Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 8

February 15, 2010

Volume 49, Issue 8

Pages 1333–1507

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
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    1. Cover Picture: Nanoparticulate Functional Materials (Angew. Chem. Int. Ed. 8/2010) (page 1333)

      Helmut Goesmann and Claus Feldmann

      Version of Record online: 8 JAN 2010 | DOI: 10.1002/anie.200907226

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      Nanoscientists boldly go to the frontiers of the smallest solids in basic science and their technical application. In their Review on page 1362 ff., H. Goesmann and C. Feldmann point to the visionary potential of nanoparticulate functional materials. After a general introduction of the topic, the optical, electrical, magnetic, and catalytic properties of nanoparticles as well as their potential for upgrading materials are summarized. Moreover, fundamentally novel shapes and compositions of matter are presented.

  2. Inside Cover

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    4. Graphical Abstract
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    8. Highlights
    9. Review
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    1. Inside Cover: Thin-Film Formation of Imidazolium-Based Conjugated Polydiacetylenes and Their Application for Sensing Anionic Surfactants (Angew. Chem. Int. Ed. 8/2010) (page 1334)

      Xiaoqiang Chen, Sunwoo Kang, Min Jung Kim, Joohee Kim, Youn Sang Kim, Heejin Kim, Bo Chi, Sung-Jin Kim, Jin Yong Lee and Juyoung Yoon

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.201000113

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      The stimulus-induced blue-to-red transition of polydiacetylenes (PDAs) has led to the development of a variety of PDA-based chemosensors. In their Communication on page 1422 ff., J. Yoon, J. Y. Lee, and co-workers describe an anionic-surfactant-selective sensor based on PDA and imidazolium, which shows selective color response to anionic surfactants. Furthermore, this system easily distinguishes between the anionic surfactants sodium dodecyl sulfate (SDS) and sodium dodecylbenzenesulfonate (SDBS).

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
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  4. News

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
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  5. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
    10. Communications
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    1. Norbert Krause (page 1354)

      Version of Record online: 19 JAN 2010 | DOI: 10.1002/anie.200906813

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      “The best advice I have ever been given is honesty is the best policy. The worst advice I have ever been given was to give up my academic career …” This and more about Norbert Krause can be found on page 1354.

  6. Book Review

    1. Top of page
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    1. Chirality at the Nanoscale. Nanoparticles, Surfaces, Materials and more. Edited by David B. Amabilino. (page 1355)

      Davide Bonifazi

      Version of Record online: 9 FEB 2010 | DOI: 10.1002/anie.200905648

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      Wiley-VCH, Weinheim 2009. 418 pp., hardcover € 149.00.—ISBN 978-3527320134

  7. Highlights

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    1. Molecular Electronics

      Advanced Molecular Logic with Memory Function (pages 1356–1358)

      Uwe Pischel

      Version of Record online: 25 JAN 2010 | DOI: 10.1002/anie.200906705

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      Commit to memory: Whereas combinational logic devices are indifferent with respect to the history of input application, sequential logic is related to a memory function. A proof-of-principle of the sequential logic concept at the molecular level was demonstrated recently with a surface-confined osmium complex (see picture). This is an important conceptual advance toward molecular information processing.

    2. Expanded Porphyrins

      Lucky Seven: Characterization of Stable T-Shaped Copper(II) Complexes of [32]Heptaphyrins (pages 1359–1361)

      Piotr J. Chmielewski

      Version of Record online: 10 DEC 2009 | DOI: 10.1002/anie.200905577

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      Luck and skill were both needed to find out that tetraaryl[32]heptaphyrin(1.1.1.1.1.1.1) and its fourfold-fused derivative stabilize divalent copper in an unprecedented T-shaped geometry of the coordinating environment (see picture; Cu red, F blue, N light gray, C dark gray).

  8. Review

    1. Top of page
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    1. Nanoscience

      Nanoparticulate Functional Materials (pages 1362–1395)

      Helmut Goesmann and Claus Feldmann

      Version of Record online: 27 JAN 2010 | DOI: 10.1002/anie.200903053

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      At the very beginning was the dyeing of glass, a first application of nanoparticular functional materials (see picture). Today diverse perspectives for the increasing complexity of technical developments are offered. To prepare high-value nanoparticles a number of influences must be considered, and evaluation of particle properties requires the expertise of different fields. This background defines both the challenge and the attraction of nanoscience.

  9. Communications

    1. Top of page
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    4. Graphical Abstract
    5. News
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    10. Communications
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    1. Biosensors

      Quantum Dot Biosensors for Ultrasensitive Multiplexed Diagnostics (pages 1396–1401)

      Daniel Geißler, Loïc J. Charbonnière, Raymond F. Ziessel, Nathaniel G. Butlin, Hans-Gerd Löhmannsröben and Niko Hildebrandt

      Version of Record online: 27 JAN 2010 | DOI: 10.1002/anie.200906399

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      Colorful bioassays: Time- and color-resolved detection of Förster resonance energy transfer (FRET) from luminescent terbium complexes to different semiconductor quantum dots results in a fivefold multiplexed bioassay with sub-picomolar detection limits for all five bioanalytes (see picture). The detection of up to five biomarkers occurs with a sensitivity that is 40–-240-fold higher than one of the best-established single-analyte reference assays.

    2. Dihydrogen Activation

      The Mechanism of Dihydrogen Activation by Frustrated Lewis Pairs Revisited (pages 1402–1405)

      Stefan Grimme, Holger Kruse, Lars Goerigk and Gerhard Erker

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/anie.200905484

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      A new picture of H2activation is given by state-of-the-art quantum chemical calculations of potential energy surfaces and transition states and a thorough theoretical analysis. Key factors for activation of H2 and other small molecules by so-called frustrated Lewis pairs (FLP) are entrance (preparation) steps and the electric field strength inside the FLP cavity.

    3. Conjugated Polymers

      Correlation of Intramolecular Excimer Emission with Lamellar Layer Distance in Liquid-Crystalline Polymers: Verification by the Film-Swelling Method (pages 1406–1409)

      Wang-Eun Lee, Jin-Woo Kim, Chang-Jin Oh, Toshikazu Sakaguchi, Michiya Fujiki and Giseop Kwak

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/anie.200906621

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      Swollen up: Poly(diphenylacetylene) derivatives with different alkyl groups show intramolecular excimer emission that arises from the phenyl–phenyl stack structure in the side chains. The excimer emission is intrinsically correlated with lamellar layer distance. Film-swelling experiments verify that the excimer emission can be modulated by changing the lamella layer distance (see picture).

    4. Spin Transitions

      An Unprecedented Charge Transfer Induced Spin Transition in an Fe–Os Cluster (pages 1410–1413)

      Matthew G. Hilfiger, Meimei Chen, Tatiana V. Brinzari, Tanya M. Nocera, Michael Shatruk, Doros T. Petasis, Janice L. Musfeldt, Catalina Achim and Kim R. Dunbar

      Version of Record online: 18 JAN 2010 | DOI: 10.1002/anie.200906264

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      High 'n low: The novel {[Fe(tmphen)2]3[Os(CN)6]2} complex (see structure) is the first example of a cluster in which a high-spin FeIII ion is in a coordination environment of four imine nitrogen atoms and two N-coordinated cyanides. Magnetic studies reveal an unprecedented type of reversible charge transfer induced spin transition (CTIST) between the low-spin FeII[BOND]N[TRIPLE BOND]C[BOND]OsIII and high-spin FeIII[BOND]N[TRIPLE BOND]C[BOND]OsII systems.

    5. DNA Nanotechnology

      A Route to Scale Up DNA Origami Using DNA Tiles as Folding Staples (pages 1414–1417)

      Zhao Zhao, Hao Yan and Yan Liu

      Version of Record online: 26 JAN 2010 | DOI: 10.1002/anie.200906225

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      Into the fold: A new strategy is presented to scale up DNA origami using multi-helical DNA tiles as folding staples. Atomic force microscopy images (see picture) demonstrate the two-dimensional structures formed by using this strategy.

    6. Polymers

      Multimode Diffusion of Ring Polymer Molecules Revealed by a Single-Molecule Study (pages 1418–1421)

      Satoshi Habuchi, Norihiro Satoh, Takuya Yamamoto, Yasuyuki Tezuka and Martin Vacha

      Version of Record online: 18 JAN 2010 | DOI: 10.1002/anie.200904394

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      Molecular twister: A single-molecule study in a semi-dilute regime on a synthetic ring polymer containing a fluorescent perylene diimide unit (see picture, orange) reveals the heterogeneity of the system. The investigation indicates partial threading of the cyclic chains with the linear polymer matrix.

    7. Sensors

      Thin-Film Formation of Imidazolium-Based Conjugated Polydiacetylenes and Their Application for Sensing Anionic Surfactants (pages 1422–1425)

      Xiaoqiang Chen, Sunwoo Kang, Min Jung Kim, Joohee Kim, Youn Sang Kim, Heejin Kim, Bo Chi, Sung-Jin Kim, Jin Yong Lee and Juyoung Yoon

      Version of Record online: 19 JAN 2010 | DOI: 10.1002/anie.200905041

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      Showing their true colors: Polymers based on polydiacetylene and imidazolium show selective color response to anionic surfactants. Furthermore, this system easily distinguishes between the anionic surfactants sodium dodecyl sulfate (SDS) and sodium dodecylbenzenesulfonic acid (SDBS).

    8. Drug Design

      Drug Design for G-Protein-Coupled Receptors by a Ligand-Based NMR Method (pages 1426–1429)

      Stefan Bartoschek, Thomas Klabunde, Elisabeth Defossa, Viktoria Dietrich, Siegfried Stengelin, Christian Griesinger, Teresa Carlomagno, Ingo Focken and K. Ulrich Wendt

      Version of Record online: 18 JAN 2010 | DOI: 10.1002/anie.200905102

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      A nonradioactive binding assay relying on NMR methods has been devised for a G-protein-coupled receptor; in addition the INPHARMA methods give access to the relative orientation of multiple ligands and supports ligand-based drug design (see picture of superimposed ligands). The method is fast and does not require any structural information from protein crystal structures.

    9. Helicity

      Control of the Helicity of Poly(phenylacetylene)s: From the Conformation of the Pendant to the Chirality of the Backbone (pages 1430–1433)

      Iria Louzao, José M. Seco, Emilio Quiñoá and Ricardo Riguera

      Version of Record online: 18 JAN 2010 | DOI: 10.1002/anie.200905222

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      Helix sense selection: Tuning the conformational equilibrium of the pendants of poly(phenylacetylene)s allows selection of the helicity of the polymer in a reversible way. Complexation with appropriate metal cations (e.g. Ba2+) or changing the polarity of the solvent permits the reversible selection of the desired helix sense. A full picture of the mechanism explaining this phenomenon is presented.

    10. Functional Monolayers

      Orienting Zeolite L Microcrystals with a Functional Linker (pages 1434–1438)

      Yu Wang, Huanrong Li, Yu Feng, Hongjie Zhang, Gion Calzaferri and Tiezhen Ren

      Version of Record online: 27 JAN 2010 | DOI: 10.1002/anie.200905354

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      A glowing endorsement: Arranging zeolite L crystals into luminescent macroscopic structures allows preparation of dense, homogeneous, well-oriented, stable, and highly organized functional monolayers (see picture). The color of the luminescence of the resulting layers can be fine-tuned by changing the type and number of lanthanide ions coordinated to the linker, the guest inside the channels of the zeolite host, and the excitation wavelength.

    11. Mass Spectrometry of Proteins

      Multiple Soft Ionization of Gas-Phase Proteins and Swift Backbone Dissociation in Collisions with ≤99 eV Electrons (pages 1439–1441)

      Roman A. Zubarev and Hongqian Yang

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/anie.200905977

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      Contrary to the dominant paradigm, electrons with an energy above 20 eV can ionize polypeptides multiple times (see picture) without destroying their primary or even elements of their tertiary structure. Concomitant electronic excitation can cause rapid backbone-bond cleavage, with weak molecule–molecule bonding remaining intact. This “soft-fragmentation” technique should enable the detailed structural characterization of protein complexes.

    12. Nanotechnology

      Diffusion-Facilitated Fabrication of Gold-Decorated Zn2SiO4 Nanotubes by a One-Step Solid-State Reaction (pages 1442–1446)

      Yang Yang, Ren Bin Yang, Hong Jin Fan, Roland Scholz, Zhipeng Huang, Andreas Berger, Yong Qin, Mato Knez and Ulrich Gösele

      Version of Record online: 22 JAN 2010 | DOI: 10.1002/anie.200906022

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      A ZnO-Au-SiO2sandwich nanowire structure has been used to fabricate Zn2SiO4 nanotubes with inlaid gold nanocrystallites on the outer surface. The thin gold interlayer not only acts as a precursor for the gold nanocrystallites, but also facilitates the Kirkendall voids at the ZnO-SiO2 interface and then accelerates the formation of the Zn2SiO4 nanotubes (see picture).

    13. Nanolithography

      Biomimetic Crystallization Nanolithography: Simultaneous Nanopatterning and Crystallization (pages 1447–1450)

      Roberto de La Rica, Kristina Ivana Fabijanic, Antonio Baldi and Hiroshi Matsui

      Version of Record online: 19 JAN 2010 | DOI: 10.1002/anie.200906200

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      The write stuff: The title method (BCN) is demonstrated for the simultaneous fabrication and patterning of oxide semiconductors at room temperature. BCN involves the production of relatively stable amorphous inks of ZnO, which are nanopatterned with the tip of an atomic force microscope as a pen, which also induces crystallization (see picture). The semiconducting nanostructures could be applied in nanoelectronics and nanooptics applications.

    14. Biorecognition

      Drug-Free Macromolecular Therapeutics: Induction of Apoptosis by Coiled-Coil-Mediated Cross-Linking of Antigens on the Cell Surface (pages 1451–1455)

      Kuangshi Wu, Jihua Liu, Russell N. Johnson, Jiyuan Yang and Jindřich Kopeček

      Version of Record online: 25 JAN 2010 | DOI: 10.1002/anie.200906232

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      Peptide biorecognition: The heterodimerization of complementary randomly coiled peptides, one (red) bound to an antibody fragment (gray) and one (green) grafted to a copolymer (black), to form coiled coils resulted in the cross-linking of CD20 target antigens (orange) on Raji B cells and consequently the initiation of apoptosis (see schematic representation).

    15. ATP Detection

      A Luciferase/Single-Walled Carbon Nanotube Conjugate for Near-Infrared Fluorescent Detection of Cellular ATP (pages 1456–1459)

      Jong-Ho Kim, Jin-Ho Ahn, Paul W. Barone, Hong Jin, Jingqing Zhang, Daniel A. Heller and Michael S. Strano

      Version of Record online: 27 JAN 2010 | DOI: 10.1002/anie.200906251

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      Take the tube: The title conjugate provides spatiotemporal information of ATP in living cells by a two-step fluorescence quenching mechanism. OxyLrin, which is generated enzymatically in the reaction between ATP and D-luciferin (Lrin), is adsorbed onto the nanotubes and quenches their fluorescence (see picture). The sensor is highly selective toward ATP.

    16. Polyketide Biosynthesis

      Functionally Distinct Modules Operate Two Consecutive α,β[RIGHTWARDS ARROW]β,γ Double-Bond Shifts in the Rhizoxin Polyketide Assembly Line (pages 1460–1464)

      Björn Kusebauch, Benjamin Busch, Kirstin Scherlach, Martin Roth and Christian Hertweck

      Version of Record online: 23 DEC 2009 | DOI: 10.1002/anie.200905467

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      Shift work: Biochemical analysis of the rhizoxin pathway revealed that the diene moiety is not shifted all at once, but through distinct enzymatic operations. The first shift occurs by a formal β,γ-dehydration in module 7, while the second double bond is first generated by module 8 and then shifted by an unprecedented “shift module” with a novel type of DH* domain (see scheme). ACP=acyl carrier protein, DH*=dehydratase-like shift domain.

    17. The Final Steps of Bacillaene Biosynthesis in Bacillus amyloliquefaciens FZB42: Direct Evidence for β,γ Dehydration by a trans-Acyltransferase Polyketide Synthase (pages 1465–1467)

      Jana Moldenhauer, Daniel C. G. Götz, Christian R. Albert, Sebastian K. Bischof, Kathrin Schneider, Roderich D. Süssmuth, Marianne Engeser, Harald Gross, Gerhard Bringmann and Jörn Piel

      Version of Record online: 19 JAN 2010 | DOI: 10.1002/anie.200905468

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      Caught in the act: Genetic pathway engineering in conjunction with HPLC–NMR spectroscopy of highly labile intermediates provided direct evidence for the installation of β,γ double bonds during polyketide elongation to form the antibiotic bacillaene. The novel congener bacillaene B (1) was also discovered as an elusive true end product of the pathway in Bacillus amyloliquefaciens.

    18. Homogeneous Catalysis

      Direct Synthesis of Imines from Alcohols and Amines with Liberation of H2 (pages 1468–1471)

      Boopathy Gnanaprakasam, Jing Zhang and David Milstein

      Version of Record online: 25 JAN 2010 | DOI: 10.1002/anie.200907018

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      A clean sweep: Aryl and aliphatic imines can be synthesized directly and efficiently from alcohols and amines under mild, neutral conditions with the liberation of only molecular hydrogen and water (see scheme; R=isopropyl, tert-butyl). This general, environmentally benign reaction is catalyzed by a de-aromatized ruthenium PNP pincer complex (0.2 mol %), and can proceed in toluene under an inert atmosphere or under air.

    19. Copper-Catalyzed Hydrosilylation with a Bowl-Shaped Phosphane Ligand: Preferential Reduction of a Bulky Ketone in the Presence of an Aldehyde (pages 1472–1476)

      Tetsuaki Fujihara, Kazuhiko Semba, Jun Terao and Yasushi Tsuji

      Version of Record online: 25 JAN 2010 | DOI: 10.1002/anie.200906348

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      Hollywood bowl: A highly active copper catalyst with a bowl-shaped phosphane (bsp) ligand was used in the hydrosilylation reaction of bulky ketones. The preferential reduction of a bulky ketone in the presence of an unprotected aldehyde is unprecedented.

    20. Metal–Organic Frameworks

      Metal–Organic Framework MIL-101 for High-Resolution Gas-Chromatographic Separation of Xylene Isomers and Ethylbenzene (pages 1477–1480)

      Zhi-Yuan Gu and Xiu-Ping Yan

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/anie.200906560

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      It's time for application: Chromium terephthalate MIL-101, a metal–organic framework (MOF) with coordinatively unsaturated sites, was utilized as the stationary phase to fabricate the first MOF-coated capillary column for high-resolution gas-chromatographic separation of xylene isomers and ethylbenzene with excellent selectivity.

    21. Cascade Reactions

      Iminium–Allenamine Cascade Catalysis: One-Pot Access to Chiral 4H-Chromenes by a Highly Enantioselective Michael–Michael Sequence (pages 1481–1484)

      Xinshuai Zhang, Shilei Zhang and Wei Wang

      Version of Record online: 18 JAN 2010 | DOI: 10.1002/anie.200906050

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      Taking the Michael-Michael: A cascade Michael–Michael reaction of aryl or alkyl alkynals, involving an unprecedented iminium–allenamine sequence, is efficiently catalyzed by a chiral diphenylprolinol TBDMS ether, and affords highly functionalized 4H-chromenes in high yields. TBDMS=tert-butyldimethylsilyl.

    22. Biosensors

      Fluorescence Turn-On Detection of a Protein through the Reduced Aggregation of a Perylene Probe (pages 1485–1488)

      Bin Wang and Cong Yu

      Version of Record online: 21 JAN 2010 | DOI: 10.1002/anie.200905237

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      Sensitivity that won't break the bank: The addition of an anti-lysozyme DNA aptamer (a polyanion) to a cationic perylene probe that exists in aqueous solution as a mixture of the fluorescent free monomer and aggregate forms shifted the equilibrium and resulted in fluorescence quenching (see schematic representation). The subsequent introduction of lysozyme weakened DNA binding to the perylene aggregates and led to fluorescence recovery.

    23. Expanded Porphyrins

      A Stable Organic Radical Delocalized on a Highly Twisted π System Formed Upon Palladium Metalation of a Möbius Aromatic Hexaphyrin (pages 1489–1491)

      Harapriya Rath, Sumito Tokuji, Naoki Aratani, Ko Furukawa, Jong Min Lim, Dongho Kim, Hiroshi Shinokubo and Atsuhiro Osuka

      Version of Record online: 26 JAN 2010 | DOI: 10.1002/anie.200906017

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      One more twist of a Möbius strip: Metalation of Möbius-aromatic hexakis(pentafluorophenyl)[28]hexaphyrin (see picture; Pd red, Cl green, N blue, phenyl rings omitted) provides a highly stable organic radical that is delocalized over a doubly twisted π-conjugation system. The two-photon absorption cross-section is distinctly larger than that of non-aromatic expanded porphyrins.

    24. Carbohydrate Recognition

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      Design, Synthesis, and Screening of a Library of Peptidyl Bis(Boroxoles) as Oligosaccharide Receptors in Water: Identification of a Receptor for the Tumor Marker TF-Antigen Disaccharide (pages 1492–1495)

      Arnab Pal, Marie Bérubé and Dennis G. Hall

      Version of Record online: 18 JAN 2010 | DOI: 10.1002/anie.200906620

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      Mini lectins: A new class of oligosaccharide receptors (see example) was designed by exploiting several modes of molecular recognition, including the unique ability of benzoboroxoles to complex hexopyranosides. The synthesis is modular, thus well suited to targeting specific oligosaccharides using combinatorial libraries.

    25. Homogeneous Catalysis

      Enantioselective Synthesis of 2,3-Dihydro-1H-benzo[b]azepines: Iridium-Catalyzed Tandem Allylic Vinylation/Amination Reaction (pages 1496–1499)

      Hu He, Wen-Bo Liu, Li-Xin Dai and Shu-Li You

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/anie.200906638

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      Making azacycles: The [{Ir(cod)Cl}2]/L complex efficiently catalyzes the tandem allylic vinylation and asymmetric allylic amination of (E)-2 with ortho-amino styrene derivatives 1 to afford the title compounds 3 with excellent enantioselectivity. cod=1,5-cyclooctadiene, DABCO=1,4-diazabicyclo[2.2.2]octane.

    26. Solar Cells

      A Polybenzo[1,2-b:4,5-b′]dithiophene Derivative with Deep HOMO Level and Its Application in High-Performance Polymer Solar Cells (pages 1500–1503)

      Lijun Huo, Jianhui Hou, Shaoqing Zhang, Hsiang-Yu Chen and Yang Yang

      Version of Record online: 25 JAN 2010 | DOI: 10.1002/anie.200906934

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      Sun catcher: The new benzo[1,2-b:4,5-b′]dithiophene-containing polymer PBDTTBT exhibits a power conversion efficiency of up to 5.66 %. The high open-circuit voltage (0.92 V) originates from the low HOMO level of the polymer and the high internal and external quantum efficiencies over a wide spectral range. PBDTTBT is a promising donor material for application in polymer solar cells.

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    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Review
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