Chemistry - A European Journal

Cover image for Vol. 19 Issue 30

July 22, 2013

Volume 19, Issue 30

Pages 9725–10056

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: The Ligand-Based Quintuple Bond-Shortening Concept and Some of Its Limitations (Chem. Eur. J. 30/2013) (page 9725)

      Dr. Awal Noor, Tobias Bauer, Dr. Tanya K. Todorova, Prof. Dr. Birgit Weber, Prof. Dr. Laura Gagliardi and Prof. Dr. Rhett Kempe

      Version of Record online: 15 JUL 2013 | DOI: 10.1002/chem.201390109

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      Quintuple bonds between chromium atoms are the first choice for looking at how short a metal–metal bond can be. In their Full Paper on page 9825 ff., L. Gagliardi, R. Kempe et al. describe a rational concept of shortening quintuple bonds based on ligand design. A Cr–Cr distance of 1.7056(12) Å is the value finally reached. Most importantly, the potential limitations of the shortening concept and the formation of other coordination isomers or over-reduction are described.

    2. You have free access to this content
      Back Cover: Importance of Size and Distribution of Ni Nanoparticles for the Hydrodeoxygenation of Microalgae Oil (Chem. Eur. J. 30/2013) (page 10060)

      Wenji Song, Dr. Chen Zhao and Prof. Dr. Johannes A. Lercher

      Version of Record online: 15 JUL 2013 | DOI: 10.1002/chem.201390112

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      Highly enhanced activity and better stability for hydrodeoxygenation of stearic acid and microalgae oil has been reported for Ni/HBEA catalysts by C. Zhao, J. A. Lercher, and W. Song in their Full Paper on page 9833 ff. Improved synthetic techniques realize much smaller and more homogeneously dispersed Ni particles in the resultant catalysts, and the roles of average size and uniformity are thus highlighted.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
  3. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Corrigendum: Diels–Alder and Retro-Diels–Alder Cycloadditions of (1,2,3,4,5-Pentamethyl)cyclopentadiene to La@C2v-C82: Regioselectivity and Product Stability (page 9739)

      Marc Garcia-Borràs, Dr. Josep M. Luis, Prof. Dr. Marcel Swart and Prof. Dr. Miquel Solà

      Version of Record online: 15 JUL 2013 | DOI: 10.1002/chem.201302382

  4. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
  5. Minireview

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. Nanoparticle Synthesis

      Recent Developments in Colloidal Synthesis of CuInSe2 Nanoparticles (pages 9746–9753)

      Dr. Elena Witt and Prof. Dr. Joanna Kolny-Olesiak

      Version of Record online: 20 JUN 2013 | DOI: 10.1002/chem.201301076

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      How to synthesize CuInSe2 nanocrystals: The progress in the colloidal synthesis and size and shape control of semiconductor CuInSe2 nanoparticles and the advances in the understanding of the underlying reaction mechanisms are reported in this Minireview.

  6. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. Asymmetric catalysis

      Enantioselective Construction of Dihydropyran-Fused Indoles through Chiral Calcium Phosphate Catalyzed Oxo-Hetero-Diels–Alder Reactions by Using 2-Oxoindolin-3-ylidenes as Heterodienes (pages 9754–9759)

      Zhijie Mao, Weipeng Li, Yan Shi, Haibin Mao, Aijun Lin, Prof. Dr. Chengjian Zhu and Prof. Dr. Yixiang Cheng

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/chem.201301039

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      Carbon–carbon bond formation: A highly efficient method for the oxo-hetero-Diels–Alder reaction of 2-oxoindolin-3-ylidenes based on chiral calcium phosphate is described. In general, adducts were obtained with high yields and excellent diastereo- and enantioselectivities (up to 96 % yield, >99:1 endo/exo, >99 % ee; see scheme, Boc=tert-butoxycarbonyl).

    2. Fluorescence Probes

      Solvatochromic Pyrene Analogues of Prodan Exhibiting Extremely High Fluorescence Quantum Yields in Apolar and Polar Solvents (pages 9760–9765)

      Yosuke Niko, Dr. Susumu Kawauchi and Prof. Dr. Gen-ichi Konishi

      Version of Record online: 6 JUN 2013 | DOI: 10.1002/chem.201301020

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      True colors: Novel pyrene analogues of Prodan exhibit outstanding photophysical properties with remarkably high fluorescence quantum yield (QY) in solvents ranging from apolar hexane to polar methanol (see figure). This is accompanied by strong solvatochromism and large Stokes shifts. These properties have not been previously achieved in enormous solvatochromic dyes, but are quite useful for emitting materials and imaging tools.

    3. Cell Recognition

      Fluorescent Labeling Agents for Quorum-Sensing Receptors (FLAQS) in Live Cells (pages 9766–9770)

      José Gomes, Natalie Huber, Alexander Grunau, Prof. Dr. Leo Eberl and Prof. Dr. Karl Gademann

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201301387

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      Lighten up: A selective fluorescent-labeling agent for quorum sensing (FLAQS) can be used for the visualization of the communication pathway of bacteria in live cells (see figure). This represents a new, operationally simple, fast, and inexpensive tool for the imaging of quorum-sensing receptors by using fluorescently labeled signaling-molecule analogues.

    4. Organic Semiconductors

      Self-Assembled π-Extended Condensed Benzothiophene Nanoribbons for Field-Effect Transistors (pages 9771–9774)

      Zhe Pan, Yao Liu, Fei Fan, Prof. Dr. Yu Chen, Yongxi Li, Prof. Dr. Xiaowei Zhan and Yi Song

      Version of Record online: 28 JUN 2013 | DOI: 10.1002/chem.201300603

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      Nanostructures: A new air-stable π-extended condensed benzothiophene was prepared by starting from 4,8-dioctyl-oxybenzo[1,2-b:4,5-b′]dithiophene in about 54 % overall yield. Highly ordered 1D organic nanoribbons of the resultant compound were formed by molecular self-assembly. An individual nanoribbon-based organic field-effect transistor (see figure) exhibited an average mobility of 0.05 cm2 V−1 s−1.

    5. Organocatalysis

      Shedding Light on Organocatalysis—Light-Assisted Asymmetric Ion-Pair Catalysis for the Enantioselective Hydrogenation of Pyrylium Ions (pages 9775–9779)

      Chien-Chi Hsiao, Hsuan-Hung Liao, Dr. Erli Sugiono, Dr. Iuliana Atodiresei and Prof. Dr. Magnus Rueping

      Version of Record online: 6 JUN 2013 | DOI: 10.1002/chem.201300766

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      A new light-driven asymmetric ion-pair catalysis procedure for the metal-free enantioselective hydrogenation of in situ generated pyrylium ions from readily available chalcones was developed (see scheme). The photo-assisted Brønsted acid catalyzed procedure has broad scope and allows, for the first time, access to valuable 4H-chromenes in good yields and with excellent enantioselectivities.

    6. Mixed-Valent Compounds

      Refining the Interpretation of Near-Infrared Band Shapes in a Polyynediyl Molecular Wire (pages 9780–9784)

      Matthias Parthey, Dr. Josef B. G. Gluyas, Dr. Phil A. Schauer, Dr. Dmitry S. Yufit, Prof. Dr. Judith A. K. Howard, Prof. Dr. Martin Kaupp and Prof. Dr. Paul J. Low

      Version of Record online: 12 JUN 2013 | DOI: 10.1002/chem.201301747

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      Spinning to improve (band) shape: A blend of theoretical and experimental work demonstrates that the rotational conformation of mixed-valence complexes influences the low-energy (NIR) transitions in such molecules. Interpretations of the NIR band shapes are presented.

    7. Hydroalkoxylation

      Nickel-Catalysed Hydroalkoxylation Reaction of 1,3-Butadiene: Ligand Controlled Selectivity for the Efficient and Atom-Economical Synthesis of Alkylbutenyl Ethers (pages 9785–9788)

      Dr. Sandra Bigot, Dr. Mohammed Samir Ibn El Alami, Alexis Mifleur, Prof. Yves Castanet, Dr. Isabelle Suisse, Prof. André Mortreux and Prof. Mathieu Sauthier

      Version of Record online: 12 JUN 2013 | DOI: 10.1002/chem.201300633

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      The nickel-catalysed hydroalkoxylation of butadiene is promoted by a nickel(0)/dppb catalyst (dppb=1,4-bis(diphenylphosphino)butane; see scheme). By following this new synthetic procedure, alkylbutenyl ethers are readily obtained from an alcohol and 1,3-butadiene with exclusion of dimerisation and telomerisation products.

    8. Synthetic Methods

      Copper-Catalyzed Direct Synthesis of Iodoenamides from Ketoximes (pages 9789–9794)

      Hao Liang, Zhi-Hui Ren, Prof. Yao-Yu Wang and Prof. Dr. Zheng-Hui Guan

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201301785

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      Iodide in copper's pathway: A new, efficient, and practical copper-catalyzed synthesis of Z-iodoenamides from readily available ketoximes has been developed (see scheme). The reaction was believed to proceed through a single-electron-transfer pathway. The corresponding Z-iodoenamides have been applied to the synthesis of substituted oxazoles, dienes, β-phenoxyl enamides, eneynes, β-acylenamides, and pyrroles (DCE=1,2-dichloroethane).

    9. Synthesis

      ICl-Induced Intramolecular Electrophilic Cyclization of 1-[4′-Methoxy(1,1′-biphenyl)2-yl]alkynones—A Facile Approach to Spiroconjugated Molecules (pages 9795–9799)

      Prof. Dr. Yu Chen, Xiaochen Liu, Minwook Lee, Chenlong Huang, Igor Inoyatov, Zhiwei Chen, Abraham C. Perl and Prof. Dr. William H. Hersh

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201301582

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      Spiro compounds: An iodine monochloride-induced intramolecular cyclization of 1-[4′-methoxy(1,1′-biphenyl)2-yl]alkynones has been developed (see scheme). An electrophilic iodocyclization selectively takes place at the ipso position (versus the ortho electrophilic aromatic substitution) to afford 4′H-spiro(cyclohexa[2,5]diene-1,1′-naphthalene)-4,4′-diones, a new group of spiroconjugated compounds.

    10. Host–Guest Systems

      Stepwise Coordination of PtII-180° and PdII-90° Metal Fragments to the Purine Nucleobase 9-Methylhypoxanthine Affords a Closed Octadecanuclear Pt6Pd12 Cluster (pages 9800–9806)

      Dr. Francisca M. Albertí, Witold Zielinski, Marta Morell Cerdà, Dr. Pablo J. Sanz Miguel, Oliver Troeppner, Prof. Dr. Ivana Ivanović-Burmazović and Prof. Dr. Bernhard Lippert

      Version of Record online: 6 JUN 2013 | DOI: 10.1002/chem.201300446

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      Crossing the line: A pH-induced “crossover” in 3D shapes of supramolecular constructs derived from trans(NH3)2PtII, [PdII(en)], and the purine model nucleobase 9-methylhypoxanthine (see figure) is reported in which [Pd(en)(H2O)]2+ and [Pd(en)(OH)]+ are the decisive players (en=ethylenediamine).

    11. Olefin Metathesis

      Isomerizing Ethenolysis as an Efficient Strategy for Styrene Synthesis (pages 9807–9810)

      Sabrina Baader, Dr. Dominik M. Ohlmann and Prof. Dr. Lukas J. Gooßen

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201301336

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      A shrinking chain: A bimetallic system consisting of [{Pd(μ-Br)(tBu3P)}2] and a ruthenium metathesis catalyst has been found to efficiently promote the cross-metathesis between substituted alkenes and ethylene, while continuously migrating the double bond along the alkenyl chain (see scheme). When alkenylarenes, such as the natural products eugenol, safrol, or estragol, were treated with this catalyst under an ethylene atmosphere, they were cleanly converted into the corresponding styrenes and propylene gas.

    12. Nanostructures

      Facile Synthesis of Transition-Metal Oxide Nanocrystals Embedded in Hollow Carbon Microspheres for High-Rate Lithium-Ion-Battery Anodes (pages 9811–9816)

      Dr. Jun Liu, Wei Liu, Kunfeng Chen, Dr. Shaomin Ji, Prof. Yichun Zhou, Yanling Wan, Prof. Dongfeng Xue, Prof. Peter Hodgson and Dr. Yuncang Li

      Version of Record online: 20 JUN 2013 | DOI: 10.1002/chem.201300357

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      Charged up: A general soft-template route for the synthesis of uniform hollow carbon microspheres embedded with transition-metal oxide nanocrystals (OHCMs) has been developed (see figure). The obtained OHCMs possess a microsized spherical shape, embedded transition-metal oxide nanocrystals, and fully encapsulating conductive carbon shells, which endow the resulting anode materials with high specific capacities, rate capabilities, electrode densities, and cycle stabilities.

  7. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. Nanotube Catalysis

      Mechanistic Insight into the Catalytic Oxidation of Cyclohexane over Carbon Nanotubes: Kinetic and In Situ Spectroscopic Evidence (pages 9818–9824)

      Xixian Yang, Dr. Hongjuan Wang, Jing Li, Dr. Wenxu Zheng, Dr. Rong Xiang, Prof. Zikang Tang, Prof. Hao Yu and Prof. Feng Peng

      Version of Record online: 20 JUN 2013 | DOI: 10.1002/chem.201300676

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      Cyclohexane oxidation over nanotubes: A weak interaction between radicals and graphene skeletons significantly promotes the catalytic oxidation of cyclohexane by confining the radicals around the surfaces of CNTs (see scheme). This, in turn, enhances the electron-transfer catalysis of peroxides to yield the corresponding alcohol and ketone.

    2. Multiple Bonds

      The Ligand-Based Quintuple Bond-Shortening Concept and Some of Its Limitations (pages 9825–9832)

      Dr. Awal Noor, Tobias Bauer, Dr. Tanya K. Todorova, Prof. Dr. Birgit Weber, Prof. Dr. Laura Gagliardi and Prof. Dr. Rhett Kempe

      Version of Record online: 2 JUL 2013 | DOI: 10.1002/chem.201301240

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      A sterically tailor-made guanidinate ligand is the key to the shortest metal–metal bond observed to date. The Cr[BOND]Cr quintuple bond is of the same length as the longest C[BOND]C bond in stable alkanes. The ligand-based metal–metal bond-shortening concept has a few limitations. Most importantly, the formation of coordination isomers with an unsupported Cr[BOND]Cr bond of significantly lower bond order was determined by CASSCF/CASPT2 calculations (see figure).

    3. Biomass

      Importance of Size and Distribution of Ni Nanoparticles for the Hydrodeoxygenation of Microalgae Oil (pages 9833–9842)

      Wenji Song, Dr. Chen Zhao and Prof. Dr. Johannes A. Lercher

      Version of Record online: 21 JUN 2013 | DOI: 10.1002/chem.201301005

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      The small matter of size: Nearly 5–8-fold enhancements of initial rates and improved recyclability have been achieved with Ni/HBEA catalysts, prepared by improved synthesis techniques, on the hydrodeoxygenation of stearic acid and microalgae oil. The average size and uniformity of Ni particles are crucial for maintaining the highly active and stable catalyst. The small metal sites facilitate high initial rates and the good uniformity ensures high catalyst stability (see figure).

    4. Graphene

      Exploiting Multivalent Nanoparticles for the Supramolecular Functionalization of Graphene with a Nonplanar Recognition Motif (pages 9843–9848)

      Dr. Fulvio G. Brunetti, Helena Isla, Dr. Juan Aragó, Prof. Dr. Enrique Ortí, Dr. Emilio M. Pérez and Prof. Dr. Nazario Martín

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201301102

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      Mismatched, yet attracted to each other: The supramolecular modification of planar graphene with the geometrically mismatched, curved 9,10-di(1,3-dithiole-2-ylidene)-9,10-dihydroanthracene (exTTF) molecule is demonstrated. The exTTF–graphene interaction is amplified by utilizing gold nanoparticles (AuNPs) as multivalent scaffolds. The resulting graphene–exTTFAuNP conjugates form sandwich-type nanostructures (see figure).

    5. Epoxidation

      Thermal Restructuring of Silica-Grafted TiClx Species and Consequences for Epoxidation Catalysis (pages 9849–9858)

      Philipp Mania, Dr. René Verel, Florian Jenny, Dr. Ceri Hammond and Prof. Dr. Ive Hermans

      Version of Record online: 18 JUN 2013 | DOI: 10.1002/chem.201300842

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      Anchoring titanium: Grafting of TiCl4 to site-isolated silanol groups on silica initially leads to freely rotating species. Upon heating, a thermal restructuring takes place, causing the elimination of TiCl4 and the formation of more strongly anchored titanium species, which were found to be highly active and stable epoxidation catalysts (see figure).

    6. Dye Alignment

      Modulating Dye Aggregation by Incorporation into 1D-MgAPO Nanochannels (pages 9859–9865)

      Dr. Virginia Martínez-Martínez, Dr. Raquel García, Dr. Luis Gómez-Hortigüela, Prof. Joaquín Pérez-Pariente and Prof. Iñigo López-Arbeloa

      Version of Record online: 18 JUN 2013 | DOI: 10.1002/chem.201301285

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      A perfect fit: A computer-aided rational choice of a host framework for dyes enables fine tuning of their aggregation state. Pyronine Y (PY) can be forced to rearrange from undesirable H-type dimers in MgAPO-5 (APO=aluminophosphates) to red-emissive J-type aggregates in MgAPO-36 (ATS), resulting in an organized multicolour emission system interesting for energy transport. Total suppression of aggregation is achieved in an MgAPO-11-type framework, providing a highly fluorescent hybrid system with an extraordinarily preferential alignment of chromophores.

    7. Coaxial Nanocables

      CNT@Fe3O4@C Coaxial Nanocables: One-Pot, Additive-Free Synthesis and Remarkable Lithium Storage Behavior (pages 9866–9874)

      Dr. Jianli Cheng, Dr. Bin Wang, Prof. Dr. Cheol-Min Park, Prof. Dr. Yuping Wu, Dr. Hui Huang and Dr. Fude Nie

      Version of Record online: 12 JUN 2013 | DOI: 10.1002/chem.201300037

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      In charge: Carbon nanotube (CNT)@Fe3O4@C porous core/sheath coaxial nanocables are synthesized by a simple one-pot hydrothermal process. Neither a surfactant/ligand nor a CNT pretreatment is needed in the synthetic process. The CNT@Fe3O4@C nanocables show enhanced cycling performance and high rate capability when used as the anode material of lithium-ion batteries (see figure).

    8. Nonlinear Optics

      Tuning the Dipolar Second-Order Nonlinear Optical Properties of Cyclometalated Platinum(II) Complexes with Tridentate N^C^N Binding Ligands (pages 9875–9883)

      Dr. Ester Rossi, Dr. Alessia Colombo, Dr. Claudia Dragonetti, Dr. Stefania Righetto, Prof. Dr. Dominique Roberto, Prof. Dr. Renato Ugo, Dr. Adriana Valore, Prof. Dr. J. A. Gareth Williams, Dr. Maria Grazia Lobello, Dr. Filippo De Angelis, Dr. Simona Fantacci, Prof. Dr. Isabelle Ledoux-Rak, Dr. Anu Singh and Prof. Dr. Joseph Zyss

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201301131

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      Minding our L and X: Appropriate functionalization of the cyclometalated 1,3-di(2-pyridyl)benzene ligand, L, and the choice of the ancillary X ligand allow the dipolar second-order nonlinear optical response of [PtLX] complexes to be controlled (see figure; MLCT=metal-to-ligand charge transfer, ILCT=Intraligand charge transfer).

    9. Metal–DNA Binding

      Formation of a Thymine-HgII-Thymine Metal-Mediated DNA Base Pair: Proposal and Theoretical Calculation of the Reaction Pathway (pages 9884–9894)

      Dr. Jakub Šebera, Prof. Jaroslav Burda, Dr. Michal Straka, Prof. Akira Ono, Prof. Chojiro Kojima, Prof. Yoshiyuki Tanaka and Dr. Vladimír Sychrovský

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201300460

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      The bridging mercury within DNA: The formation of the first HgII[BOND]T bond during the reaction mechanism for the generation of a T-HgII-T metal-mediated base pair (see scheme; T=thymine) is triggered by a hydroxo ligand on the HgII ion. The second linkage, as the rate-limiting step, proceeds through water-assisted tautomerization of the thymine base. A positive ΔSR value was due to both dehydration of the HgII ion and the change in chemical bonding during the reaction.

    10. R2P5+ Cages

      Synthesis of Cationic R2P5+ Cages and Subsequent Chalcogenation Reactions (pages 9895–9907)

      Dr. Michael H. Holthausen, Dr. Alexander Hepp and Prof. Dr. Jan J. Weigand

      Version of Record online: 12 JUN 2013 | DOI: 10.1002/chem.201204337

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      Phosphorus–chalcogen cations: Chalcogenation reactions of R2P5+ and Ph6P73+ cages with α-S8 or Segrey yield a series of phosphorus–chalcogen cations (see scheme). The reactions proceed by insertion of Ch (Ch=S, Se) into P[BOND]P bonds or exchange of a tetra-coordinated P moiety. Nortricyclane-type structures are obtained, these being formally derived by stepwise isolobal exchange of chalcogen moieties in P4Ch3 by [R2P]+ moieties. In addition, synthetic protocols for the synthesis of a series of R2P5+ cages are presented.

    11. Peptidomimetics

      Unusual Folding Propensity of an Unsubstituted β,γ-Hybrid Model Peptide: Importance of the C[BOND]H⋅⋅⋅O Intramolecular Hydrogen Bond (pages 9908–9915)

      Paloth Venugopalan and Dr. Raghuvansh Kishore

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201300630

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      Everywhere U-turn: The characterisation of non-functionalised β-turn-like structures across an unsubstituted β,γ-hybrid peptide unit is reported. X-ray diffraction analysis revealed the existence of four crystallographically independent molecules. Unusual β-turn-like folded structures predominate and the U-shaped conformers (see figure) are seemingly stabilised by an effective unconventional C[BOND]H⋅⋅⋅O intramolecular hydrogen bond.

    12. Asymmetric Synthesis

      You have full text access to this OnlineOpen article
      Asymmetric Synthesis of 2,4,5-Trisubstituted Δ2-Thiazolines (pages 9916–9922)

      Dr. Christoffer Bengtsson, Hanna Nelander and Prof. Dr. Fredrik Almqvist

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201301120

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      Paving the way: A route to 2,4,5-trisubstituted Δ2-thiazolines has been developed by starting from α,β-unsaturated methyl esters, with a dihydroxylation and tandem azide reduction/O[RIGHTWARDS ARROW]N acyl migration reaction as key steps (see figure). Asymmetric versions of the reaction have also been developed with use of the Sharpless asymmetric dihydroxylation to give the final products in high enantiomeric excess.

    13. DNA Recognition

      Sequence-Selective DNA Recognition with Peptide–Bisbenzamidine Conjugates (pages 9923–9929)

      Mateo I. Sánchez, Dr. Olalla Vázquez, Prof. M. Eugenio Vázquez and Prof. José L. Mascareñas

      Version of Record online: 18 JUN 2013 | DOI: 10.1002/chem.201300519

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      Bound by recognition: Conjugation of fragments of bZIP and zinc finger transcription factors to bisbenzamidines allows selective DNA recognition of composite DNA sequences containing the original target site of the peptide fragment in tandem with A/T-rich sequences targeted by the minor-groove binder unit (see figure). The fluorogenic aza-bisbenzamidine is exploited for the spectroscopic characterization of the DNA-recognition process.

    14. Stacking Interactions

      Unidirectional Molecular Stacking of Tribenzotriquinacenes in the Solid State: A Combined X-ray and Theoretical Study (pages 9930–9938)

      Jan Gerit Brandenburg, Prof. Dr. Stefan Grimme, Prof. Dr. Peter G. Jones, Dr. Georgios Markopoulos, Prof. Dr. Henning Hopf, Prof. Dr. Michał K. Cyranski and Prof. Dr. Dietmar Kuck

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201300761

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      The superbowl: Crystal structures of tribenzotriquinacenes 1 and 2 were determined by X-ray diffraction and calculated by using dispersion-corrected density functional theory. The London dispersion correction was crucial and all details of the unidirectional molecular stacking showed excellent agreement for both systems, including the slight alternating rotation of neighboring molecules parallel to the crystallographic c axis of compound 1.

    15. Helical Structures

      Heterohelicenes with Embedded P-Chiral 1H-Phosphindole or Dibenzophosphole Units: Diastereoselective Photochemical Synthesis and Structural Characterization (pages 9939–9947)

      Keihann Yavari, Dr. Pascal Retailleau, Dr. Arnaud Voituriez and Dr. Angela Marinetti

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201300844

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      From phosphindoles to helicenes: Olefins with 1H-phosphindole or dibenzophosphole substituents are suitable precursors for P/N-bi-heterosubstituted dimeric helicenes, as well as for new [6]- and [8]phosphahelicenes. The highly diastereoselective oxidative photocyclization of these olefins opens up access to enantiomerically pure helical derivatives. The structural characterization of a helical phosphine oxide, sulfide, and gold complex is reported.

    16. Donor–Acceptor Systems

      Small D–π–A Systems with o-Phenylene-Bridged Accepting Units as Active Materials for Organic Photovoltaics (pages 9948–9960)

      Dr. Antoine Leliège, M. Sc. Jérémie Grolleau, M. Sc. Magali Allain, Dr. Philippe Blanchard, Dr. Dora Demeter, Dr. Théodulf Rousseau and Dr. Jean Roncali

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/chem.201301054

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      Good things in small packages: The bridging of a dicyanovinyl group to the vicinal thiophene by an ortho-phenylene bridge leads to a new electron-withdrawing building block, which has been used for the synthesis of small donor–π–acceptor molecular donors with tailored electronic properties. Efficient planar heterojunction solar cells based on these donors of reduced molecular size and C60 or C70 are reported.

    17. Polynuclear Complexes

      Polynuclear Complexes with Alkoxo and Phenoxo Bridges from In Situ Generated Hydroxy-Rich Schiff Base Ligands: Syntheses, Structures, and Magnetic Properties (pages 9961–9972)

      Caixia Ding, Chen Gao, Prof. Dr. Seikweng Ng, Prof. Dr. Bingwu Wang and Prof. Dr. Yongshu Xie

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201301041

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      A magnetic presence: The reaction of 1-aminoglycerol with various aldehydes in the presence of metal ions affords di-, tetra-, penta- and heptanuclear complexes with interesting structures and magnetic properties (see figure).

    18. Asymmetric Catalysis

      Enantioselective Aza-Michael Addition of Imides by Using an Integrated Strategy Involving the Synthesis of a Family of Multifunctional Catalysts, Usage of Multiple Catalysis, and Rational Design of Experiment (pages 9973–9978)

      Mattia Silvi, Polyssena Renzi, Deborah Rosato, Cristiana Margarita, Alessio Vecchioni, Ivan Bordacchini, Diego Morra, Alessandro Nicolosi, Riccardo Cari, Dr. Fabio Sciubba, Dr. Daniele M. Scarpino Schietroma and Dr. Marco Bella

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201301493

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      Eureka! versus rational: No “eureka!” moment, but rather a rational step-by-step improvement. The optimization of a challenging reaction was achieved by using an integrated approach involving the synthesis of a family of organocatalysts, multiple catalysis, and through a rational exploration of chemical space with the application of the experiment design in asymmetric catalysis (see figure).

    19. Sensors

      Tetra(p-tolyl)borate-Functionalized Solvent Polymeric Membrane: A Facile and Sensitive Sensing Platform for Peroxidase and Peroxidase Mimetics (pages 9979–9986)

      Xuewei Wang and Prof. Wei Qin

      Version of Record online: 12 JUN 2013 | DOI: 10.1002/chem.201300284

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      Peroxidase-sensing platform: A membrane sensor allows facile, sensitive, and cost-effective determination of catalytic activities of peroxidase or its mimetics (see figure). Reaction intermediates in the peroxidative oxidation of o-phenylenediamine are transferred into a tetra(p-tolyl)borate-functionalized solvent polymeric membrane and induce changes at the sample–membrane interface, by which the peroxidase activities can be measured.

    20. Supramolecular Gels

      Cholesterol-/Estradiol-Appended Alkynylplatinum(II) Complexes as Supramolecular Gelators: Synthesis, Characterization, Photophysical and Gelation Studies (pages 9987–9994)

      Dr. Yongguang Li, Elizabeth Suk-Hang Lam, Dr. Anthony Yiu-Yan Tam, Dr. Keith Man-Chung Wong, Dr. Wai Han Lam, Prof. Dr, Lixin Wu and Prof. Dr. Vivian Wing-Wah Yam

      Version of Record online: 12 JUN 2013 | DOI: 10.1002/chem.201301510

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      Platinum gels: A series of cholesterol-/estradiol-appended alkynylplatinum(II) complexes of a tridentate N-donor ligand, 2,6-bis(1-alkylpyrazol-3-yl)pyridine, has been designed and synthesized. Some complexes have been found to be capable of forming stable supramolecular gels.

    21. Photosensitive Complexes

      Synthesis and Characterization of Various Photosensitive Copper(II) Complexes with 5-(1-Methylhydrazinyl)-1H-tetrazole as Ligand and Perchlorate, Nitrate, Dinitramide, and Chloride as Anions (pages 9995–10003)

      Manuel Joas, Prof. Thomas M. Klapötke, Dr. Jörg Stierstorfer and Norbert Szimhardt

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201300688

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      Explosive complexes: Various copper(II) complexes with 5-(1-methylhydrazinyl)-1H-tetrazole as a ligand were synthesized and characterized. The complexes were further tested upon laser irradiation and as possible primary explosives. The figure shows the detonation of [Cu(ClO4)(μ-MHT)(H2O)] and the molecular unit of [{Cu(ClO4)(μ-MHT)(HMHT)}2], which are similar in their behaviors as primary explosives.

    22. Natural Products

      A Dioxane Template for Highly Selective Epoxy Alcohol Cyclizations (pages 10004–10016)

      Dr. James J. Mousseau, Dr. Christopher J. Morten and Prof. Dr. Timothy F. Jamison

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201300845

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      Reversed selectivity: 1,3-Dioxan-5-ol templated epoxy alcohols undergo a remarkably selective cyclization, which occurs with near complete endo selectivity that is opposite to that predicted by Baldwin's rules. This endo preference in water near pH 7.0 is an order of magnitude larger relative to that of a previously disclosed THP-templated cyclization (see scheme), suggesting that “templates” may be important in the biosynthesis of marine ladder polyethers.

    23. Zeolites

      Dual-Mesoporous ZSM-5 Zeolite with Highly b-Axis-Oriented Large Mesopore Channels for the Production of Benzoin Ethyl Ether (pages 10017–10023)

      Dr. Xiaoxia Zhou, Prof. Hangrong Chen, Dr. Yan Zhu, Yudian Song, Dr. Yu Chen, Dr. Yongxia Wang, Dr. Yun Gong, Dr. Guobin Zhang, Dr. Zhu Shu, Dr. Xiangzhi Cui, Dr. Jinjin Zhao and Prof. Jianlin Shi

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201300245

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      An aggregation–assembly process was developed for the synthesis of dual-mesoporous zeolite ZSM-5 with b-axis-aligned larger mesopores and smaller wormlike mesopores by using nonionic copolymer F127 and cationic surfactant CTAB as co-templates (see figure). It shows excellent catalytic performance in the condensation of benzaldehyde with ethanol due to the free access of bulky reactants provided by the dual-mesoporous structure, especially the b-axis-oriented large mesopores, and the large number of active sites and strong acidity offered by the zeolite framework.

    24. Microporous Materials

      Novel Functionalized Microporous Organic Networks Based on Triphenylphosphine (pages 10024–10029)

      Dr. Qiang Zhang, Dr. Yanqin Yang and Prof. Suobo Zhang

      Version of Record online: 14 JUN 2013 | DOI: 10.1002/chem.201300334

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      Phosphine sponges: Microporous polymers (see figure) with phosphine or phosphine oxide as connecting nodes were prepared. These materials exhibit high surface areas and excellent carbon dioxide capture capacities. Pd nanoparticles supported on the polymeric networks were also prepared; they exhibit high catalytic activity for Suzuki reactions.

    25. Homogeneous Catalysis

      Highly Active and Selective Catalysis of Copper Diphosphine Complexes for the Transformation of Carbon Dioxide into Silyl Formate (pages 10030–10037)

      Dr. Ken Motokura, Daiki Kashiwame, Naoki Takahashi, Dr. Akimitsu Miyaji and Prof. Dr. Toshihide Baba

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201300935

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      What a turnover! Copper diphosphine complexes are highly active and selective homogeneous catalysts for the hydrosilylation of CO2. The turnover number (TON) reaches 70 000 after 24 h with 1,2-bis(diisopropylphosphino)benzene as a ligand under 1 atmosphere of CO2 (see scheme; PMHS=polymethylhydrosiloxane).

    26. Synthetic Methods

      Synthesis of Trisubstituted Ureas by a Multistep Sequence Utilizing Recyclable Magnetic Reagents and Scavengers (pages 10038–10045)

      Quirin M. Kainz, Martin Zeltner, Dr. Michael Rossier, Prof. Dr. Wendelin J. Stark and Prof. Dr. Oliver Reiser

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/chem.201300358

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      Do it magnetically! A small library of trisubstituted ureas and thioureas was synthesized in high yields and purities by a multistep sequence exclusively applying magnetic reagents and scavengers. No purification steps were necessary apart from magnetic decantation, and the resins were recycled if possible. The novel resins were conveniently and efficiently prepared starting from polymer-coated magnetic Co/C or Fe/C nanobeads by microwave protocols.

    27. Electron transport calculations

      Elementary Photoelectronic Processes at a Porphyrin Dye/Single-Walled TiO2 Nanotube Hetero-interface in Dye-Sensitized Solar Cells: A First-Principles Study (pages 10046–10056)

      Dr. Cunku Dong, Prof. Xin Li, Wei Zhao, Pengfei Jin, Xiujuan Fan and Prof. Jingyao Qi

      Version of Record online: 13 JUN 2013 | DOI: 10.1002/chem.201301035

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      Electron transport in solar cells: The elementary interfacial photoelectronic processes in one-dimensional single-walled TiO2 nanotube-based dye-sensitized solar cells (DSSCs) have been elucidated by quantum-chemical calculations. The photogenerated electron undergoes ultrafast injection into the conduction band of a TiO2 nanotube and is then transported along the nanotube by means of the Ti 3dmath image orbitals, offering a unidirectional charge-carrier pathway for massive electron collection in the electrode (see graphic).

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