Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 22

May 26, 2014

Volume 53, Issue 22

Pages 5475–5710

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. You have free access to this content
      Cover Picture: Engineering Multifunctional Capsules through the Assembly of Metal–Phenolic Networks (Angew. Chem. Int. Ed. 22/2014) (page 5475)

      Junling Guo, Dr. Yuan Ping, Dr. Hirotaka Ejima, Dr. Karen Alt, Mirko Meissner, Joseph J. Richardson, Dr. Yan Yan, Prof. Karlheinz Peter, Prof. Dominik von Elverfeldt, Assoc. Prof. Christoph E. Hagemeyer and Prof. Frank Caruso

      Version of Record online: 15 APR 2014 | DOI: 10.1002/anie.201401143

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      Multifunctional capsules were assembled through interactions between metal ions and a single organic ligand. In their Communication on page 5546 ff., F. Caruso et al. show that a common phenolic plant compound, tannic acid, can be used to coordinate a variety of metals, yielding a library of metal–phenolic network (MPN) capsules. The functional properties of the MPN capsule are determined by the coordinated metals and can be tailored for various applications.

    2. You have free access to this content
      Inside Cover: High Degree of Polymerization in a Fullerene-Containing Supramolecular Polymer (Angew. Chem. Int. Ed. 22/2014) (page 5476)

      Dr. Helena Isla, Dr. Emilio M. Pérez and Prof. Dr. Nazario Martín

      Version of Record online: 9 APR 2014 | DOI: 10.1002/anie.201403680

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      Including a preorganized macrocyclic host in a self-recognizing monomer and using fullerenes as guests leads to supramolecular polymers with a very high degree of polymerization. E. M. Pérez, N. Martín, and H. Isla show in their Communication on page 5629 ff. that molecular weights above 150 kDa were determined in solution, whereas up to 90 kDa could be detected through MALDI-TOF mass spectrometry. Very long and straight fibers of lengths in the micrometer range were observed by atomic force microscopy.

    3. You have free access to this content
      Inside Back Cover: Telluride Misfit Layer Compounds: [(PbTe)1.17]m(TiTe2)n (Angew. Chem. Int. Ed. 22/2014) (page 5711)

      Daniel B. Moore, Prof. Matt Beekman, Dr. Sabrina Disch and Dr. David C. Johnson

      Version of Record online: 15 APR 2014 | DOI: 10.1002/anie.201401144

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      Much like skiers taking different lifts to different ski runs down a mountain, designed precursors can be used to direct the self-assembly of targeted intergrowth structures, as described by D. C. Johnson et al. in their Communication on page 5672 ff. The image of Oregon's Mount Hood represents the potential energy landscape, and the colored lines illustrate how different starting points lead to the self-assembly of different metastable compounds.

    4. You have free access to this content
      Back Cover: Three-Dimensional Protein Networks Assembled by Two-Photon Activation (Angew. Chem. Int. Ed. 22/2014) (page 5712)

      Dr. Volker Gatterdam, Dr. Radhan Ramadass, Dr. Tatjana Stoess, Manuela A. H. Fichte, Prof. Dr. Josef Wachtveitl, Prof. Dr. Alexander Heckel and Prof. Dr. Robert Tampé

      Version of Record online: 9 MAY 2014 | DOI: 10.1002/anie.201401149

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      In situ three-dimensional orientation of proteins is a hot topic in life and material science. The manipulation of protein networks allows artificial signal cascades thus controlling protein and cell behavior. In their Communication on page 5680 ff., R. Tampé et al. describe a new way to arrange fusion proteins in a biocompatible hydrogel with minimal distortion by two-photon activation.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. You have free access to this content
      Frontispiece: [B30]: A Quasiplanar Chiral Boron Cluster

      Wei-Li Li, Dr. Ya-Fan Zhao, Dr. Han-Shi Hu, Prof. Dr. Jun Li and Prof. Dr. Lai-Sheng Wang

      Version of Record online: 25 MAY 2014 | DOI: 10.1002/anie.201482271

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      The [B30] cluster exists as a pair of planar structures with a hexagonal hole at different positions. J. Li, L.-S. Wang, and co-workers show in their Communication on page 5540 ff. that these two isomers are enantiomers.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
  4. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
  5. Book Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. Modern Methods in Stereoselective Aldol Reactions. Edited by Rainer Mahrwald. (page 5498)

      Claude Spino

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201400982

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      Wiley-VCH, Weinheim, 2013. 485 pp., hardcover, € 149.00.—ISBN 978-3527332052

  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. René Peters (page 5499)

      Version of Record online: 7 FEB 2014 | DOI: 10.1002/anie.201311144

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      “In a spare hour, I enjoy being in nature with my husky. My favorite way to spend a holiday is to relax by the sea …” This and more about René Peters can be found on page 5499.

  7. Correspondence

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. Chemical Bonding

      Comment on “Fluorine in Shark Teeth: Its Direct Atomic-Resolution Imaging and Strengthening Function” (pages 5502–5503)

      Dr. Antti J. Karttunen and Priv.-Doz. Dr. Florian Kraus

      Version of Record online: 24 APR 2014 | DOI: 10.1002/anie.201402426

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      No covalency: Based on quantum chemical calculations it is shown that the computational results presented in a recent publication of Wang and co-workers do not support the claim that Ca[BOND]F bonding in Ca5(PO4)3F is covalent. Consequently, Ca[BOND]F covalency cannot be held responsible for tooth strengthening or decay.

  8. Reviews

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. Synthetic Methods

      A New Golden Age for Donor–Acceptor Cyclopropanes (pages 5504–5523)

      Dr. Tobias F. Schneider, Dr. Johannes Kaschel and Prof. Dr. Daniel B. Werz

      Version of Record online: 25 APR 2014 | DOI: 10.1002/anie.201309886

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      Tug-of-war on cyclopropanes: Even though donor–acceptor-substituted cyclopropanes were already investigated 30 years ago, the last few years have brought about a renaissance in their chemistry. This Review highlights the most recent developments regarding ring opening, cycloadditions, and ring enlargement.

    2. Strictly Biphasic Janus Structures

      Strictly Biphasic Soft and Hard Janus Structures: Synthesis, Properties, and Applications (pages 5524–5538)

      Dr. Xinchang Pang, Congshan Wan, Mengye Wang and Prof. Zhiqun Lin

      Version of Record online: 1 APR 2014 | DOI: 10.1002/anie.201309352

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      Best of both worlds: Janus structures comprise two hemistructures with different compositions and functionalities. This Review summarizes the synthetic routes to soft, hard, and hybrid soft/hard Janus structures, and discusses their properties and applications.

  9. Communications

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Author Profile
    8. Correspondence
    9. Reviews
    10. Communications
    1. Chiral Boron Cluster

      [B30]: A Quasiplanar Chiral Boron Cluster (pages 5540–5545)

      Wei-Li Li, Dr. Ya-Fan Zhao, Dr. Han-Shi Hu, Prof. Dr. Jun Li and Prof. Dr. Lai-Sheng Wang

      Version of Record online: 3 APR 2014 | DOI: 10.1002/anie.201402488

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      Holey chiral: The [B30] cluster was characterized by photoelectron spectroscopy and ab initio calculations. A pair of planar structures with a hexagonal hole at different positions are found to be degenerate with identical electronic structures. These two isomers are enantiomers, suggesting that [B30] is the first chiral boron cluster.

    2. Organic–Inorganic Hybrid Materials | Hot Paper

      Engineering Multifunctional Capsules through the Assembly of Metal–Phenolic Networks (pages 5546–5551)

      Junling Guo, Dr. Yuan Ping, Dr. Hirotaka Ejima, Dr. Karen Alt, Mirko Meissner, Joseph J. Richardson, Dr. Yan Yan, Prof. Karlheinz Peter, Prof. Dominik von Elverfeldt, Assoc. Prof. Christoph E. Hagemeyer and Prof. Frank Caruso

      Version of Record online: 2 APR 2014 | DOI: 10.1002/anie.201311136

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      Multifunctional capsules: A common plant phenolic compound, tannic acid, can be used to coordinate a variety of metals through a one-step assembly process, thereby yielding a broad library of metal–phenolic network (MPN; see picture) capsules. The properties of the MPN capsules are determined by the coordinated metals.

    3. Synthetic Methods

      Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (−)-Filiformin (pages 5552–5555)

      Daniel J. Blair, Dr. Catherine J. Fletcher, Dr. Katherine M. P. Wheelhouse and Prof. Dr. Varinder K. Aggarwal

      Version of Record online: 22 APR 2014 | DOI: 10.1002/anie.201400944

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      True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary-tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel-type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (−)-filiformin.

    4. Environmental Chemistry

      A Superhydrophobic Sponge with Excellent Absorbency and Flame Retardancy (pages 5556–5560)

      Changping Ruan, Kelong Ai, Xingbo Li and Prof. Lehui Lu

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201400775

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      Coming clean: A robust and flame-retardant sponge has been prepared from the commercially available melamine sponge through a simple and mild two-step strategy. The superhydrophobicity, high porosity, robust stability, and intrinsic flame-retardant nature of the sponge enable the absorption and recycling of crude oil (see picture) as well as organic solvents. The fabrication of this sponge is easy to scale up.

    5. Metal–Organic Framework Films

      Lithographic Deposition of Patterned Metal–Organic Framework Coatings Using a Photobase Generator (pages 5561–5565)

      Dr. Benjamin K. Keitz, Chung Jui Yu, Prof. Jeffrey R. Long and Dr. Rob Ameloot

      Version of Record online: 9 APR 2014 | DOI: 10.1002/anie.201400580

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      A photobase generator and UV irradiation were used to generate the metal–organic frameworks HKUST-1 and {Cu2(trans-1,4-cyclohexanedicarboxylate)2} at room temperature. This method was subsequently applied to the preparation of patterned metal–organic framework coatings.

    6. Bioluminescence

      A Novel Type of Luciferin from the Siberian Luminous Earthworm Fridericia heliota: Structure Elucidation by Spectral Studies and Total Synthesis (pages 5566–5568)

      Valentin N. Petushkov, Maxim A. Dubinnyi, Aleksandra S. Tsarkova, Natalja S. Rodionova, Mikhail S. Baranov, Vadim S. Kublitski, Osamu Shimomura and Ilia V. Yampolsky

      Version of Record online: 15 APR 2014 | DOI: 10.1002/anie.201400529

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      Feeling blue: UV, fluorescence, NMR, and HRMS spectroscopy studies were used to elucidate the structure of the luciferin from the recently discovered luminous earthworm Fridericia heliota. The luciferin, which is part of a novel ATP-dependent bioluminescent system, was found to be a peptide formed from oxalic acid, lysine, a modified tyrosine residue, and γ-aminobutyric acid.

    7. Natural Products

      A Concise and Versatile Synthesis of Alkaloids from Kopsia tenuis: Total Synthesis of (±)-Lundurine A and B (pages 5569–5572)

      Prof. Shigeru Arai, Masaya Nakajima and Prof. Atsushi Nishida

      Version of Record online: 25 MAY 2014 | DOI: 10.1002/anie.201400464

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      To the core: The total synthesis of (±)-lundurines A and B is described. One of the key reactions is a SmI2-mediated cyclopropanation, which delivered the core structure with perfect stereocontrol of the quaternary carbon centers. Palladium- and ruthenium-catalyzed cyclizations were also effective for constructing seven- and five-membered heterocycles, respectively, to complete the total syntheses.

      Corrected by:

      Corrigendum: Corrigendum: A Concise and Versatile Synthesis of Alkaloids from Kopsia tenuis: Total Synthesis of (±)-Lundurine A and B

      Vol. 53, Issue 52, 14295, Version of Record online: 17 DEC 2014

    8. Molecular Imaging

      DNA-Templated Assembly of a Heterobivalent Quantum Dot Nanoprobe For Extra- and Intracellular Dual-Targeting and Imaging of Live Cancer Cells (pages 5573–5577)

      Wei Wei, Xuewen He and Prof. Nan Ma

      Version of Record online: 16 APR 2014 | DOI: 10.1002/anie.201400428

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      Put two and two together: Two spatially isolated cancer markers (nucleolin and mRNA) present on the cell surface and in cell cytosol, respectively, have been targeted with a DNA-templated heterobivalent quantum dot (QD) nanoprobe. Fluorescence resonance energy transfer based confocal microscopy allows imaging and unambiguous signal deconvolution of the mRNA-targeting QD nanoprobes inside cancer cells.

    9. Mixed-Matrix Membranes

      Simultaneous Spray Self-Assembly of Highly Loaded ZIF-8–PDMS Nanohybrid Membranes Exhibiting Exceptionally High Biobutanol-Permselective Pervaporation (pages 5578–5582)

      Hongwei Fan, Dr. Qi Shi, Hao Yan, Prof. Shulan Ji, Prof. Jinxiang Dong and Prof. Guojun Zhang

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201309534

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      Thin and functional: A ZIF-8/polymer suspension and a cross-linker/catalyst solution were simultaneously sprayed onto a polysulfone substrate (see picture). The nanoparticles of the zeolitic imidazolate framework ZIF-8 were dispersed uniformly and separated from one another by the polymer chains. The resulting ZIF-8/polymer nanohybrid membranes exhibited excellent biobutanol-permselective pervaporation.

    10. Metal–Organic Frameworks

      Pressure-Induced Bond Rearrangement and Reversible Phase Transformation in a Metal–Organic Framework (pages 5583–5586)

      Dr. Elinor C. Spencer, Dr. Mangalampalli S. R. N. Kiran, Dr. Wei Li, Prof. Upadrasta Ramamurty, Prof. Nancy L. Ross and Prof. Anthony K. Cheetham

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201310276

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      A reversible pressure-induced phase transformation associated with a substantial bond rearrangement is discovered in the metal–organic framework [tmenH2][Er(HCOO)4]2 (tmenH22+=N,N,N′,N′-tetramethylethylenediammonium). The transition is first-order and is accompanied by a unit cell volume change of about 10 %. X-ray diffraction studies reveal the complex bond rearrangement process.

    11. Rare-Cell Enrichment

      You have full text access to this OnlineOpen article
      Rare-Cell Enrichment by a Rapid, Label-Free, Ultrasonic Isopycnic Technique for Medical Diagnostics (pages 5587–5590)

      Dr. Yannyk Bourquin, Dr. Abeer Syed, Dr. Julien Reboud, Dr. Lisa C. Ranford-Cartwright, Prof. Michael P. Barrett and Prof. Jonathan M. Cooper

      Version of Record online: 26 MAR 2014 | DOI: 10.1002/anie.201310401

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      Subtle differences in the physical properties of specific cell types are exploited in a new low-cost ultrasonic system to enrich specific cell populations (see picture; SAW=surface acoustic wave). To demonstrate the efficiency and simplicity of this method, the causative agents of malaria and sleeping sickness in blood were enriched. In this way the infection can be detected at low levels not suitable for conventional diagnostic methods.

    12. Supramolecular Isomers

      Distortional Supramolecular Isomers of Polyrotaxane Coordination Polymers: Photoreactivity and Sensing of Nitro Compounds (pages 5591–5595)

      In-Hyeok Park, Raghavender Medishetty, Ja-Yeon Kim, Prof. Dr. Shim Sung Lee and Prof. Dr. Jagadese J. Vittal

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201310536

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      Polyrotaxane isomers! Of the four supramolecular isomers of coordination polymers synthesized, two have polyrotaxane structures that differ only in the relative positions of the wheel in the neighboring axle. They show different photoreactivity under UV light as well as sensing abilities of a number of organic nitro compounds.

    13. Vibrational Imaging

      Live-Cell Quantitative Imaging of Proteome Degradation by Stimulated Raman Scattering (pages 5596–5599)

      Yihui Shen, Fang Xu, Lu Wei, Fanghao Hu and Prof. Wei Min

      Version of Record online: 15 APR 2014 | DOI: 10.1002/anie.201310725

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      Breaking it down: Stimulated Raman scattering microscopy was coupled with metabolic labeling with 13C-phenylalanine to visualize global proteolysis activity in living cells with subcellular resolution. Through 12C/(12C+13C) ratio maps, the protein decay kinetics of mammalian cells under steady-state conditions and various perturbations, including oxidative stress, cell differentiation, and huntingtin protein aggregation, were quantified.

    14. Asymmetric Catalysis

      Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3-Diazenated Pyrroloindolines (pages 5600–5603)

      Dr. Hosea M. Nelson, Solomon H. Reisberg, Hunter P. Shunatona, Jigar S. Patel and Prof. Dr. F. Dean Toste

      Version of Record online: 8 APR 2014 | DOI: 10.1002/anie.201310905

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      Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99 % yield and 96 % ee (MTBE=methyl tert-butyl ether).

    15. Organophotocatalysis

      Enantioselective Organo-Photocatalysis Mediated by Atropisomeric Thiourea Derivatives (pages 5604–5608)

      Nandini Vallavoju, Dr. Sermadurai Selvakumar, Dr. Steffen Jockusch, Prof. Dr. Mukund P. Sibi and Prof. Dr. Jayaraman Sivaguru

      Version of Record online: 16 APR 2014 | DOI: 10.1002/anie.201310940

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      Organo-photocatalysts that are based on atropisomeric thioureas and display lower excited-state energies than the reactive substrates have been developed. These photocatalysts were found to be efficient in promoting the [2+2] photocycloaddition of 4-alkenyl-substituted coumarins, which led to the corresponding products with high enantioselectivity (77–96 % ee) at low catalyst loading (1–10 mol %).

    16. Anion Transport

      A Flexible Solution to Anion Transport: Powerful Anionophores Based on a Cyclohexane Scaffold (pages 5609–5613)

      James A. Cooper, Steven T. G. Street and Prof. Anthony P. Davis

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201311071

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      Speedy shuttling: New anionophores were developed which are simpler and far more accessible than conceptually related earlier systems. They are also less preorganized and anion affinities are lower (as expected), but transport activities set new records. This surprising performance suggests a role for controlled flexibility in the design of transmembrane anion carriers.

    17. Multiple Bonds

      Terminal Imido Rhodium Complexes (pages 5614–5618)

      Ana M. Geer, Dr. Cristina Tejel, Dr. José A. López and Prof. Miguel A. Ciriano

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201400023

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      A missing link: Terminal imido rhodium complexes with a Rh[DOUBLE BOND]N multiple bond have been prepared, thus providing compounds which have been elusive to synthesis. Preliminary studies indicate rhodium imides are somewhat ambiphilic and can therefore undergo protonation at the nitrogen atom, as well as hydrogenation at the Rh[DOUBLE BOND]N bond. These systems also engage in nitrene-group transfer and cycloaddition reactions.

    18. Graphene Quantum Dots

      White-Light-Emitting Edge-Functionalized Graphene Quantum Dots (pages 5619–5623)

      Prof. Dr. Ryo Sekiya, Yuichiro Uemura, Prof. Dr. Hideki Murakami and Prof. Dr. Takeharu Haino

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201311248

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      In the dotlight: Graphene quantum dots (GQDs) functionalized with bulky Fréchet's dendritic wedges at the GQD periphery were synthesized. The single-layered, size-regulated structures of the dendronized GQDs were revealed by atomic force microscopy. The edge-functionalization of the GQDs led to white-light emission, which is an uncommon feature.

    19. Protein Structure

      Conformation and Topology of Diacylglycerol Kinase in E.coli Membranes Revealed by Solid-state NMR Spectroscopy (pages 5624–5628)

      Yanke Chen, Dr. Zhengfeng Zhang, Xinqi Tang, Jianping Li, Prof. Clemens Glaubitz and Prof. Jun Yang

      Version of Record online: 2 APR 2014 | DOI: 10.1002/anie.201311203

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      Native structure: Multidimensional solid-state NMR was used to reveal the secondary structure and topology of diacylglycerol kinase (DAGK) in E. coli membranes. This technique enables the structural characterization of membrane proteins in a native-like environment. The results obtained were different to those obtained from solution NMR and X-ray crystallography, thus highlighting the influence of solubilization environment on the structure of membrane proteins.

    20. Supramolecular polymers

      High Degree of Polymerization in a Fullerene-Containing Supramolecular Polymer (pages 5629–5633)

      Dr. Helena Isla, Dr. Emilio M. Pérez and Prof. Dr. Nazario Martín

      Version of Record online: 28 MAR 2014 | DOI: 10.1002/anie.201402828

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      Tight embrace makes polymers longer: A self-recognizing monomer containing a fullerene guest and an exTTF-based macrocyclic host self-assembles to form linear supramolecular polymers with an extreme degree of polymerization. Polymers of MW up 90 kDa in the gas phase and over 150 kDa in solution have been detected. These materials might find use in the construction of self-organized optoelectronic devices, where polymers of high molecular weight are typically found to yield more efficient devices.

    21. Structure Elucidation

      Magnesiacyclopentadienes as Alkaline-Earth Metallacyclopentadienes: Facile Synthesis, Structural Characterization, and Synthetic Application (pages 5634–5638)

      Junnian Wei, Liang Liu, Ming Zhan, Ling Xu, Prof. Dr. Wen-Xiong Zhang and Prof. Dr. Zhenfeng Xi

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201310116

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      Mg in the middle: The first series of spiro-dilithio magnesiacyclopentadienes, magnesiacyclopentadienes, and dimagnesiabutadienes has been synthesized and structurally characterized. Unique structural characteristics and bonding were revealed, and the reaction chemistry and synthetic applications were studied. An efficient method for synthesizing amino cyclopentadienes was established by using thioformamides.

    22. Synthetic Methods

      Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines (pages 5639–5642)

      Dr. Vincent Bizet, Laura Buglioni and Prof. Dr. Carsten Bolm

      Version of Record online: 9 APR 2014 | DOI: 10.1002/anie.201310790

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      Double duty: A one-pot sulfur imidation/oxidation sequence using a single ruthenium complex for both steps was developed (see scheme). Photochemical decarboxylations of 1,4,2-dioxazol-5-ones provide N-acyl nitrenes, which imidate sulfides at ambient temperature. The subsequent oxidation then occurs under mild phase-transfer catalysis conditions. In this manner, N-acyl sulfimides and sulfoximines can be obtained in high yields starting from sulfides.

    23. Phosphine Catalysis

      Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation (pages 5643–5647)

      Dr. Xiaoyu Han, Dr. Weijun Yao, Dr. Tianli Wang, Yong Ren Tan, Ziyu Yan, Jacek Kwiatkowski and Prof. Dr. Yixin Lu

      Version of Record online: 15 APR 2014 | DOI: 10.1002/anie.201311214

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      Optically enriched 4-spiro-5-pyrazolones were prepared through phosphine-catalyzed enantioselective [4+1] annulation. In this study, substituted pyrazolones were used as a C1 synthon in cycloaddition for the first time. Moreover, this is the first report in which α-substituted allenoates were utilized in an asymmetric [4+1] annulation.

    24. Catalytic Oxidation | Hot Paper

      Trinuclear Pd3O2 Intermediate in Aerobic Oxidation Catalysis (pages 5648–5652)

      Andrew J. Ingram, Dr. Diego Solis-Ibarra, Prof. Richard N. Zare and Prof. Robert M. Waymouth

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201400134

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      Catalytic ménage à trois: A catalytically active trinuclear Pd3O2 complex was identified during Pd-mediated aerobic oxidation of alcohols. Synthesis, structural characterization, and catalytic studies of the trinuclear compound show that it is a product of oxygen activation by reduced palladium species and is a competent intermediate in the catalytic aerobic oxidation of alcohols. These results illuminate a new pathway for O2 reduction by Pd complexes.

    25. Heterocycle Synthesis

      Visible-Light-Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal-Free Conditions (pages 5653–5656)

      Jun Xuan, Xu-Dong Xia, Ting-Ting Zeng, Zhu-Jia Feng, Prof. Dr. Jia-Rong Chen, Dr. Liang-Qiu Lu and Prof. Dr. Wen-Jing Xiao

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201400602

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      Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.

    26. Synthetic Methods

      CO/C-H as an Acylating Reagent: A Palladium-Catalyzed Aerobic Oxidative Carbonylative Esterification of Alcohols (pages 5657–5661)

      Lu Wang, Yanxia Wang, Dr. Chao Liu and Prof. Aiwen Lei

      Version of Record online: 16 APR 2014 | DOI: 10.1002/anie.201400612

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      New choice: A palladium-catalyzed oxidative carbonylative esterification of a variety of functionalized alcohols under base- and ligand-free conditions is demonstrated, and a CO/olefin combination is utilized as the acylating reagent with O2 as a benign oxidant. Notably, scope of the substrate alcohols has been greatly broadened.

    27. Cycloaddition

      The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(II)-Catalyzed Cycloadditions of 1-Sulfonyl 1,2,3-Triazoles with 1,3-Dienes (pages 5662–5666)

      Dr. Hai Shang, Yuanhao Wang, Dr. Yu Tian, Juan Feng and Prof. Dr. Yefeng Tang

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201400426

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      On the (di)verge: Rhodium(II)-catalyzed cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed and enable the efficient and divergent synthesis of two types of synthetically valuable nitrogen heterocycles, 2,5-dihydroazepines and 2,3-dihydropyrroles, by formal [4+3] and [3+2] cycloadditions, respectively. Ts=4-toluenesulfonyl.

    28. Synthetic Methods

      Rhodium-Catalyzed Tandem Cyclization/Si[BOND]C Activation Reaction for the Synthesis of Siloles (pages 5667–5671)

      Dr. Qing-Wei Zhang, Kun An and Prof. Dr. Wei He

      Version of Record online: 8 APR 2014 | DOI: 10.1002/anie.201400828

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      Bare your siloles: The title reaction involving Si[BOND]C(sp3) bond activation was developed for the synthesis of photoluminescent siloles. An external proton source promotes the rhodium catalyst turnover. In addition, the selective activation of Si[BOND]C(sp2) bonds was discovered through the use of a π-acid additive. This method enabled the first synthesis of benzofuran siloles and provided rapid access to conjugated siloles by facile derivatization.

    29. Targeted Synthesis

      Telluride Misfit Layer Compounds: [(PbTe)1.17]m(TiTe2)n (pages 5672–5675)

      Daniel B. Moore, Prof. Matt Beekman, Dr. Sabrina Disch and Dr. David C. Johnson

      Version of Record online: 9 APR 2014 | DOI: 10.1002/anie.201401022

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      Challenging the limits of solid-state synthesis: A synthetic method that entails the design of precursors to form targeted products that are not accessible by traditional solid-state synthesis is put to the test. This method is used to produce the first reported family of telluride misfit layer compounds.

    30. Artificial Signal Cascades

      Nanobiomolecular Multiprotein Clusters on Electrodes for the Formation of a Switchable Cascadic Reaction Scheme (pages 5676–5679)

      Dr. Sven C. Feifel, Andreas Kapp, Dr. Roland Ludwig and Prof. Dr. Fred Lisdat

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201310437

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      Triprotein-containing architectures on electrodes for dual analyte detection: Interprotein electron transfer chains have been established for a multilayer system with three different proteins, namely cellobiose dehydrogenase (CDH), laccase (Lac), and cytochrome c (cyt c). The activity of the individual enzymes can be switched by the applied electrode potential.

    31. Two-Photon Protein Assembly

      Three-Dimensional Protein Networks Assembled by Two-Photon Activation (pages 5680–5684)

      Dr. Volker Gatterdam, Dr. Radhan Ramadass, Dr. Tatjana Stoess, Manuela A. H. Fichte, Prof. Dr. Josef Wachtveitl, Prof. Dr. Alexander Heckel and Prof. Dr. Robert Tampé

      Version of Record online: 11 APR 2014 | DOI: 10.1002/anie.201309930

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      Chemical biology aims at controlling protein interactions and cell behavior by external stimuli. Tools are needed to manipulate and structure target molecules in a non-invasive manner, and this is best achieved by light. A two-photon-activatable glutathione can be used for the light-guided three-dimensional patterning of glutathione S-transferase at superior spatiotemporal resolution.

    32. Fluorescent Dyes

      Geminate Recombination as a Photoprotection Mechanism for Fluorescent Dyes (pages 5685–5688)

      Phil Holzmeister, Andreas Gietl and Prof. Dr. Philip Tinnefeld

      Version of Record online: 8 APR 2014 | DOI: 10.1002/anie.201310300

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      Single-molecule spectroscopy reveals a new mechanism for diffusion-limited photoprotection. Geminate recombination after reduction of organic dyes by thiols enhances photostabilization by avoiding the buildup of photobleaching intermediates such as photo-oxidized states. Stable and long-lasting fluorescence can be achieved in combination with ROXS buffers.

    33. Diborenes

      Boron Radical Cations from the Facile Oxidation of Electron-Rich Diborenes (pages 5689–5693)

      Dr. Philipp Bissinger, Prof. Dr. Holger Braunschweig, Dr. Alexander Damme, Dr. Thomas Kupfer, Dr. Ivo Krummenacher and Dr. Alfredo Vargas

      Version of Record online: 7 APR 2014 | DOI: 10.1002/anie.201311110

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      The NHC- and phosphine-stabilized diborenes IMe⋅(Dur)B[DOUBLE BOND]B(Dur)⋅IMe and PEt3⋅(Mes)B[DOUBLE BOND]B(Mes)⋅PEt3 possess an unusually high boron-centered electron density, making them very strong neutral reductants. Thus, removal of one electron from the B[BOND]B π systems occurs readily by chemical oxidation with (C7H7)BArf4 to afford the corresponding radical cations. The nature of the Lewis base exerts strong influence on the electronic structure of the neutral and cationic diborene systems.

    34. Host–Guest Chemistry

      Noncovalent Chirality Sensing Ensembles for the Detection and Reaction Monitoring of Amino Acids, Peptides, Proteins, and Aromatic Drugs (pages 5694–5699)

      Dr. Frank Biedermann and Prof. Dr. Werner M. Nau

      Version of Record online: 9 APR 2014 | DOI: 10.1002/anie.201400718

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      Strong and diagnostic induced circular dichroism signals in the near-UV or visible region are obtained when chiral, optically transparent analytes bind to an achiral chemosensing ensemble composed of a macrocyclic host and dye. This affords a novel, supramolecular detection method for chiral aromatic analytes in water.

    35. Biomimetics of Carbohydrate Nucleotides

      Fluorescent Mimetics of CMP-Neu5Ac Are Highly Potent, Cell-Permeable Polarization Probes of Eukaryotic and Bacterial Sialyltransferases and Inhibit Cellular Sialylation (pages 5700–5705)

      Dr. Johannes J. Preidl, Dr. Vinayaga S. Gnanapragassam, Dr. Michael Lisurek, Dr. Jörn Saupe, Prof. Dr. Rüdiger Horstkorte and Prof. Dr. Jörg Rademann

      Version of Record online: 15 APR 2014 | DOI: 10.1002/anie.201400394

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      You can't run, you can't hide: Sialyltransferases cover cancer cells with neuraminic acids, enabling them to escape from tissues and to metastasize. Cell-permeable chemical probes targeting this class of enzymes might help to study, understand, and inhibit such processes.

    36. Thermoresponsive Membranes

      Temperature-Modulated Water Filtration Using Microgel-Functionalized Hollow-Fiber Membranes (pages 5706–5710)

      Daniel Menne, Fee Pitsch, Dr. John E. Wong, Prof. Andrij Pich and Prof. Matthias Wessling

      Version of Record online: 16 APR 2014 | DOI: 10.1002/anie.201400316

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      Hollow-fiber membranes can be modified in a straightforward fashion with thermoresponsive microgels when the microgels are infiltrated into the porous structure of the membrane in dead-end mode at constant flux. The resulting membranes show thermoresponsive properties in terms of resistance and retention.

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