Chemistry - A European Journal

Cover image for Vol. 19 Issue 5

January 28, 2013

Volume 19, Issue 5

Pages 1513–1834

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: Giant Residual Dipolar 13C–1H Couplings in High-Spin Organoiron Complexes: Elucidation of Their Structures in Solution by 13C NMR Spectroscopy (Chem. Eur. J. 5/2013) (page 1513)

      Matthias Kruck, Prof. Dr. Hubert Wadepohl, Prof. Dr. Markus Enders and Prof. Dr. Lutz H. Gade

      Version of Record online: 17 JAN 2013 | DOI: 10.1002/chem.201390010

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      The paramagnetic FeII high-spin complexes which partially align in the magnetic field of the NMR spectrometer. This results in giant residual diploar couplings (RDCs), the analysis of which allows the structural refinement of the iron complexes. The approach provides an additional analytical tool for the characterization of small paramagnetic complexes in solution. The study has been carried out in Heidelberg and its castle is shown in the background. For more details see the Full Paper by M. Enders, L. Gade et al. on page 1599 ff.

  2. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Corrigendum: Pnicogen Bonds: A New Molecular Linker? (page 1526)

      Stefan Zahn, René Frank, Prof. Evamarie Hey-Hawkins and Prof. Barbara Kirchner

      Version of Record online: 17 JAN 2013 | DOI: 10.1002/chem.201204538

      This article corrects:

      Pnicogen Bonds: A New Molecular Linker?

      Vol. 17, Issue 22, 6034–6038, Version of Record online: 18 APR 2011

  4. News

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

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

      Basic Principles and Current Trends in Colloidal Synthesis of Highly Luminescent Semiconductor Nanocrystals (pages 1534–1546)

      Dr. Pavel Samokhvalov, Dr. Mikhail Artemyev and Prof. Dr. Igor Nabiev

      Version of Record online: 10 JAN 2013 | DOI: 10.1002/chem.201202860

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      Joining the (quantum) dots: Recent progress in the synthesis of highly luminescent CdSe, CdS, ZnSe, and other AIIBVI core–shell colloidal quantum dots and the influence of the core structure and the core–shell interface on their luminescence quantum yield (see figure) is reported in this Minireview. Short- and long-term prospects for the development of techniques for producing fluorescent quantum dots for biological and technological applications are discussed.

  6. Communications

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

      Ratiometric Detection of Viscosity Using a Two-Photon Fluorescent Sensor (pages 1548–1553)

      Fei Liu, Dr. Tong Wu, Jianfang Cao, Shuang Cui, Dr. Zhigang Yang, Dr. Xinxin Qiang, Dr. Shiguo Sun, Dr. Fengling Song, Dr. Jiangli Fan, Jingyun Wang and Prof. Xiaojun Peng

      Version of Record online: 19 DEC 2012 | DOI: 10.1002/chem.201202646

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      In the thick of it: A carbazole-based cyanine derivative has been used as a ratiometric fluorescent sensor to detect mitochondrial viscosities over the range 1–950 cP within live cells and living tissues by using two-photon microscopy. Its success is based on the fast- and low-barrier rotation around its methine bond (see figure) and the huge increase of the fluorescence quantum yield (QY) from the loss of mobility in viscous media.

    2. Homogeneous Catalysis

      A Neutral, Chiral, Bis(imidazolidine)-Derived NCN-Type Palladium Pincer Complex with Catalytic Activity (pages 1554–1557)

      Prof. Dr. Takayoshi Arai, Ikiyo Oka, Takuma Morihata, Atsuko Awata and Prof. Dr. Hyuma Masu

      Version of Record online: 4 JAN 2013 | DOI: 10.1002/chem.201204017

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      Caught in a pincer: A chiral, imidazolidine-derived NCN-type palladium pincer complex has been prepared using a ligand introduction technique. Single-crystal X-ray diffraction analysis of this complex showed a well-organized asymmetric sphere. The neutral palladium/chloride version exhibited significant catalytic activity for the reaction of nitroalkenes with malononitrile to give products in a highly enantioselective manner (see scheme).

    3. Magnesium Silicate Nanotubes

      Programmed Synthesis of Magnetic Magnesium Silicate Nanotubes with High Adsorption Capacities for Lead and Cadmium Ions (pages 1558–1562)

      Dr. Chang-Yan Cao, Fang Wei, Jin Qu and Prof. Wei-Guo Song

      Version of Record online: 4 JAN 2013 | DOI: 10.1002/chem.201203986

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      Magnetic nanotubes formed with magnesium silicate (γ-Fe2O3@MgSNTs) were produced by a well-controlled programmed synthesis from carbon nanotubes (CNTs, see scheme). The nanotubes show high adsorption capacities for PbII and CdII. An ion-exchange mechanism between the MgII ions and PbII or CdII ions was proposed and confirmed.

    4. Photocatalysis

      Photocatalytic Oxidation of Organic Compounds in Water by Using Ruthenium(II)–Pyridylamine Complexes as Catalysts with High Efficiency and Selectivity (pages 1563–1567)

      Shingo Ohzu, Dr. Tomoya Ishizuka, Yuichirou Hirai, Prof. Dr. Shunichi Fukuzumi and Prof. Dr. Takahiko Kojima

      Version of Record online: 13 DEC 2012 | DOI: 10.1002/chem.201203430

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      The photocatalytic oxidation of organic substrates such as alcohols was conducted in the presence of RuII–aqua complexes as oxidation catalysts, [RuII(bpy)3]2+ as a photosensitizer and electron mediator, and a CoIII complex as a sacrificial oxidant (see scheme). The catalytic systems exhibited high efficiency to achieve turnover numbers of over 8000.

    5. Mesoporous Materials

      Synthesis of Porous Amorphous FePO4 Nanotubes and Their Lithium Storage Properties (pages 1568–1572)

      Ren Cai, Dr. Yaping Du, Wenyu Zhang, Huiteng Tan, Tao Zeng, Xin Huang, Hongfen Yang, Chunping Chen, Hai Liu, Jixin Zhu, Shengjie Peng, Jing Chen, Prof. Yuliang Zhao, Prof. Haichen Wu, Prof. Yizhong Huang, Prof. Rong Xu, Prof. Tuti Mariana Lim, Prof. Qichun Zhang, Prof. Hua Zhang and Prof. Qingyu Yan

      Version of Record online: 20 DEC 2012 | DOI: 10.1002/chem.201203935

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      Holey pipes: An oil-phase chemical route was used to prepare porous amorphous a-FePO4 nanotubes. In the etching process, Fe2O3 reacted with weak acid, resulting in nanotubes with a pore size of 2–10 nm. The porous nanotubes show good cathode performance in lithium ion batteries owing to their hollow structure and small pore size.

    6. Diazo Compounds

      Reactivity of Stabilized Vinyl Diazo Derivatives toward Unsaturated Hydrocarbons: Regioselective Gold-Catalyzed Carbon–Carbon Bond Formation (pages 1573–1576)

      Prof. José Barluenga, Giacomo Lonzi, Prof. Miguel Tomás and Dr. Luis A. López

      Version of Record online: 19 DEC 2012 | DOI: 10.1002/chem.201203217

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      They struck gold! New reaction modes were observed in the gold-catalyzed reaction of alkenyldiazo compounds and unsaturated substrates. The process represents a new C[BOND]C bond-formation reaction in which alkenes, alkynes, and arenes are active reagents for the Cγ-allylation, -allenylation, and -arylation, respectively, of alkenyldiazo substrates (see scheme). The reactivity pattern is likely to rely on the formation of a highly electrophilic alkenylgold carbenoid, which may be involved in a carbocation-type mechanism.

    7. Janus Particles

      Wireless Electrografting of Molecular Layers for Janus Particle Synthesis (pages 1577–1580)

      Chawanwit Kumsapaya, Marie-France Bakaï, Dr. Gabriel Loget, Bertrand Goudeau, Dr. Chompunuch Warakulwit, Prof. Jumras Limtrakul, Prof. Alexander Kuhn and Dr. Dodzi Zigah

      Version of Record online: 28 DEC 2012 | DOI: 10.1002/chem.201204198

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      Glassy carbon beads are selectively functionalized on one side with an ultrathin organic layer by bipolar electrochemical reduction of diazonium salts to give Janus-type beads with a hybrid organic–inorganic composition (see scheme). The presence of the grafted organic layers is revealed either by co-adsorption of gold nanoparticles or by coupling with a fluorescent molecule.

    8. Click Chemistry

      “Click” Bis-Triazoles as Neutral C[BOND]H⋅⋅⋅Anion-Acceptor Organocatalysts (pages 1581–1585)

      Stephan Beckendorf, Sören Asmus, Dr. Christian Mück-Lichtenfeld and Dr. Olga García Mancheño

      Version of Record online: 20 DEC 2012 | DOI: 10.1002/chem.201203360

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      A new player on the field! “Click” bis-triazoles have been introduced as a highly efficient new class of neutral C[BOND]H⋅⋅⋅anion-binding organocatalysts (see scheme). DFT and NMR studies were used to confirm this activation modus and identify the optimal catalyst.

    9. Nerve Agents

      Neutral 1,3-Diindolylureas for Nerve Agent Remediation (pages 1586–1590)

      Andrea Barba-Bon, Prof. Ana M. Costero, Prof. Margarita Parra, Prof. Salvador Gil, Prof. Ramón Martínez-Máñez, Dr. Félix Sancenón, Prof. Philip A. Gale and Dr. Jennifer R. Hiscock

      Version of Record online: 23 DEC 2012 | DOI: 10.1002/chem.201202028

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      Efficient neutralization of nerve-agent simulants by 1,3-diindolylureas in a neutral medium was investigated (see scheme; DCP=diethylchlorophosphate, DCNP=diethylcyanophosphonate). The rate of hydrolysis of the simulants was found to increase by as much as 45 % in the presence of these compounds. A mechanism based on the simulant complexation was established.

  7. Full Papers

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

      Controlled Stacking and Unstacking of Peripheral Chlorophyll Units Drives the Spring-Like Contraction and Expansion of a Semi-Artificial Helical Polymer (pages 1592–1598)

      Prof. Dr. Munenori Numata, Daiki Kinoshita, Naoya Hirose, Dr. Tomohiro Kozawa, Prof. Hitoshi Tamiaki, Yoshihiro Kikkawa and Dr. Masatoshi Kanesato

      Version of Record online: 10 JAN 2013 | DOI: 10.1002/chem.201203569

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      Spring to life: The self-assembly of peripheral amphiphilic chlorophyll units endows a helical semi-artificial polysaccharide with a dynamic spring-like motion. Strong π–π stacking of these peripheral chlorophyll units led to the contraction of the polymer; expansion occurred after cooperative molecular recognition of bipyridyl-type ligands with pairs of chlorophyll units (see scheme).

    2. NMR Spectroscopy

      Giant Residual Dipolar 13C–1H Couplings in High-Spin Organoiron Complexes: Elucidation of Their Structures in Solution by 13C NMR Spectroscopy (pages 1599–1606)

      Matthias Kruck, Prof. Dr. Hubert Wadepohl, Prof. Dr. Markus Enders and Prof. Dr. Lutz H. Gade

      Version of Record online: 10 JAN 2013 | DOI: 10.1002/chem.201203450

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      Aligning the dipoles: Giant residual dipolar couplings (RDCs) of up to 30 Hz have been observed in paramagnetic NMR spectra of high-spin FeII–alkyl complexes. Analysis of the measured RDCs allowed the structural refinement of these relatively small molecules in solution and hence adds a valuable analytical tool for the identification of paramagnetic complexes in solution (see figure).

    3. Metal–Organic Frameworks

      Crystal Structures and Proton Conductivities of a MOF and Two POM–MOF Composites Based on CuII Ions and 2,2′-Bipyridyl-3,3′-dicarboxylic Acid (pages 1607–1616)

      Prof. Dr. Meilin Wei, Xiaoxiang Wang and Dr. Xianying Duan

      Version of Record online: 13 DEC 2012 | DOI: 10.1002/chem.201203154

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      MOF connections: Three types of proton carriers are assembled in 1D hydrophilic channels of 3D metal–organic frameworks (MOFs) with two traditional but distinct building blocks, the metal N-heterocyclic multi-carboxylic acid frameworks and polyoxometalates (POMs), for the first time (see figure). These ordered poly-POM–MOFs show good proton conductivity across a wide range of temperature and relative humidity (RH). They could be models to provide valuable points for establishing structure–activity relationships.

    4. Macrocycles

      Topology Switching in [32]Heptaphyrins Controlled by Solvent, Protonation, and meso Substituents (pages 1617–1628)

      Dr. Mercedes Alonso, Prof. Paul Geerlings and Prof. Frank De Proft

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201203295

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      Flicking the magnetic switch: [32]Heptaphyrin can switch between three distinct π-conjugation topologies without breaking the macrocycle (see scheme). Protonation, solvent, and meso substituents control the topology. In the neutral state, the antiaromatic figure-eight conformation is preferred by most substituents. However, mono- and triprotonated species adopt an aromatic Möbius structure. Topology switching induces a large change in magnetic properties.

    5. Mixed-Valent Compounds

      Hydride Reactivity of NiII[BOND]X[BOND]NiII Entities: Mixed-Valent Hydrido Complexes and Reversible Metal Reduction (pages 1629–1636)

      Henrike Gehring, Ramona Metzinger, Christian Herwig, Julia Intemann, Prof. Dr. Sjoerd Harder and Prof. Dr. Christian Limberg

      Version of Record online: 4 JAN 2013 | DOI: 10.1002/chem.201203201

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      Ni–H in the claw: An investigation of the chemistry of nickel hydride within a ligand framework that is composed of two β-diketiminato binding sites has led to the observation of remarkable reactivities and rare structural features, including a mixed-valent dinickel–hydride core (see figure) and a thiolate-bridged NiINiI complex.

    6. Reaction Mechanisms

      A Theoretical Investigation on the Strecker Reaction Catalyzed by a TiIV-Complex Catalyst Generated from a Cinchona Alkaloid, Achiral Substituted 2,2′-Biphenol, and Tetraisopropyl Titanate (pages 1637–1646)

      Dr. Zhishan Su, Dr. Weiyi Li, Dr. Jun Wang, Prof. Changwei Hu and Prof. Xiaoming Feng

      Version of Record online: 12 DEC 2012 | DOI: 10.1002/chem.201202237

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      The asymmetric Strecker reaction was shown by DFT calculations to occur through a dual activation mechanism in which TiIV acts as a Lewis acid to activate the aldimine electrophile, whereas the cinchona alkaloid acts as a Lewis base to promote the activation and isomerization of HCN. Asymmetric activation is achieved by the transfer of asymmetry from the chiral cinchonine ligand to the axially flexible achiral biphenol ligand through an interaction with TiIV (see figure).

    7. Macrodipoles

      Theoretical Investigation of Macrodipoles in Supramolecular Columnar Stackings (pages 1647–1657)

      Prof. Dr. Rodrigo Q. Albuquerque, Andreas Timme, Roman Kress, Prof. Dr. Jürgen Senker and Prof. Dr. Hans-Werner Schmidt

      Version of Record online: 12 DEC 2012 | DOI: 10.1002/chem.201202507

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      Vide, supra! Monomers of trisamide derivatives are able to self-assemble to form supramolecular columns that exhibit macrodipoles (μd; see figure). This report shows how the nature of the monomer influences the magnitude of the formed macrodipole and the final properties of these columnar stackings.

    8. Synthetic Methods

      Concise Synthesis of Well-Defined Linear and Branched Oligothiophenes with Nickel-Catalyzed Regiocontrolled Cross-Coupling of 3-Substituted Thiophenes by Catalytically Generated Magnesium Amide (pages 1658–1665)

      Shota Tanaka, Daiki Tanaka, Go Tatsuta, Kohei Murakami, Shunsuke Tamba, Dr. Atsushi Sugie and Prof. Dr. Atsunori Mori

      Version of Record online: 19 DEC 2012 | DOI: 10.1002/chem.201203331

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      Dendrimers: A single-step per extension protocol allows stepwise formation of the thiophene–thiophene bond, with which linear and branched oligothiophenes are synthesized in a remarkably concise manner (see scheme).

    9. Organocatalysis

      One-Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols (pages 1666–1671)

      Dr. Qipu Dai, Dr. Hadi Arman and Prof. Dr. John Cong-Gui Zhao

      Version of Record online: 13 DEC 2012 | DOI: 10.1002/chem.201203104

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      A poor reaction saved! The tandem Henry–Michael reaction of nitromethane and 7-oxo-hept-5-en-1-als catalyzed by quinidine thiourea 1 generates a mixture of diastereomers. A subsequent one-pot tetramethyl guanidine (TMG)-catalyzed tandem retro-Henry–Henry reaction on this diastereomeric mixture provided the corresponding trisubstituted cyclohexanols in high enantioselectivities (up to 96 % ee) and excellent diastereoselectivities (>99:1 d.r.; see scheme).

    10. Prodrugs

      Facile Preparation of Mono-, Di- and Mixed-Carboxylato Platinum(IV) Complexes for Versatile Anticancer Prodrug Design (pages 1672–1676)

      Dr. Jenny Z. Zhang, Dr. Paul Bonnitcha, Ezequiel Wexselblatt, Alice V. Klein, Prof. Yousef Najajreh, Prof. Dan Gibson and Prof. Trevor W. Hambley

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201203159

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      Unsymmetry is beautiful: Platinum(IV) anticancer prodrugs have two axial sites that can be individually functionalized with a diverse range of ligands using controlled strategies to confer additive pharmacological advantages to the platinum component.

    11. Structure–Property Relationships

      Interplay between the Diradical Character and Third-Order Nonlinear Optical Properties in Fullerene Systems (pages 1677–1685)

      Dr. Shabbir Muhammad, Kotaro Fukuda, Takuya Minami, Dr. Ryohei Kishi, Dr. Yasuteru Shigeta and Dr. Masayoshi Nakano

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201203463

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      Heroes in open-shell singlets: The topological dependence of the diradical character and the second hyperpolarizability (γ) in fullerenes was studied (see figure). Fullerene systems have been categorized into three groups, that is, closed-shell (yi=0), intermediate open-shell (0<yi<1), and almost pure open-shell compounds (yi≅1). Interestingly, the γ values of fullerenes with intermediate diradical values are remarkably larger than those of the other two groups.

    12. Dyes/Pigments

      Bioconjugatable Azo-Based Dark-Quencher Dyes: Synthesis and Application to Protease-Activatable Far-Red Fluorescent Probes (pages 1686–1699)

      Arnaud Chevalier, Dr. Cédrik Massif, Prof. Pierre-Yves Renard and Dr. Anthony Romieu

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201203427

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      Black is beautiful! The azo-coupling reaction between Methylene Violet 3RAX and functionalized tertiary anilines has been revisited to obtain a series of novel BHQ-3 dyes with various reactive handles (see figure). The bioconjugation ability of such modified dark quenchers was illustrated by the preparation of urokinase-sensitive fluorogenic probes in good yields.

    13. Microporous Materials

      Diol-Linked Microporous Networks of Cubic Siloxane Cages (pages 1700–1705)

      Yuko Wada, Kenta Iyoki, Dr. Ayae Sugawara-Narutaki, Prof. Dr. Tatsuya Okubo and Prof. Dr. Atsushi Shimojima

      Version of Record online: 30 NOV 2012 | DOI: 10.1002/chem.201202883

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      Out of the cage: A new class of inorganic–organic hybrid microporous materials has been synthesized by treating octa(hydridosilsesquioxane) (H8Si8O12; see figure, D4R=double-four-ring structure) with various diols, including 1,3-propanediol (PD), 1,4-cyclohexanediol (CHD), and 1,3-adamantanediol (AD). The AD-linked product is highly stable against hydrolysis, possibly owing to the higher steric hindrance and the high hydrophobicity of AD links.

    14. Metal–Organic Explosives

      Metal–Organic Frameworks (MOFs) as Safer, Structurally Reinforced Energetics (pages 1706–1711)

      Oleksandr S. Bushuyev, Dr. Geneva R. Peterson, Dr. Preston Brown, Dr. Amitesh Maiti, Dr. Richard H. Gee, Prof. Brandon L. Weeks and Prof. Louisa J. Hope-Weeks

      Version of Record online: 13 DEC 2012 | DOI: 10.1002/chem.201203610

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      More than the sum of the parts: Crystal engineering efforts have generated energetic 2D MOFs to replace conventional heavy-metal-based primers. The building blocks were selected for their structural characteristics and energetic contribution. The long-range structural reinforcement in these layered, multidimensional structures affords desirably attenuated sensitivity to detonation (see figure).

    15. Electrosynthesis

      An Original Electrochemical Pathway for the Synthesis of Porphyrin Oligomers (pages 1712–1719)

      Dr. Delphine Schaming, Dr. Yun Xia, Dr. René Thouvenot and Prof. Laurent Ruhlmann

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/chem.201203271

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      An electrosynthesis process, which allows the formation of four oligomers, containing three, four, or five macrocycles, has been developed. This method is based on nucleophilic attack of porphyrins substituted with several pendant pyridyl groups to the electrogenerated radical cation of zinc β-octaethylporphyrin (see scheme). The newly obtained compounds were investigated with regard to their electrochemical behavior.

    16. Radiochemistry

      A Resin-Linker-Vector Approach to Radiopharmaceuticals Containing 18F: Application in the Synthesis of O-(2-[18F]-Fluoroethyl)-L-tyrosine (pages 1720–1725)

      Dr. Amy C. Topley, Valerio Isoni, Dr. Thomas A. Logothetis, Dr. Duncan Wynn, Dr. Harry Wadsworth, Dr. Alex M. R. Gibson, Imtiaz Khan, Dr. Neil J. Wells, Prof. Cécile Perrio and Prof. Richard C. D. Brown

      Version of Record online: 19 DEC 2012 | DOI: 10.1002/chem.201202474

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      Detachable labels: A resin-linker-vector (RLV) strategy has been developed for the radiosynthesis of tracer molecules containing the radionuclide 18F, in which the linker has tosylate-like reactivity. The potential for the application of the 4-alkylphenylsulfonate in practical radiosyntheses has been illustrated herein by the synthesis of the positron-emission tomography radiotracer O-(2-[18F]-fluoroethyl)-L-tyrosine ([18F]-FET; see scheme).

    17. Cancer Therapy

      Photoactivatable Prodrugs of Highly Potent Duocarmycin Analogues for a Selective Cancer Therapy (pages 1726–1731)

      Prof. Lutz F. Tietze, Dr. Michael Müller, Svenia-C. Duefert, Dr. Kianga Schmuck and Dr. Ingrid Schuberth

      Version of Record online: 7 DEC 2012 | DOI: 10.1002/chem.201202773

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      Retoxification by light: Evaluation of the photochemical properties and the in vitro cytotoxicity in the presence and absence of light revealed for the shown prodrug an excellent suitability for an application in selective cancer therapy. The compound is more than two million times less cytotoxic than the corresponding seco-drug with an IC50=110 fM (see picture).

    18. Nanostructures

      Facile Low-Temperature Synthesis of Ultralong Monodisperse ZnSe Quantum Wires with the Assistance of Ag2S (pages 1732–1739)

      Prof. Zhipeng Huang, Lei Pan, Peng Zhong, Maoying Li, Prof. Feng Tian and Prof. Chi Zhang

      Version of Record online: 30 NOV 2012 | DOI: 10.1002/chem.201202462

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      Bird on a quantum wire: Monodisperse Ag2S (or Ag2Se)[BOND]ZnSe quantum wires can be synthesized at 120 °C with the assistance of Ag2S. These quantum wires are uniform in structure and morphology and have an aspect ratio of larger than 100. This method can be also used to fabricate CdSe quantum rods.

    19. Annulene Aromaticity

      Counter-Rotating Spin-Polarised Ring Currents in Odd-Electron Carbocycles (pages 1740–1746)

      Dr. Alessandro Soncini and Prof. Patrick W. Fowler

      Version of Record online: 6 DEC 2012 | DOI: 10.1002/chem.201202572

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      Aromaticity: an open and shut case? Orbital ring currents from π electrons of opposite spin are opposed in odd-electron systems, but reinforce in even-electron systems (see figure).

    20. Asymmetric Synthesis

      Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael–Cyclization Reaction (pages 1747–1753)

      Hao Wu, Li-Li Zhang, Zhi-Qing Tian, Dr. Yao-Dong Huang and Prof. Yong-Mei Wang

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201203221

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      Cascade to complexity: Bispirooxindole derivatives containing three stereocenters, including two spiro quarternary centers, were synthesized in a high-yielding, atypically rapid, and stereocontrolled cascade Michael–cyclization reaction between methyleneindolinones and isothiocyanato oxindoles catalyzed by a bi- or multifunctional organocatalyst (see scheme).

    21. Histidine Complexes

      pH-Dependent Coordination of AgI Ions by Histidine: Experiment, Theory, and a Model for SilE (pages 1754–1761)

      Laurent Mirolo, Tobias Schmidt, Dr. Sonja Eckhardt, Prof. Dr. Markus Meuwly and Prof. Dr. Katharina M. Fromm

      Version of Record online: 13 DEC 2012 | DOI: 10.1002/chem.201201844

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      SilE billy: Histidine–silver complexes were synthesized at different pH values and a model was proposed for the mode of action of the silver-binding protein SilE, which is involved in the defense mechanism of bacteria against silver ions (see figure).

    22. Peptide Design

      Multimerization of an Apoptogenic TRAIL-Mimicking Peptide by Using Adamantane-Based Dendrons (pages 1762–1768)

      Dr. Giuseppe Lamanna, Dr. Cristian R. Smulski, Neila Chekkat, Dr. Karine Estieu-Gionnet, Dr. Gilles Guichard, Prof. Sylvie Fournel and Dr. Alberto Bianco

      Version of Record online: 13 DEC 2012 | DOI: 10.1002/chem.201202415

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      TRAIL-blazers: Multimerization of an apoptogenic peptide that mimics the natural tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) by using adamantane-based dendrons remarkably increased the selective binding affinity to TRAIL receptor 2 (TR2; see scheme). Only multimeric forms of the ligands could induce cell death in TR2-expressing cells, thus triggering a substantial TR2-dependent apoptotic response in vitro. This multivalency effect is important in biological ligand/receptor interactions.

    23. Helical Structures

      Sonication-Induced Coiled Fibrous Architectures of Boc-L-Phe-L-Lys(Z)-OMe (pages 1769–1777)

      Rouzbeh Afrasiabi and Prof. Dr. Heinz-Bernhard Kraatz

      Version of Record online: 19 DEC 2012 | DOI: 10.1002/chem.201202268

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      Mobilis in mobili: A novel dipeptide organogelator capable of forming highly organised helical assemblies was reported (see figure). Boc-L-Phe-L-Lys(Z)-OMe (Z=carbobenzyloxy) not only organises into multi-hierarchical assemblies but also demonstrates temperature-dependent chiroptical switching and thixotropic behaviour. This small dipeptide may provide new avenues for understanding and fabricating novel and readily accessible nanomaterials.

    24. Cancer Therapy

      Bioresponsive Hyaluronic Acid-Capped Mesoporous Silica Nanoparticles for Targeted Drug Delivery (pages 1778–1783)

      Zhaowei Chen, Zhenhua Li, Youhui Lin, Meili Yin, Prof. Dr. Jinsong Ren and Prof. Dr. Xiaogang Qu

      Version of Record online: 9 JAN 2013 | DOI: 10.1002/chem.201202038

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      Go nano! Mesoporous silica nanoparticle-based nanoreservoirs that are end-capped with hyaluronic acid have been constructed and demonstrate great potential for cell-specific targeting and controlled drug release in response to specific enzymes present at the tumor site (see figure).

    25. Carborates

      Quantum-Chemical and Electrochemical Investigation of the Electrochemical Windows of Halogenated Carborate Anions (pages 1784–1795)

      Prof. Dr. René T. Boeré, Christoph Bolli, Prof. Dr. Maik Finze, Dr. Alexander Himmelspach, Prof. Dr. Carsten Knapp and Dr. Tracey L. Roemmele

      Version of Record online: 11 DEC 2012 | DOI: 10.1002/chem.201202475

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      To the limit: Halogenated carborates are very important, weakly coordinating anions that are strongly resistant to electrochemical oxidation and reduction. Electrochemical measurements of the oxidation and reduction processes, supported by quantum-chemical calculations, have established the range of electrochemical stability for a wide variety of halogenated carborates (see figure; R=H, Me; X=H, Me, F, Cl, Br, I; Y=F, Cl, Br, I).

    26. Hydride–Iridafuran Formation

      Aldehyde-Assisted Hydrogen Transfer during the Formation of Hydride–Iridafurans from Alkynes and Aldehydes (pages 1796–1809)

      Dr. Cristina M. Posadas, Dr. Nuria Rendón, Dr. Joaquín López-Serrano, Dr. Yohar A. Hernández, Dr. Eleuterio Álvarez, Prof. Dr. Margarita Paneque and Prof. Dr. Manuel L. Poveda

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201202794

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      Aldehydes as a shuttle for H transfer: One equivalent each of CO2Me-substituted alkynes (DMAD: dimethyl acetylenecarboxylate, MP: methyl propiolate) and aldehydes (both aromatic and aliphatic) undergo oxidative coupling to IrI compounds to form hydride–iridafurans (see scheme). This process is assisted by a second molecule of aldehyde, which acts as a shuttle for the aldehyde H atom.

    27. Oxidation

      Remarkable Solvent, Porphyrin Ligand, and Substrate Effects on Participation of Multiple Active Oxidants in Manganese(III) Porphyrin Catalyzed Oxidation Reactions (pages 1810–1818)

      Min Young Hyun, Young Dan Jo, Jun Ho Lee, Hong Gyu Lee, Hyun Min Park, In Hong Hwang, Kyeong Beom Kim, Prof. Suk Joong Lee and Prof. Cheal Kim

      Version of Record online: 23 NOV 2012 | DOI: 10.1002/chem.201202640

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      MnV[DOUBLE BOND]O versus MnIII[BOND]OOR: Three active oxidants (MnV[DOUBLE BOND]O, MnIV[DOUBLE BOND]O, and MnIII[BOND]OOR) operate simultaneously in Mn(porphyrin)–complex-catalyzed oxidation reactions. The participation of the active oxidants is remarkably influenced by the solvent polarity, the concentration and type of substrate, and the porphyrin ligands (see figure).

    28. Sensitizers

      The Role of π Bridges in High-Efficiency DSCs Based on Unsymmetrical Squaraines (pages 1819–1827)

      Dr. Jared H. Delcamp, Dr. Yanrong Shi, Dr. Jun-Ho Yum, Dr. Tissa Sajoto, Elisa Dell'Orto, Dr. Stephen Barlow, Dr. Mohammad K. Nazeeruddin, Prof. Seth R. Marder and Prof. Michael Grätzel

      Version of Record online: 18 DEC 2012 | DOI: 10.1002/chem.201202677

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      Bridge to success: The squaraine sensitizer (see figure) demonstrates a power conversion efficiency of 7.3 % for liquid-electrolyte dye-sensitized solar cells and 7.9 % for co-sensitized cells with another metal-free dye. A near-ideal IPCE curve shape is realized for this dye, with an excellent short circuit current of 18.0 mA cm−2. This strong current is, in part, due to a high molar absorptivity of >5 000 M−1 cm−1 from 400 to 724 nm.

    29. Bipolar Host Materials

      Simple Bipolar Hosts with High Glass Transition Temperatures Based on 1,8-Disubstituted Carbazole for Efficient Blue and Green Electrophosphorescent Devices with “Ideal” Turn-on Voltage (pages 1828–1834)

      Dr. Hong Huang, Yixin Wang, Biao Pan, Xiao Yang, Prof. Dr. Lei Wang, Dr. Jiangshan Chen, Prof. Dr. Dongge Ma and Prof. Dr. Chuluo Yang

      Version of Record online: 23 NOV 2012 | DOI: 10.1002/chem.201202329

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      Glow in the dark: Two hybrids based on 1,8-disubstituted carbazole with a twist structure were designed and synthesized. Blue phosphorescent organic light-emitting devices (PhOLEDs) containing benzimidazole units exhibited a similar performance to a similarly structured device based on the mCP host (mCP = N,N′-dicarbazoyl-3,5-benzene). Green PhOLEDs employing the new host material 1,8-OXDCz exhibited an ideal turn-on voltage (2.5 V at 1.58 cd m−2), a maximum current efficiency of 73.9 cd A−1, and a power efficiency of 89.7 lm W−1 (see figure).

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