Chemistry - A European Journal

Cover image for Vol. 14 Issue 19

June 27, 2008

Volume 14, Issue 19

Pages 5699–6007

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    1. Cover Picture: Supramolecular Sensing with Phosphonate Cavitands (Chem. Eur. J. 19/2008) (page 5699)

      Monica Melegari, Michele Suman, Laura Pirondini, Davide Moiani, Chiara Massera, Franco Ugozzoli, Elina Kalenius, Pirjo Vainiotalo, Jean-Christophe Mulatier, Jean-Pierre Dutasta and Enrico Dalcanale

      Version of Record online: 23 JUN 2008 | DOI: 10.1002/chem.200890071

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      The entropic route… to boost molecular recognition in gas sensing has been successfully implemented. In their Full paper on page 5772 ff., E. Dalcanale et al. validate this approach for the phosphonate cavitands/alcohol receptor–analyte pairs in mass sensors. The cover shows the molecular structure of a tetraphosphonate cavitand–methanol complex, in which the guest hydrogen bonding is equally distributed among four isoenergetic positions. The underlying graphics illustrate the ESI-MS experiments and the QCM responses supporting the enhanced complexation at the gas–solid interface.

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  3. Correction

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      On the Mechanism of the Thermal Retro-Cycloaddition of Fulleropyrrolidines (Retro-Prato Reaction) (page 5709)

      Salvatore Fillipone, Marta Izquierdo Barroso, Ángel Martín-Domenech, Silvia Osuna, Miquel Solà and Nazario Martin

      Version of Record online: 23 JUN 2008 | DOI: 10.1002/chem.200890073

      This article corrects:

      On the Mechanism of the Thermal Retrocycloaddition of Pyrrolidinofullerenes (Retro-Prato Reaction)

      Vol. 14, Issue 17, 5198–5206, Version of Record online: 25 APR 2008

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  5. Concept

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    1. Ring-Closing Metathesis: Novel Routes to Aromatic Heterocycles (pages 5716–5726)

      Timothy J. Donohoe, Lisa P. Fishlock and Panayiotis A. Procopiou

      Version of Record online: 28 MAR 2008 | DOI: 10.1002/chem.200800130

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      Piecing together the puzzle: Ring-closing metathesis has recently been established as a powerful tool for the construction of a variety of aromatic heterocycles (see graphic). The approaches to five- and six-membered motifs that contain both nitrogen and oxygen are described.

  6. Communications

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    1. A Novel Platform for Modeling Oxidative Catalysis in Non-Heme Iron Oxygenases with Unprecedented Efficiency (pages 5727–5731)

      Anna Company, Laura Gómez, Xavier Fontrodona, Xavi Ribas and Miquel Costas

      Version of Record online: 15 MAY 2008 | DOI: 10.1002/chem.200800724

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      Bioinspired: A novel family of bioinspired non-heme iron complexes is described that catalyzes the H2O2 stereospecific alkane hydroxylation and olefin cis-dihydroxylation and epoxidation with unprecedented efficiency (K = ketone, A = alcohol, E = epoxide, D = diol, TN = turnover number).

    2. TTF-Modified DNA (pages 5732–5736)

      Nicolas Bouquin, Vladimir L. Malinovskii, Xavier Guégano, Shi-Xia Liu, Silvio Decurtins and Robert Häner

      Version of Record online: 13 MAY 2008 | DOI: 10.1002/chem.200800505

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      Highly organized: Tetrathiafulvalene(TTF)-modified oligonucleotides form stable double strands (see graphic). Exciton coupling reveals a high degree of structural organization in the modified region of a hetero-duplex formed by TTF and perylene diimide-containing strands. Fluorescence quenching in TTF/pyrene-modified hetero-hybrids is demonstrated. The results presented are important for the development of redox-active, oligonucleotide-based diagnostics or optical sensors.

    3. Enantioselective and Regioselective Ruthenium-Catalyzed Decarboxylative Etherification of Allyl Aryl Carbonates (pages 5737–5741)

      Martina Austeri, David Linder and Jérôme Lacour

      Version of Record online: 21 MAY 2008 | DOI: 10.1002/chem.200800619

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      Simple ligand, catalyst and conditions: The combination of readily-prepared pyridylmonooxazolines (pymox) ligands and [CpRu(CH3CN)3][PF6] affords a regio- and enantioselective decarboxylative etherification of allyl aryl carbonates (see scheme). This is the first successful example of this type of etherification reaction.

    4. Mutual Responsive Hydrazide-Based Low-Molecular-Mass Organic Gelators: Probing Gelation on the Molecular Level (pages 5742–5746)

      Yong Yang, Ting Chen, Jun-Feng Xiang, Hui-Juan Yan, Chuan-Feng Chen and Li-Jun Wan

      Version of Record online: 13 MAY 2008 | DOI: 10.1002/chem.200800540

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      Organic gelator: Diacetyl- and dinaphthyl-terminated hydrazide-based oligomers displayed gelation ability in apolar solvents due to hydrogen bonding and/or π–π stacking interactions, which promoted aggregation along one dimension. Their gels were solvent polarity sensitive. Because of complementary hydrogen-bonding sites, when the ratio of the two gelators was 1:1 in apolar solvents, a multipoint directed supramolecular substitution reaction led to gel–sol transition (shown here).

    5. Efficient Thia-Bridged Triarylamine Heterohelicenes: Synthesis, Resolution, and Absolute Configuration Determination (pages 5747–5750)

      Giuseppe Lamanna, Cristina Faggi, Francesco Gasparrini, Alessia Ciogli, Claudio Villani, Philip J. Stephens, Frank J. Devlin and Stefano Menichetti

      Version of Record online: 13 MAY 2008 | DOI: 10.1002/chem.200800705

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      One, two, three, four: twist! Four consecutive (one-pot) electrophilic sulfur insertions on triarylamines with phthalimidesulfenyl chloride (see scheme), offer an easy access to chiral hetero[4]- and -[6]helicenes that are remarkably stable against a reversal of the helicity. These heterohelicenes were resolved by HPLC on an amylose-based chiral stationary phase, and the absolute configuration was established by ab initio calculations and experimental vibrational circular dichroism spectra.

    6. Synthesis and Oxidation-Induced DNA Cross-Linking Capabilities of Bis(catechol) Quaternary Ammonium Derivatives (pages 5751–5754)

      Zhibin Song, Xiaocheng Weng, Liwei Weng, Jing Huang, Xiaolin Wang, Minghui Bai, Yangyang Zhou, Guangfu Yang and Xiang Zhou

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200800783

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      Design and synthesis: A series of bis(catechol) compounds has been designed and synthesized and their abilities to cross-link plasmid DNA and oligonucleotides after periodate oxidation or tyrosinase were investigated (see graphic). The oxidative process was monitored by UV/Vis spectroscopy.

  7. Full Papers

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    1. 1,2,4-Triazolium-Cation-Based Energetic Salts (pages 5756–5771)

      Chaza Darwich, Thomas M. Klapötke and Carles Miró Sabaté

      Version of Record online: 3 JUN 2008 | DOI: 10.1002/chem.200800340

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      Things that go bang: Salts based on the novel methylguanazinium cation with classical energetic anions were synthesised and fully characterised (an example is illustrated here). All compounds have low sensitivities toward classical stimuli, good thermal stabilities (DSC) and high (calculated) performances, yielding a new family of heterocycle-based compounds with prospective use as high-explosives and/or propellants.

    2. Supramolecular Sensing with Phosphonate Cavitands (pages 5772–5779)

      Monica Melegari, Michele Suman, Laura Pirondini, Davide Moiani, Chiara Massera, Franco Ugozzoli, Elina Kalenius, Pirjo Vainiotalo, Jean-Christophe Mulatier, Jean-Pierre Dutasta and Enrico Dalcanale

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200800327

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      Molecular recognition and gas sensing: The combined used of ESI-MS, crystal structure analyses and QCM testing allows to probe the gas-sensing properties of cavitands (see graphic). The predicting value of the methodology has been successfully tested on the latest generation of tetraphosphonate cavitand receptors, demonstrating the importance of energetically equivalent multiple interactions on sensor selectivity and sensitivity.

    3. Ultralong Carbon–Carbon Bonds in Dispirobis(10-methylacridan) Derivatives with an Acenaphthene, Pyracene, or Dihydropyracylene Skeleton (pages 5780–5793)

      Hidetoshi Kawai, Takashi Takeda, Kenshu Fujiwara, Makoto Wakeshima, Yukio Hinatsu and Takanori Suzuki

      Version of Record online: 14 MAY 2008 | DOI: 10.1002/chem.200702028

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      The big one! The real ultralong C[BOND]C bond is here in novel hexaphenylethane derivatives that have two units of spiroacridan incorporated in pyracene (1.771(3) Å) and dihydropyracylene (1.749(2) Å) skeletons (see scheme).

    4. Supramolecular Synthons on Surfaces: Controlling Dimensionality and Periodicity of Tetraarylporphyrin Assemblies by the Interplay of Cyano and Alkoxy Substituents (pages 5794–5802)

      Nikolai Wintjes, Jens Hornung, Jorge Lobo-Checa, Tobias Voigt, Tomáš Samuely, Carlo Thilgen, Meike Stöhr, François Diederich and Thomas A. Jung

      Version of Record online: 30 MAY 2008 | DOI: 10.1002/chem.200800746

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      Optimum coverage: The self-assembly of three different tetrakis(meso-phenyl)porphyrins with cyano and different alkyloxy substituents is studied on Cu(111) by STM (see graphic). At coverages below 0.8 monolayers (ML), two of these porphyrins show chainlike assemblies, which transform into nanoporous networks with different pore-to-pore distances at higher coverages, whereas the third molecular component self-assembles directly into a nanoporous network.

    5. Highly Effective and Reversible Control of the Rocking Rates of Rotaxanes by Changes to the Size of Stimulus-Responsive Ring Components (pages 5803–5811)

      Keiji Hirose, Kazuaki Ishibashi, Yoshinobu Shiba, Yasuko Doi and Yoshito Tobe

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200800257

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      Rock on! The rates of the rocking motion of rotaxanes were reversibly switched by a change in the size of the ring component. This ring component incorporates a metaphenylene unit, which swings like a pendulum, and a dianthrylethane unit, which undergoes reversible isomerization in response to photochemical and thermal stimuli and changes its size (see graphic). The change in the ring size substantially changes the rocking rates.

    6. Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging (pages 5812–5819)

      Qingdong Zheng, Gaixia Xu and Paras N. Prasad

      Version of Record online: 21 MAY 2008 | DOI: 10.1002/chem.200800309

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      Green for go! Highly fluorescent BODIPY dyes that emit light ranging from the green to near-IR region have been synthesized by introducing a bulky naphthalenyl group at the meso position. The one- and two-photon fluorescence imaging of living cells with these dyes has been successfully demonstrated (see graphic).

    7. The Importance of the Long Type 1 Copper-Binding Loop of Nitrite Reductase for Structure and Function (pages 5820–5828)

      Katsuko Sato, Susan J. Firbank, Chan Li, Mark J. Banfield and Christopher Dennison

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200701997

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      Are you in the loop? Dramatic shortening of the 15-residue type 1 copper-binding loop of nitrite reductase (NIR; see graphic) results in unusual flexibility at this metal centre, which gives rise to dramatically decreased activity and lowered stability of the native trimer structure.

    8. Protonated Macrobicyclic Hosts Containing Pyridine Head Units for Anion Recognition (pages 5829–5838)

      David Esteban-Gómez, Carlos Platas-Iglesias, Andrés de Blas, Luigi Fabbrizzi and Teresa Rodríguez-Blas

      Version of Record online: 21 MAY 2008 | DOI: 10.1002/chem.200800092

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      Fit into place: The interaction of macrobicyclic receptors (L1 (•) and L2 (○)) containing a mixture of ammonium, pyridinium and secondary aniline hydrogen-bonding donor sites with different anions has been investigated. The stability trend observed for the recognition of halide anions and the sulfate-to-nitrate binding selectivity have been rationalised by means of DFT calculations.

    9. Pillaring of CdCl2-Like Layers in Lanthanide Metal–Organic Frameworks: Synthesis, Structure, and Photophysical Properties (pages 5839–5850)

      Partha Mahata, K. V. Ramya and Srinivasan Natarajan

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200800240

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      A colorful life: Lanthanide pyridine-2,3-dicarboxylate layers resembling CdCl2 layers (see picture) are pillared by 1,4-benzenedicarboxylate units to form a 3D mixed carboxylate compound. Doping of Eu3+ and Tb3+ in place of La3+ gives rise to ligand-sensitized metal-centered emission (Eu=pink, Tb=green) with lifetimes of 29.4 and 14.3 μs, respectively. The Nd-containing compound shows a two-photon up-conversion behavior when excited at 580 nm.

    10. Pyridine-Catalyzed Stereoselective Addition of Acyclic 1,2-Diones to Acetylenic Esters: Synthetic and Theoretical Studies of an Unprecedented Rearrangement (pages 5851–5860)

      Abhilash N. Pillai, Cherumuttathu H. Suresh and Vijay Nair

      Version of Record online: 8 MAY 2008 | DOI: 10.1002/chem.200800250

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      Pyridine catalysis: The pyridine-catalyzed C[BOND]C bond-forming reaction of acyclic 1,2-diones with activated acetylenes provides a unique synthetic protocol for the stereoselective synthesis of 1,2-diaroyl maleates (see scheme). Mechanistic details of the reaction were unravelled by DFT methods.

    11. Fluorescent, Synthetic Amphiphilic Heptapeptide Anion Transporters: Evidence for Self-Assembly and Membrane Localization in Liposomes (pages 5861–5870)

      Lei You and George W. Gokel

      Version of Record online: 15 MAY 2008 | DOI: 10.1002/chem.200800147

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      Synthetic anion pores: Novel fluorescence probes provide detailed information about the distribution and assembly of synthetic anion transporters in bilayer membranes (see scheme).

    12. Aggregation Behavior and Dynamics of Synthetic Amphiphiles That Self-Assemble to Anion Transporters (pages 5871–5879)

      Elizabeth K. Elliott, Megan M. Daschbach and George W. Gokel

      Version of Record online: 15 MAY 2008 | DOI: 10.1002/chem.200800148

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      An array of analytical methods has been used to probe how synthetic anion transporters (SATs) organize in the aqueous phase prior to membrane insertion and pore formation (see scheme). Dynamic light scattering, electron microscopy, and Langmuir trough methods were used to give insight into the mechanism of active ion channel formation.

    13. Mechanism of the Reaction of Radicals with Peroxides and Dimethyl Sulfoxide in Aqueous Solution (pages 5880–5889)

      Ronit Herscu-Kluska, Alexandra Masarwa, Magal Saphier, Haim Cohen and Dan Meyerstein

      Version of Record online: 16 MAY 2008 | DOI: 10.1002/chem.200800218

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      Methyl and methylperoxyl radicals derived from dimethyl sulfoxide react with hydrogen peroxide, peroxymonocarbonate (HCO4), and persulfate (see scheme). The major reaction observed for the hydroperoxide species is abstraction of hydrogen atoms by the radical species and methanol and formaldehyde are produced. Furthermore, it is shown that the formation of methyl radical species in the presence of DMSO is not a proof of the formation of the hydroxyl radical species.

    14. Spectroelectrochemical and Computational Studies on the Mechanism of Hypoxia Selectivity of Copper Radiopharmaceuticals (pages 5890–5907)

      Jason P. Holland, Peter J. Barnard, David Collison, Jonathan R. Dilworth, Ruth Edge, Jennifer C. Green and Eric J. L. McInnes

      Version of Record online: 21 MAY 2008 | DOI: 10.1002/chem.200800539

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      Just breathe! Tumour hypoxia plays a pivotal role in the clinical management of cancer patients and understanding its consequences is crucial in the development of hypoxia-selective radiopharmaceuticals. Detailed spectroelectrochemical and computational studies on hypoxia-selective copper complexes (see scheme) have been conducted and a new mechanistic scheme consistent with all available chemical and biological data is presented.

    15. A Novel Linker Methodology for the Synthesis of Tailored Conjugate Vaccines Composed of Complex Carbohydrate Antigens and Specific TH-Cell Peptide Epitopes (pages 5908–5917)

      Sebastian Dziadek, Sandra Jacques and David R. Bundle

      Version of Record online: 14 MAY 2008 | DOI: 10.1002/chem.200800065

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      A novel immunologically neutral linker methodology (see figure) has been developed for the efficient preparation of highly defined glycoconjugate vaccines against cancer and microbial infections.

    16. Syntheses, Reactivity and DFT Studies of Group 2 and Group 12 Metal Complexes of Tris(pyrazolyl)methanides Featuring “Free” Pyramidal Carbanions (pages 5918–5934)

      Helen R. Bigmore, Jens Meyer, Ivo Krummenacher, Heinz Rüegger, Eric Clot, Philip Mountford and Frank Breher

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200800181

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      Zwitterionic methanide complexes of Group 2 and 12 metals have been obtained for the first time by reaction of tris(3,5-dimethylpyrazolyl)methane with dimethylzinc or dialkyl magnesium reagents (see scheme). These contain one or two “naked” sp3-hybridised carbanions that are fully separated from the mono- or dicationic metal centres. Aspects of the formation and bonding of these novel species were examined by means of density functional calculations.

    17. Synthesis and Characterization of Chiral Benzylic Ether-Bridged Periodic Mesoporous Organosilicas (pages 5935–5940)

      Jürgen Morell, Sangam Chatterjee, Peter J. Klar, Daniel Mauder, Ilja Shenderovich, Frank Hoffmann and Michael Fröba

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200800239

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      A chiral periodic mesoporous organosilica (PMO) carrying benzylic ether bridging groups has been synthesized by hydrolysis and condensation of the new organosilica precursor 1,4-bis(triethoxysilyl)-2-(1-methoxyethyl)benzene in the presence of the surfactant Brij 76 as a supramolecular structure-directing agent under acidic conditions. The evidence for the presence of the chiral units in the organosilica precursor as well as inside the PMO material is provided by optical activity measurements.

    18. Synthesis, Fluorescence, and Two-Photon Absorption of Bidentate Phosphane Oxide Derivatives: Complexation with Pb2+ and Cd2+ Cations (pages 5941–5950)

      Minh-Huong Ha-Thi, Maël Penhoat, Delphine Drouin, Mireille Blanchard-Desce, Véronique Michelet and Isabelle Leray

      Version of Record online: 15 MAY 2008 | DOI: 10.1002/chem.200800084

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      Fluorescent phosphane oxide sensors: The design and synthesis, the photophysical properties, and the linear and nonlinear spectral properties of some novel fluorescent phosphane oxide derivatives are reported. Upon complexation with heavy metal ions such as Pb2+ and Cd2+ (see figure), a red shift of the one- and two-photon excitation spectra is observed in absorption and emission spectroscopy. The first biphotonic Cd2+ sensors are described.

    19. Controlled Synthesis and Luminescence of Semiconductor Nanorods (pages 5951–5956)

      Peng Li, Leyu Wang, Lun Wang and Yadong Li

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200701958

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      Nanorods of luminescence: A new wet chemical synthesis method is described for the preparation of luminescent semiconductor nanorods (see figure) of CdS, ZnS, and ZnS:Mn with controllable aspect ratios by using stable inorganic precursors such as nitrates and chlorides.

    20. Generation and Reactivity of Enantiomeric (BINOLato)Ni+ Complexes with Chiral Secondary Alcohols in the Gas Phase (pages 5957–5965)

      Francesca R. Novara, Philipp Gruene, Detlef Schröder and Helmut Schwarz

      Version of Record online: 21 MAY 2008 | DOI: 10.1002/chem.200800090

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      Chiral metal complexes: Nickel(II) complexes, each containing an optically pure BINOLato ligand and one enantiomer of a secondary alcohol, have been investigated in the gas phase. Collision-induced dissociation of those complexes leads to the loss either of the entire alcohol (A) or of the corresponding ketone (B). Differences in the branching ratios between these channels for the two diastereomers provide insight into the diastereoselectivity operative in the C[BOND]H- and O[BOND]H-bond activation processes.

    21. Regulation of the Near-IR Spectral Properties of Individually Dissolved Single-Walled Carbon Nanotubes in Aqueous Solutions of dsDNA (pages 5966–5973)

      Yuichi Noguchi, Tsuyohiko Fujigaya, Yasuro Niidome and Naotoshi Nakashima

      Version of Record online: 6 MAY 2008 | DOI: 10.1002/chem.200800070

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      Modulate the gap: Single-walled carbon nanotubes (SWNTs) dissolve in aqueous solutions of double-stranded DNA (dsDNA). The band gaps of the individually solubilized SWNTs can be modulated by changing the pH of the solutions (see picture). A very small pH change causes a dramatic spectral change. The results have been rationalized in terms of reversible SWNT oxidation.

    22. Reversible Transitions between Peptide Nanotubes and Vesicle-Like Structures Including Theoretical Modeling Studies (pages 5974–5980)

      Xuehai Yan, Yue Cui, Qiang He, Kewei Wang, Junbai Li, Weihua Mu, Bolin Wang and Zhong-can Ou-yang

      Version of Record online: 14 MAY 2008 | DOI: 10.1002/chem.200800012

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      From tubes to spheres and back again: A reversible shape transition between self-assembled dipeptide nanotubes and vesicle-like structures is observed by changing the peptide concentration. A theoretical equation is presented to help with the understanding of this transition (see figure).

    23. Synthesis and Characterization of a Grapevine Nanostructure Consisting of Single-Walled Carbon Nanotubes with Covalently Attached [60]Fullerene Balls (pages 5981–5987)

      Wei Wu, Huarui Zhu, Louzhen Fan and Shihe Yang

      Version of Record online: 19 MAY 2008 | DOI: 10.1002/chem.200701655

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      On the grapevine: A grapevine nanostructure is created by covalently grafting fullerene [60] balls onto single-walled carbon nanotubes (SWNTs; see figure). The cyclic voltammetric response of the nanostructure film dramatically resembles that of the C60 derivative in solution with multiple reversible electrochemical reactions, which manifest the covalent attachment of C60 to SWNTs in the monomeric form.

    24. Preparation of Highly Active and Dispersed Platinum Nanoparticles on Mesoporous Al-MCM-48 and Their Activity in the Hydroisomerisation of n-Octane (pages 5988–5995)

      Juan M. Campelo, Adam F. Lee, Rafael Luque, Diego Luna, Jose M. Marinas and Antonio A. Romero

      Version of Record online: 15 MAY 2008 | DOI: 10.1002/chem.200800182

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      Naturally nano: Highly active and well-dispersed platinum nanoparticles supported on Al-MCM-48 have been found to be very efficient in catalysing the hydroisomerisation of n-octane (see picture). These catalysts provide high selectivities in favour of methylheptanes at low platinum loadings.

    25. Flutelike Porous Hematite Nanorods and Branched Nanostructures: Synthesis, Characterisation and Application for Gas-Sensing (pages 5996–6002)

      Xinglong Gou, Guoxiu Wang, Xiangyang Kong, David Wexler, Joseph Horvat, Juan Yang and Jinsoo Park

      Version of Record online: 24 APR 2008 | DOI: 10.1002/chem.200701705

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      Branched nanostructures: Flutelike porous Fe2O3 nanorods and branched nanostructures, such as pentapods and hexapods (see figure), were prepared through dehydration and recrystallisation of the hydrothermally produced β-FeOOH precursor. These nanostructures exhibit not only unique magnetic behaviour, but also are excellent sensors for selectively detecting ethanol, formaldehyde and acetic acid among other flammable, toxic and corrosive gases.

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    1. Preview: Chem. Eur. J. 20/2008 (page 6007)

      Version of Record online: 23 JUN 2008 | DOI: 10.1002/chem.200890075

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