Chemistry - A European Journal

Cover image for Vol. 18 Issue 16

April 16, 2012

Volume 18, Issue 16

Pages 4797–5115

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Communications
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      Cover Picture: Disposable Electrochemical Immunosensor by Using Carbon Sphere/Gold Nanoparticle Composites as Labels for Signal Amplification (Chem. Eur. J. 16/2012) (page 4797)

      Qiunan Xu, Feng Yan, Dr. Jianping Lei, Chuan Leng and Prof. Huangxian Ju

      Version of Record online: 4 APR 2012 | DOI: 10.1002/chem.201290060

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      A sensitive immunoassay method has been developed by combining a disposable electrochemical immunosensor with a carbon sphere/gold nanoparticle composite as an electrochemical label, which exhibits a wide linear range, low detection limit, good specificity, and acceptable accuracy for the detection of antigen. For more details see the Full Paper by H. Ju, J. Lei et al. on page 4994 ff.

  2. Inside Cover

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    4. Graphical Abstract
    5. Corrigendum
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    1. Inside Cover: Chiral Transcription and Retentive Helical Memory: Probing Peptide Auxiliaries Appended with Naphthalenediimides for Their One-Dimensional Molecular Organization (Chem. Eur. J. 16/2012) (page 4798)

      M. Pandeeswar, M. B. Avinash and Dr. T. Govindaraju

      Version of Record online: 4 APR 2012 | DOI: 10.1002/chem.201290061

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      Homo, hetero, and achiral peptide conjugates of naphthalenediimide were designed to gain insights into nature's mysterious selection of homochirality and future chiral technological applications. Chiral induction and amplification was demonstrated by sergeants and soldiers, and majority rules methods. Homochiral conjugates resulted in hierarchical 1D supramolecular chiral assemblies and a new phenomenon coined as retentive helical memory is described. These results in principle support spontaneous deracemization and chiral amplification pathways for biological homochirality. For more details see the communication by T. Govindaraju et al. on page 4818 ff.

  3. Graphical Abstract

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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
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  4. Corrigendum

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
    6. News
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  5. News

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    4. Graphical Abstract
    5. Corrigendum
    6. News
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  6. Communications

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    5. Corrigendum
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    1. Chirality

      Chiral Transcription and Retentive Helical Memory: Probing Peptide Auxiliaries Appended with Naphthalenediimides for Their One-Dimensional Molecular Organization (pages 4818–4822)

      M. Pandeeswar, M. B. Avinash and Dr. T. Govindaraju

      Version of Record online: 20 MAR 2012 | DOI: 10.1002/chem.201200197

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      Right or left paradox: Homochiral, heterochiral and achiral peptide auxiliaries appended with naphthalenediimide (NDI, see figure) were employed to demonstrate chiral transcription. We report an interesting phenomenon coined as retentive helical memory. Remarkably, NDI–peptide conjugates were tuned into hierarchical 1D molecular assemblies of opposite helicity in case of homochiral peptide auxiliaries.

    2. Nanocomposite

      Synthesis of Dendritic Platinum Nanoparticles/Lucigenin/Reduced Graphene Oxide Hybrid with Chemiluminescence Activity (pages 4823–4826)

      Dr. Yi He and Prof. Hua Cui

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/chem.201104044

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      Multifunctional hybrid: A dendritic platinum nanoparticle/lucigenin/reduced graphene oxide (RGO) hybrid with chemiluminescence (CL) activity was prepared for the first time by using lucigenin as a linker through simultaneous reduction of H2PtCl4 and a lucigenin-functionalized graphene oxide composite by sodium borohydride (see scheme). The hybrid may have potential applications as a CL sensor, in catalysis, energy conversion, and opto-electronic systems.

    3. Carbonylative Coupling

      Palladium-Catalyzed Carbonylative Heck Reaction of Aryl Bromides with Vinyl Ethers to 3-Alkoxy Alkenones and Pyrazoles (pages 4827–4831)

      Johannes Schranck, Xiao-Feng Wu, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/chem.201103643

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      Three COming together: The first carbonylative Heck coupling reaction of aryl bromides and vinyl ethers leading to 1-aryl-3-alkoxy-2-propen-1-ones has been established (see scheme). Based on this coupling methodology, a novel one-pot synthesis of aryl-substituted pyrazoles was also realized.

    4. Organocatalysis

      Asymmetric Michael Addition of N-Boc-Protected Oxindoles to Nitroalkenes Catalyzed by a Chiral Secondary Amine (pages 4832–4835)

      Dr. Chuan Wang, Dipl.-Chem. Xuena Yang and Prof. Dr. Dieter Enders

      Version of Record online: 20 MAR 2012 | DOI: 10.1002/chem.201200079

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      New mission for prolinol ethers: A secondary-amine-catalyzed Michael addition of N-Boc-protected oxindoles to nitroalkenes through a Brønsted base activation mode has been developed, furnishing the products in excellent yields (88–98 %), diastereoselectivities (d.r.=98:2–>99:1) and high to excellent enantioselectivities (82–>99 % ee; see scheme).

    5. Amyloid Beta Peptides

      Inhibition of Cu-Amyloid-β by using Bifunctional Peptides with β-Sheet Breaker and Chelator Moieties (pages 4836–4839)

      Madeleine Jensen, Anne Canning, Sabri Chiha, Pierre Bouquerel, Dr. Jeppe Trudslev Pedersen, Prof. Dr. Jesper Østergaard, Dr. Olivier Cuvillier, Isabelle Sasaki, Dr. Christelle Hureau and Prof. Dr. Peter Faller

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/chem.201103546

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      Breaking the mold: Inhibition of toxic amyloid-β (Aβ) aggregates and disruption of Cu-Aβ with subsequent redox-silencing of Cu have been considered promising strategies against Alzheimer's disease. The design and proof of concept of simple peptides containing a Cu-chelating/redox-silencing unit and an Aβ-aggregation inhibition unit (β-sheet breaker) is described (see scheme).

    6. Aqueous Catalysis

      Cu-Catalyzed Three-Component Synthesis of Substituted Benzothiazoles in Water (pages 4840–4843)

      Hang Deng, Zhengkai Li, Dr. Fang Ke and Prof. Dr. Xiangge Zhou

      Version of Record online: 19 MAR 2012 | DOI: 10.1002/chem.201103525

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      Three in one: Copper-catalyzed three-component reactions, involving 2-iodoanilines, aldehydes, and sulfur powder, afford 2-phenylbenzothiazoles in water. A variety of 2-substituted benzothiazoles can be obtained in good to excellent yields of up to 96 % (see scheme).

    7. Enantiospecific Annulation

      Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones (pages 4844–4849)

      Dr. Fides Benfatti, Florian de Nanteuil and Prof. Dr. Jérôme Waser

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/chem.201103971

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      An almost familiar ring: The first enantiospecific [3+2] annulation of donor–acceptor aminocyclopropanes with ketones is reported (see scheme; Phth=phthaloyl). The reaction is catalysed by tin(IV) chloride (5 mol %) at −78 °C and gives aminotetrahydrofurans bearing a quaternary C5 atom in high yield, diastereoselectivity and enantiospecificity (see scheme).

    8. Carbohydrates

      Organotin-Catalyzed Highly Regioselective Thiocarbonylation of Nonprotected Carbohydrates and Synthesis of Deoxy Carbohydrates in a Minimum Number of Steps (pages 4850–4853)

      Prof. Dr. Wataru Muramatsu, Satoko Tanigawa, Yuki Takemoto, Hirofumi Yoshimatsu and Prof. Dr. Osamu Onomura

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201104007

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      Nonprotected carbohydrates: The catalytic regioselective thiocarbonylation of carbohydrates by using organotin dichloride under mild conditions was demonstrated. The reaction afforded various deoxy saccharides in high yields and excellent regioselectivity in a minimum number of steps. The regioselectivity of the thiocarbonylation is attributed to the intrinsic character of the carbohydrates based on the stereorelationship of their hydroxy groups (see scheme).

    9. C[BOND]H Activation

      A New Dirhodium Catalyst with Hemilabile Tropolonato Ligands for C[BOND]H Bond Functionalization (pages 4854–4858)

      Dr. Frauke Thrun, Dipl.-Chem. Burkhard Butschke and Dr. Timm Graening

      Version of Record online: 19 MAR 2012 | DOI: 10.1002/chem.201102427

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      Don't hold on too tightly! In a new dirhodium catalyst for C[BOND]H functionalization reactions, two tropolonato ligands are introduced as hemilabile chelating ligands (see scheme). Only two bridges hold the Rh[BOND]Rh core together. The tropolonato ligands can liberate a binding site in the equatorial coordination sphere of the catalyst. This opens a doorway to new mechanistic channels in C[BOND]H functionalization.

    10. Intramolecular Decarboxylation

      Palladium-Catalyzed Intramolecular Decarboxylative Coupling of Arene Carboxylic Acids/Esters with Aryl Bromides (pages 4859–4865)

      Prof. Dr. Zengming Shen, M. Sc. Zhenjie Ni, Song Mo, Jing Wang and Yamin Zhu

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/chem.201103438

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      Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Communications
    8. Full Papers
    9. Preview
    1. Intramolecular Cyclizations

      Synthesis and Optoelectronic Properties of Hexahydroxylated 10-O-R-Substituted Anthracenes via a New Modification of the Friedel–Crafts Reaction Using O-Protected ortho-Acetal Diarylmethanols (pages 4866–4876)

      Dr. Agnieszka Bodzioch, Dr. Bernard Marciniak, Dr. Ewa Różycka-Sokołowska, Prof. Jeremiasz K. Jeszka, Dr. Paweł Uznański, Dr. Sylwester Kania, Janusz Kuliński and Prof. Piotr Bałczewski

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/chem.201101909

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      A new modification of Friedel–Crafts type intramolecular cyclization reactions, involving O-protected ortho-acetal diarylmethanols, led to a series of electron-rich hexahydroxylated 10-O-R-substituted anthracenes (see figure). Given its optoelectronic properties, the methoxy derivative is a promising material for device applications, particularly in the area of organic field-effect transistors (OFETs).

    2. Nucleobases

      Isoguanine Formation from Adenine (pages 4877–4886)

      Dr. Qianyi Cheng, Dr. Jiande Gu, Katherine R. Compaan and Prof. Dr. Henry F. Schaefer III

      Version of Record online: 12 MAR 2012 | DOI: 10.1002/chem.201102415

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      Attack: Several possible mechanisms underlying isoguanine formation when a OH radical attacks the C2 position of adenine (Amath image) are investigated theoretically for the first time. The findings explain why only the N1H and O2H tautomers of isolated isoguanine and isoguanosine have been observed experimentally.

    3. Supported Catalysts

      Supported Pd–Cu Bimetallic Nanoparticles That Have High Activity for the Electrochemical Oxidation of Methanol (pages 4887–4893)

      Dr. Zhen Yin, Dr. Wu Zhou, Yongjun Gao, Prof. Dr. Ding Ma, Prof. Dr. Christopher J. Kiely and Prof. Dr. Xinhe Bao

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201103674

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      Army of two: Supported bimetallic Pd–Cu nanoparticles, which were synthesized by a one-step multiphase method, showed enhanced electrocatalytic activity towards MeOH oxidation, comparable to the state-of-the-art commercially available Pt/C catalysts.

    4. Heterogeneous Catalysis

      Scandium(III)-Zeolites as New Heterogeneous Catalysts for Imino-Diels–Alder Reactions (pages 4894–4901)

      Dr. Andrea Olmos, Dr. Benoit Louis and Prof. Dr. Patrick Pale

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201103624

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      A zeolite for the DA: ScIII-zeolite acts as a very efficient and highly recyclable heterogeneous ligand-free catalyst for imino-Diels–Alder reactions. Piperidinyl peptidomimetics and indoloquinolizidine alkaloid-type derivatives have been obtained in one or two steps from simple components (amino acids, aldehydes and electron-rich dienes; see scheme) with overall yields of over 80 %.

    5. Drug Delivery

      Efficient Intracellular Delivery of Camptothecin by Silica/Titania Hollow Nanoparticles (pages 4902–4908)

      Chanhoi Kim, Sojin Kim, Wan-Kyu Oh, Moonjung Choi and Prof. Jyongsik Jang

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/chem.201200043

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      Effective and selective: Inorganic hollow nanoparticles (HNPs) composed of SiO2 and TiO2 have a well-defined uniform size (50 nm) and can undergo facile antibody-conjugation and drug-loading processes. The HNP drug-delivery system exhibits efficient comptothecin delivery, high selectivity for cancer cells, high uptake ratio into the cells, and low toxicity, which implies that HNPs have a remarkable potential for cancer therapy.

    6. Cluster Compounds

      Oligonuclear Molecular Models of Intermetallic Phases: A Case Study on [Pd2Zn6Ga2(Cp*)5(CH3)3] (pages 4909–4915)

      Dr. Timo Bollermann, Mariusz Molon, Dr. Christian Gemel, Kerstin Freitag, Dr. Rüdiger W. Seidel, Dr. Moritz von Hopffgarten, Paul Jerabek, Prof. Dr. Gernot Frenking and Prof. Dr. Roland A. Fischer

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201102758

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      A model student: [Pd2(μ-GaCp*)3(GaCp*)2] reacts with ZnMe2 to yield [Pd2Zn6Ga2(Cp*)5(CH3)3] as the first example of an oligonuclear Zn/Ga mixed-ligand transition-metal (M) cluster (see picture, M′=Ga, Zn). Structural characterization and DFT calculations revealed distinct similarities to related M/Zn/Ga Hume–Rothery intermetallic solid-state compounds, such as Zn/Ga site preferences and direct M[BOND]M bonding.

    7. Chiral Recognition

      Amphiphilic Schiff Base Organogels: Metal-Ion-Mediated Chiral Twists and Chiral Recognition (pages 4916–4922)

      Qingxian Jin, Dr. Li Zhang, Xuefeng Zhu, Dr. Pengfei Duan and Prof. Dr. Minghua Liu

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201103187

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      Let's twist again: An amphilphilic Schiff base organogelator that contained an ortho-substituted OH group formed gels in many organic solvents. The addition of Cu2+ ions caused the nanofiber gel to perform a chiral twist, whilst the addition of Mg2+ ions enhanced the fluorescence of the gel. More interestingly, the Mg2+-mediated organogel showed chiral recognition ability for D-tartaric acid.

    8. Graphene

      n-Type Reduced Graphene Oxide Field-Effect Transistors (FETs) from Photoactive Metal Oxides (pages 4923–4929)

      Heejoun Yoo, Youngmin Kim, Dr. Junghyun Lee, Hyemi Lee, Yeoheung Yoon, Giyoun Kim and Prof. Hyoyoung Lee

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/chem.201103967

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      The straight dope: Photoactive and semiconducting metal oxides, such as TiO2- and ZnO-doped graphene FETs, show n-type electric properties even under conditions of no irradiation. On exposure to UV light, these FETs show strong n-type electric behavior within seconds. These n-doping effects show saturation curves and slowly return back to their original state in darkness (see figure).

    9. Hydrogen-Bond Dynamics

      On the Role of Hydrogen Bonds in Photoinduced Electron-Transfer Dynamics between 9-Fluorenone and Amine Solvents (pages 4930–4937)

      Dr. Hirendra N. Ghosh, Dr. Katrin Adamczyk, Sandeep Verma, Dr. Jens Dreyer and Dr. Erik T. J. Nibbering

      Version of Record online: 2 MAR 2012 | DOI: 10.1002/chem.201102994

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      Ultrafast fluorescence upconversion and infrared measurements of the photoinduced reductive electron transfer between 9-fluorenone and diethylamine or triethylamine solvents indicate that the forward charge-separation and backward charge-recombination rates do not follow a direct relationship with the driving forces for electron transfer, thus suggesting a key role of hydrogen-bond modes coupled to the electron-transfer coordinates (see figure).

    10. Immunoassays

      Paper-Based Electrochemiluminescent 3D Immunodevice for Lab-on-Paper, Specific, and Sensitive Point-of-Care Testing (pages 4938–4945)

      Dr. Jixian Yan, Dr. Lei Ge, Prof. Xianrang Song, Prof. Mei Yan, Dr. Shenguang Ge and Prof. Jinghua Yu

      Version of Record online: 5 MAR 2012 | DOI: 10.1002/chem.201102855

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      Paperback writer: A paper-based electrochemiluminescent 3D immunodevice detected carcinoembryonic antigen in human serum. This technique combined high sensitivity and selectivity with the low cost and simplicity of paper-based analytical devices.

    11. Natural Products

      An Improved Route to (+)-Tedanolide and Analysis of Its Subtle Effects Controlling Conformation and Biological Behaviour (pages 4946–4952)

      Dr. Nina Diaz, Dr. Mingzhao Zhu, Dr. Gunnar Ehrlich, Ulrike Eggert, Yazh Muthukumar, Dr. Florenz Sasse and Prof. Dr. Markus Kalesse

      Version of Record online: 5 MAR 2012 | DOI: 10.1002/chem.201103038

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      Unfolding activity: Des-epoxy-tedanolide unfolds its biological activity through a different mode of action compared to deoxytedanolide. The biological effect of the epoxide present in tedanolide and deoxytedanolide could be investigated through the synthesis of its des-epoxy analogue. During the course of its synthesis it also became apparent that the hybridization at C5 significantly contributes to a conformational behaviour, which in turn is responsible for potential hemiacetal formation.

    12. Photochemistry

      Ruthenium(II)–Polyimine–Coumarin Light-Harvesting Molecular Arrays: Design Rationale and Application for Triplet–Triplet-Annihilation-Based Upconversion (pages 4953–4964)

      Wanhua Wu, Shaomin Ji, Wenting Wu, Jingyin Shao, Dr. Huimin Guo, Prof. Tony D. James and Prof. Jianzhang Zhao

      Version of Record online: 8 MAR 2012 | DOI: 10.1002/chem.201101377

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      Ru being served? RuII–bipyridine complexes typically absorb below 450 nm and ε<16 000 M−1 cm−1. The first visible-light-harvesting RuII–coumarin array absorbs at 475 nm (ε=63 300 M−1 cm−1) and the energy-transfer from the antenna to the coordination center is efficient.

    13. Graphene Modification

      Graphene Functionalisation with a Conjugated Poly(fluorene) by Click Coupling: Striking Electronic Properties in Solution (pages 4965–4973)

      Marta Castelaín , Dr. Gerardo Martínez, Pablo Merino, Prof. José Á. Martín-Gago , Prof. José L. Segura, Dr. Gary Ellis and Dr. Horacio J. Salavagione

      Version of Record online: 8 MAR 2012 | DOI: 10.1002/chem.201102008

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      Something just clicked! The click coupling of graphene and a polyfluorene derivative produces a material in which the emission properties depend on the affinity of the surrounding medium for graphene (see figure).

    14. Nanostructures

      Graphene–CdS Nanocomposites: Facile One-Step Synthesis and Enhanced Photoelectrochemical Cytosensing (pages 4974–4981)

      Xiaomei Zhao, Shiwei Zhou, Dr. Li-Ping Jiang, Prof. Wenhua Hou, Dr. Qingming Shen and Prof. Jun-Jie Zhu

      Version of Record online: 8 MAR 2012 | DOI: 10.1002/chem.201102379

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      The hard cell: Graphene-CdS nanocomposites were prepared by a one-step synthesis in aqueous solution. These as-prepared nanocomposites exhibited enhanced photocurrent (see figure). Based on these nanocomposites, an advanced photoelectrochemical cytosensor was fabricated, which showed good photoelectronic effect and cell-capture ability, and had a wide linear range and low detection limit for Hela cells.

    15. Repulsive Bond Paths

      A Bond Path and an Attractive Ehrenfest Force Do Not Necessarily Indicate Bonding Interactions: Case Study on M2X2 (M=Li, Na, K; X=H, OH, F, Cl) (pages 4982–4993)

      Dr. Piotr Dem'yanov and Pavel Polestshuk

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201101863

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      Similar are repulsed: Two anions linked by a bond path in dimers M2X2 (M=Li, Na, K, X=H, OH, F, Cl) were found to experience strong repulsion. The interaction between two anions or two cations that are not linked by a bond path is also strongly repulsive. Repulsive anion–anion and cation–cation interactions are outweighed by much stronger anion–cation interactions, and the molecules of the dimers are therefore stable.

    16. Screen-Printed Electrodes

      Disposable Electrochemical Immunosensor by Using Carbon Sphere/Gold Nanoparticle Composites as Labels for Signal Amplification (pages 4994–4998)

      Qiunan Xu, Feng Yan, Dr. Jianping Lei, Chuan Leng and Prof. Huangxian Ju

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/chem.201200171

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      A convenient and low-cost immunosensor was designed by using a polyethylene-glycol-film-modified screen-printed carbon electrode combined with a self-synthesized carbon sphere/gold nanoparticle composite as an electrochemical label for signal amplification (see scheme). This efficient method provides a potential application for clinical detection of protein markers.

    17. Total Synthesis

      Total Synthesis of Exiguamines A and B Inspired by Catecholamine Chemistry (pages 4999–5005)

      Vladimir Sofiyev, Jean-Philip Lumb, Matthew Volgraf and Prof. Dirk Trauner

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201103605

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      Be inspired: The presented biomimetic total synthesis of exiguamines A and B draws inspiration from catecholamine chemistry and is heavily influenced by biosynthetic considerations, in particular with respect to pericyclic reactions. The key steps are a challenging biaryl coupling, oxidation of a phenol to a para-quinone, and a cascade reaction in the final step.

    18. Metal–Organic Frameworks

      2D Porous Honeycomb Polymers versus Discrete Nanocubes from Trigonal Trinuclear Complexes and Ligands with Variable Topology (pages 5006–5012)

      Victoria N. Dorofeeva, Dr. Sergey V. Kolotilov, Dr. Mikhail A. Kiskin, Ruslan A. Polunin, Dr. Zhanna V. Dobrokhotova, Dr. Olivier Cador, Dr. Stéphane Golhen, Prof. Dr. Lahcène Ouahab, Prof. Dr. Igor L. Eremenko and Prof. Dr. Vladimir M. Novotortsev

      Version of Record online: 12 MAR 2012 | DOI: 10.1002/chem.201103688

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      A nanobox of tricks: A combination of trinuclear complexes and organic ligands with D3h symmetry led to a 2D coordination polymer with honeycomb pores, capable of adsorbing significant quantities of N2 and H2. Removal of one donor group from the ligand, leading to its transformation into a C2v bridge, switched the reaction pathway towards the formation of a discrete nanocube, in which eight trinuclear units are linked by twelve bidentate bridges.

    19. Alkali Metals

      Rubidium Polyhydrides Under Pressure: Emergence of the Linear H3 Species (pages 5013–5021)

      Dr. James Hooper and Prof. Eva Zurek

      Version of Record online: 5 MAR 2012 | DOI: 10.1002/chem.201103205

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      A pressing motif: At a pressure of 15 GPa, RbH5 is predicted to become stable with respect to decomposition into H2 and RbH. The unit cell contains Rb+ ions, H2 molecules, and the symmetric linear equation image molecule, which is the simplest example of a three-center four-electron bond. At higher pressures equation image is further stabilized in an RbH3 phase, which metallizes at 220 GPa.

    20. C[BOND]H Activation

      Synthesis of 2- and 2,7-Functionalized Pyrene Derivatives: An Application of Selective C[BOND]H Borylation (pages 5022–5035)

      Dr. Andrew G. Crawford, Prof. Dr. Zhiqiang Liu, Prof. Dr. Ibraheem A. I. Mkhalid, Dr. Marie-Hélène Thibault, Dr. Nicolle Schwarz, Dr. Gilles Alcaraz, Dr. Andreas Steffen, Dr. Jonathan C. Collings, Dr. Andrei S. Batsanov, Prof. Dr. Judith A. K. Howard and Prof. Dr. Todd B. Marder

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201103774

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      The point of catalytic C[BOND]H borylation! Regioselective iridium-catalyzed borylation of pyrene takes place at the 2- and 2,7-positions. The resulting mono- and bisboronate esters can be readily converted into both nucleophilic and electrophilic cross-coupling partners and serve as useful precursors to a wide range of pyrene derivatives of significant photophysical and structural interest, which are otherwise difficult to prepare (see scheme).

    21. DFT Calculations

      A DFT and TD-DFT Approach to the Understanding of Statistical Kinetics in Substitution Reactions of M3Q4 (M=Mo, W; Q=S, Se) Cuboidal Clusters (pages 5036–5046)

      Dr. Andrés G. Algarra, Dr. M. Jesús Fernández-Trujillo and Dr. Manuel G. Basallote

      Version of Record online: 8 MAR 2012 | DOI: 10.1002/chem.201102629

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      Let's play together: The validity of the simplifications required for the observation of statistical kinetics in the substitution reactions of cuboidal M3Q4 clusters are explored by using DFT and TD-DFT (time-dependent DFT) calculations. Whereas the activation barriers for the three consecutive substitutions (see scheme) are close to each other, the three metal centres cannot be considered to behave as independent chromophores.

    22. C[BOND]H Activation

      Direct Arylation of Benzene with Aryl Bromides using High-Temperature/High-Pressure Process Windows: Expanding the Scope of C[BOND]H Activation Chemistry (pages 5047–5055)

      Bartholomäus Pieber, Dr. David Cantillo and Prof. Dr. C. Oliver Kappe

      Version of Record online: 7 MAR 2012 | DOI: 10.1002/chem.201103748

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      Cobalt and some heat: Processing direct arylation reactions in sealed tubes at high temperatures allows rapid catalyst/ligand screening and reaction optimization, ultimately reducing processing times from two days to five minutes (see figure).

    23. Heterocycles

      New Types of Reactivity of α,β-Unsaturated N,N-Dimethylhydrazones: Chemodivergent Diastereoselective Synthesis of Functionalized Tetrahydroquinolines and Hexahydropyrrolo[3,2-b]indoles (pages 5056–5063)

      Dr. Vellaisamy Sridharan, Pascual Ribelles, Verónica Estévez, Prof. Mercedes Villacampa, Prof. M. Teresa Ramos, Prof. Paramasivan T. Perumal and Prof. J. Carlos Menéndez

      Version of Record online: 5 MAR 2012 | DOI: 10.1002/chem.201103562

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      Playing dominos: The reaction between anilines, aldehydes, and α,β-unsaturated N,N-dimethylhydrazones afforded C4-functionalized 1,2,3,4-tetrahydroquinolines or 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles through domino mechanisms, depending on the solvent and catalyst employed (see scheme).

    24. Microbiology

      Aminopyrrolic Synthetic Receptors for Monosaccharides: A Class of Carbohydrate-Binding Agents Endowed with Antibiotic Activity versus Pathogenic Yeasts (pages 5064–5072)

      Prof. Cristina Nativi, Dr. Oscar Francesconi, Gabriele Gabrielli, Irene De Simone, Dr. Benedetta Turchetti, Dr. Tommaso Mello, Dr. Lorenzo Di Cesare Mannelli, Prof. Carla Ghelardini, Prof. Pietro Buzzini and Dr. Stefano Roelens

      Version of Record online: 5 MAR 2012 | DOI: 10.1002/chem.201103318

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      Antibiotic agents: Synthetic aminopyrrolic receptors for carbohydrate recognition represent a new class of biologically active compounds endowed with antibiotic activity, which effectively inhibit the proliferation of yeast and yeast-like pathogens, such as Candida and Prototheca (see figure).

    25. Hematite Nanochains

      Sacrificial Templating Synthesis of Hematite Nanochains from [Fe18S25](TETAH)14 Nanoribbons: Their Magnetic, Electrochemical, and Photocatalytic Properties (pages 5073–5079)

      Dr. Yu-Xue Zhou, Dr. Hong-Bin Yao, Dr. Wei-Tang Yao, Zhu Zhu and Prof. Dr. Shu-Hong Yu

      Version of Record online: 8 MAR 2012 | DOI: 10.1002/chem.201102736

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      Templated synthesis of nanochains: Unique hematite nanochains, self-assembled from α-Fe2O3 nanoparticles, were synthesized by a sacrificial template method through thermal decomposition of [Fe18S25](TETAH)14 as a nanoribbon precursor (see scheme; TETAH=protonated triethylenetetramine). Magnetic studies have shown greatly enhanced coercivity of the 1D hematite nanochains compared with that of dispersed α-Fe2O3 nanoparticles at 5 K.

    26. Mesoporous Materials

      A Strategy for the Synthesis of Mesostructured Metal Oxides with Lower Oxidation States (pages 5080–5086)

      Dr. Harun Tüysüz, Dr. Claudia Weidenthaler and Prof. Dr. Ferdi Schüth

      Version of Record online: 12 MAR 2012 | DOI: 10.1002/chem.201103650

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      As strong as an Ox: A detailed study on the pseudomorphic conversion of ordered mesoporous Co3O4 and ferrihydrite into CoO and Fe3O4, respectively, by using alcohol/water vapor as a gentle reducing agent is described. The reduction conditions for the transformation were optimized. In addition, the first one-pot synthesis of mesostructured CoO by using cubic ordered silica as a hard template is demonstrated.

    27. Supramolecular Polymers

      Cucurbituril-Modulated Supramolecular Assemblies: From Cyclic Oligomers to Linear Polymers (pages 5087–5095)

      Hai Qian, Dr. Dong-Sheng Guo and Prof. Dr. Yu Liu

      Version of Record online: 8 MAR 2012 | DOI: 10.1002/chem.201101904

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      Cucurbit[8]uril (blue) not only modulates the topology of supramolecular assemblies of bis(p-sulfonatocalix[4]arenes) (green) and hexamethylene-bridged bisviologen (orange; see figure), but also stimulates their switching between assembly and disassembly.

    28. Conformation Analysis

      Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids (pages 5096–5104)

      Dr. Fernando Rodríguez, Víctor J. Somovilla, Dr. Francisco Corzana, Dr. Jesús H. Busto, Prof. Alberto Avenoza and Prof Jesús M. Peregrina

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/chem.201103089

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      Presentation is important! The synthesis and conformational analysis of different glycosyl amino acids and glycopeptides, containing the nonnatural β-hydroxycyclohexane-α-amino acid residue, have been investigated. The cyclohexane ring can effectively modulate the presentation of the sugar moiety with respect to the underlying amino acid residue (see figure). These features allow the molecule to adopt novel conformations that are not found in natural derivatives.

    29. Mechanochromism

      Reversible Phase Transformation and Mechanochromic Luminescence of ZnII-Dipyridylamide-Based Coordination Frameworks (pages 5105–5112)

      Prof. Biing-Chiau Tzeng, Tsung-Yi Chang, Sheng-Luen Wei and Dr. Hwo-Shuenn Sheu

      Version of Record online: 12 MAR 2012 | DOI: 10.1002/chem.201103405

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      Wet and dry: A 1D double-zigzag framework, {[Zn(paps)2(H2O)2](ClO4)2}n (paps=N,N′-bis(pyridylcarbonyl)-4,4′-diaminodiphenyl thioether), has been synthesized. A similar reaction in dry solvents led to the formation of a 2D polyrotaxane framework, [Zn(paps)2(ClO4)2]n. The structures can be interconverted by heating and grinding in the presence of moisture (see figure) and display mechanochromic luminescence.

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      Preview: Chem. Eur. J. 17/2012 (page 5115)

      Version of Record online: 4 APR 2012 | DOI: 10.1002/chem.201290064

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