Chemistry – An Asian Journal

Cover image for Vol. 5 Issue 7

July 5, 2010

Volume 5, Issue 7

Pages 1501–1707

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
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    1. Cover Picture: RhI-Catalyzed Two-Component [(5+2)+1] Cycloaddition Approach toward [5-8-5] Ring Systems (Chem. Asian J. 7/2010) (page 1501)

      Feng Huang, Zhong-Ke Yao, Yi Wang, Yuanyuan Wang, Jialing Zhang and Zhi-Xiang Yu

      Article first published online: 1 JUL 2010 | DOI: 10.1002/asia.201090020

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      Cycloaddition Reactions… … catalyzed by transition metal complexes have been of continuing interest to chemists owing to their efficiency in constructing complicated molecules from much simpler starting materials in atom- and step-economical fashions. It has been found that eight-membered carbocycles in many natural products are fused or bridge-fused with one or more five- or six-membered carbocycles. In their Communication on page 1555 ff., Z.-X. Yu et al. present [Rh(CO)2Cl]2-catalyzed two-component [(5+2)+1] cycloaddition of ene-vinylcyclopropanes that have various tether types and substituents with CO designed for one-pot synthesis of fused tricyclic cyclooctenones with atom and step economies.

  2. Graphical Abstract

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    3. Graphical Abstract
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    1. Graphical Abstract: Chem. Asian J. 7/2010 (pages 1504–1510)

      Article first published online: 1 JUL 2010 | DOI: 10.1002/asia.201090021

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
    7. Full Papers
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  4. Focus Reviews

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
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    1. Fluorophores

      Organic Fluorophores Exhibiting Highly Efficient Photoluminescence in the Solid State (pages 1516–1531)

      Masaki Shimizu and Tamejiro Hiyama

      Article first published online: 25 JUN 2010 | DOI: 10.1002/asia.200900727

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      The Charge of the Light Brigade: Small organic molecules that exhibit fluorescence in the visible region with high photoluminescence quantum yields in the solid state, such as crystal, neat film, and powder are reviewed with an emphasis on the characteristics of the molecular structures.

    2. Diamond Chemistry

      The Chemistry of C[BOND]H Bond Activation on Diamond (pages 1532–1540)

      Yu Lin Zhong and Kian Ping Loh

      Article first published online: 23 APR 2010 | DOI: 10.1002/asia.201000027

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      Diamond surfaces, when terminated with hydrogen, exhibit special properties, such as negative electron affinity and surface conductivity which enhance the reactivity for C[BOND]H bond activation. This Focus Review covers the chemistry of C[BOND]H bond activation by UV photochemical and diazonium chemistry and the subsequent C[BOND]C coupling chemistry.

  5. Communications

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    1. Annulation Reactions

      An Unexpected Phosphine-Catalyzed Regio- and Diastereoselective [4+1] Annulation Reaction of Modified Allylic Compounds with Activated Enones (pages 1542–1545)

      Zuliang Chen and Junliang Zhang

      Article first published online: 21 MAY 2010 | DOI: 10.1002/asia.201000193

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      Rapid access: An unexpected regio- and diastereoselective phosphine-catalyzed [4+1] annulation reaction of modified allylic compounds with activated enones was revealed, providing a simple, efficient route to synthesis of highly substituted 2,3-dihydrofurans with convertible functional groups.

    2. Nanomaterials

      Organic-Stabilizer-Free Synthesis of Layered Protonic Titanate Nanosheets (pages 1546–1549)

      Bin Zhao, Feng Chen, Xiaona Gu and Jinlong Zhang

      Article first published online: 5 MAY 2010 | DOI: 10.1002/asia.201000018

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      Stress-free zone: Protonic dititanate (H2Ti2O5H2O) nanosheets were synthesized directly using a novel alkalescent route free from any washing and protonation processes. The formation of the protonic dititanate nanosheets (but not nanotubes) is likely due to the adequate relaxation of the internal stress in the hydrothermal process.

    3. Thin-Film Transistors

      Hexathienoacene: Synthesis, Characterization, and Thin-Film Transistors (pages 1550–1554)

      Ying Liu, Xiangnan Sun, Chong-an Di, Yunqi Liu, Chunyan Du, Kun Lu, Shanghui Ye and Gui Yu

      Article first published online: 17 MAY 2010 | DOI: 10.1002/asia.201000001

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      A new linear six thiophene-fused system of hexathienoacene (HTA) has been synthesized, which has also been compared with pentathienoacene (PTA) in terms of optical, electrochemical, and charge-transfer properties of organic semiconductors. The highest mobility of 0.06 cm2 V−1 s−1 with a current on/off ratio of 105 on n-octadecyltrichlorosilane (OTS)-treated SiO2/Si substrates has been achieved.

    4. Cycloaddition

      RhI-Catalyzed Two-Component [(5+2)+1] Cycloaddition Approach toward [5-8-5] Ring Systems (pages 1555–1559)

      Feng Huang, Zhong-Ke Yao, Yi Wang, Yuanyuan Wang, Jialing Zhang and Zhi-Xiang Yu

      Article first published online: 26 MAR 2010 | DOI: 10.1002/asia.201000053

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      Bringing it all together: [{Rh(CO)2Cl}2]-catalyzed two-component [(5+2)+1] cycloaddition of ene-vinylcyclopropanes with various tether types and substituents with CO has been designed for the one-pot synthesis of fused tricyclic cyclooctenones with atom and step economies.

    5. Glycolipids

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      Rational Design and Evaluation of a Branched-Chain-Containing Glycolipid Antigen That Binds to CD1d (pages 1560–1564)

      Dong Jae Baek, Yoon-Sook Lee, Chaemin Lim, Doohyun Lee, Taeho Lee, Jae-Young Lee, Kyoo-A Lee, Won-Jea Cho, Chang-Yuil Kang and Sanghee Kim

      Article first published online: 21 APR 2010 | DOI: 10.1002/asia.201000120

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      Circumnavigating or clamping: CD1 molecules recognize glycolipid antigens with a straight alkyl chain moiety. Owing to the presence of the central pole in the A′ pocket of the CD1 binding groove, the straight alkyl chain of antigens circles around the pole like a hook. To determine whether CD1 molecules are capable of recognizing structurally dissimilar ligands, we have designed and evaluated branched-chain-containing glycolipid derivatives of the prototypical CD1d ligand α-GalCer.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
    7. Full Papers
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    1. Nanomaterials

      Use of Side-Chain Incompatibility for Tailoring Long-Range p/n Heterojunctions: Photoconductive Nanofibers Formed by Self-Assembly of an Amphiphilic Donor–Acceptor Dyad Consisting of Oligothiophene and Perylenediimide (pages 1566–1572)

      Wei-Shi Li, Akinori Saeki, Yohei Yamamoto, Takanori Fukushima, Shu Seki, Noriyuki Ishii, Kenichi Kato, Masaki Takata and Takuzo Aida

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.201000111

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      Custom fit: Organic p/n heterojunctions with molecular-level precision have been tailored. An oligothiophene–perylenediimide dyad, when modified with triethylene glycol side chains at one terminus and dodecyl side chains at the other, self-assembles into a photoconducting nanofiber with a well-defined morphology (see figure).

    2. Chromoreagents

      Chromo-Fluorogenic Detection of Nerve-Agent Mimics Using Triggered Cyclization Reactions in Push–Pull Dyes (pages 1573–1585)

      Ana M. Costero, Margarita Parra, Salvador Gil, Raúl Gotor, Pedro M. E. Mancini, Ramón Martínez-Máñez, Félix Sancenón and Santiago Royo

      Article first published online: 28 MAY 2010 | DOI: 10.1002/asia.201000058

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      Detection of nerve-gas mimics: A new family of receptors are able to chromo-fluorogenically detect the presence of nerve-gas mimics in aqueous environments and in the gas phase. These chromoreagents display an intramolecular cyclization reaction coupled with a color change upon interaction with certain nerve-agent simulants.

    3. Calcite

      Rosette-Shaped Calcite Structures at Surfaces: Mechanistic Implications for CaCO3 Crystallization (pages 1586–1593)

      Sung Ho Yang and Insung S. Choi

      Article first published online: 28 MAY 2010 | DOI: 10.1002/asia.201000190

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      Rose in the matrix! Two-dimensional rosette-shaped calcite structures are formed on films of poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA). The structures are controlled by varying a number of factors, such as reaction time, amount of (NH4)2CO3, concentration of PAA, and charge of matrix-films. A mechanism is proposed by investigating the transformation from amorphous CaCO3 to calcite crystals.

    4. Hydrogen Storage

      Hydrogen Storage Properties of Ca(BH4)2–LiNH2 System (pages 1594–1599)

      Hailiang Chu, Zhitao Xiong, Guotao Wu, Jianping Guo, Xueli Zheng, Teng He, Chengzhang Wu and Ping Chen

      Article first published online: 7 MAY 2010 | DOI: 10.1002/asia.200900677

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      An effective container: Interaction of Ca(BH4)2 and LiNH2 leads to decreased dehydrogenation temperatures and increased hydrogen desorption capacity in comparison to pristine Ca(BH4)2. More than 7 wt % of hydrogen can be detached at a temperature as low as approximately 178 °C from the cobalt-catalyzed Ca(BH4)2–4 LiNH2 system.

    5. Oxidative Addition

      Reactions of 7,8-Dithiabicyclo[4.2.1]nona-2,4-diene 7-exo-Oxide with Dodecacarbonyl Triiron Fe3(CO)12: A Novel Type of Sulfenato Thiolato Diiron Hexacarbonyl Complexes (pages 1600–1610)

      Jochen Windhager, Ulf-Peter Apfel, Tomoharu Yoshino, Norio Nakata, Helmar Görls, Manfred Rudolph, Akihiko Ishii and Wolfgang Weigand

      Article first published online: 14 MAY 2010 | DOI: 10.1002/asia.200900733

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      Super model! The reaction of Fe3(CO)12 () with 7,8-dithiabicyclo[4.2.1]nona-2,4-diene 7-exo-oxide () yields the sulfenato-thiolato complex , which is used as starting material for further oxidation and substitution reactions. The electrochemistry of these complexes is discussed.

    6. Polymers

      Syntheses and Crystal Structures of a Series of Coordination Polymers Constructed From C2-Symmetric Ligand 1,3-Adamantanedicarboxylic Acid (pages 1611–1619)

      Jun-Cheng Jin, Ya-Nan Zhang, Yao-Yu Wang, Jian-Qiang Liu, Zhe Dong and Qi-Zhen Shi

      Article first published online: 8 JUN 2010 | DOI: 10.1002/asia.200900751

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      Crystal engineering: This article systematically investigates the influence of the properties of inhomogeneous N-auxiliary ligands and pH value on the helical structures of complexes based on C2-symmetric ligand 1,3-adamantanedicarboxylic acid (H2ADC) (see figure). A series of new ZnII/CoII dicarboxylates have been synthesized by slow diffusion.

    7. Pentacenes

      Synthesis of 1,2,3,4,8,9,10,11-Octasubstituted Pentacenequinone Derivatives and their Conversion into Substituted Pentacenes (pages 1620–1626)

      Shi Li, Lishan Zhou, Kiyohiko Nakajima, Ken-ichiro Kanno and Tamotsu Takahashi

      Article first published online: 7 MAY 2010 | DOI: 10.1002/asia.200900754

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      Multisubstituted pentacenes: A new synthetic method for substituted pentacenes has been developed by the combination of the quinone method and double homologation method. The substituted pentacenes prepared by double homologation were converted into their corresponding pentacenequinones by oxidation. Aryl and alkynyl groups were introduced by the reaction with aryllithiums or alkynyl Grignard reagents followed by reduction of the resulting diols.

    8. Hydrogels

      Preparation of Enzymatically Recyclable Hydrogels Through the Formation of Inclusion Complexes of Amylose in a Vine-Twining Polymerization (pages 1627–1633)

      Yoshiro Kaneko, Kazuya Fujisaki, Tsuyoshi Kyutoku, Hidemitsu Furukawa and Jun-ichi Kadokawa

      Article first published online: 17 MAY 2010 | DOI: 10.1002/asia.201000012

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      Inspired by plants! Hydrogels are prepared by the formation of an inclusion complex of amylose in a vine-twining polymerization. In addition, the enzymatic disruption and reproduction of the hydrogels are achieved by the combination of the amylase-catalyzed hydrolysis of the amylose component and the formation of amylose by the phosphorylase-catalyzed polymerization.

    9. Self-Assembly

      Hydrogen Bonding Induced Supramolecular Self-Assembly of Linear Doubly Discotic Triad Supermolecules (pages 1634–1641)

      Jianjun Miao and Lei Zhu

      Article first published online: 21 MAY 2010 | DOI: 10.1002/asia.201000017

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      Doubly discotic triad supermolecules: A series of linear doubly discotic triad supermolecules based on a porphyrin (P) core and two triphenylene (Tp) arms linked by amide bonds are synthesized. Intermolecular hydrogen bonding among amide bonds and degree of coupling between porphyrin and two triphenylene arms determined the supramolecular self-assembly of the linear discotic triad supermolecules.

    10. Mesoporous Materials

      Lanthanide (Eu3+, Tb3+) Centered Mesoporous Hybrids with 1,3-Diphenyl-1,3-Propanepione Covalently Linking SBA-15 (SBA-16) and Poly(methylacrylic acid) (pages 1642–1651)

      Ya-Juan Li, Bing Yan and Ying Li

      Article first published online: 12 MAY 2010 | DOI: 10.1002/asia.201000032

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      Linking up: 1,3-Diphenyl-1,3-propanepione (DBM)-functionalized ordered meso-porous silica (SBA-15 and SBA-16) and organic polymer chains can be combined through a standardized method of assembling mesoporous luminescent lanthanide molecular-based polymeric hybrids with chemical bonds. The products contain long, organic carbon chains and ordered organic networks (Si[BOND]O[BOND]Si).

    11. Organocatalysis

      Asymmetric Catalytic Aziridination of Cyclic Enones (pages 1652–1656)

      Francesco De Vincentiis, Giorgio Bencivenni, Fabio Pesciaioli, Andrea Mazzanti, Giuseppe Bartoli, Patrizia Galzerano and Paolo Melchiorre

      Article first published online: 28 MAY 2010 | DOI: 10.1002/asia.201000040

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      Access to aziridine antipodes: The first catalytic method for the asymmetric aziridination of cyclic enones is described (see scheme). The presented organocatalytic strategy is effective for a wide variety of substrates, thereby providing fast access to both of the antipodes of the aziridines with very high enantiomeric purity.

    12. Dehydrogenative Coupling

      C[BOND]H Bond Activation/Borylation of Furans and Thiophenes Catalyzed by a Half-Sandwich Iron N-Heterocyclic Carbene Complex (pages 1657–1666)

      Tsubasa Hatanaka, Yasuhiro Ohki and Kazuyuki Tatsumi

      Article first published online: 10 JUN 2010 | DOI: 10.1002/asia.201000140

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      An iron grip on carbon bonds: A newly synthesized iron-methyl complex (see scheme) was found to activate the C[BOND]H bonds of furan, thiophene, and benzene. These reactions were applied to the coupling of furans/thiophenes with pinacolborane (HBpin) in the presence of tert-butylethylene and a catalytic amount of iron complex (10 mol % to HBpin).

    13. Mass Spectrometry

      Intramolecular Scrambling of Aryl Groups in Organopalladium Complexes [ArPd(PPh3)2]+: From Solution to the Gas Phase, Back Again, and In-Between (pages 1667–1676)

      Divya Agrawal, Emilie-Laure Zins and Detlef Schröder

      Article first published online: 28 MAY 2010 | DOI: 10.1002/asia.201000086

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      Aryl pick ‘n’ mix: Gas-phase experiments reveals the intramolecular scrambling of aryl groups between palladium and phosphorus in organopalladium complexes [ArPd(PPh3)2]+ generated by means of electrospray ionization (ESI). Gas-phase-data analysis implies that this scrambling process has a relatively low energy demand and heating the reagents in solution reveals the same reaction as that found by using ESI (see figure).

    14. Carbene Complexes

      Triazole-Functionalized N-Heterocyclic Carbene Complexes of Palladium and Platinum and Efficient Aqueous Suzuki–Miyaura Coupling Reaction (pages 1677–1686)

      Shaojin Gu, Hui Xu, Na Zhang and Wanzhi Chen

      Article first published online: 25 MAY 2010 | DOI: 10.1002/asia.201000071

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      First click, then couple! A series of NHC ligands containing a triazole group were readily synthesized via click chemistry. The structures of Ag, Pd, and Pt complexes containing carbene-triazole ligands were confirmed by single crystal X-ray structural analysis. The nonsymmetrical pincer palladium complex shows high activity in aqueous Suzuki–Miyaura cross coupling reactions of aryl bromides or 1,1-dibromo-1-alkenes in neat water under an air atmosphere.

    15. Iron Catalysis

      Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones (pages 1687–1691)

      Daniele Addis, Nadim Shaikh, Shaolin Zhou, Shoubhik Das, Kathrin Junge and Matthius Beller

      Article first published online: 14 MAY 2010 | DOI: 10.1002/asia.201000064

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      Economical iron catalyst: A general protocol for both racemic and stereoselective iron-catalyzed hydrosilylation of ketones with readily available PMHS has been developed. The reaction is highly chemoselective, even in the presence of other functional groups.

    16. Chromogenic Probes

      A Selective Chromogenic Probe for Mercury(II) and Cyanide in Aqueous Buffered Solution from a Cycloaddition Reaction of an Ynamine to Polycyclic Dithiolethiones (pages 1692–1699)

      Pedro Fuertes, Daniel Moreno, José V. Cuevas, María García-Valverde and Tomás Torroba

      Article first published online: 8 JUN 2010 | DOI: 10.1002/asia.201000063

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      Mercury rising! A new polysulfur-nitrogen heterocycle is described as a new selective chromogenic probe for the naked-eye detection of mercury(II), by a dramatic change of color from purple to blue-violet in a HEPES-buffered water/acetonitrile 1:1 mixture, with sub-micromolar sensitivity. The chemical probe also changes from purple to red in the presence of cyanide.

  7. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Reviews
    6. Communications
    7. Full Papers
    8. Preview
    1. You have free access to this content
      Preview: Chem. Asian J. 8/2010 (page 1707)

      Article first published online: 1 JUL 2010 | DOI: 10.1002/asia.201090023

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