Chemistry - A European Journal

Cover image for Vol. 16 Issue 36

September 24, 2010

Volume 16, Issue 36

Pages 10901–11191

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: Modulation of the Aerobic Oxidative Polymerization in Phenylazomethine Dendrimers Assembling Copper Complexes (Chem. Eur. J. 36/2010) (page 10901)

      Dr. Takane Imaoka, Yuki Kawana, Masahiro Tsuji and Prof. Dr. Kimihisa Yamamoto

      Article first published online: 20 SEP 2010 | DOI: 10.1002/chem.201090178

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      Dendrimer ligands that assemble copper complexes, which efficiently catalyze the oxidative polymerization of a fluorinated phenol derivative without adding pyridine or other bases, are described by K. Yamamoto et al. in their Full Paper on page 11003 ff. The resulting assembly could be regarded as an all-in-one catalyst, which remains highly active under dilute or base-free conditions.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
    1. Inside Cover: (Chem. Eur. J. 36/2010) (page 10902)

      Article first published online: 20 SEP 2010 | DOI: 10.1002/chem.201090179

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      Thermodynamics and kinetics, represented by the classical Aesop fable of “The Tortoise and the Hare”, have been shown to influence the yield of (bio)catalyzed hydrogen-transfer processes of different ketone/alcohol pairs. The picture illustrates ketones as acrobats walking on a tightrope represented by an IR spectrum. These equilibria are related to the IR frequency of the carbonyl bond; the shorter the bond, the more displaced the equilibrium is towards the alcohol and vice versa.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
  5. Concept

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
    1. Cancer Therapy

      Selenium- and Tellurium-Containing Multifunctional Redox Agents as Biochemical Redox Modulators with Selective Cytotoxicity (pages 10920–10928)

      Dr. Vincent Jamier, Dr. Lalla A. Ba and Prof. Dr. Claus Jacob

      Article first published online: 30 JUL 2010 | DOI: 10.1002/chem.201000884

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      Programmed destruction: Selenium- and tellurium-based agents turn the oxidizing redox environment present in certain cancer cells into a lethal cocktail of reactive species, which pushes these cells over a critical redox threshold and ultimately kills them through apoptosis (see figure).

  6. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
    1. Polyelectrolytes

      Ionic Mixed Interactions in Macromolecules (pages 10930–10945)

      Alberto Ciferri 

      Article first published online: 19 AUG 2010 | DOI: 10.1002/chem.201000763

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      Hidden gems! A synthetic classification of systems displaying ionic mixed interactions and a discussion of underlying molecular mechanisms is presented. An elongated, fully charged chain has been the accepted model for the conformation of strong polyelectrolytes. However, it appears that a wide variety of attractive interactions favor a pearling conformation (see figure).

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
    1. Electron Transfer

      Nanographite Impurities Dominate Electrochemistry of Carbon Nanotubes (pages 10946–10949)

      Dr. Adriano Ambrosi and Prof. Martin Pumera

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001584

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      Junk does the work: The observed heterogeneous electron-transfer (HET) rate of multiwalled carbon nanotube (MWCNT) materials is comparable to that of graphite only because CNT materials contain large quantities of nanographite impurities. When pure CNTs are used, the observed HET rate is actually significantly lower than that of graphitic materials. In other words, most of the electrochemical activity of CNTs is due to the presence of the nanographite impurities contained within them.

    2. Homogeneous Catalysis

      Rhodium-Catalysed Intermolecular Alkyne Hydroacylation: The Enantioselective Synthesis of α- and β-Substituted Ketones by Kinetic Resolution (pages 10950–10954)

      Dr. Carlos González-Rodríguez, Scott R. Parsons, Dr. Amber L. Thompson and Dr. Michael C. Willis

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001748

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      Cleared up! Intermolecular alkyne hydroacylation represents a new addition to the range of transition-metal-catalysed hydroacylation reactions that can be performed in an enantioselective manner. By using a kinetic resolution procedure, both racemic α- and β-substituted aldehydes can be converted into the corresponding enantiomerically enriched substituted enone products (see scheme).

    3. Organocatalysis

      Highly Enantioselective Michael Addition of Malononitrile to Vinylogous Imine Intermediates Generated in situ from Arylsulfonyl Indoles (pages 10955–10958)

      Linhai Jing, Jiangtao Wei, Li Zhou, Zhiyong Huang, Zhengkai Li, Dr. Di Wu, Haifeng Xiang and Prof. Dr. Xiangge Zhou

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001662

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      Malononitrile on rare form: Highly enantioselective Michael addition of malononitrile to vinylogous imine intermediates 2, generated in situ from arylsulfonyl indoles 1, is described (see scheme). This protocol provides easy and convenient access to valuable 3-indolyl derivatives 3 in high yields and enantioselectivities. A possible catalytic mechanism is proposed.

    4. Synthetic Methods

      Scaling Out by Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS): Multi-Gram Synthesis of Bromo- and Fluoro-benzofused Sultams Benzthiaoxazepine-1,1-dioxides (pages 10959–10962)

      Dr. Farman Ullah, Dr. Thiwanka Samarakoon, Dr. Alan Rolfe, Ryan D. Kurtz, Prof. Paul R. Hanson and Prof. Michael G. Organ

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001651

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      Go with the flow! Using a combination of continuous-flow techniques and microwave irradiation, a 19-member collection of 5–10 gram quantities of benzthiaoxazepine-1,1-dioxides has been produced (see scheme). The elimination of intermediate- and large-scale process optimization by invoking the concept of scale-out (rather than scale up) has significantly reduced the time necessary to prepare these compounds.

    5. Conjugated Polymers

      Chirally Organized Oligothiophenes: Towards Modeling Interchain Interactions Within π-Conjugated Systems (pages 10963–10967)

      David Cornelis, Prof. Dr. Thierry Verbiest and Dr. Guy Koeckelberghs

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001079

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      Interchain modeling: A model is proposed to compare the strength of the interaction between two conjugated oligomers (see graphic). It consists of probing changes in the angle between the parts of a binaphthalene hinge, invoked by the interaction between the oligomers. This allows the strength of the interaction between any set of oligomers to be compared or changes in the interactions upon oxidation or deprotonation to be monitored.

    6. Homogeneous Catalysis

      Palladium(II)-Catalyzed Highly Regio- and Stereoselective Synthesis of 2-Chloro-1,3-diene Derivatives from Alkynols and Alkenes (pages 10968–10970)

      Prof. Dr. Huanfeng Jiang, Chunli Qiao and Weibing Liu

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001318

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      Diene or not diene: A facile and efficient palladium-catalyzed highly regio- and stereoselective strategy is depicted for the synthesis of chloro-substituted 1,3-dienes from alkynols and alkenes (see scheme). This protocol provides a good alternative for the construction of halo-substituted 1,3-dienes.

    7. Inorganic Chemistry

      Non-innocent Behaviour of Dithiocarboxylate Ligands Based on N-Heterocyclic Carbenes (pages 10971–10974)

      Saira Naeem, Dr. Amber L. Thompson, Dr. Lionel Delaude and Dr. James D. E. T. Wilton-Ely

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001235

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      Not so innocent: Sterically tuneable dithiocarboxylate ligands derived from N-heterocyclic carbenes act as excellent bidentate chelates for ruthenium(II) σ-alkenyl complexes. However, the most sterically demanding member of the ligand family causes a fascinating and unexpected rearrangement to occur (see figure; ICy=1,3-dicylohexylimidazolium, IDip=1,3-bis(2,6-diisopropylphenyl)imidazolium).

    8. Gold Catalysis

      Gold(I) and Brønsted Acid Catalyzed Intramolecular Rearrangements of Vinylidenecyclopropanes (pages 10975–10979)

      Bei-Li Lu, Yin Wei and Min Shi

      Article first published online: 5 AUG 2010 | DOI: 10.1002/chem.201001433

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      Spot the difference! Different intramolecular rearrangements of vinylidenecyclopropanes containing a secondary alcohol chain were observed depending on whether the reaction was catalyzed by a gold(I) complex or a Brønsted acid (HOTf; OTf=trifluoromethanesulfonate). The corresponding adducts were obtained in moderate to good yields (see scheme). The scope and limitations of these reactions, as well as plausible mechanisms, have been discussed.

    9. Asymmetric Synthesis

      Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons (pages 10980–10983)

      Alexandre Welle, Dr. Julien Petrignet, Prof. Bernard Tinant, Prof. Johan Wouters and Prof. Olivier Riant

      Article first published online: 4 AUG 2010 | DOI: 10.1002/chem.201000907

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      Asymmetric aldol reaction: A domino silylation–aldol reaction between enoyloxazolidinones and various aldehydes has been developed (see scheme). The process catalysed by a copper complex in the presence of a borosilane led to high diastereoselectivities. Yields between 59 and 90 % and d.r. values between 78:22 to 95:5 were obtained. When methacryloyloxazolidinones were used, a controlled chiral quaternary carbon was generated. BPin=4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl.

      Corrected by:

      Corrigendum: Corrigendum: Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons

      Vol. 17, Issue 44, 12227, Article first published online: 17 OCT 2011

    10. Vitamin Derivatives

      Isovitamin B12: A Vitamin B12 Derivative That Flips Its Tail (pages 10984–10988)

      Prof. Dr. Shahzad Murtaza, Markus Ruetz, Prof. Dr. Karl Gruber and Prof. Dr. Bernhard Kräutler

      Article first published online: 5 AUG 2010 | DOI: 10.1002/chem.201001616

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      Base on: Vitamin B12 is well known as a compact and cobalt-coordinated base-on corrinoid, in which the corrin and nucleotide moieties are connected by their natural linker, (R)-isopropanolamine. In the synthetic isomer, isovitamin B12, an n-propanolamine linker produces a structural mismatch. X-ray crystallography revealed two distinct base-on conformers of isovitamin B12 (magenta; inward conformer, yellow: outward conformer).

    11. Natural Products

      Bufogargarizins A and B: Two Novel 19-Norbufadienolides with Unprecedented Skeletons from the Venom of Bufo bufo gargarizans (pages 10989–10993)

      Hai-Yan Tian, Dr. Lei Wang, Dr. Xiao-Qi Zhang, Dr. Ying Wang, Dr. Dong-Mei Zhang, Prof. Dr. Ren-Wang Jiang, Dr. Zhong Liu, Jun-Shan Liu, Prof. Dr. Yao-Lan Li and Prof. Dr. Wen-Cai Ye

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000847

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      Toad venom: Bufogargarizins A and B with unprecedented skeletons were discovered from the venom (middle) of Bufo bufo gargarizans (left). The absolute configurations were elucidated by spectroscopic data, X-ray crystal diffraction, modified Mosher's method and computational analysis.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Concept
    7. Review
    8. Communications
    9. Full Papers
    10. Preview
    1. Supramolecular Chemistry

      Electronic and Optical Properties in the Solid-State Molecular Assemblies of Anion-Responsive Pyrrole-Based π-Conjugated Systems (pages 10994–11002)

      Prof. Dr. Hiromitsu Maeda, Yuya Bando, Yohei Haketa, Yoshihito Honsho, Prof. Dr. Shu Seki, Hiromi Nakajima and Prof. Dr. Norimitsu Tohnai

      Article first published online: 6 SEP 2010 | DOI: 10.1002/chem.201001852

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      Any old (an)ion? Solid-state assemblies of π-conjugated acyclic anion receptors exhibit anion-dependent properties that are in sharp contrast to those in the solution state. Anion complexation, along with structural differences in the pyrrole subunits, such as a benzo-fused pyrrole, plays an essential role not only in the formation of the assembled modes, but also in determining the electronic and optical properties, as well as the charge-carrier mobilities (see graphic).

    2. Copper Catalysts

      Modulation of the Aerobic Oxidative Polymerization in Phenylazomethine Dendrimers Assembling Copper Complexes (pages 11003–11011)

      Dr. Takane Imaoka, Yuki Kawana, Masahiro Tsuji and Prof. Dr. Kimihisa Yamamoto

      Article first published online: 27 AUG 2010 | DOI: 10.1002/chem.201001516

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      New branches: A phenylazomethine dendrimer complexed with copper ions (see figure) acts as the catalyst for the oxidative polymerization of a fluorinated phenol without any additive bases. Not only is high catalytic performance achieved, but also the flexible control of reaction conditions in the dendrimer is an advantage for this type of catalyst. This property allows modulation of the branching degree of polymer products.

    3. Reaction Mechanisms

      Ketone–Alcohol Hydrogen-Transfer Equilibria: Is the Biooxidation of Halohydrins Blocked? (pages 11012–11019)

      Dr. Fabricio R. Bisogno, Dr. Eduardo García-Urdiales, Dr. Haydee Valdés, Dr. Iván Lavandera, Prof. Wolfgang Kroutil, Prof. Dimas Suárez and Prof. Dr. Vicente Gotor

      Article first published online: 27 AUG 2010 | DOI: 10.1002/chem.201001233

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      Finding the balance: To provide a rationale for the quasi-irreversibility of the hydrogen-transfer (HT) bioreduction of α-halo carbonyl compounds (see figure), the redox equilibrium of a series of ketones was studied, with thermodynamics found to be the driving force. An IR-based method to predict the conversion of the HT reduction of a given ketone and a strategy to achieve the HT oxidation of halohydrins is also shown.

    4. Mesoporous Structures

      Highly Ordered Mesoporous Cobalt Oxide Nanostructures: Synthesis, Characterisation, Magnetic Properties, and Applications for Electrochemical Energy Devices (pages 11020–11027)

      Prof. Dr. Guoxiu Wang, Hao Liu, Prof. Josip Horvat, Bei Wang, Prof. Dr. Shizhang Qiao, Jinsoo Park and Prof. Dr. Hyojun Ahn

      Article first published online: 5 AUG 2010 | DOI: 10.1002/chem.201000562

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      Highly ordered mesoporous Co3O4 nanostructures have been prepared by using a hard-template method. Mesoporous Co3O4 (general TEM image shown) exhibits a low Néel temperature and bulk antiferromagnetic coupling. When used as electrode materials in lithium-ion cells and supercapacitors, mesoporous Co3O4 demonstrates a high reversible lithium storage capacity and a high specific supercapacitance.

    5. Charge Transfer

      Trifluoromethyl-Substituted Conjugated Oligoelectrolytes (pages 11028–11036)

      Dr. Yan Ren and Prof. Guillermo C. Bazan

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000885

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      Let's twist again: A trifluoromethyl-substituted conjugated oligoelectrolyte undergoes planarization upon absorption of light (see scheme). This geometry promotes an intramolecular charge-transfer excited state. Similar features are not observed for the unsubstituted analogue.

    6. DNA Intercalation

      AT-Specific DNA Binding of Binuclear Ruthenium Complexes at the Border of Threading Intercalation (pages 11037–11046)

      Johanna Andersson, Dr. Minna Li and Prof. Per Lincoln

      Article first published online: 2 AUG 2010 | DOI: 10.1002/chem.201000180

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      Binuclear Ru–DNA binding: An investigation of the effect of bridging ligand structure on DNA threading intercalation (see figure) has resulted in the discovery of a new threading intercalating complex, [μ-dppzip(phen)4Ru2]4+. The new complex is a weaker threading intercalator than the well-studied [μ-bidppz(phen)4Ru2]4+, but shows greater selectivity towards AT-DNA because it does not thread mixed-sequence DNA at all.

    7. Pyridinium Properties

      Expanded Pyridiniums: Bis-cyclization of Branched Pyridiniums into Their Fused Polycyclic and Positively Charged Derivatives—Assessing the Impact of Pericondensation on Structural, Electrochemical, Electronic, and Photophysical Features (pages 11047–11063)

      Dr. Jérôme Fortage, Dr. Fabien Tuyèras, Dr. Philippe Ochsenbein, Dr. Fausto Puntoriero, Dr. Francesco Nastasi, Prof. Dr. Sebastiano Campagna, Dr. Sophie Griveau, Dr. Fethi Bedioui, Dr. Ilaria Ciofini and Dr. Philippe P. Lainé

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000504

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      The properties of pyridiniums are not all equivalently sensitive to pericondensation. Extending the π-conjugated system affects the electronic and photophysical properties but not the first reduction process, which remains localized on the pyridinium core (see figure). Insights gained into this plural physicochemical behavior provide guidelines for the design of novel pyridiniums with predictable properties.

    8. Nanocatalysts

      Structural and Electronic Effects of Carbon-Supported PtxPd1−x Nanoparticles on the Electrocatalytic Activity of the Oxygen-Reduction Reaction and on Methanol Tolerance (pages 11064–11071)

      Dr. Shih-Hong Chang, Dr. Wei-Nien Su, Dr. Min-Hsin Yeh, Dr. Chun-Jern Pan, Dr. Kuan-Li Yu, Din-Goa Liu, Dr. Jyh-Fu Lee and Prof. Bing-Joe Hwang

      Article first published online: 5 AUG 2010 | DOI: 10.1002/chem.201000458

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      Pt–Pd nanocatalysts for fuel cells: The structural and electronic effects of carbon-supported PtxPd1−x nanoparticles (see figure; x=0.25, 0.5, and 0.75) on the electrocatalytic activity of the oxygen reduction reaction and on methanol tolerance are investigated. The extent of alloying and d-band vacancies of PtxPd1−x nanoclusters are shown to be key factors responsible for their synergistic and antagonistic effects on these fuel-cell reactions.

    9. Pd-based Negishi Catalyst

      [Pd(Cl)2{P(NC5H10)(C6H11)2}2]—A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings (pages 11072–11081)

      Jeanne L. Bolliger and Christian M. Frech

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001201

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      Cross-coupling catalyst: [Pd(Cl)2{P(NC5H10)(C6H11)2}2] is an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, and sterically hindered aryl bromides with various (also heterocyclic) arylzinc reagents (see scheme). The couplings are completed within a few minutes at 100 °C in the presence of just 0.01 mol % of catalyst.

    10. Magnetic Properties

      Tripodal Thiols as Ligands for Molecular Magnets: Very Strong Antiferromagnetic Exchange Interactions in Vanadium(III) Clusters (pages 11082–11088)

      Luke J. Batchelor, Emma Fitzgerald, Dr. Joanna Wolowska, Dr. Joseph J. W. McDouall and Prof. Eric J. L. McInnes

      Article first published online: 2 AUG 2010 | DOI: 10.1002/chem.201000823

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      VIIIclusters: Paramagnetic cluster chemistry of H3tmme, the tri-thiol analogue of the famous tripodal alcohols, is reported. With VIII clusters (see figure), very strong antiferromagnetic exchange interactions are observed such that only spin ground states are populated at room temperature.

    11. Calixarenes

      The Effect of Ligand Denticity in Size-Selective Synthesis of Calix[n]arene-Stabilized Gold Nanoparticles: A Multitechnique Approach (pages 11089–11099)

      Dr. Luca Pescatori, Alice Boccia, Dr. Flavio Ciesa, Dr. Francesca Rossi, Dr. Vincenzo Grillo, Prof. Arturo Arduini, Prof. Andrea Pochini, Prof. Robertino Zanoni and Dr. Andrea Secchi

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201001039

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      Small but stable: A series of Au nanoparticles (AuNPs) stabilized by monodentate, bidentate, and tridentate thiolate calix[4]arene derivatives was prepared by using the Brust–Schiffrin two-phase synthesis and characterized (see graphic). The multidentate structure of the calixarenes induced the formation of very small (≈1 nm) NPs.

    12. Aptamers

      ADLOC: An Aptamer-Displacement Assay Based on Luminescent Oxygen Channeling (pages 11100–11107)

      Dipl.-Chem. Björn Niebel, Christian Lentz, Dipl.-Biol. Monika Pofahl, Prof. Dr. Günter Mayer, Prof. Dr. Achim Hoerauf, Dr. Kenneth M. Pfarr and Prof. Dr. Michael Famulok

      Article first published online: 5 AUG 2010 | DOI: 10.1002/chem.201001192

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      Screening drugs by ADLOC: A new aptamer-based sensor is described that relies on the formation of an aptamer/protein complex, which can be detected by luminescent oxygen channeling. The system also senses the displacement of an aptamer from its protein target, induced by small molecules and thus can be used for drug screening.

    13. Asymmetric Catalysis

      New Chiral Calixsalen Chromium Complexes: Recyclable Asymmetric Catalysts (pages 11108–11114)

      Dr. Anaïs Zulauf, Dr. Mohamed Mellah and Dr. Emmanuelle Schulz

      Article first published online: 4 AUG 2010 | DOI: 10.1002/chem.201001012

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      Just reuse it! Chiral calixsalen (salen=N,N′-bis(salicylidene)ethylenediamine) chromium complexes (see scheme) were prepared and used as heterogeneous asymmetric catalysts. They proved to be particularly competent for epoxide ring opening compared with their linear analogues in terms of selectivity. These cyclic polymers could be easily recovered by simple filtration and efficiently reused.

    14. Nanostructures

      Pt–NiCo Nanostructures with Facilitated Electrocatalytic Activities for Sensitive Determination of Intracellular Thiols with Long-Term Stability (pages 11115–11120)

      Feng Zhang, Dr. Ming Wen, Mingzhu Cheng, Di Liu, Anwei Zhu and Prof. Yang Tian

      Article first published online: 4 AUG 2010 | DOI: 10.1002/chem.201000574

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      Thiol detection: A Pt–NiCo nanomaterial has been synthesized for the sensitive electrochemical determination of biological thiols that include L-cysteine (CySH), homocysteine (HCySH), and gluthione (GSH) with high sensitivity and long-term stability (see figure). The striking analytical performance, together with the characteristic properties of the Pt–NiCo nanomaterial itself, establishes a reliable and durable approach for the detection of protein and nonprotein thiols in liver cancer cells, Hep G2.

    15. Detection of NO

      Pyrene-Based Fluorescent Nitric Oxide Cheletropic Traps (FNOCTs) for the Detection of Nitric Oxide in Cell Cultures and Tissues (pages 11121–11132)

      Dipl.-Chem. Peter M. Düppe, Dr. Peter M. Talbierski, Dr. Frank S. Hornig, Prof. Dr. Ursula Rauen, Dr. Hans-Gert Korth, Dr. Timo Wille, Prof. Dr. Roland Boese, Dr. Thorsten Omlor, Prof. Dr. Herbert de Groot and Prof. Dr. Reiner Sustmann

      Article first published online: 2 AUG 2010 | DOI: 10.1002/chem.201000029

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      Catching NO: Stable pyrene-based o-quinodimethane derivatives give rise to strong fluorescence emission after cheletropic reaction with nitric oxide and reduction (see picture; iNOS: inducible NO synthase). Monitoring of NO radical release from N-diazeniumdiolates, rat liver macrophages, and the endothelium of porcine aorta demonstrates the versatility of the method.

    16. Hydrogen Generation

      Water Stable Zr–Benzenedicarboxylate Metal–Organic Frameworks as Photocatalysts for Hydrogen Generation (pages 11133–11138)

      Dr. Cláudia Gomes Silva, Ignacio Luz, Dr. Francesc X. Llabrés i Xamena, Prof. Dr. Avelino Corma and Prof. Dr. Hermenegildo García

      Article first published online: 4 AUG 2010 | DOI: 10.1002/chem.200903526

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      Let there be light! We describe the photocatalytic hydrogen generation of water/methanol using UiO-66 as photocatalyst. We show that this photocatalytic activity can be increased by rational design of the material and by adding a hydrogen evolution co-catalyst. By using laser flash photolysis, the photocatalytic activity for hydrogen formation has been correlated with the generation of charge separated states.

    17. Cluster Compounds

      Construction of a Novel Topological Frustrated System: A Frustrated Metal Cluster in a Helical Space (pages 11139–11144)

      Ryuta Ishikawa, Prof. Dr. Motohiro Nakano, Dr. Akira Fuyuhiro, Dr. Tetsuya Takeuchi, Dr. Shojiro Kimura, Takanari Kashiwagi, Prof. Dr. Masayuki Hagiwara, Prof. Dr. Koichi Kindo, Prof. Dr. Sumio Kaizaki and Prof. Dr. Satoshi Kawata

      Article first published online: 5 AUG 2010 | DOI: 10.1002/chem.201000676

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      A unique pentanuclear frustrated cluster with a helical arrangement of ligands around the central metal core has been constructed (see picture). Dzyaloshinsky–Moriya interactions are essential components to observe a gradual magnetization and forbidden transitions of high-field/multi-frequency (HF/MF)-ESR. The origin of the magnetic anisotropy of this compound is influenced by the helical spin structure.

    18. Zintl Ions

      Studies on the Reactivity of [Ge9]4− towards [Fe(cot)(CO)3]: Synthesis and Characterization of [Ge8Fe(CO)3]3− and of the Anionic Organometallic Species [Fe(cot)(CO)3] (pages 11145–11150)

      Binbin Zhou and Dr. Jose M. Goicoechea

      Article first published online: 2 AUG 2010 | DOI: 10.1002/chem.201000507

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      Strike while the iron is hot! Reaction of [Fe(cot)(CO)3] (COT=cyclooctatetraene) with K4Ge9 yielded [K(2,2,2-crypt)]3[Ge8Fe(CO)3] (see scheme; 2,2,2-crypt=4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane). In addition, a reduction product of the [Fe(cot)(CO)3] precursor was also isolated, [K(2,2,2-crypt)][Fe(η3-C8H8)(CO)3]. All species were characterized by EPR and IR spectroscopy and ES-MS spectrometry when possible.

    19. Phthalocyanines

      Azaphenalene Phthalocyanines: Phthalocyanine Analogues with Six-Membered-Ring Units Instead of Five-Membered-Ring Units (pages 11151–11159)

      Dr. Soji Shimizu, Hua Zhu and Prof. Dr. Nagao Kobayashi

      Article first published online: 2 AUG 2010 | DOI: 10.1002/chem.201000642

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      Bigger rings: Mixed-condensation reaction of 1,8-naphthalenedicarbonitrile and a 4,5-disubstituted phthalonitrile provided a series of novel phthalocyanine analogues with azaphenalene moieties in place of the isoindole moieties. Monosubstituted species, APPc, and the two structural isomers of disubstituted species, adj-AP2Pc and opp-AP2Pc (see graphic; adj=adjacent, opp=opposite), were successfully isolated and characterized.

    20. β-Peptide Conformation

      Synthesis and Conformational Characterisation of Hexameric β-Peptide Foldamers by Using Double POAC Spin Labelling and cw-EPR (pages 11160–11166)

      Dr. Karen Wright, Dr. Michel Wakselman, Dr. Jean-Paul Mazaleyrat, Dr. Lorenzo Franco, Prof. Antonio Toffoletti, Prof. Fernando Formaggio and Prof. Claudio Toniolo

      Article first published online: 4 AUG 2010 | DOI: 10.1002/chem.201000821

      Thumbnail image of graphical abstract

      Labels make it easier: β-Hexapeptides that contain two nitroxide-based residues (i.e., (3R,4R)-4-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid (POAC)) at different relative positions were synthesised by solution methods and fully characterised. The biradical exchange interaction between two POAC residues within each peptide indicates unambiguously that the secondary structure overwhelmingly adopted is the 12-helix (see picture).

    21. Organometallic Compounds

      A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups (pages 11167–11177)

      Dr. Aiichiro Nagaki, Heejin Kim, Yuya Moriwaki, Chika Matsuo and Prof. Jun-ichi Yoshida

      Article first published online: 16 AUG 2010 | DOI: 10.1002/chem.201000876

      Thumbnail image of graphical abstract

      Go micro! A flow microreactor system serves as a straightforward method for the generation and reaction of aryllithium compounds bearing an alkoxycarbonyl group (see scheme).

    22. Natural Products

      Curvularides A–E: Antifungal Hybrid Peptide–Polyketides from the Endophytic Fungus Curvularia geniculata (pages 11178–11185)

      Dr. Porntep Chomcheon, Dr. Suthep Wiyakrutta, Dr. Thammarat Aree, Dr. Nongluksna Sriubolmas, Dr. Nattaya Ngamrojanavanich, Prof. Chulabhorn Mahidol, Prof. Somsak Ruchirawat and Dr. Prasat Kittakoop

      Article first published online: 2 AUG 2010 | DOI: 10.1002/chem.201000652

      Thumbnail image of graphical abstract

      From plant to fungus to drug: Five new hybrid peptide–polyketides, curvularides A–E, were isolated from an endophytic fungus (see image). The structures (15) were elucidated by spectroscopic and crystallographic methods. Curvularide B (2) was shown to exhibit antifungal activity against Candida albicans and synergistic activity with a fluconazole drug.

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      Preview: Chem. Eur. J. 37/2010 (page 11191)

      Article first published online: 20 SEP 2010 | DOI: 10.1002/chem.201090182

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