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Chemistry - A European Journal

Cover image for Vol. 13 Issue 1

December 18, 2006

Volume 13, Issue 1

Pages 3–363

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Concept
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      Cover Picture: Heavy-Metal-Ion Capture, Ion-Exchange, and Exceptional Acid Stability of the Open-Framework Chalcogenide (NH4)4In12Se20 (Chem. Eur. J. 1/2007) (page 3)

      Manolis J. Manos, Christos D. Malliakas and Mercouri G. Kanatzidis

      Article first published online: 11 DEC 2006 | DOI: 10.1002/chem.200790001

      Purely inorganic open-framework compounds (NH4)4In12Se20 (1) and (NH4)2In12Se19 (2) have been synthesized and their ion-exchange properties are reported by M. Kanatzidis et al. in their Full Paper on page 51ff. The chalcogenide framework has innate reactivity towards soft heavy-metal ions (Hg2+, Pb2+, Ag+) and its pores are well suited for their capture. The authors show that 1 can effectively and selectively remove such metal ions from water.

  2. Editorial

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  3. Graphical Abstract

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      Graphical Abstract: Chem. Eur. J. 1/2007 (pages 12–20)

      Article first published online: 11 DEC 2006 | DOI: 10.1002/chem.200790000

  4. Concept

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      Catalytic Applications of Metal Nanoparticles in Imidazolium Ionic Liquids (pages 32–39)

      Pedro Migowski and Jaïrton Dupont

      Article first published online: 20 NOV 2006 | DOI: 10.1002/chem.200601438

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      Catalysis with metal nanoparticles (NPs): Transition-metal NPs in ionic liquids are stabilized by loosely bound supramolecular anionic species and/or NHC carbenes together with an oxide layer that is responsible for their high catalytic activity (see scheme). However, these loosely bound layers are also responsible for their relatively low stability that leads to aggregation/agglomeration and eventually to the bulk metal.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Concept
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      Configurations of Nickel–Cyclam Antiviral Complexes and Protein Recognition (pages 40–50)

      Tina M. Hunter, Iain W. McNae, Daniel P. Simpson, Alison M. Smith, Stephen Moggach, Fraser White, Malcolm D. Walkinshaw, Simon Parsons and Peter J. Sadler

      Article first published online: 22 NOV 2006 | DOI: 10.1002/chem.200601334

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      Protein recognition: The configurations adopted by antiviral nickel–(bi)cyclam complexes are important for specific recognition of the membrane co-receptor protein CXCR4. We show that axial ligands such as acetate and nitrate can have dramatic effects on nickel–cyclam configurations both in the solid state and in solution.

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      Heavy-Metal-Ion Capture, Ion-Exchange, and Exceptional Acid Stability of the Open-Framework Chalcogenide (NH4)4In12Se20 (pages 51–58)

      Manolis J. Manos, Christos D. Malliakas and Mercouri G. Kanatzidis

      Article first published online: 22 NOV 2006 | DOI: 10.1002/chem.200600892

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      The hydrothermal synthesis of the two purely inorganic open-framework indium selenides (for example, (NH4)4In12Se201) are reported. Compound 1 exhibits a unique 3D open-framework structure (shown here). It also possesses ion-exchange capacity for Cs+, Rb+, NH4+, but it has selectivity against Na+ and Li+.

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      Solid-State Self-Assembly of Polymeric Double Helicates Leading to Linear Arrays of Silver(I) Ions and Reversible Strand/Double Helix Interconversion in Solution (pages 59–68)

      Adrian-Mihail Stadler, Nathalie Kyritsakas, Gavin Vaughan and Jean-Marie Lehn

      Article first published online: 29 SEP 2006 | DOI: 10.1002/chem.200600726

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      Polycationic wires: Depending on the ligand employed, discontinuous or continuous polynuclear Ag+ ionic sequences may be obtained (see picture).

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      Redox-Controlled Interaction of Biferrocenyl-Terminated Dendrimers with β-Cyclodextrin Molecular Printboards (pages 69–80)

      Christian A. Nijhuis, Karolina A. Dolatowska, Bart Jan Ravoo, Jurriaan Huskens and David N. Reinhoudt

      Article first published online: 16 OCT 2006 | DOI: 10.1002/chem.200600777

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      Turning the switch—on, off, and in between: Biferrocenes form stable inclusion complexes with β-cyclodextrin host molecules and biferrocene dendrimers bind strongly to a β-cyclodextrin host surface. Oxidation of the biferrocene to the mixed-valence state weakens the interaction dramatically and results in effective desorption of the guest dendrimer from the host surface (see figure).

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      “Pocket Dendrimers” as Nanoscale Receptors for Bimolecular Guest Accommodation (pages 81–89)

      Satoshi Shinoda, Masakazu Ohashi and Hiroshi Tsukube

      Article first published online: 6 OCT 2006 | DOI: 10.1002/chem.200600076

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      What has it got in its pockets? Molecular modeling, NMR measurements, and zinc-coordination experiments revealed that unsymmetrical zinc(II) porphyrin dendrimers have pockets accessible to external substrates (see figure). When a diamidopyridine moiety was further introduced into the unsymmetrical dendrimer of the 3rd generation, a thymine derivative and a pyridine derivative were simultaneously bound in its nanoscale pocket.

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      Structure of the α-Homo-DNA:RNA Duplex and the Function of Twist and Slide To Catalogue Nucleic Acid Duplexes (pages 90–98)

      Koen Nauwelaerts, Eveline Lescrinier and Piet Herdewijn

      Article first published online: 22 SEP 2006 | DOI: 10.1002/chem.200600363

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      Twist and slide: High-resolution NMR studies of an α-homo-DNA:RNA duplex reveal the formation of a right-handed parallel-oriented helix (see picture). The structure differs from that of an A- or B-type DNA helix. A mathematical and geometrical model based on slide and twist parameters has been developed to classify the geometry of nucleic acid duplexes.

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      Two Methods for the Determination of Enantiomeric Excess and Concentration of a Chiral Sample with a Single Spectroscopic Measurement (pages 99–104)

      Lei Zhu, Shagufta H. Shabbir and Eric V. Anslyn

      Article first published online: 26 OCT 2006 | DOI: 10.1002/chem.200600402

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      Two for the price of one! Utilization of a dual-chamber quartz cuvette has enabled the concentration and enantiomeric excess (ee) of a chiral sample to be determined in one spectroscopic measurement.

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      meso–meso-Linked Corrole Dimers with Modified Cores: Synthesis, Characterization, and Properties (pages 105–114)

      Jeyaraman Sankar, Harapriya Rath, Viswanathan Prabhuraja, Sabapathi Gokulnath, Tavarekere K. Chandrashekar, Chandra Shekhar Purohit and Sandeep Verma

      Article first published online: 22 SEP 2006 | DOI: 10.1002/chem.200600457

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      mesomeso-Linked corrole dimers were synthesized by the AgI-catalyzed coupling reaction and were characterized by using various spectrochemical techniques. The photonic properties of these dimers and their use as DNA-cleaving agents (see graphic) were explored.

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      Total Syntheses of the Actin-Binding Macrolides Latrunculin A, B, C, M, S and 16-epi-Latrunculin B (pages 115–134)

      Alois Fürstner, Dominic De Souza, Laurent Turet, Michaël D. B. Fenster, Liliana Parra-Rapado, Conny Wirtz, Richard Mynott and Christian W. Lehmann

      Article first published online: 8 NOV 2006 | DOI: 10.1002/chem.200601135

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      Metal-catalyzed C[BOND]C-bond formation, most notably, ring-closing alkyne metathesis (RCAM) and iron-catalyzed cross-coupling reactions, provides the basis for a concise and efficient approach to the entire family of the latrunculins (see scheme). These macrolides of marine origin are superb probe molecules for chemical biology for testing the many fundamental roles of the actin cytoskeleton.

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      Latrunculin Analogues with Improved Biological Profiles by “Diverted Total Synthesis”: Preparation, Evaluation, and Computational Analysis (pages 135–149)

      Alois Fürstner, Douglas Kirk, Michaël D. B. Fenster, Christophe Aïssa, Dominic De Souza, Cristina Nevado, Tell Tuttle, Walter Thiel and Oliver Müller

      Article first published online: 8 NOV 2006 | DOI: 10.1002/chem.200601136

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      The power of “diverted total synthesis”, that is, the de novo synthesis of “natural product like” structures, is illustrated by a concise approach to a focused library of latrunculin analogues. The best compounds of this series surpass the activity of the naturally occurring macrolide latrunculin B (see figure) in their effect on the actin cytoskeleton. A computational analysis of the bonding situation in the binding site of the protein allows us to rationalize these experimental results.

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      Biaryls Made Easy: PEPPSI and the Kumada–Tamao–Corriu Reaction (pages 150–157)

      Michael G. Organ, Mirvat Abdel-Hadi, Stephanie Avola, Niloufar Hadei, Joanna Nasielski, Christopher J. O'Brien and Cory Valente

      Article first published online: 4 DEC 2006 | DOI: 10.1002/chem.200601360

      Thumbnail image of graphical abstract

      An easily employed, highly versatile Kumada–Tamao–Corriu (KTC) protocol utilizing the PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization and Initiation) precatalysts 1 and 2 is detailed. The ease-of-use of these catalysts and the synthesis of a wide range of hindered biaryls, large coupling partners and drug-like heterocycles, in high yield, makes the PEPPSI-KTC protocol very attractive.

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      MTO Schiff-Base Complexes: Synthesis, Structures and Catalytic Applications in Olefin Epoxidation (pages 158–166)

      Ming-Dong Zhou, Jin Zhao, Jun Li, Shuang Yue, Chang-Nian Bao, Janos Mink, Shu-Liang Zang and Fritz E. Kühn

      Article first published online: 26 OCT 2006 | DOI: 10.1002/chem.200600863

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      Rhenium-based epoxidation catalysts: Several Schiff bases readily form complexes with methyltrioxorhenium(VII) (MTO) by undergoing a hydrogen transfer from a ligand-bound OH group to a ligand N atom. The resulting complexes (see picture) are stable at room temperature and can be handled and stored in air. Their catalytic behaviour is strongly influenced by the coordinated Schiff bases, which lead either to high selectivities and good activities or to catalyst decomposition.

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      Stereoselective Preparation of Six Diastereomeric Quatercyclopropanes from Bicyclopropylidene and Some Derivatives (pages 167–177)

      Malte von Seebach, Sergei I. Kozhushkov, Heiko Schill, Daniel Frank, Roland Boese, Jordi Benet-Buchholz, Dmitry S. Yufit and Armin de Meijere

      Article first published online: 6 OCT 2006 | DOI: 10.1002/chem.200600799

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      All six possible diastereomeric quatercyclopropanes were obtained in several steps from bicyclopropylidene via the meso- (diastereomers on yellow) and d,l-bis(bicyclopropylidenyl)s (diastereomers on blue). The different conformers both in the solid phase and in solution are also described.

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      Fluorescent Sensors for Hg2+ in Micelles: A New Approach that Transforms an ON–OFF into an OFF–ON Response as a Function of the Lipophilicity of the Receptor (pages 178–187)

      Piersandro Pallavicini, Yuri Antonio Diaz-Fernandez, Francesco Foti, Carlo Mangano and Stefano Patroni

      Article first published online: 16 OCT 2006 | DOI: 10.1002/chem.200600879

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      An ON–OFF micellar fluorescent sensor can be transformed into a sensor of the OFF–ON type by using a “not too lipophilic” ligand that is released from micelles after complexation (see figure).

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      Preparation and Structure of Mono- and Binuclear Half-Sandwich Iridium, Ruthenium, and Rhodium Carbene Complexes Containing 1,2-Dichalcogenolao 1,2-Dicarba-closo-Dodecaboranes (pages 188–195)

      Xin Wang, Shuang Liu, Lin-Hong Weng and Guo-Xin Jin

      Article first published online: 16 OCT 2006 | DOI: 10.1002/chem.200600854

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      Half-sandwich Ir, Rh, and Ru carbene complexes (2, 3, 5, and 6) containing 1,2-dichalcogenolato carborane ligands have been synthesized (see scheme) and characterized structurally. Addition of mono-N-heterocyclic carbenes such as 1 yielded mononuclear compounds 2 and 3, where bis-NHC ligands yielded centrosymmetric binuclear complexes (5 and 6).

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      Conformational Control of [26]Hexaphyrins(1.1.1.1.1.1) by meso-Thienyl Substituents (pages 196–202)

      Masaaki Suzuki and Atsuhiro Osuka

      Article first published online: 6 OCT 2006 | DOI: 10.1002/chem.200601147

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      Conformational control of meso-aryl-substituted [26]hexaphyrins(1.1.1.1.1.1) (types I and II) has been achieved by using small aryl substituents, such as thienyl groups. The type-I conformation leads to new metalation products through C[BOND]H bond activation of the thienyl group.

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      Enyne Metathesis–Oxidation Sequence for the Synthesis of 2-Phosphono Pyrroles: Proof of the “Yne-then-Ene” Pathway (pages 203–214)

      Nicolai Dieltiens, Kristof Moonen and Christian V. Stevens

      Article first published online: 2 OCT 2006 | DOI: 10.1002/chem.200600789

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      Two steps in one! A new tandem reaction sequence has been developed for the synthesis of 2-phosphono pyrroles. The sequence consists of ring-closing enyne metathesis in combination with in situ oxidation of the produced 3-pyrrolines. It was found that the reaction proceeds by means of the “yne-then-ene” pathway. During the initiation phase, the Grubbs carbene is converted into a new ruthenium carbene which continues the propagation cycle (see scheme).

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      The Mg-Oppenauer Oxidation as a Mild Method for the Synthesis of Aryl and Metallocenyl Ketones (pages 215–227)

      Ralf J. Kloetzing, Arkady Krasovskiy and Paul Knochel

      Article first published online: 6 OCT 2006 | DOI: 10.1002/chem.200600738

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      Benzaldehyde as an oxidant: An efficient method for the synthesis of unsymmetrical aryl and heteroaryl ketones starting from easily accessible Grignard reagents and aldehydes has been developed (see scheme). The mild reaction conditions enable the preparation of various ketones bearing a metallocene unit, of which most were previously unavailable.

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      The Self-Ordering Properties of Novel Phthalocyanines with Out-of-Plane Alkyl Substituents (pages 228–234)

      Neil B. McKeown, Madeleine Helliwell, Bashir M. Hassan, David Hayhurst, Hong Li, Neil Thompson and Simon J. Teat

      Article first published online: 2 OCT 2006 | DOI: 10.1002/chem.200600697

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      Twist and tilt: After attaching alkyl chains to five-membered rings fused to the peripheral sites of the phthalocyanine ring, cofacial aggregation still occurred despite the out-of-plane substituents. A crystal structure of the octahexyl derivative showed that this is achieved by the tilting of the macrocyclic plane of the phthalocyanine rings (see figure).

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      Highly Luminescent Gold(I)–Silver(I) and Gold(I)–Copper(I) Chalcogenide Clusters (pages 235–246)

      Olga Crespo, M. Concepción Gimeno, Antonio Laguna, Carmen Larraz and M. Dolores Villacampa

      Article first published online: 29 SEP 2006 | DOI: 10.1002/chem.200600566

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      Illuminating examples: The synthesis and luminescence properties of the clusters [E(AuL)3M]+ have been studied as a function of the chalcogenide (E=O, S, Se), the heterofunctional ligand (L=PPh2py, PPh2CH2CH2py), or the metal (M=Ag, Cu) (see picture).

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      Studies on Pd0-Catalyzed Cyclization of N-3,4-Alkadienyl Toluenesulfonamides with Organic Halides: Selective Synthesis of 2,3-Dihydropyrroles, 1,2,3,6-Tetrahydropyrridines, and Azetidines (pages 247–254)

      Shengming Ma, Fei Yu, Jing Li and Wenzhong Gao

      Article first published online: 27 SEP 2006 | DOI: 10.1002/chem.200600431

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      A switch made possible by subsituents! The substituents of the allene moiety and the nitrogen atom act as a switch in determining the reaction pathways in palladium-catalyzed coupling–cyclizations, such as that depicted.

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      Atoms-in-Molecules Analysis of Extended Hypervalent Five-Center, Six-Electron (5c–6e) C2Z2O Interactions at the 1,8,9-Positions of Anthraquinone and 9-Methoxyanthracene Systems (pages 255–268)

      Waro Nakanishi, Takashi Nakamoto, Satoko Hayashi, Takahiro Sasamori and Norihiro Tokitoh

      Article first published online: 26 OCT 2006 | DOI: 10.1002/chem.200600471

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      A factor to control fine structures: σ*(Z[BOND]C)[LEFTWARDS ARROW]np(O)[RIGHTWARDS ARROW]σ*(Z[BOND]C) interactions (Z=Se and S) are demonstrated to be 5c–6e in nature for 1,8-(MeZ)2C14H6O2 and 9-MeO-1,8-(MeZ)2C14H7, based on atoms-in-molecules (AIM) and natural bond orbital (NBO) analyses. The scheme shows how 5c–6e C2Z2O is formed from 3c–4e CZO; such weak interactions determine the fine structures of compounds.

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      On the Lack of Ring-Current Aromaticity of (Heteroatom) [N]Radialenes and their Dianions (pages 269–276)

      Carmen Domene, Patrick W. Fowler, Leonardus W. Jenneskens and Erich Steiner

      Article first published online: 29 SEP 2006 | DOI: 10.1002/chem.200600507

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      Aromatic or not? The lack of diatropic ring currents in neutral and dianionic (heteroatom) [N]radialene-like systems CNYNq− with N=4, 5, 6 and q=0 or 2 (shown here) is an inevitable consequence of the nodal structure of their π (HOMO) and π* (LUMO) orbitals; only for N=3 and q=2 is a weak diatropic π ring current discernible.

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      Density Functional Embedded Cluster Study of Cu4, Ag4 and Au4 Species Interacting with Oxygen Vacancies on the MgO(001) Surface (pages 277–286)

      Konstantin M. Neyman, Chan Inntam, Lyudmila V. Moskaleva and Notker Rösch

      Article first published online: 13 SEP 2006 | DOI: 10.1002/chem.200600545

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      Tetramers Cu4, Ag4 and Au4 at oxygen vacancies Fs and Fs+ of an MgO(001) terrace were studied computationally in comparison to analogous complexes at the defect-free surface. The propensity of smallest supported particles to agglomerate to di-, tri- and tetramers was examined.

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      Supported Ionic-Liquid Films (SILF) as Two-Dimensional Nanoreactors for Enantioselective Reactions: Surface-Mediated Selectivity Modulation (SMSM) (pages 287–291)

      María R. Castillo, Leslie Fousse, José M. Fraile, José I. García and José A. Mayoral

      Article first published online: 27 SEP 2006 | DOI: 10.1002/chem.200600557

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      The close proximity of bis(oxazoline)–copper complexes to the surface support in clay-supported ionic-liquid films (SILF; see scheme) of nanometric thickness produces steric interactions between the surface and the catalytic complex, which leads to a complete reversal of the overall selectivity of the cyclopropanation reactions.

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      Highly Selective Hydrogenation of Carbon–Carbon Multiple Bonds Catalyzed by the Cation [(C6Me6)2Ru2(PPh2)H2]+: Molecular Structure of [(C6Me6)2Ru2(PPh2)(CHCHPh)H]+, a Possible Intermediate in the Case of Phenylacetylene Hydrogenation (pages 292–299)

      Mathieu J.-L. Tschan, Georg Süss-Fink, Frédéric Chérioux and Bruno Therrien

      Article first published online: 12 SEP 2006 | DOI: 10.1002/chem.200600576

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      Complex catalysis: The cation [(C6Me6)2Ru2(PPh2)H2]+ (1) has been found to catalyze the hydrogenation of carbon–carbon double and triple bonds (see scheme) with high selectivity for olefin functions in molecules also containing reducible carbonyl functions.

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      Exploring Base-Pair-Specific Optical Properties of the DNA Stain Thiazole Orange (pages 300–310)

      Dilip Venkatrao Jarikote, Nils Krebs, Sebastian Tannert, Beate Röder and Oliver Seitz

      Article first published online: 6 OCT 2006 | DOI: 10.1002/chem.200600699

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      Forced intercalation is a binding mode that allows the embedding of thiazole orange between two selected matched and mismatched base pairs, despite there being different binding preferences (see graphic). The tight contact of the “thiazole orange nucleobase” with adjacent nucleobases induced base-specific responses of steady-state and time-resolved optical properties that are not observed in “classical” dye–nucleic acid complexes. There are, for example, four different fluorescence-decay processes that respond differently to changes in the environment.

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      Nucleoside–Metallacarborane Conjugates for Base-Specific Metal Labeling of DNA (pages 311–318)

      Agnieszka B. Olejniczak, Jaromir Plešek and Zbigniew J. Leśnikowski

      Article first published online: 14 NOV 2006 | DOI: 10.1002/chem.200600740

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      Metalated nucleic acid components: The incorporation of metal centers into nucleic acids provides exceptional opportunities to create a new type of material that combines the ability of nucleic acids to store, transfer, and process information with the electronic, magnetic, or optical properties that are characteristic of metals and their complexes. Metal–nucleoside conjugates (see picture) provide versatile building blocks that fulfill such requirements.

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      Enantioselective Michael Addition of α-Substituted Cyanoacetates to Vinyl Ketones Catalyzed by Bifunctional Organocatalysts (pages 319–327)

      Tian-Yu Liu, Rui Li, Qian Chai, Jun Long, Bang-Jing Li, Yong Wu, Li-Sheng Ding and Ying-Chun Chen

      Article first published online: 13 OCT 2006 | DOI: 10.1002/chem.200600796

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      Asymmetric organocatalysis: A highly enantioselective Michael addition of α-substituted cyanoacetates to vinyl ketones synergistically promoted by simple bifunctional thiourea/tertiary amine organocatalysts is described (see scheme). The biologically important β2,2-amino acid esters with various structures could be efficiently prepared from the chiral adducts.

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      Layer-by-Layer Deposition of Rhenium-Containing Hyperbranched Polymers and Fabrication of Photovoltaic Cells (pages 328–335)

      Chui Wan Tse, Ka Yan Kitty Man, Kai Wing Cheng, Chris S. K. Mak, Wai Kin Chan, Cho Tung Yip, Zheng Tong Liu and Aleksandra B. Djurišić

      Article first published online: 2 OCT 2006 | DOI: 10.1002/chem.200600838

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      Current affairs: Multilayer thin films were prepared from a rhenium-containing hyperbranched polymer and an ionic polythiophene derivative (see picture; ITO=indium tin oxide). Photosensitization originates from the polymer junction and the films can be fabricated into photovoltaic cells. The maximum incident photon-to-electron conversion efficiency is 0.2 %.

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      Nucleophilicities and Carbon Basicities of Pyridines (pages 336–345)

      Frank Brotzel, Bernhard Kempf, Thomas Singer, Hendrik Zipse and Herbert Mayr

      Article first published online: 29 SEP 2006 | DOI: 10.1002/chem.200600941

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      Kinetic investigations of the reactions of pyridines with benzhydrylium ions have been performed to derive the nucleophilicity parameters N of the pyridines (see picture).

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      Relationship Between the Ligand Structure and the Luminescent Properties of Water-Soluble Lanthanide Complexes Containing Bis(bipyridine) Anionic Arms (pages 346–358)

      Loïc J. Charbonnière, Nicolas Weibel, Pascal Retailleau and Raymond Ziessel

      Article first published online: 29 SEP 2006 | DOI: 10.1002/chem.200600915

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      All wrapped up! The synthesis and characterisation of six new ligands (L1L6) that are able to form luminescent europium and terbium lanthanide complexes in water by wrapping around the cations are described (an example is shown here).

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    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Concept
    6. Full Papers
    7. Preview
    1. You have free access to this content
      Preview: Chem. Eur. J. 2/2007 (page 363)

      Article first published online: 11 DEC 2006 | DOI: 10.1002/chem.200790002

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