Pure FeOF Nanorods as High-Capacity Cathodes for Sodium-Ion Batteries

      Jian Zhu and Dr. Da Deng

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410572

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      Fair of phase: A new wet-chemical method was developed for the facile preparation of phase-pure FeOF nanorod structures (see SEM image). The as-prepared FeOF nanorods demonstrated a high sodium-ion-storage capacity of approximately 250 mAh g−1 and excellent cycling and rate performance (see graph).

    5. Ammonia Decomposition | Very Important Paper

      Lithium Imide Synergy with 3d Transition-Metal Nitrides Leading to Unprecedented Catalytic Activities for Ammonia Decomposition

      Jianping Guo, Peikun Wang, Prof. Dr. Guotao Wu, Prof. Dr. Anan Wu, Daqiang Hu, Prof. Dr. Zhitao Xiong, Prof. Dr. Junhu Wang, Pei Yu, Fei Chang, Zheng Chen and Prof. Dr. Ping Chen

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410773

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      Beyond an electronic promoter: A synergy between Li2NH and 3d transition-metal nitrides leads to unprecedented catalytic activities for NH3 decomposition. Li2NH acts as more than just an electronic promoter: it is an NH3 transmitting agent and favors the formation of a higher N-content intermediate, thereby altering the overall reaction energetics.

    6. Copper Arenes

      A Copper(I)–Arene Complex With an Unsupported η6 Interaction

      Dr. Ashley M. Wright, Dr. Benjamin J. Irving, Dr. Guang Wu, Dr. Anthony J. H. M. Meijer and Prof. Dr. Trevor W. Hayton

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410948

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      Addition of PR3 (R=Ph or OPh) to [Cu(η2-Me6C6)2][PF6] results in the formation of [(η6-Me6C6)Cu(PR3)][PF6], the first copper–arene complexes to feature an unsupported η6 arene interaction. A DFT analysis shows that the preference for the η6 binding mode is enforced by the steric clash between the methyl groups of the arene ligand and the phenyl rings of the phosphine co-ligand.

    7. Photocatalysis

      A Complex Perovskite-Type Oxynitride: The First Photocatalyst for Water Splitting Operable at up to 600 nm

      Dr. Chengsi Pan, Dr. Tsuyoshi Takata, Mamiko Nakabayashi, Dr. Takao Matsumoto, Prof. Naoya Shibata, Prof. Yuichi Ikuhara and Prof. Kazunari Domen

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410961

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      Overall water splitting was achieved on a new complex perovskite-type oxynitride photocatalyst, LaMgxTa1−xO1+3xN2−3x (x≥1/3), with an absorption edge at 600 nm. Coating the surface of the RhCrOy/LaMgxTa1−xO1+3xN2−3x photocatalyst particles with a layer of amorphous oxyhydroxide effectively prevented the reverse reaction and self-oxidation of the photocatalyst.

    8. Copper Complexes

      Easy Access to the Copper(III) Anion [Cu(CF3)4]

      Andrew M. Romine, Dr. Noel Nebra, Andrey I. Konovalov, Dr. Eddy Martin, Dr. Jordi Benet-Buchholz and Prof. Vladimir V. Grushin

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411348

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      Easy as it gets: The CuIII anion [Cu(CF3)4] is finally easily accessible through the newly developed exceedingly simple and highly efficient one-step procedure directly from CuCl. The reaction occurs at room temperature in air to furnish quantitatively [Cu(CF3)4], which can be used for the synthesis of other, previously unknown CF3CuIII compounds.

    9. Dendrimer Synthesis

      Fluoride-Promoted Esterification with Imidazolide-Activated Compounds: A Modular and Sustainable Approach to Dendrimers

      Dr. Sandra García-Gallego, Daniel Hult, Dr. Johan V. Olsson and Dr. Michael Malkoch

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411370

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      Esterifications with 1,1′-carbonyldiimidazole (CDI) were significantly improved by the use of cesium fluoride as the catalyst, which drives these reactions to completion. Structurally flawless and highly functional polyester dendrimers were obtained through a divergent growth approach featuring the fluoride-promoted esterification of hydroxy-functionalized scaffolds with imidazolide-activated monomers.

    10. Synthetic Methods

      Zinc(II)-Catalyzed Intermolecular Hydrative Aldol Reactions of 2-En-1-ynamides with Aldehydes and Water to form Branched Aldol Products Regio- and Stereoselectively

      Dr. Appaso Mahadev Jadhav, Dr. Vinayak Vishnu Pagar, Dr. Deepak B. Huple and Prof. Dr. Rai-Shung Liu

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411689

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      EZ­ switch: The anti and syn stereoselectivity of the title reaction can be modulated by the size of the sulfonamides to yield E- and Z-configured zinc(II) dienolates selectively. This new reaction leads to enantiopure aldol products by using an inexpensive chiral sulfonamide. EWG=electron-withdrawing group.

  22. Cover Pictures

    1. You have free access to this content
      Highly Diastereoselective and Enantioselective Olefin Cyclopropanation Using Engineered Myoglobin-Based Catalysts

      Dr. Melanie Bordeaux, Dr. Vikas Tyagi and Prof. Dr. Rudi Fasan

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201500136

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      Engineered variants of sperm whale myoglobin enable the selective cyclopropanation of aryl-substituted olefins with α-diazo esters in water. In their Communication (DOI: 10.1002/anie.201409928), R. Fasan and co-workers report the rational design of myoglobin-based catalysts capable of mediating this transformation with an unprecedented combination of high catalytic efficiency and excellent diastereo- and enantioselectivity.

  23. Communications

    1. Biradicaloids

      Stable Heterocyclopentane-1,3-diyls

      Alexander Hinz, Prof. Dr. Axel Schulz and Dr. Alexander Villinger

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410276

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      There is a house in UV light: By an unprecedented ring expansion reaction, diphosphadiazanediyls were utilized to activate carbon monoxide, leading to the first stable cyclopentane-1,3-diyl, which can be transformed into a housane by UV irradiation. Cyclopentane-1,3-diyl displays typical biradicaloid reactivity, such as activation of small molecules bearing single or multiple bonds. Ter=2,6-dimesitylphenyl.

    2. Carbenes

      Transition-Metal-Free Intramolecular Carbene Aromatic Substitution/Büchner Reaction: Synthesis of Fluorenes and [6,5,7]Benzo-fused Rings

      Zhenxing Liu, Haocheng Tan, Long Wang, Tianren Fu, Ying Xia, Dr. Yan Zhang and Prof. Dr. Jianbo Wang

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409982

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      Transition-metal-free: The synthesis of fluorenes and [6,5,7]benzo-fused rings is achieved through a transition-metal-free protocol of intramolecular aromatic substitution and Büchner reaction. The new synthetic method uses readily available aromatic N-tosylhydrazones as the diazo compound precursors and shows wide substrate scope.

    3. Molecular Recognition

      Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors

      Harry Destecroix, Charles M. Renney, Dr. Tiddo J. Mooibroek, Tom S. Carter, Patrick F. N. Stewart, Prof. Matthew P. Crump and Prof. Anthony P. Davis

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409124

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      Sticky branches: The carboxylate-terminated side chains in a series of carbohydrate receptors contributed to binding if their length was just right. If they were too long, they blocked the cavity, but shorter variants could reach round to interact with polar groups on the substrate. Binding is favored by conformational degeneracy: If one carboxylate group moves away, another can take its place.

    4. Heterogeneous Catalysis | Hot Paper

      Heterogeneous Water Oxidation: Surface Activity versus Amorphization Activation in Cobalt Phosphate Catalysts

      Diego González-Flores, Irene Sánchez, Dr. Ivelina Zaharieva, Katharina Klingan, Jonathan Heidkamp, Dr. Petko Chernev, Dr. Prashanth W. Menezes, Prof. Dr. Matthias Driess, Prof. Dr. Holger Dau and Dr. Mavis L. Montero

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409333

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      The complete transformation during catalytic operation of crystalline and surface-active Co3(PO4)2⋅8 H2O into amorphous and volume-active cobalt oxide reveals basic features of heterogeneous water oxidation catalysis, which is discussed as a convolution of three phenomena: surface catalysis, volume catalysis, and restructuring of the material under operation.

    5. Cluster Binding

      Modulation of Benzene or Naphthalene Binding to Palladium Cluster Sites by the Backside-Ligand Effect

      Yuki Ishikawa, Seita Kimura, Kohei Takase, Koji Yamamoto, Dr. Yuki Kurashige, Prof. Takeshi Yanai and Prof. Tetsuro Murahashi

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409499

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      The backside-ligand modulation strategy is used to enhance the substrate binding property of Pd clusters. The benzene or naphthalene binding ability of Pd3 or Pd4 clusters is enhanced significantly by the backside cyclooctatetraene ligand (see ovals in scheme), leading to the first isolable μ3-benzene Pd3 clusters or μ4-naphthalene Pd4 clusters.

    6. Lab-on-a-Chip

      Chip-Based Free-Flow Electrophoresis with Integrated Nanospray Mass-Spectrometry

      M. Sc. Christian Benz, Dr. Michael Boomhoff, M. Sc. Johannes Appun, Prof. Dr. Christoph Schneider and Prof. Dr. Detlev Belder

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409663

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      Going our separate weighs: Micro-free-flow electrophoresis is directly coupled with mass spectrometry and applied in a [3+2]-cycloannulation. This new method enables online purification and monitoring of chemical processes, thereby paving the way for more complex chemical synthesis on integrated lab-on-a-chip devices.

  24. Minireviews

    1. Biphasic Catalysis

      Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

      Dr. Marc Pera-Titus, Dr. Loïc Leclercq, Dr. Jean-Marc Clacens, Dr. Floryan De Campo and Prof. Dr. Véronique Nardello-Rataj

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201402069

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      What a pick! Pickering emulsions are surfactant-free dispersions of two immiscible fluids which are kinetically stabilized by colloidal particles. This review describes recent examples of hybrid and composite amphiphilic materials for the design of interfacial catalysts in Pickering emulsions for industrially relevant biphasic reactions in fine chemistry, biofuel upgrading, and depollution.

  25. Communications

    1. Analytical Methods

      Photoswitching Kinetics and Phase-Sensitive Detection Add Discriminative Dimensions for Selective Fluorescence Imaging

      Jérôme Querard, Dr. Tal-Zvi Markus, Marie-Aude Plamont, Carole Gauron, Pengcheng Wang, Dr. Agathe Espagne, Prof. Dr. Michel Volovitch, Prof. Dr. Sophie Vriz, Dr. Vincent Croquette, Dr. Arnaud Gautier, Dr. Thomas Le Saux and Prof. Dr. Ludovic Jullien

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201408985

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      OPIOM: Out-of-phase imaging after optical modulation enables selective and quantitative imaging of a photoswitching fluorescent probe in the presence of interfering species. The application of this method for selective imaging in mammalian cells and zebrafish was demonstrated.

    2. Dual Catalysis

      C[BOND]H Functionalization of Phenols using Combined Ruthenium and Photoredox Catalysis: In Situ Generation of the Oxidant

      M. Sc. David C. Fabry, B. Sc. Meria A. Ronge, Dipl.-Chem. Jochen Zoller and Prof. Dr. Magnus Rueping

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201408891

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      Air and light: The direct ortho C[BOND]H functionalization of o-(2-pyridyl)phenols provides various olefinated phenol ethers in good yields (see Scheme). The ruthenium catalyst is regenerated through oxidation by a photoredox catalyst under visible-light irradiation.

    3. Membranes

      Mapping Conformational Heterogeneity of Mitochondrial Nucleotide Transporter in Uninhibited States

      Dr. Remy Sounier, Dr. Gaetan Bellot and Dr. James J. Chou

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201408417

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      Flexing domains: Liquid-state NMR spectroscopy has been used to study conformational heterogeneity of mitochondrial GTP/GDP transporter. The data reveal that the carrier is intrinsically plastic. Despite the threefold pseudosymmetry of the carrier, the plasticity is asymmetrically distributed among the domains. GDO=generalized degree of order, RDC=residual dipolar coupling.