Chemistry - A European Journal

Cover image for Chemistry - A European Journal

August 1, 2011

Volume 17, Issue 32

Pages 8753–8995

  1. Cover Picture

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    1. Cover Picture: Understanding the Anomalous Alkane Selectivity of ZIF-7 in the Separation of Light Alkane/Alkene Mixtures (Chem. Eur. J. 32/2011) (page 8753)

      Dr. Johan van den Bergh, Canan Gücüyener, Dr. Evgeny A. Pidko, Prof. Dr. Emiel J. M. Hensen, Dr. Jorge Gascon and Prof. Dr. Freek Kapteijn

      Version of Record online: 25 JUL 2011 | DOI: 10.1002/chem.201190160

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      The efficient use of the gate-opening effect in the zeolite imidazolate framework ZIF-7 upon adsorption of light alkene/alkane mixtures might open the door to a new separation technology based on selective alkane adsorption. A detailed investigation of the adsorption and separation of alkanes and alkenes, as well as a rigorous performance assessment is reported in the Full Paper by J. Gascon et al. on page 8832 ff.

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  3. News

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  4. Minireview

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    1. Organocatalysis

      The Organocatalytic Vinylogous Aldol Reaction: Recent Advances (pages 8770–8779)

      Prof. Sunil V. Pansare and Eldho K. Paul

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201101269

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      Who needs metals? A review of the development and application of the organocatalytic version of the vinylogous aldol reaction is provided. Two variants of this reaction are discussed in detail, the organocatalysed adaptation of the vinylogous Mukaiyama aldol reaction and the more recent direct vinylogous aldol reaction of enals and 2(5H) furanones.

  5. Communications

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    1. Asymmetric Organocatalysis

      Highly Active Organocatalysts for Asymmetric anti-Mannich Reactions (pages 8780–8783)

      Dr. Rafael Martín-Rapún, Xinyuan Fan, Dr. Sonia Sayalero, Mahboubeh Bahramnejad, Dr. Félix Cuevas and Prof. Miquel A. Pericàs

      Version of Record online: 6 JUL 2011 | DOI: 10.1002/chem.201101513

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      Lighten the load! A family of enantiopure 4-oxy-substituted 3-aminopyrrolidines arising from the enantioselective ring-opening of meso-3-pyrroline oxide have been developed as catalysts for the asymmetric, anti-selective Mannich reaction (see scheme; PMP=p-methoxyphenyl; PG=protecting group). Very high catalytic activity (down to 0.01 mol % loading) and stereoselectivity have been recorded.

    2. Alkylation

      Catalytic Enantioselective β-Alkylation of α,β-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes (pages 8784–8788)

      Samson Afewerki, Palle Breistein, Kristian Pirttilä, Luca Deiana, Dr. Pawel Dziedzic, Prof. Ismail Ibrahem and Prof. Armando Córdova

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201100756

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      Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3-dehydrocurcumene and (S)-(+)-tumerone.

    3. Graphene

      Macroscopic, Free-Standing Ag-Reduced, Graphene Oxide Janus Films Prepared by Evaporation-Induced Self-Assembly (pages 8789–8793)

      Dr. Encai Ou, Xiaojuan Zhang, Zhongming Chen, Yonggong Zhan, Ying Du, Guoping Zhang, Yujun Xiang, Yuanqin Xiong and Prof. Weijian Xu

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201101256

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      A facile, efficient, and unique self-assembly process for the preparation of the macroscopic, free-standing, Ag-reduced, graphene oxide (Ag-RGO) Janus films, which exhibit a unique asymmetry of their two surfaces with macroscopic dimensions, is presented. A novel strategy using an evaporation-induced, self-assembly (EISA) process is shown to be a powerful and flexible method for synthesizing well-defined Janus thin films (see figure).

    4. Olefination Reactions

      Amine- and Sulfonamide-Promoted Wittig Olefination Reactions in Water (pages 8794–8798)

      Dr. James McNulty and David McLeod

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201101153

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      Amine-promoted olefination: The reaction of a phosphonium salt and an aldehyde in water to yield alkenes with high E-configurational control is promoted by catalytic amounts of non-basic amines in aqueous bicarbonate media (see scheme). Possible catalytic cycles involving imines and iminium intermediates are discussed.

    5. Fullerene Derivatives

      In Search of Fullerene-Based Superacids: Synthesis, X-ray Structure, and DFT Study of C60(C2F5)5H (pages 8799–8802)

      Dr. Igor V. Kuvychko, Dr. Natalia B. Shustova, Dr. Stanislav M. Avdoshenko, Dr. Alexey A. Popov, Dr. Steven H. Strauss and Dr. Olga V. Boltalina

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/chem.201101328

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      Simply super! The perfluoroalkylfullerene C60(C2F5)5H is the first structurally characterized perfluoroalkylated fullerene-based acid and is also predicted to be the first gas-phase fullerene-based superacid.

    6. Silylenes

      The Reactivity of a Silacyclopentadienylidene towards Aldehydes: Silole Ring Expansion and the Formation of Base-Stabilized Silacyclohexadienones (pages 8803–8806)

      Dr. Yihua Gao, Hongfan Hu and Prof. Dr. Chunming Cui

      Version of Record online: 29 JUN 2011 | DOI: 10.1002/chem.201100587

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      Tossing aldehydes into the ring: The reaction of a silacyclopentadienylidene with aldehydes leads to C[DOUBLE BOND]O bond cleavage with the formation of base-stabilized silanones and cyclopropanation of the adjacent C[DOUBLE BOND]C bond, followed by silole ring expansion to give silicon analogues of cyclohexadienones (see scheme).

    7. Iron Catalysis

      Fe-Catalyzed Thioesterification of Carboxylic Esters (pages 8807–8809)

      Dipl.-Chem. Silja Magens and Prof. Dr. Bernd Plietker

      Version of Record online: 6 JUL 2011 | DOI: 10.1002/chem.201101073

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      Second nature: Starting from shelf-stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical-ligation-type peptide formation, which suggests that the thiol may act as a co-catalyst for future 1,2-additions of pronucleophiles to carboxylic esters.

    8. Nanoparticles

      Synthesis of Mesoporous Pt Nanoparticles with Uniform Particle Size from Aqueous Surfactant Solutions toward Highly Active Electrocatalysts (pages 8810–8815)

      Dr. Liang Wang and Prof. Dr. Yusuke Yamauchi

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201100386

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      Pores for improved catalysis: Mesoporous Pt nanoparticles (MPNs) with large surface areas are created within 10 min by a very simple, one-step, aqueous reaction at room temperature. The obtained MPNs (see figure) exhibit significantly enhanced catalytic activity toward the methanol oxidation reaction.

    9. Hydrogen Bonds

      Remote Communication in a DNA-Based Nanoswitch (pages 8816–8818)

      Dr. Célia Fonseca Guerra, Dr. Zsolt Szekeres and Prof. Dr. F. Matthias Bickelhaupt

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201101335

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      Nano-telegraph: It is shown quantum chemically how the hydrogen-bond strength of a DNA base pair can be remotely switched (across several nanometers) between three states (weak, intermediate, and strong) through a π-conjugated “organic wire”.

  6. Full Papers

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    1. Alkali-Metal Chemistry

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      Developing a Hetero-Alkali-Metal Chemistry of 2,2,6,6-Tetramethylpiperidide (TMP): Stoichiometric and Structural Diversity within a Series of Lithium/Sodium, Lithium/Potassium and Sodium/Potassium TMP Compounds (pages 8820–8831)

      Dr. David R. Armstrong, Dr. Alan R. Kennedy, Prof. Robert E. Mulvey and Dr. Stuart D. Robertson

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/chem.201101167

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      The Magnificent Seven: By opening a library of hetero-alkali-metal chemistry of the important utility base 2,2,6,6-tetramethylpiperidide (TMP), “The Magnificent Seven”, seven new bimetallic compounds that display unprecedented open ring, closed ring, and infinite chain solid-state structures are introduced (see figure; TMEDA=N,N,N′,N′-tetramethylethylenediamine; PMDETA=N,N,N′,N′′,N′′-pentamethyldiethylenediamine).

    2. Metal–Organic Frameworks

      Understanding the Anomalous Alkane Selectivity of ZIF-7 in the Separation of Light Alkane/Alkene Mixtures (pages 8832–8840)

      Dr. Johan van den Bergh, Canan Gücüyener, Dr. Evgeny A. Pidko, Prof. Dr. Emiel J. M. Hensen, Dr. Jorge Gascon and Prof. Dr. Freek Kapteijn

      Version of Record online: 13 JUL 2011 | DOI: 10.1002/chem.201100958

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      Going their separate ways: The separation of short-chain alkanes and alkenes is accomplished by selective adsorption on the zeolite imidazolate framework ZIF-7 through a gate-opening mechanism. The difference in the partial pressure at which alkenes and alkanes are taken up by ZIF-7 makes it an excellent candidate for the design of simpler alkane/alkene PSA-based separation schemes, for which fewer cycles and less energy will be required.

    3. Magnetic Interactions

      The Dilemma of CrIIINiII Exchange Interactions: Ferromagnetism versus Antiferromagnetism (pages 8841–8849)

      Daniel Aravena and Prof. Eliseo Ruiz

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/chem.201100163

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      Orthogonal “magnetic orbitals” or not: Exchange interactions of the available dinuclear CrIIINiII complexes were analyzed using theoretical methods based on density functional theory, while the study of polynuclear CrIIINiII systems focused on the ring Cr7Ni and S-shaped Cr12Ni3 complexes (see figure).

    4. Stereoelectronic Effects

      Theoretical and X-ray Crystallographic Evidence of a Fluorine-Imine Gauche Effect: An Addendum to Dunathan’s Stereoelectronic Hypothesis (pages 8850–8857)

      Christof Sparr, Evdokiya Salamanova, Dr. W. Bernd Schweizer, Dr. Hans Martin Senn and Prof. Dr. Ryan Gilmour

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201100644

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      Fabulous fluorine! The preference of β-fluoroimines to adopt a gauche conformation has been studied by single-crystal X-ray diffraction analysis and DFT methods. Empirical and theoretical evidence for a preferential synclinal arrangement around the NCCF torsion angle (ϕ) is presented (see scheme).

    5. Polycarbonates

      Differences in Reactivity of Epoxides in the Copolymerisation with Carbon Dioxide by Zinc-Based Catalysts: Propylene Oxide versus Cyclohexene Oxide (pages 8858–8869)

      Maximilian W. Lehenmeier, Christian Bruckmeier, Stephan Klaus, Joachim E. Dengler, Dr. Peter Deglmann, Dr. Anna-Katharina Ott and Prof. Dr. Bernhard Rieger

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201100578

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      Key role of back-biting: An investigation of the different reactivities of propylene oxide and cyclohexene oxide in the copolymerisation with CO2 (see image) has been carried out. Experiments and theoretical investigations strongly hint that future research should focus on preventing the back-biting reaction.

    6. Molecular Recognition

      The Role of Chirality in Directing the Formation of Cup-Shaped Porphyrins and the Coordination Characteristics of such Hosts (pages 8870–8881)

      Bao-Yu Wang, Daniel A. Turner, Teodora Zujović, Prof. Christopher M. Hadad and Prof. Jovica D. Badjić

      Version of Record online: 15 JUN 2011 | DOI: 10.1002/chem.201100755

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      Accommodating hosts! Acid-catalyzed condensation of enantiopure pyrromethanecarbinols can be controlled to give cup-shaped porphyrins (see scheme; R=H). These molecules act as hosts and could therefore be of interest in supramolecular and catalytic chemistry.

    7. Metal–Organic Frameworks

      Probing the Dynamics of CO2 and CH4 within the Porous Zirconium Terephthalate UiO-66(Zr): A Synergic Combination of Neutron Scattering Measurements and Molecular Simulations (pages 8882–8889)

      Dr. Qingyuan Yang , Dr. Hervé Jobic, Dr. Fabrice Salles, Dr. Daniil Kolokolov , Vincent Guillerm, Dr. Christian Serre and Dr. Guillaume Maurin

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/chem.201003596

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      Diffusion in MOFs: Quasi-elastic neutron scattering (QENS) measurements were combined with molecular dynamics (MD) simulations to explore the self- (Ds) and transport diffusion (Dt) of CH4 and CO2, respectively, in the humidity-resistant MOF-type material UiO-66(Zr). The global microscopic diffusion mechanism involves a combination of intracage motions and jump sequences between tetrahedral and octahedral cages. Whereas the Ds profile of CH4 exhibits a maximum, Dt of CO2 increases continuously with increasing loading (see picture).

    8. DNA Cleavage

      Site-Specific Recognition of Guanosine by Manganese(III) Corroles in DNA Non-Duplex Regions through Active Oxygen Transfer (pages 8890–8895)

      Qianqian Zhai, Liang Xu, Yushu Ge, Dr. Tian Tian, Wendi Wu, Shengyong Yan, Yangyang Zhou, Dr. Minggang Deng, Prof. Yi Liu and Xiang Zhou

      Version of Record online: 17 JUN 2011 | DOI: 10.1002/chem.201101128

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      Beat the bulge: Manganese corroles can selectively cleave guanosine units located in DNA non-duplex structures within duplexes, such as loops and bulges. The cleavage mechanism is revealed to be a manganese-involved oxygen-transfer process. These results can provide a molecular tool that could specifically probe the guanosine units in DNA non-duplex structures (see picture).

    9. Graphene

      Facile Synthesis of Wide-Bandgap Fluorinated Graphene Semiconductors (pages 8896–8903)

      Dr. Haixin Chang, Jinsheng Cheng, Xuqing Liu, Junfeng Gao, Mingjian Li, Prof. Jinghong Li, Prof. Xiaoming Tao, Prof. Feng Ding and Prof. Zijian Zheng

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/chem.201100699

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      Fluorinated graphenes: An eco-friendly, highly effective, low-cost, and highly scalable approach has been developed to synthesize wide-bandgap fluorinated graphene (F-graphene; see figure) semiconductors. Experimental and theoretical results show the F-graphene bandgaps are largely dependent on the F coverage and configurations, and can be tuned over a very wide range.

    10. Surface Plasmon Resonance

      Amplified Surface Plasmon Resonance Based DNA Biosensors, Aptasensors, and Hg2+ Sensors Using Hemin/G-Quadruplexes and Au Nanoparticles (pages 8904–8912)

      Gilad Pelossof, Dr. Ran Tel-Vered, Dr. Xiao-Qing Liu and Prof. Itamar Willner

      Version of Record online: 1 JUL 2011 | DOI: 10.1002/chem.201100601

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      Extra sensory: Thiolated nucleic acid hairpin nanostructures that contain “caged” G-quadruplex sequences and single-stranded recognition domains were immobilized on Au surfaces or Au nanoparticles linked to Au surfaces (see scheme). The structures were implemented in the ultrasensitive and selective surface plasmon resonance detection of DNA, adenosine monophosphate, and Hg2+ ions.

    11. Arenes

      Pyrogallol[4]arenes Show Highly Variable Amphiphilic Behavior at the Air–Water Interface Dependent Upon Side Chain Length and Branching (pages 8913–8921)

      Dr. Megan M. Daschbach, Dr. Oleg V. Kulikov, Elizabeth F. Long and Prof. George W. Gokel

      Version of Record online: 17 JUN 2011 | DOI: 10.1002/chem.201100221

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      A question of the side chain: The amphiphilic behavior of various pyrogallol[4]arenes with side chains of different sizes and degrees of branching (e.g., methyl, ethyl, propyl, isopropyl) at the air–water interface was investigated by using a Langmuir trough and Brewster angel microscopy (see figure).

    12. Ligand Design

      Telomerisation of Buta-1,3-diene and Methanol: Superiority of Chromanyl-Type Phosphines in the Dow Process for the Industrial Production of 1-MOD (pages 8922–8928)

      Dr. Mathieu J.-L. Tschan, Dr. Hélène Launay, Dr. Henk Hagen, Dr. Jordi Benet-Buchholz and Dr. Piet W. N. M. van Leeuwen

      Version of Record online: 21 JUN 2011 | DOI: 10.1002/chem.201100684

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      MonoXantphos and monoSPANphos: Palladium catalysts with ligands containing 8-diphenylphosphinochromane-like substituents at phosphorus allowed efficient telomerisation of buta-1,3-diene and methanol (see scheme). MonoXantphos and monoSPANphos afforded the most active, stable and selective catalysts known to date under commercially relevant production conditions for 1-methoxyocta-2,7-diene, the precursor to oct-1-ene.

    13. Dendrimers

      Hybrid Gold-Nanoparticle-Cored Conjugated Thiophene Dendrimers: Synthesis, Characterization, and Energy-Transfer Studies (pages 8929–8940)

      Dr. Suxiang Deng, Timothy M. Fulghum, Greg Krueger, Derek Patton, Jin-Young Park and Prof. Rigoberto C. Advincula

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/chem.201100246

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      A series of nanoparticle-cored thiophene dendrimers (see picture) were synthesized, characterized, and investigated for their energy-transfer properties. The solution fluorescence of the attached thiophene dendrons is quenched progressively. Both alkyl-chain length and dendron size have a significant influence on the energy-transfer efficiency, as well as on core sizes and size distribution of the Au nanoparticles.

    14. Polymer Electrolytes

      Segmental Dynamics of PEO/LiClO4 Complex Crystals and Their Influence on the Li+-Ion Transportation in Crystal Lattices: A 13C Solid-State NMR Approach (pages 8941–8946)

      Dr. Yangwen Gao, Prof. Bingweng Hu, Prof. Yefeng Yao and Prof. Qun Chen

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/chem.201100788

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      Helical jumps: Remarkable helical jump motions of the polyethylene oxide (PEO) segments in PEO/LiClO4 complex crystals are clearly demonstrated. The jump motions are believed to provide the mechanism of ionic conductivity, inducing the transportation of the coordinated Li+ ions along the crystallographic c axis. Solid-state high-resolution 13C NMR spectroscopy is shown to be a powerful tool for elucidating phase structures, dynamics and conduction mechanisms of crystalline polymer electrolytes (see figure).

    15. Electrophosphorescence

      A New Phosphine Oxide Host based on ortho-Disubstituted Dibenzofuran for Efficient Electrophosphorescence: Towards High Triplet State Excited Levels and Excellent Thermal, Morphological and Efficiency Stability (pages 8947–8956)

      Chunmiao Han, Guohua Xie, Jing Li, Zhensong Zhang, Dr. Hui Xu, Zhaopeng Deng, Prof. Yi Zhao, Prof. Pengfei Yan and Prof. Shiyong Liu

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/chem.201100695

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      An efficient host for blue and green electrophosphorescence, 4,6-bis(diphenylphosphoryl)dibenzofuran (o-DBFDPO), with the structure of a short-axis-substituted dibenzofuran was designed and synthesised. The influence of its symmetric structure and the larger number of diphenylphosphine oxide moieties on the optical properties and frontier molecular orbitals was investigated. Stable and efficient blue and green electrophosphorescence were demonstrated (see figure).

    16. Hybrid Materials

      One-Pot Functionalization of Graphene with Porphyrin through Cycloaddition Reactions (pages 8957–8964)

      Xiaoyan Zhang, Lili Hou, Arjen Cnossen, Dr. Anthony C. Coleman, Oleksii Ivashenko, Prof. Dr. Petra Rudolf, Prof. Dr. Bart J. van Wees, Dr. Wesley R. Browne and Prof. Dr. Ben L. Feringa

      Version of Record online: 6 JUL 2011 | DOI: 10.1002/chem.201100980

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      Photoactive units on graphene: Two types of graphene-based hybrid material, graphene-TPP (TPP=tetraphenylporphyrin) and graphene-PdTPP (PdTPP=palladium tetraphenylporphyrin), were prepared directly from pristine graphene through one-pot cycloaddition reactions (see scheme). In view of the unique properties of both graphene and porphyrin, these two hybrid materials might have potential applications in a number of areas, such as solar cells and sensors.

    17. Porphyrinoids

      meso-Aryl Phenanthroporphyrins: Synthesis and Spectroscopic Properties (pages 8965–8983)

      Dr. Hai-Jun Xu, Dr. John Mack, Dr. Ana B. Descalzo, Prof. Zhen Shen, Prof. Nagao Kobayashi, Prof. Xiao-Zeng You and Dr. Knut Rurack

      Version of Record online: 16 JUN 2011 | DOI: 10.1002/chem.201002596

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      Saddle the porphyrins! Annelation with phenanthrene moieties and meso-phenyl substitution of tetrapyrrole porphyrin lead to porphyrinoids with very deep saddle distortions. This results in redshifted absorption and emission bands at wavelengths unprecedented for tetrapyrrole porphyrins (see figure).

    18. Mesoporous Silica

      SBA-15-Type Organosilica with 4-Mercapto-N,N-bis-(3-Si-propyl)butanamide for Palladium Scavenging and Cross-Coupling Catalysis (pages 8984–8994)

      Samir El Hankari, Dr. Abdelkrim El Kadib, Dr. Annie Finiels, Prof. Ahmed Bouhaouss, Prof. Joël J. E. Moreau, Prof. Cathleen M. Crudden, Dr. Daniel Brunel and Dr. Peter Hesemann

      Version of Record online: 5 JUL 2011 | DOI: 10.1002/chem.201002190

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      Materials made to measure: The use of a bulky thiol precursor combined with a high degree of condensation of the SiO2 framework enhances the catalytic properties of heterogeneous Pd-containing catalysts in Suzuki and Sonogashira cross-coupling reactions (see scheme).

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      Preview: Chem. Eur. J. 33/2011 (page 8995)

      Version of Record online: 25 JUL 2011 | DOI: 10.1002/chem.201190163

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