Chemistry - A European Journal

Cover image for Vol. 20 Issue 7

February 10, 2014

Volume 20, Issue 7

Pages 1769–2079

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Cover Profile
    4. Graphical Abstract
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: An Unexpected Fluctuating Reactivity for Odd and Even Carbon Numbers in the TiO2-Based Photocatalytic Decarboxylation of C2-C6 Dicarboxylic Acids (Chem. Eur. J. 7/2014) (page 1769)

      Yiran Sun, Dr. Wei Chang, Dr. Hongwei Ji, Dr. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Version of Record online: 2 FEB 2014 | DOI: 10.1002/chem.201490023

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      The degradation behavior… of five straight-chain dicarboxylic acids were compared in aqueous TiO2-based photocatalysis. The reactivity is found to be dependent on the number of carbon atoms. Dicarboxylic acids with an even number of carbon atoms were degraded more slowly than those with an odd number of carbon atoms. This unusual behavior is very closely related to the different pre-coordination modes of the acids with the photocatalyst. For more details, see the Full Paper by J. C. Zhao et al. on page 1861 ff.

    2. You have free access to this content
      Back Cover: Regeneration of a Conjugated sp2 Graphene System through Selective Defunctionalization of Epoxides by Using a Proven Synthetic Chemistry Mechanism (Chem. Eur. J. 7/2014) (page 2084)

      Chun Kiang Chua and Prof. Martin Pumera

      Version of Record online: 2 FEB 2014 | DOI: 10.1002/chem.201490026

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      Selective defunctionalization of epoxides on graphene oxide using proven synthetic chemistry is shown on the background of layered rock structures in Zion National Park. For more details, see the Full Paper by M. Pumera and C. K. Chua on page 1871 ff.

  2. Cover Profile

    1. Top of page
    2. Cover Pictures
    3. Cover Profile
    4. Graphical Abstract
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. You have free access to this content
      An Unexpected Fluctuating Reactivity for Odd and Even Carbon Numbers in the TiO2-Based Photocatalytic Decarboxylation of C2–C6 Dicarboxylic Acids (page 1772)

      Yiran Sun, Dr. Wei Chang, Dr. Hongwei Ji, Dr. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Version of Record online: 27 JAN 2014 | DOI: 10.1002/chem.201304931

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      The degradation behavior of straight-chain dicarboxylic acids fluctuates with the number of carbon atoms under TiO2-based photocatalysis. Dicarboxylic acids with an even number of carbon atoms degraded slower than those with an odd number of carbon atoms.” Read more about the story behind the cover in the Cover Profile and about the research itself on page 1861 ff. (DOI: 10.1002/chem.201303236).

  3. Graphical Abstract

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

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

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

      Ordered Hybrids from Template-Free Organosilane Self-Assembly (pages 1790–1806)

      Dr. Abraham Chemtob, Dr. Lingli Ni, Prof. Céline Croutxé-Barghorn and Prof. Bruno Boury

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/chem.201303070

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      A successful marriage: Periodically ordered hybrids represent the successful marriage of organosilane sol–gel polymerization and supramolecular chemistry. Their template-free and single-step synthesis procedure has no equivalent in polymer chemistry (see scheme)

  6. Communications

    1. Top of page
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    3. Cover Profile
    4. Graphical Abstract
    5. News
    6. Minireview
    7. Communications
    8. Full Papers
    1. Dyes/Pigments

      Perkin’s and Caro’s Mauveine in Queen Victoria’s Lilac Postage Stamps: A Chemical Analysis (pages 1808–1812)

      Dr. Maria da Conceição Oliveira, Ana Dias, Dr. Peter Douglas and Prof. J. Sérgio Seixas de Melo

      Version of Record online: 23 JAN 2014 | DOI: 10.1002/chem.201303232

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      Victorian dyes: Lilac postage stamps of the Victorian period have been analyzed and compared with historical samples of mauveine from W. H. Perkin and H. Caro; it is shown that many lilac stamps are not dyed with mauveine, but a small group of lilac 6d stamps dating from about 1865–1870 are, and for these there is evidence of mauveine made by both the Perkin and Caro synthetic routes.

    2. Synthetic Methods

      ZnII- and AuI-Catalyzed Regioselective Hydrative Oxidations of 3-En-1-ynes with Selectfluor: Realization of 1,4-Dioxo and 1,4-Oxohydroxy Functionalizations (pages 1813–1817)

      Dr. Appaso Mahadev Jadhav, Sagar Ashok Gawade, Dr. Dhananjayan Vasu, Dr. Ramesh B. Dateer and Prof. Dr. Rai-Shung Liu

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201304322

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      Catalytic 1,4-dioxo functionalizations of 3-en-1-ynes to Z- and E-2-en-1,4-dicarbonyl compounds are described. Regioselective difunctionalization was achieved in a one-pot operation through an initial alkyne hydration and was followed by in situ Selectfluor oxidations (see scheme). The presence of pyridine alters the chemoselectivity to provide the 4-hydroxy-2-en-1-carbonyl product instead.

    3. Ring-Opening Reactions

      Ruthenium-Catalyzed Synthesis of Indoles from Anilines and Epoxides (pages 1818–1824)

      Dr. Miguel Peña-López, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Version of Record online: 23 JAN 2014 | DOI: 10.1002/chem.201304432

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      Ru creative: A general ruthenium-catalyzed synthesis of indoles from readily available anilines and epoxides has been developed (see scheme). Generation of water and molecular hydrogen as the only by-products makes this atom-efficient process attractive for the synthesis of heteroarenes.

    4. Catalysis

      Copper-Catalyzed Cascade Cyclization Reaction of 2-Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H-Benzotriazoles in Water (pages 1825–1828)

      Xiaobo Shang, Shixian Zhao, Prof. Dr. Wanzhi Chen, Dr. Chao Chen and Prof. Dr. Huayu Qiu

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/chem.201303712

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      A new approach to the synthesis of 2 H-benzotriazoles is described. This strategy is based on the copper-catalyzed C[BOND]N coupling of 2-haloaryltriazenes or 2-haloazo compounds with sodium azide and the intramolecular addition of a nitrene species to N[DOUBLE BOND]N bonds (see scheme; TMEDA=N,N,N′,N′-tetramethylethylenediamine; CTAB=hexadecyltrimethylammonium bromide). This approach allows the synthesis of various N-amino- and N-aryl-2 H-benzotriazoles in water, in good to excellent yields.

    5. Silica Mesochannels

      Vertically Oriented Silica Mesochannels as the Template for Electrodeposition of Polyaniline Nanostructures and Their Electrocatalytic and Electroanalytical Applications (pages 1829–1833)

      Longhua Ding, Wanzhen Li, Qiaohong Wang, Qinqin Sun, Yayun He and Prof. Bin Su

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/chem.201303807

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      Caught on film: Mesoporous silica films (MSF) with vertically oriented mesochannels on a conductive substrate serve as a hard-template for electrodeposition of polyaniline (PANI; ITO=indium tin oxide; see figure). Such PANI nanostructures are confined in an orderly fashion in silica mesochannels and produce a robust hybrid film. The film displays good electrocatalytic activity toward oxidation of ascorbic acid and can be used for potentiometric pH-sensing.

    6. Catalysis

      CuI/Pd0 Cooperative Dual Catalysis: Tunable Stereoselective Construction of Tetra-Substituted Alkenes (pages 1834–1838)

      Sébastien Vercruysse, Loïc Cornelissen, Fady Nahra, Laurent Collard and Prof. Olivier Riant

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/chem.201304284

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      Two catalysts are better than one: A tunable and stereoselective dual catalytic system using copper and palladium reagents is described (see scheme; Pin = pinacol). This cooperative silylcupration and palladium-catalyzed allylation readily affords trisubstituted alkenylsilanes. Fine-tuning the reaction conditions allows selective access to one stereoisomer over the other. This new methodology tolerates different substituents on both coupling partners and is highly stereoselective.

    7. Synthetic Methods

      Copper-Promoted Oxidative Coupling of Enamides and Alkynes for the Synthesis of Substituted Pyrroles (pages 1839–1842)

      Mi-Na Zhao, Zhi-Hui Ren, Prof. Yao-Yu Wang and Prof. Dr. Zheng-Hui Guan

      Version of Record online: 22 JAN 2014 | DOI: 10.1002/chem.201304565

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      Oxidative coupling: A new method for the copper-promoted oxidative coupling of enamides with alkynes has been developed (see scheme; DCE = 1,2-dichloroethane). This reaction directly affords substituted pyrroles in good yields through C[BOND]H and N[BOND]H bond functionalization of enamides.

    8. Triple Bond Chemistry

      Alkylation of Terminal Alkynes with Transient σ-Alkylpalladium(II) Complexes: A Carboalkynylation Route to Alkyl-Substituted Alkynes (pages 1843–1846)

      Ming-Bo Zhou, Xiao-Cheng Huang, Yan-Yun Liu, Dr. Ren-Jie Song and Prof. Dr. Jin-Heng Li

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/chem.201303879

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      Three times the fun: A mild and general alkylation of terminal alkynes with transient σ-alkylpalladium(II) complexes for assembling alkyl-substituted alkynes is described (see scheme). This method represents a new way to the use of transient σ-alkylpalladium(II) complexes in organic synthesis through 1,2-carboalkynylation of alkenes.

  7. Full Papers

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

      Total Synthesis and Structure Revision of Didemnaketal B (pages 1848–1860)

      Prof. Dr. Haruhiko Fuwa, Takashi Muto, Kumiko Sekine and Prof. Dr. Makoto Sasaki

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303713

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      Twelve years after the initial isolation report, the correct stereostructure of didemnaketal B (see figure), a potent HIV-1 protease inhibitor, was established through stereoselective total synthesis.

    2. Photocatalysis

      An Unexpected Fluctuating Reactivity for Odd and Even Carbon Numbers in the TiO2-Based Photocatalytic Decarboxylation of C2-C6 Dicarboxylic Acids (pages 1861–1870)

      Yiran Sun, Dr. Wei Chang, Dr. Hongwei Ji, Dr. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201303236

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      Degrading behavior: The degradation behavior of straight-chain dicarboxylic acids fluctuates with the number of carbon atoms under TiO2-based photocatalysis. Dicarboxylic acids with an even number of carbon atoms degraded slower than those with an odd number of carbon atoms. This fluctuation arises from the difference in binding modes between the substrates and the TiO2 surface for odd and even carbon chain lengths (see figure).

    3. Graphene

      Regeneration of a Conjugated sp2 Graphene System through Selective Defunctionalization of Epoxides by Using a Proven Synthetic Chemistry Mechanism (pages 1871–1877)

      Chun Kiang Chua and Prof. Martin Pumera

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/chem.201304131

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      Removing oxygen: The use of an indium/indium(I) chloride mixture to enhance the electrical properties of reduced graphene oxide (RGO) is described. The structural characterizations based on XPS, NMR, Raman, and FTIR spectroscopy, thermogravimetric, and conductivity analyses of RGO and control experiments highlighted the feasibility of indium/indium(I) chloride in the selective removal of oxygen-containing groups based on de-epoxidation.

    4. Supramolecular Chemistry

      Supramolecular ssDNA Templated Porphyrin and Metalloporphyrin Nanoassemblies with Tunable Helicity (pages 1878–1892)

      Gevorg Sargsyan, Prof. Brian M. Leonard, Prof. Jan Kubelka and Prof. Milan Balaz

      Version of Record online: 23 JAN 2014 | DOI: 10.1002/chem.201304153

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      Porphyrin–diaminopurine conjugates form left-handed and right-handed nanowires along an oligothymidine template, giving almost mirror-image circular dichroisms signals, by directional hydrogen bonding. Porphyrin nanowires displayed high circular dichroism anisotropies, strong electronic coupling between porphyrins, and high thermal and pH stability (see figure).

    5. Zeolite Synthesis

      Topotactic Conversion of β-Helix-Layered Silicate into AST-Type Zeolite through Successive Interlayer Modifications (pages 1893–1900)

      Yusuke Asakura, Ryosuke Takayama, Dr. Toshimichi Shibue and Prof. Dr. Kazuyuki Kuroda

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303368

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      An AST-type zeolite was synthesized from a layered silicate, β-helix-layered silicate (HLS), through successive interlayer modifications and subsequent interlayer condensation. HLS intercalated with N,N-dimethylpropionamide (see picture) can be converted into an AST-type zeolite by calcination. The utilization of an amide molecule is thus an effective way to control the stacking sequence of silicate layers.

    6. Catalysis

      Reaction Mechanism for the Dual Gold-Catalyzed Synthesis of Dibenzopentalene: A DFT Study (pages 1901–1908)

      Dr. Mie Højer Vilhelmsen and Prof. Dr. A. Stephen K. Hashmi

      Version of Record online: 17 JAN 2014 | DOI: 10.1002/chem.201303636

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      Observation of high importance: A mechanism for the dibenzopentalene synthesis by dual gold activation, investigated by DFT and natural-bond-orbital (NBO) calculations, is presented. Calculations indicate that the previously characterized “dead-end” intermediate, the gem-diaurated dibenzopentalene, might be an active part of the catalytic cycle (see figure).

    7. Heterocycles

      Protonation of Pyridyl-Substituted TTF Derivatives: Substituent Effects in Solution and in the Proton–Electron Correlated Charge-Transfer Complexes (pages 1909–1917)

      Sang Chul Lee, Dr. Akira Ueda, Dr. Akiko Nakao, Prof. Dr. Reiji Kumai, Prof. Dr. Hironori Nakao, Prof. Dr. Youichi Murakami and Prof. Dr. Hatsumi Mori

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201302614

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      Substituent effects on protonated pyridyl-substituted tetrathiafulvalene electron-donor molecules (PyH+-TTF) in solution and in the proton–electron correlated charge-transfer complexes were evaluated. The introduction of the ethylenedithio group electronically and structurally modulated the charge distribution of the unique hydrogen-bonded dimer unit (see figure) as well as the overall molecular arrangement, electronic structure, and conductivity in the charge-transfer complex.

    8. Reaction Mechanisms

      The Mechanism of Gold(I)-Catalyzed Hydroalkoxylation of Alkynes: An Extensive Experimental Study (pages 1918–1930)

      Alexander Zhdanko and Prof. Dr. Martin E. Maier

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201303795

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      Golden mechanism: An extensive experimental study of the mechanism of gold(I)-catalyzed hydroalkoxylation of internal alkynes (see scheme) has been carried out by using NMR spectroscopy. This study is focused on the organogold intermediates, observations of actual catalytic intermediates in situ, and the reaction kinetics.

    9. Organic Light-Emitting Diodes

      2,5-Difluorenyl-Substituted Siloles for the Fabrication of High-Performance Yellow Organic Light-Emitting Diodes (pages 1931–1939)

      Bin Chen, Yibin Jiang, Long Chen, Han Nie, Bairong He, Dr. Ping Lu, Herman H. Y. Sung, Prof. Ian D. Williams, Prof. Hoi Sing Kwok, Prof. Anjun Qin, Prof. Zujin Zhao  and Prof. Ben Zhong Tang 

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201303259

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      Incorporating fluorenyl substituents into the 2,5-positions of silole rings generates efficient solid-state luminogenic materials. The electroluminescent devices made by using the substituted rings as host emitters show yellow light, with high luminance, current efficiency, power efficiency, and external quantum efficiency of up to 44 100 cd m−2, 18.3 cd A−1, 15.7 lm W−1, and 5.5 %, respectively (see figure).

    10. Nanomaterials

      Controllable Blinking-to-Nonblinking Behavior of Aqueous CdTeS Alloyed Quantum Dots (pages 1940–1946)

      Dr. Chaoqing Dong, Heng Liu, Aidi Zhang and Prof. Dr. Jicun Ren

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303605

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      It is nonblinking! The blinking of aqueous CdTeS alloyed quantum dots (QDs) is controlled by the concentration of the thiol ligand and its molecular structure. Highly fluorescent, completely nonblinking QDs have been prepared by using certain thiol ligands as stabilizers in aqueous phase. The suppressed blinking mechanism has been mainly attributed to the elimination of quantum-dot surface traps induced by thiol ligands (see figure).

    11. Silicon–Phosphorus Chemistry

      A Donor-Stabilized Zwitterionic “Half-Parent” Phosphasilene and Its Unusual Reactivity towards Small Molecules (pages 1947–1956)

      Kerstin Hansen, Tibor Szilvási, Dr. Burgert Blom, Dr. Elisabeth Irran and Prof. Dr. Matthias Driess

      Version of Record online: 16 JAN 2014 | DOI: 10.1002/chem.201303906

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      Stable influence: The stabilization of a labile, zwitterionic “half-parent” phosphasilene with 4-dimethylaminopyridine (DMAP) and a small N-heterocyclic carbene (NHC) is reported (see scheme). The unusual reactivity of the DMAP- and NHC-stabilized phosphasilene adduct moieties towards small molecules such as dimethylzinc and H2S, as well as towards N[BOND]H bonds in ammonia and several organoamines, leads to new functional groups in silicon–phosphorus chemistry.

    12. Mesoporous Materials

      Clickable Periodic Mesoporous Organosilicas: Synthesis, Click Reactions, and Adsorption of Antibiotics (pages 1957–1963)

      Dr. Jinsuo Gao, Xueying Zhang, Dr. Shutao Xu, Prof. Feng Tan, Prof. Xinyong Li, Prof. Yaobin Zhang, Prof. Zhenping Qu, Prof. Xie Quan and Dr. Jian Liu

      Version of Record online: 13 NOV 2013 | DOI: 10.1002/chem.201303778

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      Clickable PMOs: Azido periodic mesoporous organosilicas (PMOs) for the adsorption of antibiotics have been prepared (see scheme). Ethane-bridged PMOs, functionalized with azido groups at different densities, were synthesized by using a co-condensation method. Four different alkynes were attached to the azide-terminated PMOs by means of an efficient click reaction, the resulting clicked PMOs showing improved adsorption capacity for antibiotics.

    13. Natural Products

      A General Strategy for the Catalytic, Highly Enantio- and Diastereoselective Synthesis of Indolizidine-Based Alkaloids (pages 1964–1979)

      Falko Abels, Chris Lindemann and Prof. Dr. Christoph Schneider

      Version of Record online: 16 JAN 2014 | DOI: 10.1002/chem.201304086

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      Organocatalysis: A unified, catalytic, and highly stereocontrolled synthesis of a broad range of indolizidine-based alkaloids has been developed that delivers the target alkaloids with high overall yields and excellent optical purity. As a key step, a very convenient three-component Brønsted acid catalyzed vinylogous Mukaiyama–Mannich reaction (VMMR) was employed (see scheme).

    14. Rotational Spectroscopy

      How Water Interacts with Halogenated Anesthetics: The Rotational Spectrum of Isoflurane–Water (pages 1980–1984)

      Qian Gou, Dr. Gang Feng, Dr. Luca Evangelisti, Montserrat Vallejo-López, Lorenzo Spada, Prof. Dr. Alberto Lesarri, Dr. Emilio J. Cocinero and Prof. Dr. Walther Caminati

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201303724

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      The inhaled anesthetic isoflurane (1-chloro-2,2,2-trifluoroethyl difluoromethyl ether) contains several different sites for stereospecific interaction, which may suggest interaction through weak hydrogen or halogen bonding with neuronal ion channels and on the protein binding in the central nervous system. By using Fourier transform microwave spectroscopy, isoflurane was shown to bind to water through a C[BOND]H⋅⋅⋅O weak hydrogen bond (see figure).

    15. Porphyrinoids

      Hückel and Möbius Expanded para-Benziporphyrins: Synthesis and Aromaticity Switching (pages 1985–1997)

      Bartosz Szyszko, Dr. Natasza Sprutta, Dr. Paulina Chwalisz, Dr. Marcin Stępień and Prof. Lechosław Latos-Grażyński

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303676

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      Molecular contortionist: Hückel–Möbius aromaticity switching is observed in a family of expanded benziporphyrins. The changes of π-conjugation topology are induced by temperature changes, acid-base chemistry, as well as metal coordination, and have a marked effect on the spectral signatures of these macrocycles.

    16. Fluorescent Probes

      Rational Design of a Solvatochromic Fluorescent Uracil Analogue with a Dual-Band Ratiometric Response Based on 3-Hydroxychromone (pages 1998–2009)

      Dr. Dmytro Dziuba, Iuliia A. Karpenko, Nicolas P. F. Barthes, Dr. Benoît Y. Michel, Dr. Andrey S. Klymchenko, Dr. Rachid Benhida, Prof. Dr. Alexander P. Demchenko, Prof. Dr. Yves Mély and Prof. Dr. Alain Burger

      Version of Record online: 16 JAN 2014 | DOI: 10.1002/chem.201303399

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      Pimp my dye: A new solvatochromic ratiometric fluorophore from 3-hydroxychromones (3HCs) and uracil fragments is reported (see figure). The data indicate that uracil and 3HC fragments of this derivative are coupled into an electronic conjugated system, which upon excitation attains strong charge-transfer characteristics.

    17. Functionalized Tricyclic Cytosine Analogues Provide Nucleoside Fluorophores with Improved Photophysical Properties and a Range of Solvent Sensitivities (pages 2010–2015)

      Brittney J. Rodgers, Nada A. Elsharif, Nisha Vashisht, Macy M. Mingus, Mark A. Mulvahill, Dr. Gudrun Stengel, Prof. Robert D. Kuchta and Prof. Byron W. Purse

      Version of Record online: 5 DEC 2013 | DOI: 10.1002/chem.201303410

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      All things bright: Improved synthetic methods have been used to prepare a set of new tri- and tetracyclic 2′-deoxycytidine analogues with systematic incorporation of electron-donating and -withdrawing groups. The analogues show patterns of substituent effects on photophysical properties that will make them useful as biophysical probes (see figure).

    18. Photosensitizers

      Peripherally and Axially Carboxylic Acid Substituted Subphthalocyanines for Dye-Sensitized Solar Cells (pages 2016–2021)

      Dr. Mine Ince, Dr. Anaïs Medina, Dr. Jun-Ho Yum, Dr. Aswani Yella, Dr. Christian G. Claessens, Dr. M. Victoria Martínez-Díaz, Prof. Michael Grätzel, Dr. Mohammad K. Nazeeruddin and Prof. Tomás Torres

      Version of Record online: 17 JAN 2014 | DOI: 10.1002/chem.201303639

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      Subphthalocyanines bearing a carboxylic acid group either at the peripheral or axial positions have been synthesized. These dyes have been used for the first time as sensitizers in dye-sensitized solar cells (see figure; FTO = fluorine-doped tin oxide).

    19. Nanostructures

      Hollow and Yolk-Shell Iron Oxide Nanostructures on Few-Layer Graphene in Li-Ion Batteries (pages 2022–2030)

      Dr. Zhenyu Sun, Kunpeng Xie, Dr. Zi An Li, Dr. Ilja Sinev, Petra Ebbinghaus, Dr. Andreas Erbe, Prof. Dr. Michael Farle, Prof. Dr. Wolfgang Schuhmann, Prof. Dr. Martin Muhler and Dr. Edgar Ventosa

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303723

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      Running on empty: Hollow and yolk-shell iron oxide nanostructures supported on few-layer graphene (FLG) were found to be beneficial for the cycling stability in lithium-ion batteries, especially for electrodes with low carbon content (see figure). Further improvement of capacity retention upon cycling was achieved for composites with a hollow structure, obtaining retention values above 97 % after 120 cycles at 1000 mA g−1.

    20. Isomerization

      Solvent Migration in Microhydrated Aromatic Aggregates: Ionization-Induced Site Switching in the 4-Aminobenzonitrile–Water Cluster (pages 2031–2039)

      Takashi Nakamura, Dipl.-Phys. Matthias Schmies, Dipl.-Phys. Alexander Patzer, Prof. Dr. Mitsuhiko Miyazaki, Prof. Dr. Shun-ichi Ishiuchi, Dr. Martin Weiler, Prof. Dr. Otto Dopfer and Prof. Dr. Masaaki Fujii

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201303321

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      Solvation dynamics at the single-molecule level: IR spectroscopy of the isolated 4-aminobenzonitrile–H2O cluster illustrates that photoionization initiates the migration of the H2O ligand from the CN site to the NH site in 100 % yield (see figure).

    21. Synthetic Methods

      Palladium-Catalyzed Coupling Reaction of Perfluoroarenes with Diarylzinc Compounds (pages 2040–2048)

      Dr. Masato Ohashi, Ryohei Doi and Prof. Dr. Sensuke Ogoshi 

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303451

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      Transforming C[BOND]F into C[BOND]C: Pd0/PCy3-catalyzed cross-coupling of C6F6 with a variety of diarylzinc compounds proceeds in the presence of lithium iodide to give pentafluorobiaryl compounds in good-to-excellent yields (see scheme). The key intermediate in this catalytic reaction is a transient, three-coordinated, monophosphine-ligated species, [Pd(C6F5)I(PCy3)], which was generated by oxidative addition of the C[BOND]F bond of C6F6 to [Pd(PCy3)2], followed by dissociation of a PCy3 ligand.

    22. Photosynthesis

      A New Approach for the Photosynthetic Antenna–Reaction Center Complex with a Model Organized Around an s-Triazine Linker (pages 2049–2057)

      Susanne Kuhri, Dr. Georgios Charalambidis, Prof. Panagiotis A. Angaridis, Prof. Theodore Lazarides, Dr. Georgia Pagona, Dr. Nikos Tagmatarchis, Prof. Dr. Athanassios G. Coutsolelos and Prof. Dr. Dirk M. Guldi

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201302632

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      Well-connected: Mimics of the photosynthetic antenna–reaction center complex have been designed and synthesized. BDP-H2P-C60 and BDP-ZnP-C60 (see figure) contain a porphyrin, a boron dipyrrin (BDP), and a fulleropyrrolidine of the type C60-X-NH2 (X=spacer). The components were connected by s-triazine. The star-type arrangement of the three photo- and redox-active components around the central s-triazine unit permits direct interaction.

    23. Stereoselective Reactions

      Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines (pages 2058–2064)

      Mari Yoshida, Naotaro Sassa, Tomomitsu Kato, Dr. Shuhei Fujinami, Dr. Takahiro Soeta, Prof. Dr. Katsuhiko Inomata and Prof. Dr. Yutaka Ukaji

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/chem.201302889

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      Desymmetrization of the divinyl carbinol, 1,4-pentadien-3-ol, was achieved by the asymmetric 1,3-dipolar cycloaddition of azomethine imines by using diisopropyl (R,R)-tartrate ((R,R)-DIPT) as the chiral auxiliary to afford the corresponding optically active trans-pyrazolidines with excellent regio-, diastereo-, and enantioselectivity (see scheme).

    24. Janus Nanoparticles

      Unconventional Assembly of Bimetallic Au–Ni Janus Nanoparticles on Chemically Modified Silica Spheres (pages 2065–2070)

      Dr. Lei Jia, Dr. Xiaowei Pei, Prof. Feng Zhou and Prof. Weimin Liu

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303659

      Thumbnail image of graphical abstract

      Very special assemblies: Janus Au[BOND]Ni NPs with a thin layer of octadecylamine (ODA) can self-assemble onto catechol-modified silica spheres (SiO2[BOND]OH) to form an unconventional core–loop complex structure. While the assembly of SiO2[BOND]OH and isotropic Au, Ni, or Fe3O4 particles generates traditional core– satellite structures instead (see figure). The mechanism of formation of the assemblies has also been investigated by using thiol-terminated silica spheres (SH[BOND]SiO2).

    25. Cooperative Binding

      Artificial Nucleobase–Amino Acid Conjugates: A New Class of TAR RNA Binding Agents (pages 2071–2079)

      Jean-Patrick Joly, Guillaume Mata, Dr. Patrick Eldin, Dr. Laurence Briant, Dr. Fabien Fontaine-Vive, Dr. Maria Duca and Dr. Rachid Benhida

      Version of Record online: 15 JAN 2014 | DOI: 10.1002/chem.201303664

      Thumbnail image of graphical abstract

      Kissing interaction: The rational design, synthesis, and in vitro evaluation of new RNA binding agents are reported. The conjugation of an artificial nucleobase, which is able to interact specifically with an RNA base pair (Hoogsteen pairing), and various amino acids leads to efficient binding to the target RNA and the inhibition of viral replication in HIV-infected cells (see figure).

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