Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 26

June 25, 2012

Volume 51, Issue 26

Pages 6281–6534

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Cover Picture: A Combined Gas-Phase Photoelectron Spectroscopic and Theoretical Study of Zeise’s Anion and Its Bromine and Iodine Analogues (Angew. Chem. Int. Ed. 26/2012) (page 6281)

      Gao-Lei Hou, Hui Wen, Dr. Kenneth Lopata, Dr. Wei-Jun Zheng, Dr. Karol Kowalski, Dr. Niranjan Govind, Dr. Xue-Bin Wang and Dr. Sotiris S. Xantheas

      Article first published online: 15 JUN 2012 | DOI: 10.1002/anie.201203656

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      Zeise's anion is the quintessential organometallic compound first synthesized by William Zeise in the 1820s. In their Communication on page 6356 ff., S. S. Xantheas et al. present a combined gas-phase photoelectron spectroscopic and computational study of Zeise's anion, which provides rich and detailed chemical-bonding and interaction information on the anion and its bromine and iodine analogues (Zeise's portrait taken from the Wikipedia entry on William C. Zeise).

  2. Inside Cover

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    13. Minireview
    14. Review
    15. Communications
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    1. Inside Cover: [P9]+[Al(ORF)4], the Salt of a Homopolyatomic Phosphorus Cation (Angew. Chem. Int. Ed. 26/2012) (page 6282)

      Dr. Tobias Köchner, Dipl.-Chem. Tobias A. Engesser, Dr. Harald Scherer, Prof. Dr. Dietmar A. Plattner, M. Sc. Alberto Steffani and Prof. Dr. Ingo Krossing

      Article first published online: 15 JUN 2012 | DOI: 10.1002/anie.201203991

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      Like a sunset the pure phosphorus cation [P9]+, which was hitherto only known in the gas phase, now rises as the first member of this substance class in the liquid and solid-state phases. I. Krossing et al. describe in their Communication on page 6529 ff. how pseudo-gas-phase conditions induced by the weakly coordinating anion [Al{OC(CF3)3}4] led to the stabilization of the reactive cation in the condensed phase. Photo: Torsten Schmidt.

  3. Inside Back Cover

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    15. Communications
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    1. Inside Back Cover: One-Pot Controlled Synthesis of Hexagonal-Prismatic Cu1.94S-ZnS, Cu1.94S-ZnS-Cu1.94S, and Cu1.94S-ZnS-Cu1.94S-ZnS-Cu1.94S Heteronanostructures (Angew. Chem. Int. Ed. 26/2012) (page 6535)

      Dr. Shi-Kui Han, Ming Gong, Hong-Bin Yao, Ze-Ming Wang and Prof. Dr. Shu-Hong Yu

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201203659

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      Hexagonal-prismatic Cu1.94S-ZnS, Cu1.94S-ZnS-Cu1.94S, and Cu1.94S-ZnS-Cu1.94S-ZnS-Cu1.94S nanostructures can be synthesized with screw-, dumbbell-, and sandwich-like forms. In their Communication on page 6365 ff., S.-H. Yu et al. show that the type of product can be controlled by the molar ratio of the CuI and [Zn(S2CNEt2)2] precursors in oleylamine. Picture design: M.-R. Gao.

  4. Back Cover

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    15. Communications
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    1. Back Cover: A Light-Induced Phase Exhibiting Slow Magnetic Relaxation in a Cyanide-Bridged [Fe4Co2] Complex (Angew. Chem. Int. Ed. 26/2012) (page 6536)

      Dr. Masayuki Nihei, Yuki Okamoto, Yoshihiro Sekine, Dr. Norihisa Hoshino, Dr. Takuya Shiga, Dr. Isiah Po-Chun Liu and Prof. Dr. Hiroki Oshio

      Article first published online: 24 MAY 2012 | DOI: 10.1002/anie.201203654

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      Photoswitchable single-molecule magnets are attractive materials that may find applications in future molecular devices. In their Communication on page 6361 ff., H. Oshio and co-workers describe a cyanide-bridged [Fe4Co2] extended square-type complex that displays a thermal and light-induced electron-transfer-coupled spin transition. The light-induced phase transition at low temperature leads to ferromagnetic interactions between the metal ions and the onset of slow magnetic relaxation.

  5. Editorial

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    14. Review
    15. Communications
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  6. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 26/2012 (pages 6287–6300)

      Article first published online: 21 JUN 2012 | DOI: 10.1002/anie.201290048

  7. News

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  8. Author Profile

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    1. Frank Würthner (pages 6308–6309)

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201201949

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      “Looking back over my career, I would say that some detours were worth it. When I was eighteen I wanted to be a chemistry student, however, first I had to spend one year in the army …” This and more about Frank Würthner can be found on page 6308.

  9. News

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  10. Book Review

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    1. Supramolecular Photochemistry. Controlling Photochemical Processes. Edited by V. Ramamurthy and Yoshihisa Inoue. (pages 6311–6312)

      Alberto Credi

      Article first published online: 15 JUN 2012 | DOI: 10.1002/anie.201202588

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      John Wiley & Sons, Hoboken 2011. 640 pp., hardcover, € 129.00.—ISBN 978-0470230534

  11. Highlights

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    1. Bacterial Communication

      Deconvoluting Interspecies Bacterial Communication (pages 6314–6315)

      Dr. Roberta J. Worthington and Prof. Dr. Christian Melander

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202440

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      The universal bacterial signal molecule autoinducer-2 (AI-2) is derived from 4,5-dihydroxy-2,3-pentanedione (DPD). DPD exists in a complex equilibrium between multiple forms (see scheme), and NMR spectroscopy has now been used to establish that the extent of the structural diversity displayed by DPD over a broad pH range is even greater than previously posited.

    2. Lewis Acidic Cyclophanes

      Incorporation of Boron in the Walls of an “All-Carbon” Cyclophane: A Novel Approach to Lewis Acidic Macrocycles (pages 6316–6318)

      Prof. Dr. François P. Gabbaï

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201660

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      A p-doped conjugated cyclophane! The six boron atoms of the bora-cyclophane (see picture) recently reported by Chen and Jäkle team up to impart a set of unique properties to this novel macrocycle. In particular, this macrocycle undergoes six consecutive reversible reductions to afford the hexaanion. It also binds up to six small nucleophilic anions, a process that quenches the fluorescence of the ring and changes its character to electron-rich.

  12. Minireview

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    1. Molecular Scaffolds

      Molecular Scaffolds Using Multiple Orthogonal Conjugations: Applications in Chemical Biology and Drug Discovery (pages 6320–6326)

      David M. Beal and Dr. Lyn H. Jones

      Article first published online: 19 APR 2012 | DOI: 10.1002/anie.201200002

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      More tools, please! The toolbox of synthetic transformations that facilitate chemistry at the interface with biology, particularly in a pharmaceutical setting, is still far from adequate. Heteromultifunctional scaffolds (represented by the pocket knife in the picture) suitable for sequential “click” reactions have been developed recently that may find significant utility in the areas of chemical biology and chemically enabled biotherapeutics.

  13. Review

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    1. Supramolecular Chemistry

      Molecular Assemblies of Perylene Bisimide Dyes in Water (pages 6328–6348)

      Daniel Görl, Dr. Xin Zhang and Prof. Dr. Frank Würthner

      Article first published online: 9 MAY 2012 | DOI: 10.1002/anie.201108690

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      Fascinating functional nanostructures are formed in water by amphiphilic perylene bisimide dyes through strong hydrophobic interactions. This Review describes the current developments in the self-assembly of perylene bisimides in water to form π–π-stacked molecular aggregates.

  14. Communications

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    1. Electrochemistry

      Dynamic Electrochemistry in Flame Plasma Electrolyte (pages 6350–6355)

      Atif Elahi, Dr. Toks Fowowe and Dr. Daren J. Caruana

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201200226

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      Chemistry in flames: Dynamic electrochemistry in the gas phase is described by considering the ionized medium of a flame as an electrolyte (see picture). This study opens up the possibility of accessing redox reactions that are outside the potential limits set by the solvent in conventional liquid-phase electrochemistry.

    2. Gaseous Organometallics

      A Combined Gas-Phase Photoelectron Spectroscopic and Theoretical Study of Zeise’s Anion and Its Bromine and Iodine Analogues (pages 6356–6360)

      Gao-Lei Hou, Hui Wen, Dr. Kenneth Lopata, Dr. Wei-Jun Zheng, Dr. Karol Kowalski, Dr. Niranjan Govind, Dr. Xue-Bin Wang and Dr. Sotiris S. Xantheas

      Article first published online: 8 MAY 2012 | DOI: 10.1002/anie.201201959

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      Shining light on Zeise: In a study of Zeise's anion, [PtCl3(C2H4)], and its bromine and iodine analogues, electronic structure information for each species, derived from spectral features, is assigned through calculations at the coupled cluster level of theory. The calculations indicate that the electron binding energies decrease with halogen size and that there is a synergistic η2 interaction between C2H4 and the PtX3 anions.

    3. Photoswitchable Magnetism

      A Light-Induced Phase Exhibiting Slow Magnetic Relaxation in a Cyanide-Bridged [Fe4Co2] Complex (pages 6361–6364)

      Dr. Masayuki Nihei, Yuki Okamoto, Yoshihiro Sekine, Dr. Norihisa Hoshino, Dr. Takuya Shiga, Dr. Isiah Po-Chun Liu and Prof. Dr. Hiroki Oshio

      Article first published online: 3 MAY 2012 | DOI: 10.1002/anie.201202225

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      Single-molecule magnets: A cyanide-bridged hexanuclear complex showed a thermal electron-transfer-coupled spin transition centered at 220 K. Light irradiation at low temperature (LT; HT=high temperature) generated a metastable state showing slow magnetic relaxation in measurements of the alternating-current magnetic susceptibility (χm; see picture).

    4. Heteronanostructures

      One-Pot Controlled Synthesis of Hexagonal-Prismatic Cu1.94S-ZnS, Cu1.94S-ZnS-Cu1.94S, and Cu1.94S-ZnS-Cu1.94S-ZnS-Cu1.94S Heteronanostructures (pages 6365–6368)

      Dr. Shi-Kui Han, Ming Gong, Hong-Bin Yao, Ze-Ming Wang and Prof. Dr. Shu-Hong Yu

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202128

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      Playing six-a-side: Complex hexagonal prism Cu1.94S-ZnS heteronanostructures were synthesized by a colloidal route. Cu1.94S-ZnS, Cu1.94S-ZnS-Cu1.94S, and Cu1.94S-ZnS-Cu1.94S-ZnS-Cu1.94S structures are formed with screw-, dumbbell-, and sandwich-like shapes by using CuI and [Zn(S2CNEt2)2] as precursors in oleylamine.

    5. RNA Structures

      Strong and Selective Binding of Amiloride to an Abasic Site in RNA Duplexes: Thermodynamic Characterization and MicroRNA Detection (pages 6369–6372)

      Dr. Yusuke Sato, Toshiki Ichihashi, Dr. Seiichi Nishizawa and Prof. Dr. Norio Teramae

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201201790

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      Firmly tied: The binding affinity of amiloride for an abasic (AP) site-containing RNA duplex (see picture) is two orders of magnitude superior to the affinity of the corresponding AP site-containing DNA duplex. The observed high binding affinity for the RNA duplex arises from a favorable enthalpy gain. The binding-induced fluorescence response of amiloride is applicable to microRNA detection.

    6. Self-Assembly

      Thermoresponsive Assembly of Charged Gold Nanoparticles and Their Reversible Tuning of Plasmon Coupling (pages 6373–6377)

      Yiding Liu, Xiaogang Han, Le He and Prof. Yadong Yin

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201201816

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      Charged colloidal gold nanoparticles (AuNPs) can be assembled and disassembled in an aqueous solution in response to temperature change and display reversible thermoresponsive tuning of plasmon coupling. The reversible tuning was made possible by manipulating the electrostatic interaction through the temperature-dependent zeta potential of the charged AuNPs (see the extinction spectra of a typical AuNP dispersion).

    7. Nanotubes

      Biosupramolecular Nanowires from Chlorophyll Dyes with Exceptional Charge-Transport Properties (pages 6378–6382)

      Dr. Sanchita Sengupta, Dr. Daniel Ebeling, Dr. Sameer Patwardhan, Dr. Xin Zhang, Dr. Hans von Berlepsch, Dr. Christoph Böttcher, Dr. Vladimir Stepanenko, Dr. Shinobu Uemura, Carsten Hentschel, Prof. Dr. Harald Fuchs, Dr. Ferdinand C. Grozema, Prof. Dr. Laurens D. A. Siebbeles, Prof. Dr. Alfred R. Holzwarth, Prof. Dr. Lifeng Chi and Prof. Dr. Frank Würthner

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201961

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      Conductive tubes: Self-assembled nanotubes of a bacteriochlorophyll derivative are reminiscent of natural chlorosomal light-harvesting assemblies. After deposition on a substrate that consists of a non-conductive silicon oxide surface (see picture, brown) and contacting the chlorin nanowires to a conductive polymer (yellow), they show exceptional charge-transport properties.

    8. Photoluminescence

      Crystal-Plane-Dependent Photoluminescence of Pentacene 1D Wire and 2D Disk Crystals (pages 6383–6388)

      Ji Eun Park, Minhyeok Son, Misun Hong, Gyeongjin Lee and Hee Cheul Choi

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201971

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      Down to the wire: Pentacene exhibits crystal-plane-dependent photoluminescence (PL) activity, as demonstrated in highly crystalline 1D wires and 2D disks, which were selectively synthesized using the vaporization–condensation–recrystallization (VCR) process. Although pentacene 1D wires and 2D disks have identical triclinic crystal structures, PL activity is observed only from pentacene 1D wires owing to the presence of “PL-active” (010) planes.

    9. Nanotube Toxicology

      Degree of Chemical Functionalization of Carbon Nanotubes Determines Tissue Distribution and Excretion Profile (pages 6389–6393)

      Dr. Khuloud T. Al-Jamal, Dr. Antonio Nunes, Dr. Laura Methven, Dr. Hanene Ali-Boucetta, Dr. Shouping Li, Dr. Francesca M. Toma, Dr.  M. Antonia Herrero, Dr. Wafa' T. Al-Jamal, Dr. Huub M. M. ten Eikelder, Dr. Julie Foster, Prof. Stephen Mather, Prof. Maurizio Prato, Dr. Alberto Bianco and Prof. Kostas Kostarelos

      Article first published online: 23 MAY 2012 | DOI: 10.1002/anie.201201991

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      Getting rid of the tubes: An assessment of the retention of functionalized multi-walled carbon nanotubes (MWNTs) in the organs of mice was carried out using single photon emission computed tomography and quantitative scintigraphy (see scheme). Increasing the degree of functionalization on MWNTs enhanced renal clearance, while lower functionalization promoted reticuloendethelial system accumulation.

    10. Metal–Metal Multiple Bonds

      An Electron-Rich Molybdenum–Molybdenum Quintuple Bond Spanned by One Lithium Atom (pages 6394–6397)

      Shin-Cheng Liu, Wei-Lun Ke, Prof. Dr. Jen-Shiang K. Yu, Ting-Shen Kuo and Prof. Dr. Yi-Chou Tsai

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201200122

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      Take five: A unique quintuply bonded dimolybdenum complex [Mo2(μ-Li){μ-HC(N-2,6-Et2C6H3)2}3] (see picture) was synthesized and characterized. The Mo[BOND]Mo interaction includes an unexpected bridging Li+ ion. Calculations indicate the bridging Li+ ion does not perturb the Mo[BOND]Mo bond length (2.0612(4) Å), but results in a relatively small effective Mo[BOND]Mo bond order of 3.67.

    11. Mechanochromic Luminescence

      A Dipeptide-Based Multicolored-Switching Luminescent Solid Material: When Molecular Assemblies Meet Mechanochemical Reaction (pages 6398–6401)

      Ming-Jun Teng, Prof. Xin-Ru Jia, Dr. Xiao-Fang Chen and Prof. Yen Wei

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201200320

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      Color schemes: A mechanochromic material composed of two types of peptides bearing a pyrene group and rhodamine B moieties, respectively, displays multiluminescent colors, such as blue, green, and reddish in one sample (see picture). The mechanochromic behavior is based on a combined switching of molecular assemblies and chemical structure.

    12. Cycloaddition

      A Mild Benzannulation through Directed Cycloaddition Reactions (pages 6402–6405)

      James D. Kirkham, Dr. Roger J. Butlin and Prof. Joseph P. A. Harrity

      Article first published online: 16 MAY 2012 | DOI: 10.1002/anie.201200917

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      Simple as ABC: Alkynyl borane cycloadditions can be substrate-directed to assemble aromatic difluoroboranes within an extremely mild and efficient reaction manifold compared to that of traditional methods (see scheme). The aromatic boranes are readily transformed into a range of useful products.

    13. Catalytic Microspheres

      A General Approach to Mesoporous Metal Oxide Microspheres Loaded with Noble Metal Nanoparticles (pages 6406–6410)

      Zhao Jin, Manda Xiao, Dr. Zhihong Bao, Prof. Peng Wang and Prof. Jianfang Wang

      Article first published online: 26 APR 2012 | DOI: 10.1002/anie.201106948

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      Catalytic microspheres: A general approach is demonstrated for the facile preparation of mesoporous metal oxide microspheres loaded with noble metal nanoparticles (see TEM image in the picture). Among 18 oxide/noble metal catalysts, TiO2/0.1 mol % Pd microspheres showed the highest turnover frequency in NaBH4 reduction of 4-nitrophenol (see picture).

    14. Biomineralization

      Controlling Nanostructures of Mesoporous Silica Fibers by Supramolecular Assembly of Genetically Modifiable Bacteriophages (pages 6411–6415)

      Prof. Chuanbin Mao, Fuke Wang and Binrui Cao

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201107824

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      A useful virus: The synthesis of a new family of mesoporous silica fibers is reported. Monodisperse filamentous bacteriophages self-assembled into highly ordered hexagonal lattices that were used as templates for the formation of silica nanostructures. Removal of the bacteriophage assembly through calcination led to the formation of mesoporous silica fibers with pore structures precisely defined by the bacteriophage assembly (see picture).

    15. Artificial Cells

      Protein Expression, Aggregation, and Triggered Release from Polymersomes as Artificial Cell-like Structures (pages 6416–6420)

      Chiara Martino, Dr. Shin-Hyun Kim, Dr. Louise Horsfall, Dr. Alireza Abbaspourrad, Dr. Susan J. Rosser, Prof. Jonathan Cooper and Prof. David A. Weitz

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201443

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      Bringing droplets to life: A cytoskeletal protein (red dots, see scheme) is expressed in artificial cells composed of biocompatible polymersomes, which encapsulate expression machinery and amino acid building blocks. Release of the expressed proteins can be triggered by a negative osmotic shock.

    16. Graphene

      Linking Photo- and Redoxactive Phthalocyanines Covalently to Graphene (pages 6421–6425)

      Dr. Maria-Eleni Ragoussi, Jenny Malig, Georgios Katsukis, Dr. Benjamin Butz, Prof. Erdmann Spiecker, Dr. Gema de la Torre, Prof. Tomás Torres and Prof. Dirk M. Guldi

      Article first published online: 16 MAY 2012 | DOI: 10.1002/anie.201201452

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      “Green” graphene: For the first time, the covalent attachment of a light-harvesting and electron-donating phthalocyanine to the basal plane of few-layer graphene is reported (see picture). Physicochemical characterizations reveal an ultrafast charge separation from the photoexcited phthalocyanine to few-layer graphene followed by a slower charge recombination.

    17. Supramolecular Systems

      Consequences of Cooperativity in Racemizing Supramolecular Systems (pages 6426–6431)

      Seda Cantekin, Dr. Huub M. M. ten Eikelder, Dr. Albert J. Markvoort, Martijn A. J. Veld, Peter A. Korevaar, Prof. Dr. Mark M. Green, Dr. Anja R. A. Palmans and Prof. Dr. E. W. Meijer

      Article first published online: 16 MAY 2012 | DOI: 10.1002/anie.201201701

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      Saluting the sergeant: Phg-BTA (see scheme) cooperatively self-assembles into helical aggregates and shows unprecedented racemization behavior in the presence of base. In thermodynamically controlled conditions, the addition of a small amount of chiral auxiliary to this mixture results in a deracemization reaction and a final enantiomeric excess of 32 %. A theoretical model is presented to understand in detail the results obtained.

    18. Fluorescent Probes

      A Tunable Ratiometric pH Sensor Based on Carbon Nanodots for the Quantitative Measurement of the Intracellular pH of Whole Cells (pages 6432–6435)

      Dr. Wen Shi, Prof. Dr. Xiaohua Li and Prof. Dr. Huimin Ma

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202533

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      The whole picture: Carbon nanodots labeled with two fluorescent dyes have been developed as a tunable ratiometric pH sensor to measure intracellular pH. The nanosensor shows good biocompatibility and cellular dispersibility. Quantitative determinations on intact HeLa cells and pH fluctuations associated with oxidative stress were performed.

    19. Peptide Conformations

      Defying Entropy: Forming Large Head-to-Tail Macrocycles in the Gas Phase (pages 6436–6438)

      Marcus Tirado and Prof. Nicolas C. Polfer

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201202405

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      Spectral fingerprints: Collision-induced dissociation (CID) of protonated peptides in the gas phase results in linear fragment ions with a five-membered oxazolone ring on their C-terminal side. Infrared spectroscopy confirms that smaller fragments adopt oxazolone structures. Conversely, in mid-sized and larger fragments an isomerization to “head-to-tail” macrocycles is observed (see picture).

    20. Asymmetric Organocatalysis

      Aminocatalytic Enantioselective 1,6 Additions of Alkyl Thiols to Cyclic Dienones: Vinylogous Iminium Ion Activation (pages 6439–6442)

      Xu Tian, Dr. Yankai Liu and Prof. Dr. Paolo Melchiorre

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201202392

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      Remote transmission: In the presence of chiral amines, 2,4-dienones are activated toward the attack of a nucleophile at the δ position, a mode of activation that is termed vinylogous iminium ion catalysis. Specifically, the 1,6 addition of alkyl thiols to β-substituted cyclic dienones was catalyzed by a cinchona-based primary amine; the reaction was highly stereoselective and displayed high selectivity for reaction at the δ position.

    21. Self-Powered Nanophotonics

      Self-Powered Ultrasensitive Nanowire Photodetector Driven by a Hybridized Microbial Fuel Cell (pages 6443–6446)

      Dr. Qing Yang, Ying Liu, Zetang Li, Zongyin Yang, Xue Wang and Prof. Zhong Lin Wang

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202008

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      An integrated system consisting of a carbon fiber–ZnO hybrid nanowire (NW) multicolor photodetector is driven by a microbial fuel cell (see picture; PMMA=poly(methyl methacrylate), E=electrode). The self-powered photodetector can detect at light levels of as little as nW cm−2 intensity with a responsivity of more than 300 A W−1.

    22. Interfacial Self-Assembly

      Interfacial Self-Assembly of Water-Soluble Cationic Porphyrins for the Reduction of Oxygen to Water (pages 6447–6451)

      Astrid J. Olaya, Dr. Delphine Schaming, Prof. Dr. Pierre-Francois Brevet, Prof. Dr. Hirohisa Nagatani, Dr. Hai-Jun Xu, Dr. Michel Meyer and Prof. Dr. Hubert H. Girault

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201202266

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      Meet at the border: Assembly of the water-soluble cobalt tetrakis(N-methylpyridinium-4-yl)porphyrin [CoTMPyP]4+ at soft interfaces is enhanced and stabilized by its interfacial interaction with the lipophilic anion (C6F5)4B. The supramolecular structure thus formed (see picture) provides excellent catalytic activity in the four-electron reduction of oxygen.

    23. Photoisomerization

      Bidirectional Photocontrol of Peptide Conformation with a Bridged Azobenzene Derivative (pages 6452–6455)

      Dr. Subhas Samanta, Prof. Chuanguang Qin, Dr. Alan J. Lough and Prof.  G. Andrew Woolley

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202383

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      It goes both ways: A thiol-reactive cross-linker based on a bridged azobenzene derivative permits photoreversible control of peptide conformation on irradiation with violet (407 nm) and green (500–550 nm) light (see picture) through isomerization of the cross-linker. The large separation of the absorbance bands of the cis (yellow) and trans (red) isomers enables complete bidirectional photoswitching.

    24. Biosensors

      The Biochemiresistor: An Ultrasensitive Biosensor for Small Organic Molecules (pages 6456–6459)

      Dr. Leo M. H. Lai, Dr. Ian Y. Goon, Kyloon Chuah, Dr. May Lim, Prof. Dr. Filip Braet, Prof. Dr. Rose Amal and Prof. Dr. J. Justin Gooding

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201202350

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      New sensation: A resistance-based biosensor uses gold-coated magnetic nanoparticles (Au@MNPs) functionalized with the antibiotic enrofloxin (see picture; purple), which bind to anti-enrofloxin as analyte (blue). The Au@MNPs can be magnetically assembled between electrodes, and the measured resistance R is a function of analyte concentration.

    25. NMR Spectra Without Multiplets

      Decoupling Two-Dimensional NMR Spectroscopy in Both Dimensions: Pure Shift NOESY and COSY (pages 6460–6463)

      Dr. Juan A. Aguilar, Adam A. Colbourne, Dr. Julia Cassani, Dr. Mathias Nilsson and Prof. Gareth A. Morris

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201108888

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      An increase in the resolving power in 2D NMR spectra is obtained by collapsing 2D signals with multiplet structure into 2D singlets. This resolution gain is achieved by combining 2D experiments with pure shift techniques and covariance processing (see picture). The method should be of value in both manual and automated structure determination.

    26. Metal-Containing DNA

      AgI Ion Mediated Formation of a C–A Mispair by DNA Polymerases (pages 6464–6466)

      Tatsuya Funai, Yuki Miyazaki, Megumi Aotani, Eriko Yamaguchi, Dr. Osamu Nakagawa, Dr. Shun-ichi Wada, Prof. Hidetaka Torigoe, Prof. Akira Ono and Prof. Hidehito Urata

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201109191

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      Silver turns up the A–C: In the presence of AgI ions, a DNA polymerase incorporated deoxyadenosine (from dATP) at the site opposite cytosine in the template strand to afford the full-length product (see scheme), meaning that DNA polymerases prefer a C-AgI-A base pair to the more thermodynamically stable C-AgI-C base pair.

    27. Enantiospecific Catalysis

      Ruthenium-Catalyzed Redox Isomerization of Trifluoromethylated Allylic Alcohols: Mechanistic Evidence for an Enantiospecific Pathway (pages 6467–6470)

      Vincent Bizet, Prof. Dr. Xavier Pannecoucke, Prof. Dr. Jean-Luc Renaud and Dr. Dominique Cahard

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201200827

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      Transfer news: A synthetic approach to chiral β-CF3-substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF3-bearing allylic alcohols by an intramolecular suprafacial enantiospecific 1,3-hydrogen transfer (see scheme). This method was used for the enantioselective synthesis of (S)-CF3-citronellol.

    28. Heterocycles

      Facile Preparation of Indoles and 1,2-Benzothiazine 1,1-Dioxides: Nucleophilic Addition of Sulfonamides to Bromoacetylenes and Subsequent Palladium-Catalyzed Cyclization (pages 6471–6474)

      Masahito Yamagishi, Ken Nishigai, Azusa Ishii, Dr. Takeshi Hata and Prof. Dr. Hirokazu Urabe

      Article first published online: 13 MAY 2012 | DOI: 10.1002/anie.201201024

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      Bromine as a double agent: The bromine atom in 1-bromo-1-alkynes works as an electron-withdrawing group to effect the nucleophilic addition of sulfonamides. It again plays a pivotal role in the palladium-catalyzed cyclization of the resultant (Z)-2-(sulfonylamino)-1-bromoalkenes into nitrogen heterocycles (see scheme).

    29. PEG-DNAzymes

      Structure Formation and Catalytic Activity of DNA Dissolved in Organic Solvents (pages 6475–6479)

      Prof. Dr. Hiroshi Abe, Naoko Abe, Dr. Aya Shibata, Keiji Ito, Prof. Dr. Yoshiyuki Tanaka, Mika Ito, Dr. Hisao Saneyoshi, Prof. Dr. Satoshi Shuto and Prof. Dr. Yoshihiro Ito

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201201111

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      Equal-opportunity dissolver: By attaching polyethylene glycol at its 5′ end, DNA (PEG-DNA) can be solubilized in various organic solvents and was shown to form G-quadruplexes by CD spectroscopy. A complex containing iron(III) protoporphyrin IX (hemin) and G-quadruplex-forming PEG-DNA catalyzed an oxidative reaction in methanol (see scheme).

    30. Asymmetric Catalysis

      Highly Stereoselective Synthesis of α-Alkyl-α-Hydroxycarboxylic Acid Derivatives Catalyzed by a Dinuclear Zinc Complex (pages 6480–6483)

      Prof. Dr. Barry M. Trost and Dr. Keiichi Hirano

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201116

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      A dinuclear zinc–ProPhenol catalyst enables highly enantioselective nitro-Michael reactions with oxazol-4(5H)-ones as nucleophilic substrates (see scheme, Nap=2-naphthyl). This work highlights the utility of the ProPhenol family of ligands. The modular nature of these ligands proved crucial in the optimization of reaction conditions to achieve excellent stereoselectivities.

    31. Natural Product Synthesis

      Enantioselective Total Synthesis of Marine Diterpenoid Clavulactone (pages 6484–6487)

      Dr. Zhen-Yu Yang, Hong-Ze Liao, Kang Sheng, Dr. Yong-Fei Chen and Prof. Dr. Zhu-Jun Yao

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201369

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      The key steps in the synthesis of clavulactone are formation of an enantiopure cyclopentane precursor by epoxide rearrangement and intramolecular carbonyl–ene reaction, construction of the 3,4-dihydro-2H-pyran ring by intermolecular hetero-Diels–Alder reaction, closure of the eleven-membered ring, and finally generation of the lactone functionality by chemoselective allylic C(sp3)[BOND]H oxidation.

    32. C[BOND]H Functionalization

      Catalytic C[BOND]H Amination with Aromatic Amines (pages 6488–6492)

      Raymond T. Gephart III, Daria L. Huang, Mae Joanne B. Aguila, Graham Schmidt, Andi Shahu and Prof. Timothy H. Warren

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201201921

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      Aniline joins the club: A β-diketiminato copper(I) catalyst enables C[BOND]H amination of anilines employing low catalyst loadings to preclude oxidation to the diazene ArN[DOUBLE BOND]NAr (see scheme). Electron-poor anilines are particularly resistant towards diazene formation and participate in the amination of strong and unactivated C[BOND]H bonds. N-alkyl anilines also take part in C[BOND]H amination.

    33. Synthetic Methods

      Gold-Catalyzed Cascade Cyclizations of 1,6-Diynyl Carbonates to Benzo[b]fluorenes Involving Arylation of Oxocarbenium Ion Intermediates and Decarboxylative Etherification (pages 6493–6497)

      Yifeng Chen, Ming Chen and Prof. Yuanhong Liu

      Article first published online: 16 MAY 2012 | DOI: 10.1002/anie.201201799

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      Rearranged: The described gold-catalyzed cycloisomerizations give access to highly substituted benzo[b]fluorenes under mild reaction conditions (see scheme). Experimental results indicate that the in situ formed oxocarbenium ion intermediates, derived from gold-catalyzed 3,3-rearrangement and 6-endo-dig cyclization, undergo intramolecular arylation and subsequent decarboxylative etherification to furnish the final ether products.

    34. Thermal Transport Materials

      Polymer/Boron Nitride Nanocomposite Materials for Superior Thermal Transport Performance (pages 6498–6501)

      Wei-Li Song, Ping Wang, Dr. Li Cao, Ankoma Anderson, Dr. Mohammed J. Meziani, Andrew J. Farr and Prof. Dr. Ya-Ping Sun

      Article first published online: 15 MAY 2012 | DOI: 10.1002/anie.201201689

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      Boron nitride nanosheets were dispersed in polymers to give composite films with excellent thermal transport performances approaching the record values found in polymer/graphene nanocomposites. Similarly high performance at lower BN loadings was achieved by aligning the nanosheets in poly(vinyl alcohol) matrix by simple mechanical stretching (see picture).

    35. Protein Modifications

      Chemoselective Ligation of Sulfinic Acids with Aryl-Nitroso Compounds (pages 6502–6505)

      Dr. Mauro Lo Conte and Dr. Kate S. Carroll

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201812

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      Making a comeback: The inefficient condensation of sulfinic acid and aryl nitroso compounds has been transformed into a chemoselective process that converts sulfinic acid into stable cyclic sulfonamide analogues (see scheme). This ligation proceeds rapidly under aqueous conditions in high yield, and lays the groundwork for the development of sulfinic acid detection methods in biological systems.

    36. Nanocrystal Growth

      An Electron Paramagnetic Resonance Spectroscopic Investigation on the Growth Mechanism of NaYF4:Gd Nanocrystals (pages 6506–6510)

      Dr. Rajesh Komban, Dr. Johann P. Klare, Benjamin Voss, Jörg Nordmann, Prof. Dr. Heinz-Jürgen Steinhoff and Prof. Dr. Markus Haase

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201201025

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      Doped nanocrystals of NaYF4 and NaGdF4 are currently studied as upconversion luminescence markers and magnetic resonance imaging contrast agents. An EPR investigation on the growth mechanism of NaYF4:Gd and NaGdF4 nanocrystals showed that these nanomaterials grow in the standard oleic acid-based reaction medium by a dissolution/recrystallization mechanism and not by the aggregation or oriented attachment of smaller particles.

    37. Direct N-Trifluoromethylation

      Direct Electrophilic N-Trifluoromethylation of Azoles by a Hypervalent Iodine Reagent (pages 6511–6515)

      Katrin Niedermann, Natalja Früh, Remo Senn, Barbara Czarniecki, Dr. René Verel and Prof. Dr. Antonio Togni

      Article first published online: 22 MAY 2012 | DOI: 10.1002/anie.201201572

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      Effective CF3 transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed CF3 transfer, provides ready access to a series of new and previously challenging or inaccessible NCF3 compounds.

    38. Epigenetics

      Mechanism and Stem-Cell Activity of 5-Carboxycytosine Decarboxylation Determined by Isotope Tracing (pages 6516–6520)

      Stefan Schiesser, Benjamin Hackner, Toni Pfaffeneder, Markus Müller, Dr. Christian Hagemeier, Dr. Matthias Truss and Prof. Dr. Thomas Carell

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201202583

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      Eraserhead: Stem cells seem to erase epigenetic information by decarboxylation of the newly discovered epigenetic base 5-carboxycytosine (caC; see picture). This reaction is likely to involve a nucleophilic attack of the C5[BOND]C6 double bond.

    39. Biomaterials

      Artificial Egg Stalks Made of a Recombinantly Produced Lacewing Silk Protein (pages 6521–6524)

      Felix Bauer and Prof. Dr. Thomas Scheibel

      Article first published online: 16 MAY 2012 | DOI: 10.1002/anie.201200591

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      Rigid threads: Lacewings protect their eggs from predators by laying them on small stalks (see picture). The stalks have good mechanical properties and, unlike most other silks, a cross β structure. An artificial egg stalk was produced using a designed recombinant variant of a sequenced lacewing egg stalk protein, and it attained 90 % of the tensile strength of a natural egg stalk.

    40. Natural Product Synthesis

      Stereoselective Total Syntheses of Herbicidin C and Aureonuclemycin through Late-Stage Glycosylation (pages 6525–6528)

      Dominik Hager, Peter Mayer, Christian Paulitz, Jörg Tiebes and Prof. Dr. Dirk Trauner

      Article first published online: 29 MAY 2012 | DOI: 10.1002/anie.201201826

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      Better late than never! Two herbicidins, members of an important family of nucleoside antibiotics, have been synthesized for the first time. The route integrates a stereoselective C-glycosylation with several reagent-controlled stereoselective transformations and a surprisingly facile and highly diastereoselective late-stage N-glycosylation.

    41. Cationic Phosphorus

      [P9]+[Al(ORF)4], the Salt of a Homopolyatomic Phosphorus Cation (pages 6529–6531)

      Dr. Tobias Köchner, Dipl.-Chem. Tobias A. Engesser, Dr. Harald Scherer, Prof. Dr. Dietmar A. Plattner, M. Sc. Alberto Steffani and Prof. Dr. Ingo Krossing

      Article first published online: 25 MAY 2012 | DOI: 10.1002/anie.201201262

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      Positive at last: The first condensed-phase homopolyatomic phosphorus cation [P9]+ was prepared using a combination of the oxidant [NO]+ and weakly coordinating anion, [Al{OC(CF3)3}4]. [P9]+ consists of two P5 cages linked by a phosphonium atom to give a D2d-symmetric Zintl cluster. NMR (see picture), Raman, and IR spectroscopy, mass spectrometry, and quantum-chemical calculations confirmed the structure.

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      Article first published online: 21 JUN 2012 | DOI: 10.1002/anie.201290049

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