Chemistry - A European Journal

Cover image for Vol. 14 Issue 15

May 19, 2008

Volume 14, Issue 15

Pages 4443–4747

  1. Cover Picture

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    1. Cover Picture: Hydroxycruciforms: Amine-Responsive Fluorophores (Chem. Eur. J. 15/2008) (page 4443)

      Psaras L. McGrier, Kyril M. Solntsev, Shaobin Miao, Laren M. Tolbert, Oscar R. Miranda, Vincent M. Rotello and Uwe H. F. Bunz

      Version of Record online: 8 MAY 2008 | DOI: 10.1002/chem.200890054

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      Fishing out amines as shown in a panel in which the fluorescence response of the tetrahydroxycruciforms upon addition of different amines is depicted. Surprisingly, the amine responses are mediated by the solvent, so that a single cruciform structure forms a small sensory nose/tongue array. For more details see the Full Paper on page 4503 ff. by U. H. F. Bunz et al.

  2. Graphical Abstract

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  3. News

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  4. Concept

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    1. New Architectures for Dye-Sensitized Solar Cells (pages 4458–4467)

      Alex B. F. Martinson, Thomas W. Hamann, Michael J. Pellin and Joseph T. Hupp

      Version of Record online: 25 MAR 2008 | DOI: 10.1002/chem.200701667

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      Advanced architectures: Recently, a number of pseudo-1D photoanodes that exhibit accelerated charge transport and greater materials flexibility were fabricated. The potential of these alternative photoanode architectures for advancing, both directly and indirectly, the performance of dye-sensitized solar cells is explored (see figure).

  5. Communications

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    1. Novel Contributions to the Mechanism of the Enantioselective Hydrogenation of Dimethyl Itaconate with Rhodium Complexes (pages 4469–4471)

      Thomas Schmidt, Zhenya Dai, Hans-Joachim Drexler, Wolfgang Baumann, Christian Jäger, Dietmar Pfeifer and Detlef Heller

      Version of Record online: 9 APR 2008 | DOI: 10.1002/chem.200800389

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      Easy transformation of itaconic acid and its derivatives, such as dimethyl itaconate, into pharmaceutically interesting chiral methyl succinates by enantioselective hydrogenation is described. The X-ray structure of the major catalyst–substrate complex, [Rh((S,S)-dipamp)(dimethyl itaconate)]BF4, of the reaction is shown.

    2. Synthesis, Structure, and Transport Property of Perfluorinated Oligofluorenes (pages 4472–4474)

      Kimitaka Ohkubo, Youichi Sakamoto, Toshiyasu Suzuki, Toshimitsu Tsuzuki, Daisuke Kumaki and Shizuo Tokito

      Version of Record online: 9 APR 2008 | DOI: 10.1002/chem.200800406

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      Amorphous n-type semiconductors with high electron affinity and mobility have been obtained from perfluorinated oligo(9,9-dimethylfluorene)s, which have been synthesized from octafluorofluorene, up to the tetramer (see figure).

    3. Protection by Conformationally Restricted Mobility: First Solid-Phase Synthesis of Triostin A (pages 4475–4478)

      Judit Tulla-Puche, Eleonora Marcucci, Manuel Fermin, Núria Bayó-Puxan and Fernando Albericio

      Version of Record online: 11 APR 2008 | DOI: 10.1002/chem.200800372

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      Conformationally restricted mobility: The application of an efficient solid-phase strategy based on protection by conformationally restricted mobility (see scheme) has allowed, for the first time, the synthesis and determination of the biological activity of the two triostin A conformers, which result from the isomerization cis/trans of the N-methyl group of Cys. The most polar conformer showed the greatest inhibitory effect on cell growth.

    4. [Cu@Sn9]3− and [Cu@Pb9]3−: Intermetalloid Clusters with Endohedral Cu Atoms in Spherical Environments (pages 4479–4483)

      Sandra Scharfe, Thomas F. Fässler, Saskia Stegmaier, Stephan D. Hoffmann and Klaus Ruhland

      Version of Record online: 16 APR 2008 | DOI: 10.1002/chem.200800429

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      Highest possible symmetry! Nine Sn atoms are arranged to give an almost perfect sphere around a Cu atom in the endohedrally filled Zintl ion [Cu@Sn9]3−. The rapid equilibration of the nine Sn atoms on the spectral NMR timescale leads to an exceptionally sharp 63Cu NMR signal. In contrast to the more common endohedrally filled fullerenes, the title complexes can be synthesized in macroscopic quantities as [K([2.2.2]crypt)]+ salts.

    5. Highly Enantioselective Strecker Reaction of Ketoimines Catalyzed by an Organocatalyst from (S)-BINOL and L-Prolinamide (pages 4484–4486)

      Zongrui Hou, Jun Wang, Xiaohua Liu and Xiaoming Feng

      Version of Record online: 9 APR 2008 | DOI: 10.1002/chem.200800454

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      A novel and efficient organocatalyst was developed to promote the Strecker reaction of ketoimines (see scheme). Wide substrate scope and excellent enantioselectivities (up to 99 % ee) were obtained with low catalyst loading (2 mol %) under mild reaction conditions.

  6. Full Papers

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    1. Supramolecular Bidentate Ligands by Metal-Directed in situ Formation of Antiparallel β-Sheet Structures and Application in Asymmetric Catalysis (pages 4488–4502)

      Andy C. Laungani, John M. Slattery, Ingo Krossing and Bernhard Breit

      Version of Record online: 30 APR 2008 | DOI: 10.1002/chem.200800359

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      A new concept of in situ generation of bidentate P-ligands for transition-metal catalysis, in which two complementary, monodentate, peptide-based ligands are brought together by employing peptide secondary structure motifs as construction tools to direct the self-assembly process, is achieved through formation of stable β-sheet motifs (see scheme) and subsequent control of selectivity.

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      Hydroxycruciforms: Amine-Responsive Fluorophores (pages 4503–4510)

      Psaras L. McGrier, Kyril M. Solntsev, Shaobin Miao, Laren M. Tolbert, Oscar R. Miranda, Vincent M. Rotello and Uwe H. F. Bunz

      Version of Record online: 18 APR 2008 | DOI: 10.1002/chem.200800296

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      Amine detection made easy: One fluorophore in eight different solvents (columns in graphic) allows the unambiguous identification of twelve different amines (along one row) based on the distinct fluorescence changes through excited-state proton transfer.

    3. Coordination Chemistry of the cyclo-(P5tBu4) Ion: Monomeric and Oligomeric Copper(I), Silver(I) and Gold(I) Complexes (pages 4511–4520)

      Santiago Gómez-Ruiz, Robert Wolf, Sebastian Bauer, Henry Bittig, Andrea Schisler, Peter Lönnecke and Evamarie Hey-Hawkins

      Version of Record online: 28 MAR 2008 | DOI: 10.1002/chem.200800007

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      Coinage Complexes: The synthesis and structural characterization of unusual, monomeric CuI and AuI oligophosphanido complexes, and rare examples of oligomeric coinage metal oligophosphanides, such as the tetranuclear compounds [M4{cyclo-(P4tBu3)PtBu}4] (M=Cu, Ag, Au; see figure), in which the cyclo-(P5tBu4) ligand has rearranged to a {cyclo-(P4tBu3)PtBu} group, is described.

    4. Control of Porosity Geometry in Amino Acid Derived Nanoporous Materials (pages 4521–4532)

      Jorge Perez Barrio, Jean-Noël Rebilly, Benjamin Carter, Darren Bradshaw, John Bacsa, Alexey Y. Ganin, Hyunsoo Park, Abbie Trewin, Ramanathan Vaidhyanathan, Andrew I. Cooper, John E. Warren and Matthew J. Rosseinsky

      Version of Record online: 28 MAR 2008 | DOI: 10.1002/chem.200701556

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      Pillar talk! Channel shape and dimensions in a family of nanoporous homochiral frameworks (an example of which is shown here) can be controlled through the choice of the pillaring ligand. This approach also allows the introduction of flexibility or basic functionalities within the framework.

    5. Is the μ-Oxo-μ-Peroxodiiron Intermediate of a Ribonucleotide Reductase Biomimetic a Possible Oxidant of Epoxidation Reactions? (pages 4533–4541)

      Sam P. de Visser

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701802

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      Too slow: Density functional calculations on the μ-oxo-μ-peroxodiiron complex with a tetrapodal ligand BPP (BPP=N,N-bis(2-pyridylmethyl)-3-aminopropionate; see picture), a possible oxidant of oxo-peroxodiiron catalysts, show that it is a sluggish oxidant of epoxidations and can be ruled out as an active catalyst.

    6. Polyhedral Structures with Three-, Four-, and Five Fold Symmetry in Metal-Centered Ten-Vertex Germanium Clusters (pages 4542–4550)

      R. Bruce King, Ioan Silaghi-Dumitrescu and Matei-Maria Uţă

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701582

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      Clustered together: Analysis of density functional theory studies indicates that the relative energies of structures with three-, four-, and fivefold symmetry for centered 10-vertex bare germanium clusters of the general type M@Ge10z (M=Ni, Cu, Zn) depend on the central metal atom M and the skeletal electron count (see graphic).

    7. High-Relaxivity Magnetic Resonance Imaging (MRI) Contrast Agent Based on Supramolecular Assembly between a Gadolinium Chelate, a Modified Dextran, and Poly-β-Cyclodextrin (pages 4551–4561)

      Elisa Battistini, Eliana Gianolio, Ruxandra Gref, Patrick Couvreur, Silvia Fuzerova, Mohammad Othman, Silvio Aime, Bernard Badet and Philippe Durand

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701587

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      Nanoscale contrast agent with high relaxivity: A self-assembled nanoscale contrast agent for magnetic resonance imaging is obtained through host–guest interactions between a GdIII chelate, a polymer of β-cyclodextrin, and a dextran grafted with alkyl chains (see figure). This noncovalent gadolinium supramolecular assembly exhibits high relaxivity and GdIII payload.

    8. Luminescent Alkynylplatinum(II) Complexes of 2,6-Bis(N-alkylbenzimidazol-2′-yl)pyridine-Type Ligands with Ready Tunability of the Nature of the Emissive States by Solvent and Electronic Property Modulation (pages 4562–4576)

      Anthony Yiu-Yan Tam, Wai Han Lam, Keith Man-Chung Wong, Nianyong Zhu and Vivian Wing-Wah Yam

      Version of Record online: 7 APR 2008 | DOI: 10.1002/chem.200701914

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      Light up your chemistry! A new class of luminescent alkynylplatinum(II) complexes of tridentate 2,6-bis(N-alkylbenzimidazol-2′-yl)pyridines has been synthesized and characterized (see figure), and their electrochemical, electronic absorption, and luminescence properties have been investigated experimentally and theoretically. The nature of the emissive states was found to be easily tuned by modifications to the electronic properties of the ligands and changes in the solvent polarity.

    9. Polyelectrolyte-Induced Self-Assembly of Positively Charged Alkynylplatinum(II)–Terpyridyl Complexes in Aqueous Media (pages 4577–4584)

      Cong Yu, Kenneth Hoi-Yiu Chan, Keith Man-Chung Wong and Vivian Wing-Wah Yam

      Version of Record online: 7 APR 2008 | DOI: 10.1002/chem.200800276

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      It all depends on the polyelectrolyte: Several water-soluble alkynylplatinum(II)–terpyridine complexes with different cationic charges and ligands of different hydrophobicity have been synthesized, and polyelectrolytes carrying multiple negative charges were found to induce the aggregation and self-assembly of such complexes in aqueous media. The UV/Vis and emission spectral changes were studied and correlated to the nature of the complexes, polymer, and the media.

    10. An Iminoboronate Construction Set for Subcomponent Self-Assembly (pages 4585–4593)

      Marie Hutin, Gérald Bernardinelli and Jonathan R. Nitschke

      Version of Record online: 3 APR 2008 | DOI: 10.1002/chem.200800074

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      Building regulations: Iminoboronate esters incorporate three different dynamic linkages: C[DOUBLE BOND]N, B[BOND]O, and B[RIGHTWARDS ARROW]N bonds. We describe the rules governing iminoboronate ester formation from a variety of diol and amine subcomponents. These rules were used to build a series of increasingly complex structures, including a macrocycle and a cage. The reversibility of these bonds allowed these compounds to rearrange in well-defined ways (see scheme).

    11. New M3N@C2n Endohedral Metallofullerene Families (M=Nd, Pr, Ce; n=40–53): Expanding the Preferential Templating of the C88 Cage and Approaching the C96 Cage (pages 4594–4599)

      Manuel N. Chaur, Frederic Melin, Bevan Elliott, Amar Kumbhar, Andreas J. Athans and Luis Echegoyen

      Version of Record online: 9 APR 2008 | DOI: 10.1002/chem.200800044

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      Having a ball! The Nd3N, Pr3N, and Ce3N clusters are the largest isolated endohedral metallofullerenes to have been preferentially encapsulated in a C88 cage. The mass spectra (see graphic) and HPLC chromatograms also show a gradual increase in the yield of clusters encapsulated by a C96 cage, which indicates the next stage of templates for larger metallofullerenes.

    12. Symmetrically Tetrasubstituted [2.2]Paracyclophanes: Their Systematization and Regioselective Synthesis of Several Types of Bis-Bifunctional Derivatives by Double Electrophilic Substitution (pages 4600–4617)

      Natalia V. Vorontsova, Valeria I. Rozenberg, Elena V. Sergeeva, Evgenii V. Vorontsov, Zoya A. Starikova, Konstantin A. Lyssenko and Henning Hopf

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701683

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      Highly regioselective, double electrophilic substitution of symmetrical chiral and achiral disubstituted [2.2]paracyclophanes provides efficient synthesis of the tetrasubstituted bis-bifunctional derivatives, such as those depicted, with diverse substitution patterns and 3D structures. For unambiguous nomination of the whole set of such compounds, a trivial descriptor system (based on ortho-, meta-, para-, and pseudo-prefixes) is introduced.

    13. Optically Active Zwitterionic λ5Si,λ5Si′-Disilicates: Syntheses, Crystal Structures, and Behavior in Aqueous Solution (pages 4618–4630)

      Bastian Theis, Christian Burschka and Reinhold Tacke

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701858

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      Remarkably stable: Optically active (Δ,Δ,R,R,R,R configuration) zwitterionic λ5Si,λ5Si′-disilicates containing two pentacoordinate (formally negatively charged) silicon atoms and two tetracoordinate (formally positively charged) nitrogen atoms were synthesized and characterized (see picture). Although these λ5Si,λ5Si′-disilicates contain SiO4C skeletons, some of them display a remarkable stability in aqueous solution.

    14. Nucleophilic Additions to Alkylidene Bis(sulfoxides)—Stereoelectronic Effects in Vinyl Sulfoxides (pages 4631–4639)

      Tobias Wedel, Timo Gehring, Joachim Podlech, Elena Kordel, Angela Bihlmeier and Wim Klopper

      Version of Record online: 28 MAR 2008 | DOI: 10.1002/chem.200701847

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      The same but not the same: Though alkylidene sulfoxides behave, in some respects, in a similar manner to α,β-unsaturated carbonyl compounds, the stereoelectronic effects ruling the attack of a nucleophile are significantly different (see picture).

    15. Oxidation of Aromatic Alcohols in Irradiated Aqueous Suspensions of Commercial and Home-Prepared Rutile TiO2: A Selectivity Study (pages 4640–4646)

      Vincenzo Augugliaro, Tullio Caronna, Vittorio Loddo, Giuseppe Marcì, Giovanni Palmisano, Leonardo Palmisano and Sedat Yurdakal

      Version of Record online: 8 APR 2008 | DOI: 10.1002/chem.200702044

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      Selective photocatalysis: Oxidation of two aromatic alcohols to aldehydes has been carried out in suspensions of water and rutile TiO2 prepared at low temperature. Selectivity 3- to 7-fold higher than that obtained with commercial or calcined catalysts was observed. The catalysts were characterised by using analyses such as X-ray diffraction and scanning electron microscopy (see figure).

    16. Serine Hydroxymethyl Transferase from Streptococcus thermophilus and L-Threonine Aldolase from Escherichia coli as Stereocomplementary Biocatalysts for the Synthesis of β-Hydroxy-α,ω-diamino Acid Derivatives (pages 4647–4656)

      Mariana L. Gutierrez, Xavier Garrabou, Eleonora Agosta, Stefano Servi, Teodor Parella, Jesús Joglar and Pere Clapés

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200800031

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      Glycine-dependent aldolases: A hydroxymethyl transferase from S. thermophilus (SHMT) at 4 °C and L-threonine aldolase from E. coli at 25 °C gave L-erythro and L-threo aldol adducts, respectively (see scheme; Cbz=benzyloxycarbonyl). SHMT turned out to be among the most stereoselective glycine aldolases. Both enzymes were applied to the synthesis of 2,4-diamino-3-hydroxy acid derivatives, which are polyfunctional intermediates for the preparation of bioactive molecules.

    17. High-Throughput Kinetic Study of Hydrogenation over Palladium Nanoparticles: Combination of Reaction and Analysis (pages 4657–4666)

      Oliver Trapp, Sven K. Weber, Sabrina Bauch, Tobias Bäcker, Werner Hofstadt and Bernd Spliethoff

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701780

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      Active service: Hydrogenation over highly active Pd nanoparticles has been studied by synchronous catalysis and separation in microcapillaries (see picture). High-throughput reaction-rate measurements of reactant libraries show that the size and morphology of the nanoparticles and hence the catalytic activity depends on the ratio of the two stabilizing polysiloxanes, the activation temperature, and the loading of the Pd precursor.

    18. Optically Active Mixed Phthalocyaninato–Porphyrinato Rare-Earth Double-Decker Complexes: Synthesis, Spectroscopy, and Solvent-Dependent Molecular Conformations (pages 4667–4674)

      Xiaomei Zhang, Atsuya Muranaka, Wei Lv, Yuexing Zhang, Yongzhong Bian, Jianzhuang Jiang and Nagao Kobayashi

      Version of Record online: 11 APR 2008 | DOI: 10.1002/chem.200701853

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      Double-deckers: The solvent-dependent nature of optically active mixed phthalocyaninato–porphyrinato rare-earth double-deckers has been shown through experimental and theoretical studies. This suggests a useful method of tuning the optical and electrochemical properties of double-decker compounds in solution by changing the solvent, for example, from DMF to CHCl3 (see graphic).

    19. Total Synthesis of (−)-Balanol, All Stereoisomers, Their N-Tosyl Analogues, and Fully Protected Ophiocordin: An Easy Route to Hexahydroazepine Cores from Garner Aldehydes (pages 4675–4688)

      Ajay Kumar Srivastava and Gautam Panda

      Version of Record online: 9 APR 2008 | DOI: 10.1002/chem.200701991

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      Synthesis of protein kinase C inhibitors: Total syntheses of (−)-balanol and all of its stereoisomers starting from easily available Garner aldehydes are described. Diastereoselective Grignard reactions on Garner aldehydes and ring-closing metatheses are the key steps for the construction of hexahydroazepine subunits. The methodology is further explored for the synthesis of N-tosyl analogues of balanol and fully protected ophiocordin.

    20. A General Method for the Rapid Synthesis of Hollow Metallic or Bimetallic Nanoelectrocatalysts with Urchinlike Morphology (pages 4689–4695)

      Shaojun Guo, Shaojun Dong and Erkang Wang

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200800077

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      Nano-urchins: By taking advantage of the recent advances in nanotechnology, we have reported a facile and general method for rapid synthesis of metallic or bimetallic hollow nanostructures with urchinlike morphology (see figure). Most importantly, the hollow urchinlike platinum nanospheres obtained here exhibit higher electrocatalytic activities than solid platinum nanospheres.

    21. Synthesis of Copper Dendrite Nanostructures by a Sonoelectrochemical Method (pages 4696–4703)

      Iris Haas, Sangaraju Shanmugam and Aharon Gedanken

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701744

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      Gridlocked! The formation of copper dendrites (see figure) obtained by a sonoelectrochemical technique has been investigated. By varying the deposition conditions, we have revealed that the nature of the TEM grid is responsible for dendrite formation and is accounted for by employing the “drying-mediated self-assembly of nanoparticles” theory.

    22. Encapsulation of Ferrocene and Peripheral Electrostatic Attachment of Viologens to Dimeric Molecular Capsules Formed by an Octaacid, Deep-Cavity Cavitand (pages 4704–4710)

      Dagmara Podkoscielny, Ivy Philip, Corinne L. D. Gibb, Bruce C. Gibb and Angel E. Kaifer

      Version of Record online: 28 MAR 2008 | DOI: 10.1002/chem.200701961

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      Captivated audience! Ferrocene and simple viologen derivatives interact strongly, although in very different ways, with dimeric molecular capsules formed by an octaacid cavitand. Ferrocene is encapsulated and its anodic voltammetric response is eliminated, whereas the viologens are bound to the periphery of the capsule and the electrochemical kinetics for their reduction is attenuated (see figure).

    23. Tuning the Nucleophilicity in Cyclopropenylidenes (pages 4711–4718)

      Wolfgang W. Schoeller, Guido D. Frey and Guy Bertrand

      Version of Record online: 11 APR 2008 | DOI: 10.1002/chem.200701926

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      Calculated nucleophilicity: Cyclopropenylidenes are highly nucleophilic carbenes that can be even more nucleophilic than their five-membered ring congeners, namely, imidazol-2-ylidenes, as revealed by quantum chemical calculations (see figure).

    24. A Highly Selective and Sensitive Fluorescence Probe for the Hypochlorite Anion (pages 4719–4724)

      Xinqi Chen, Xiaochun Wang, Shujuan Wang, Wen Shi, Ke Wang and Huimin Ma

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200701677

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      A new fluorescent probe, N-benzoyl rhodamine B–hydrazide, for the hypochlorite anion has been designed and synthesized. The probe displays a highly selective fluorescence-on response to OCl only, and not to any of the other ions and oxidants that were examined (see scheme). This remarkable property gives the probe great potential for the detection of OCl directly in the presence of other species.

    25. New Highly Asymmetric Henry Reaction Catalyzed by CuII and a C1-Symmetric Aminopyridine Ligand, and Its Application to the Synthesis of Miconazole (pages 4725–4730)

      Gonzalo Blay, Luis R. Domingo, Victor Hernández-Olmos and José R. Pedro

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200800069

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      Enantioselective Henry reaction: A new copper(II) complex with a C1-symmetric chiral aminopyridine ligand catalyzes the asymmetric Henry reaction between nitroalkanes and a broad range of aldehydes (see scheme) to provide the expected nitroalkanols in high yields (up to 99 %) and excellent enantioselectivities (up to 98 %). The reaction has been applied to the enantioselective synthesis of miconazole.

    26. Synthesis, Characterization, and Field-Effect Transistor Properties of Carbazolenevinylene Oligomers: From Linear to Cyclic Architectures (pages 4731–4740)

      Yabin Song, Chong-an Di, Zhongming Wei, Tianyue Zhao, Wei Xu, Yunqi Liu, Deqing Zhang and Daoben Zhu

      Version of Record online: 2 APR 2008 | DOI: 10.1002/chem.200800008

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      A clever device! New cyclic carbazolenevinylene oligomers and a linear compound (see figure) have been synthesized and characterized. The structure–property relationships reveal that the cyclic conformation significantly affects the molecular ordering in the solid state. Importantly, the cyclic compounds also had a reduced reorganization energy compared with the linear compound. Their field-effect transistor properties are discussed.

  7. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Concept
    6. Communications
    7. Full Papers
    8. Preview
    1. Preview: Chem. Eur. J. 16/2008 (page 4747)

      Version of Record online: 8 MAY 2008 | DOI: 10.1002/chem.200890057

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