Chemistry - A European Journal

Cover image for Vol. 18 Issue 13

March 26, 2012

Volume 18, Issue 13

Pages 3785–4127

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
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    1. You have free access to this content
      Cover Picture: Ruthenium(II) Photosensitizers of Tridentate Click-Derived Cyclometalating Ligands: A Joint Experimental and Computational Study (Chem. Eur. J. 13/2012) (page 3785)

      Benjamin Schulze, Dr. Daniel Escudero, Christian Friebe, Dr. Ronald Siebert, Dr. Helmar Görls, Stephan Sinn, Martin Thomas, Sebastian Mai, Prof. Dr. Jürgen Popp, Prof. Dr. Benjamin Dietzek, Prof. Dr. Leticia González and Prof. Dr. Ulrich S. Schubert

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/chem.201290046

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      A photosensitizer exhibition of ruthenium(II) complexes featuring click-derived tridentate cyclometalating ligands is reported. Systematic structural manipulations and detailed electrochemical, photophysical, and computational investigations have been performed, allowing a deeper understanding and revealing great potential for application in dye-sensitized solar cells. For more details, see the Full Paper by U. S. Schubert, B. Dietzek, L. González et al. on page 4010 ff.

  2. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
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  4. Review

    1. Top of page
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    3. Graphical Abstract
    4. News
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    6. Communications
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    1. Directed Metalation

      Directed Remote Aromatic Metalations: Mechanisms and Driving Forces (pages 3804–3820)

      Dr. David Tilly, Dr. Jakob Magolan and Prof. Jacques Mortier

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/chem.201103920

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      Long-distance directed metalation: Directed remote aromatic metalation is a valuable synthetic tool that has been utilized for the efficient preparation of elaborate aromatic scaffolds (see scheme). This review tackles the mechanistic nuances and driving forces behind directed remote aromatic metalations in order to unravel the causes of the observed regiochemical outcomes and enable enhanced predictability of these remarkable synthetic transformations.

  5. Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Review
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    1. Catalytic Amidation

      Direct Amide Coupling of Non-activated Carboxylic Acids and Amines Catalysed by Zirconium(IV) Chloride (pages 3822–3826)

      Helena Lundberg, Fredrik Tinnis and Prof. Hans Adolfsson

      Version of Record online: 24 FEB 2012 | DOI: 10.1002/chem.201104055

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      Amidst the green: A green, mild and effective protocol for the direct formation of secondary and tertiary amides from non-activated carboxylic acids and amines in good to excellent yields by employing ZrCl4 as the catalyst is presented (see scheme). The amide coupling protocol proved to be suitable for scaled up syntheses, and the mild reaction conditions conserve the enantiopurity of chiral starting materials.

    2. Gold Complexes

      Regioselective Formation of Saturated Abnormal NHC–Gold(I) Complexes by [3+2] Cycloaddition of Azomethine Ylides and Isonitrile Gold(I) Complexes (pages 3827–3830)

      Prof. Dr. A. Stephen K. Hashmi, Dipl.-Chem. Dominic Riedel, Dr. Matthias Rudolph, Dr. Frank Rominger and Dr. Thomas Oeser

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201200217

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      Abnormally easy: The first saturated abnormal NHC–gold(I) complexes are synthesized in a two-step procedure from commercially available gold(I) precursors. The reaction of gold-coordinated isonitriles with in situ generated azomethine ylides circumvents regioselectivity problems during the carbene formation (see scheme). The scope of the reaction turned out to be general and abnormal carbenes with unusual substitution patterns are thus accessible.

    3. Alkoxycarbonylation

      A General and Efficient Palladium-Catalyzed Alkoxycarbonylation of Phenols To Form Esters through In Situ Formed Aryl Nonaflates (pages 3831–3834)

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

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201103797

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      Esters made easy! A general and efficient methodology for the palladium-catalyzed alkoxycarbonylation of in situ formed aryl nonaflates has been developed (see scheme). Both homo- and cross-esterifications are possible. DPPF=1,1′-bis(diphenylphosphino)ferrocene.

    4. Gene Technology

      A Cationic Phospholipid–Detergent Conjugate as a New Efficient Carrier for siRNA Delivery (pages 3835–3839)

      Dr. Philippe Pierrat, Dr. Gaëlle Creusat, Dr. Gilles Laverny, Prof. Françoise Pons, Dr. Guy Zuber and Dr. Luc Lebeau

      Version of Record online: 23 FEB 2012 | DOI: 10.1002/chem.201103645

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      A “grapnel” lipid: Conjugation of Triton X-100 with DOPC provides a new class of nucleic acid carriers (see figure). The lamellar phase forming a cationic conjugate has no hemolytic activity and efficiently delivers siRNA into the cytosol of mammalian cells. Covalent anchoring of the detergent to the phospholipid and the dangling hydrophobic part of the detergent moiety appear to be essential for siRNA delivery and efficient gene silencing.

    5. Allenes

      Pd-Catalyzed Asymmetric Synthesis of N-Allenyl Amides and Their Au-Catalyzed Cycloisomerizative Hydroalkylation: A New Route Toward Enantioenriched Pyrrolidones (pages 3840–3844)

      Audrey Boutier, Dr. Claire Kammerer-Pentier, Prof. Dr. Norbert Krause, Prof. Dr. Guillaume Prestat and Prof. Dr. Giovanni Poli

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201103902

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      Palladium to make them, gold to cyclize them! Gold-catalyzed cycloisomerizative hydroalkylation of N-allenyl amides affords regioselectively 4-vinyl-γ-lactams. This transformation is stereospecific and takes place with a total axis-to-center chirality transfer. The required enantioenriched N-allenyl amide is successfully obtained from an original Pd-catalyzed dynamic kinetic asymmetric transformation (see scheme).

    6. Polyoxometalates

      A Stable Hybrid Bisphosphonate Polyoxometalate Single-Molecule Magnet (pages 3845–3849)

      Dr. Hani El Moll, Dr. Anne Dolbecq, Dr. Jérôme Marrot, Guillaume Rousseau, Dr. Mohamed Haouas, Dr. Francis Taulelle, Dr. Guillaume Rogez, Dr. Wolfgang Wernsdorfer, Dr. Bineta Keita and Prof. Pierre Mialane

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/chem.201200140

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      A new functionalizable polyoxometalate platform: The heptanuclear CoII polyoxometalate complex [{(B-α- PW9O34)Co3(OH)(H2O)2(O3PC(O)- (C3H6NH3)PO3)}2Co]14− represents a unique example of a magnetic, stable, functionalizable polyoxotungstate platform, and behaves as a single-molecule magnet (see figure).

    7. Prodrugs

      ROS-Inducible DNA Cross-Linking Agent as a New Anticancer Prodrug Building Block (pages 3850–3854)

      Dr. Sheng Cao, Yibin Wang and Prof. Xiaohua Peng

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201200075

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      Down at the crossed code: Novel arylboronic ester and biarylboronic ester derivatives were synthesized. Compound 1 can be activated by hydrogen peroxide to release 2,5-bis(trimethylammonium) benzyl-1,4-diol (2), which leads to interstrand cross-link formation and DNA alkylation (see scheme). Compound 1 provides a novel building block for the development of H2O2-targeting anticancer prodrugs.

    8. Alkynes

      Mannich Reactions of Alkynes: Mechanistic Insights and the Role of Sub-Stoichiometric Amounts of Alkynylcopper(I) Compounds in the Catalytic Cycle (pages 3855–3858)

      Dr. Benjamin R. Buckley, Amna N. Khan and Prof. Dr. Harry Heaney

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201103987

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      Yellow polymeric alkynylcopper(I) compounds observed in the three-component Mannich reactions of alkynes, secondary amines and aldehydes are shown to be pre-catalysts that give rise to catalytic copper(I) alkyne complexes by interaction with secondary amines (see scheme). Interaction of these complexes with iminium ions (formed from aldehydes or their equivalents, including CH2Cl2), results in the formation of Mannich bases in high yields.

    9. DNA Recognition

      Kinetic Differentiation between Homo- and Alternating AT DNA by Sterically Restricted Phosphonium Dyes (pages 3859–3864)

      Dr. Lidija-Marija Tumir, Dr. Ivo Crnolatac, Prof. Todor Deligeorgiev, Aleksey Vasilev, Dr. Stefka Kaloyanova, Marina Grabar Branilović, Dr. Sanja Tomić and Dr. Ivo Piantanida

      Version of Record online: 24 FEB 2012 | DOI: 10.1002/chem.201102968

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      Poly has a tracker: By sterically controlling monomer–dimer equilibria, novel dyes can kinetically differentiate between homo-AT and alternating AT–AT polynucleotides. In this way, the width and steric occupation of the DNA minor groove can be finely probed and can be easily assessed by induced CD signals (see figure).

    10. Organocatalysis

      Highly Enantioselective Assembly of Functionalized Tetrahydroquinolines with Creation of an All-Carbon Quaternary Center (pages 3865–3870)

      Hao Rui Tan, Hui Fen Ng, Dr. Jun Chang and Prof. Dr. Jian Wang

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201103136

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      A Mannich–Michael combo: An efficient and highly enantioselective cascade process by H-bonding catalysis for the synthesis of functionalized tetrahydroquinolines has been developed. An indane amine-thiourea small molecule has been discovered to catalyze this process in high yields and with good diastereomeric ratios and excellent enantioselectivities (see scheme).

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Preview
    1. Molecular Dynamics

      A Non-damaging Method to Analyze the Configuration and Dynamics of Nitrotyrosines in Proteins (pages 3872–3878)

      Dr. Irene Díaz-Moreno, Dr. Pedro M. Nieto, Dr. Rebecca Del Conte, Dr. Margarida Gairí, Dr. José M. García-Heredia, Prof. Miguel A. De la Rosa and Dr. Antonio Díaz-Quintana

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201103413

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      Nitrotyrosines in a protein context: Unveiling of the configuration and dynamics of nitrotyrosines in proteins, such as cytochrome c, requires the development of a non-damaging method based on recording 1H-15N heteronuclear single quantum coherence (HSQC) NMR spectra optimized for the detection of 3J(N[BOND]H) couplings between a 15N-tagged nitro group and the adjacent aromatic proton (see figure).

    2. Sonochemical Reductions

      Mechanism of PtIV Sonochemical Reduction in Formic Acid Media and Pure Water (pages 3879–3885)

      Dr. Tony Chave, Nathalie M. Navarro, Serge Nitsche and Dr. Sergey I. Nikitenko

      Version of Record online: 23 FEB 2012 | DOI: 10.1002/chem.201102355

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      A complex mechanism for the sonochemical reduction of PtIV has been found, which involves in situ formed reactive species, as well as reactivity enhancement due to local heating around the cavitation bubble. For the first time, the design of a synthetic route for monodispersed Pt nanoparticles in pure water without any templates or capping agents by using ultrasonic irradiation at low-frequency ultrasound has been reported (see figure).

    3. Dendrons

      Dendron-Containing Tetraphenylethylene Compounds: Dependence of Fluorescence and Photocyclization Reactivity on the Dendron Generation (pages 3886–3892)

      Guangxi Huang, Baode Ma, Jianming Chen, Dr. Qian Peng, Dr. Guanxin Zhang, Prof. Qinghua Fan and Prof. Deqing Zhang

      Version of Record online: 23 FEB 2012 | DOI: 10.1002/chem.201103675

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      A flick of the switch: Covalent interactions with high-generation dendrons “turned on” the fluorescence and facilitated the photocyclization of tetraphenylethylene (TPE) compounds.

    4. Dyes/Pigments

      Synthesis, Computational Modeling, and Properties of Benzo-Appended BODIPYs (pages 3893–3905)

      Timsy Uppal, Dr. Xiaoke Hu, Dr. Frank R. Fronczek, Stephanie Maschek, Prof. Petia Bobadova-Parvanova and Prof. M. Graça H. Vicente

      Version of Record online: 24 FEB 2012 | DOI: 10.1002/chem.201103002

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      Two synthetic routes to benzo- BODIPYs from a pyrrolic precursor were investigated. Computational calculations showed similar relative energies for all reaction intermediates and products in both routes. X-ray analyses indicated that benzannulation enhances the planarity of the BODIPY core (see figure). The benzo-BODIPYs show red-shifted absorptions and emissions, ca. 50–60 nm per benzoannulated ring, and high fluorescence quantum yields.

    5. Host–Guest Systems

      Restricted Conformational Flexibility of a Triphenylamine Derivative on the Formation of Host–Guest Complexes with Various Macrocyclic Hosts (pages 3906–3917)

      Amal Kumar Mandal, Moorthy Suresh, Priyadip Das and Dr. Amitava Das

      Version of Record online: 17 FEB 2012 | DOI: 10.1002/chem.201103079

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      Locked in place: Fluorescence enhancement results from restricted internal rotation of a new triphenylamine on the formation of a host–guest complex with hosts cucurbit[7]uril (CB[7]) and β-cyclodextrin (β-CD; see picture). Furthermore, a [4]pseudorotaxane formed between dibenzo[24]crown-8 ether (DB24C8) and triphenylamine undergoes fluorescence resonance energy transfer, as shown by electrochemical analysis.

    6. Nucleophilic Substitution

      Oligoethylene Glycols as Highly Efficient Mutifunctional Promoters for Nucleophilic-Substitution Reactions (pages 3918–3924)

      Dr. Vinod H. Jadhav, Seung Ho Jang, Dr. Hwan-Jeong Jeong, Dr. Seok Tae Lim, Dr. Myung-Hee Sohn, Ju-Young Kim, Prof. Dr. Sungyul Lee, Ji Woong Lee, Prof. Dr. Choong Eui Song and Prof. Dr. Dong Wook Kim

      Version of Record online: 16 FEB 2012 | DOI: 10.1002/chem.201102455

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      The EG race: OligoEGs, such as pentaethylene glycol (pentaEG), act as mutifunctional promoters for nucleophilic-substitution reactions with the corresponding alkali-metal salts. The combination of pentaEG and a tert-alcohol media system showed tremendous efficiency in the fluorination and methoxylation of base-sensitive substrates by using the corresponding basic nucleophiles (see figure).

    7. Domino Reactions

      Alternative Reaction Pathways in Domino Reactions of Hydrazinediidozirconium Complexes with Alkynes (pages 3925–3941)

      Dr. Thorsten Gehrmann, Solveig A. Scholl, Dr. Julio Lloret Fillol, Prof. Dr. Hubert Wadepohl and Prof. Dr. Lutz H. Gade

      Version of Record online: 17 FEB 2012 | DOI: 10.1002/chem.201103497

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      A fork in the road: Azirinidozirconium species A is the key intermediate for two reaction pathways in the metal-catalyzed coupling of diarylhydrazines and alkynes. Electrophilic metal–azirinide attack at the ortho C atom (C) affords substituted indoles.

    8. Single-Chain Magnets

      Cyano-Bridged MnIII[BOND]MIII Single-Chain Magnets with MIII=CoIII, FeIII, MnIII, and CrIII (pages 3942–3954)

      Prof. Dr. Hitoshi Miyasaka, Tomokura Madanbashi, Ayumi Saitoh, Dr. Natsuko Motokawa, Ryuta Ishikawa, Prof. Dr. Masahiro Yamashita, Dr. Stefan Bahr, Prof. Dr. Wolfgang Wernsdorfer and Dr. Rodolphe Clérac

      Version of Record online: 16 FEB 2012 | DOI: 10.1002/chem.201102738

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      New SCM systems: A series of isostructural cyano-bridged MnIII(h.s.)–MIII(l.s.) alternating chains was synthesized by assembling a tricationic MnIII salen-type complex and [MIII(CN)6]3− complexes (see scheme). The three compounds with M=Fe, Mn, and Cr behave as single-chain magnets (SCMs) despite their different spin states and correlations, whereas the M=Co system displays simple paramagnetism. These hetero-spin SCMs offer a unique system to test future SCM models between the Ising and Heisenberg limits.

    9. Enzyme Models

      Dioxygen Activation of a Trinuclear CuICuICuI Cluster Capable of Mediating Facile Oxidation of Organic Substrates: Competition between O-Atom Transfer and Abortive Intercomplex Reduction (pages 3955–3968)

      Dr. Suman Maji, Dr. Jason C.-M. Lee, Yu-Jhang Lu, Dr. Chang-Li Chen, Mu-Cheng Hung, Dr. Peter P.-Y. Chen, Prof. Steve S.-F. Yu and Prof. Sunney I. Chan

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201103075

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      Three does it better: Low-temperature oxygenation of [CuICuICuI(L)]1+ leads to the formation of two oxidized tricopper complexes: a green dioxygen adduct and a blue species (see scheme), which were isolated and characterized as [CuIICuII(μ-η22-peroxo)CuII(L)]2+ and [CuIICuII(μ-O)CuII(L)]2+, respectively. The results are reminiscent of the abortive dioxygen chemistry observed for the particulate methane monooxygenase in the absence of substrate.

    10. Ligand Effects

      Unraveling Complex Small-Molecule Binding Mechanisms by Using Simple NMR Spectroscopy (pages 3969–3974)

      Dr. Marc Quinternet, Dr. Jean-Philippe Starck, Dr. Marc-André Delsuc and Prof. Bruno Kieffer

      Version of Record online: 15 FEB 2012 | DOI: 10.1002/chem.201101983

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      So fast so furious: Methyl SOFAST correlation enabled the determination of site-specific equilibrium binding constants with unlabeled proteins. Very accurate dissociation constants were determined in the binding of L- and D-tryptophan to serum albumin (see figure).

    11. Chiral Selection

      Chiral-Symmetry Selection in Soft Monolayers under Vortical Flow (pages 3975–3980)

      Núria Petit-Garrido, Dr. Josep Claret, Dr. Jordi Ignés-Mullol, Dr. Joan Anton Farrera and Prof. Dr. Francesc Sagués

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201102358

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      A swirl of surfactants: The orientational chirality of sub-millimeter domains that arise spontaneously in Langmuir monolayers of achiral surfactants was selected by using a vortical flow under the surface. The enantiomeric excess was directly assessed by polarizing optical microscopy, and depended on the forcing conditions and on the initial monolayer state (see figure).

    12. Ion–Molecule Reactions

      Dihydrogen Generation from Amine/Boranes: Synthesis, FT-ICR, and Computational Studies (pages 3981–3991)

      Prof. Dr. José-Luis M. Abboud, Dr. Balázs Németh, Prof. Dr. Jean-Claude Guillemin, Prof. Dr. Peeter Burk, Aiko Adamson and Eva Roos Nerut

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201102611

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      Hydrogen generation and storage: FT-ICR and ab initio techniques were applied to the quantitative study of the protonation in the gas phase of sixteen amine/boranes with a variety of structures. This reaction generates dihydrogen in all cases (see figure). The structural study led to the observation of the onset of frustrated Lewis pairs. Conclusions about possible structures of compounds suitable for the generation/storage of dihydrogen were reached.

    13. Biosensing

      Enzyme-Regulated Activation of DNAzyme: A Novel Strategy for a Label-Free Colorimetric DNA Ligase Assay and Ligase-Based Biosensing (pages 3992–3999)

      Kaiyu He, Wang Li, Prof. Zhou Nie, Yan Huang, Zhuoliang Liu, Lihua Nie and Prof. Shouzhuo Yao

      Version of Record online: 15 FEB 2012 | DOI: 10.1002/chem.201102290

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      Connect and activate: Enzyme-regulated DNAzyme activity is demonstrated and successfully employed in developing a DNAzyme-based strategy for a colorimetric DNA ligase assay and ligase-related biosensing (see scheme). The ligase-activated hemin-bound horseradish peroxidase mimicking DNAzyme was used for the colorimetric readout. This novel strategy is facile, versatile, sensitive and label-free.

    14. Morphogenesis

      Mimicking the Growth of a Pathologic Biomineral: Shape Development and Structures of Calcium Oxalate Dihydrate in the Presence of Polyacrylic Acid (pages 4000–4009)

      Dr. Annu Thomas, Dr. Elena Rosseeva, Dr. Oliver Hochrein, Dr. Wilder Carrillo-Cabrera, Dr. Paul Simon, Dipl.-Inform. Patrick Duchstein, Prof. Dr. Dirk Zahn and Prof. Dr. Rüdiger Kniep

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201102228

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      Crystal branching: yes or no? The shape development of calcium oxalate dihydrate (COD) in the presence of increasing amounts of polyacrylic acid (PAA) is caused by COD–PAA interactions (adsorption and incorporation) with the prismatic zones of COD (see figure). Morphologies and structures of the biomimetic individuals are closely related to so-called “pathologic” specimens (including urinary stones).

    15. Ruthenium(II) Photosensitizers

      Ruthenium(II) Photosensitizers of Tridentate Click-Derived Cyclometalating Ligands: A Joint Experimental and Computational Study (pages 4010–4025)

      Benjamin Schulze, Dr. Daniel Escudero, Christian Friebe, Dr. Ronald Siebert, Dr. Helmar Görls, Stephan Sinn, Martin Thomas, Sebastian Mai, Prof. Dr. Jürgen Popp, Prof. Dr. Benjamin Dietzek, Prof. Dr. Leticia González and Prof. Dr. Ulrich S. Schubert

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/chem.201103451

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      Making sense of sensitization: A systematic series of heteroleptic bis(tridentate) ruthenium(II) complexes of 1,3-bis(1,2,3-triazol-4-yl)benzene N C N-coordinating ligands and 2,2′:6′,2′′-terpyridine was synthesized, analyzed by single-crystal X-ray diffraction, investigated photophysically and electrochemically, and studied by computational methods (see figure) revealing great potential for application in dye-sensitized solar cells.

    16. Nanotubes

      One-Step Solvothermal Synthesis of Single-Crystalline TiOF2 Nanotubes with High Lithium-Ion Battery Performance (pages 4026–4030)

      Dr. Yi Zeng, Wenyu Zhang, Chen Xu, Ni Xiao, Prof. Yizhong Huang, Dr. Denis Y. W. Yu, Prof. Huey Hoon Hng and Prof. Qingyu Yan

      Version of Record online: 23 FEB 2012 | DOI: 10.1002/chem.201103879

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      The superiority of the tube: Single-crystalline TiOF2 nanotubes were prepared by a simple solvothermal method (see figure) and show superior capacities for Li+ storage compared with other types of TiOF2 nanoparticles. This high capacity makes the nanotubes potentially interesting anode materials in rechargeable lithium batteries.

    17. Nickel Complexes

      Pentacoordinate NiII Complexes: Preparation, Magnetic Measurements, and Ab Initio Calculations of the Magnetic Anisotropy Terms (pages 4031–4040)

      Dr. Jean-Pierre Costes , Dr. Rémi Maurice  and Dr. Laure Vendier 

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201103641

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      A stepwise process, in which a tridentate ligand (generated by monocondensation of a diamine with a ketone) chelates a Ni center with subsequent introduction of a bidentate ligand, allows preparation of genuine pentacoordinate nickel complexes (e.g., see picture) with large zero-field splitting parameters, which were determined experimentally and theoretically. C gray, N blue, O red, H omitted.

    18. Luminescent Dyads

      Excited State Properties and Energy Transfer within Dipyrrin-Based Binuclear Iridium/Platinum Dyads: The Effect of ortho-Methylation on the Spacer (pages 4041–4050)

      Dr. Catherine Bronner, Dr. Manoel Veiga, Dr. Aurélie Guenet, Prof. Dr. Luisa De Cola, Prof. Dr. Mir Wais Hosseini, Dr. Cristian A. Strassert and Dr. Stéphane A. Baudron

      Version of Record online: 24 FEB 2012 | DOI: 10.1002/chem.201103836

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      Luminescent, cyclometalated iridium complexes based on pyridyl-appended dipyrrin ligands were prepared and characterized both in the solid state and in solution. The consequence of the functionalization of the peripheral pyridyl moiety or its coordination to metal centers on the emission properties of mononuclear or heterobinuclear complexes was studied by systematic photophysical investigations.

    19. Energetic Materials

      Nitrogen-Rich 5,5′-Bistetrazolates and their Potential Use in Propellant Systems: A Comprehensive Study (pages 4051–4062)

      Niko Fischer, Dániel Izsák, Prof. Dr. Thomas M. Klapötke, Sebastian Rappenglück and Dr. Jörg Stierstorfer

      Version of Record online: 24 FEB 2012 | DOI: 10.1002/chem.201103737

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      The thrust generation: The synthesis and complete characterization of a series of nitrogen-rich salts of 5,5′-bistetrazole gave promising materials with potential applications in novel propellant systems (see figure). In addition to their good thermal and chemical stability, the high nitrogen content leads to good N2/CO ratios when combusted, which is desirable to avoid environmental and corrosion problems.

    20. Hydrogels

      Molecular Hydrogels from Bolaform Amino Acid Derivatives: A Structure–Properties Study Based on the Thermodynamics of Gel Solubilization (pages 4063–4072)

      Vicent J. Nebot, José Armengol, Dr. Johan Smets, Susana Fernández Prieto, Dr. Beatriu Escuder and Dr. Juan F. Miravet

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201103193

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      Heating up the jelly: Molecular hydrogels derived from amino acids show a strengthening upon increasing the temperature (see figure). This behavior is associated to the thermodynamics of their formation, which reveal an entropy-controlled aggregation. The role played by the hydrophobic effect in the aggregation of molecular gels is discussed.

    21. Cascade Reactions

      Hydrogen-Bond-Mediated Asymmetric Cascade Reaction of Stable Sulfur Ylides with Nitroolefins: Scope, Application and Mechanism (pages 4073–4079)

      Dr. Liang-Qiu Lu, Dr. Fang Li, Jing An, Ying Cheng, Dr. Jia-Rong Chen and Prof. Dr. Wen-Jing Xiao

      Version of Record online: 23 FEB 2012 | DOI: 10.1002/chem.201104021

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      Controlled cascade: A hydrogen-bond-mediated asymmetric [4+1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins was developed (see scheme). This reaction provides a facile route to enantioenriched 4,5-substituted oxazolidinones. Stereocontrolled modes and a mechanism are proposed to explain the origin of the stereochemistry.

    22. DNA

      Synthesis of Aldehyde-Linked Nucleotides and DNA and Their Bioconjugations with Lysine and Peptides through Reductive Amination (pages 4080–4087)

      Veronika Raindlová, Dr. Radek Pohl and Prof. Dr. Michal Hocek

      Version of Record online: 15 FEB 2012 | DOI: 10.1002/chem.201103270

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      Joining forces: DNA–peptide conjugation through reductive amination of aldehyde-modified DNA with lysine-containing peptides was developed (see scheme). Formylaryl-linked dCTP derivatives were prepared by cross-coupling and incorporated into DNA by polymerases. The reductive amination of aldehyde-modified nucleotides and DNA was studied and optimized.

    23. Organocatalysis

      Noncovalent Bifunctional Organocatalysts: Powerful Tools for Contiguous Quaternary-Tertiary Stereogenic Carbon Formation, Scope, and Origin of Enantioselectivity (pages 4088–4098)

      Prof. Dr. Thomas C. Nugent, Abdul Sadiq, Ahtaram Bibi, Prof. Dr. Thomas Heine, Lei Liu Zeonjuk, Dr. Nina Vankova and Dr. Bassem S. Bassil

      Version of Record online: 22 FEB 2012 | DOI: 10.1002/chem.201103005

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      Noncovalent by nature: Commercially available building blocks allow in situ formation of bifunctional organocatalysts for the enantioselective formation of quaternary carbons (see scheme). This new catalyst approach is general in nature and the catalyst platform is readily adaptable.

    24. Hybrid Materials

      Surface Diels–Alder Reactions as an Effective Method to Synthesize Functional Carbon Materials (pages 4099–4106)

      Dr. Helena Kaper, Dr. Agnes Grandjean, Dr. Claudia Weidenthaler, Prof. Dr. Ferdi Schüth and Dr. Frédéric Goettmann

      Version of Record online: 15 FEB 2012 | DOI: 10.1002/chem.201102718

      Thumbnail image of graphical abstract

      Making grafting on carbon as easy as grafting on silica? A new and easy approach, based on surface Diels–Alder reactions, allows the introduction of organic functionalities into the framework of mesoporous carbon (see figure).

    25. Gold Nanoparticles

      Reversible Synthesis of Sub-10 nm Spherical and Icosahedral Gold Nanoparticles from a Covalent Au(CN)2 Precursor and Recycling of Cyanide to form Ferric Ferrocyanide for Cell Staining (pages 4107–4114)

      Dr. Chih-Chia Huang, Wei-Cheng Lai, Chia-Yi Tsai, Prof. Chih-Hui Yang and Prof. Chen-Sheng Yeh

      Version of Record online: 17 FEB 2012 | DOI: 10.1002/chem.201103024

      Thumbnail image of graphical abstract

      Reversible nanoparticle formation: A one-pot synthesis of nanospheres (≈2.4 nm) and highly monodisperse icosahedral Au nanoparticles (≈8 nm) in aqueous solution using Au(CN)2 as a precursor at room temperature is reported. The Au(CN)2 chemistry involves a reversible formation–dissolution process that repeatedly produces Au nanospheres and icosahedra (see scheme).

    26. Polysilsesquioxanes

      Synthesis of Dibenzothiophene-Containing Ladder Polysilsesquioxane as a Blue Phosphorescent Host Material (pages 4115–4123)

      Dr. Zhongjie Ren, Dianming Sun, Prof. Huihui Li, Qiang Fu, Prof. Dongge Ma, Prof. Jianming Zhang and Prof. Shouke Yan

      Version of Record online: 17 FEB 2012 | DOI: 10.1002/chem.201103684

      Thumbnail image of graphical abstract

      Climb the ladder: A new wide-band semiconducting ladder polysilsesquioxane BS-LPSQ was successfully designed and synthesized. Its performance as a host for the blue-light-emitting dopant iridium bis(4,6-difluorophenyl)pyridinato-N,C2-picolinate (FIrpic), and subsequent application in electrophosphorescent organic light-emitting diodes (OLED) is much greater than ringed BS-PSQ (see figure).

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      Preview: Chem. Eur. J. 14/2012 (page 4127)

      Version of Record online: 21 MAR 2012 | DOI: 10.1002/chem.201290049

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