Chemistry – An Asian Journal

Cover image for Vol. 4 Issue 8

August 3, 2009

Volume 4, Issue 8

Pages 1155–1371

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
    8. Full Papers
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    1. Cover Picture: Superior Electron-Transport Ability of π-Conjugated Redox Molecular Wires Prepared by the Stepwise Coordination Method on a Surface (Chem. Asian J. 8/2009) (page 1155)

      Yoshihiko Nishimori, Katsuhiko Kanaizuka, Tomochika Kurita, Toshiaki Nagatsu, Yu Segawa, Fumiyuki Toshimitsu, Satoshi Muratsugu, Mitsuya Utsuno, Shoko Kume, Masaki Murata and Hiroshi Nishihara

      Article first published online: 29 JUL 2009 | DOI: 10.1002/asia.200990025

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      Electronic conductivity of molecular wires is a critical fundamental issue in molecular electronics. π-Conjugated redox molecular wires with a superior long-range electron-transport ability are constructed on a gold surface through the stepwise ligand–metal coordination method. H. Nishihara et al. investigate the influences on the electron-transfer rate constant by the chemical structure of molecular wires and the terminal redox units, temperature, electric field, and electrolyte concentration. The results indicate that facile sequential electron hopping between neighboring metal–complex units within the wire is responsible for the high electron-transport ability. For the details, turn to their Full Paper on page 1361 ff.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
    8. Full Papers
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    1. You have free access to this content
      Cooperative Effect (pages 1156–1157)

      Brian Johnson

      Article first published online: 29 JUL 2009 | DOI: 10.1002/asia.200900259

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
    8. Full Papers
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    1. Graphical Abstract: Chem. Asian J. 8/2009 (pages 1158–1165)

      Article first published online: 29 JUL 2009 | DOI: 10.1002/asia.200990026

  4. News

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

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

      π-Conjugation Enlargement Toward the Creation of Multi-Porphyrinic Systems with Large Two-Photon Absorption Properties (pages 1172–1182)

      Naoki Aratani, Dongho Kim and Atsuhiro Osuka

      Article first published online: 9 JUN 2009 | DOI: 10.1002/asia.200900045

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      Arrays the way! Recent progress in the synthesis of covalently linked porphyrin arrays with large two-photon absorption (TPA) cross-section values has been reviewed with a particular focus on the relation of TPA properties with molecular structures. This will help understand the structural requirements of porphyrin arrays with large TPA values, which will be useful for future applications in optical communication in the IR region.

    2. Ionic Liquids

      Functionalized Chiral Ionic Liquids: A New Type of Asymmetric Organocatalysts and Nonclassical Chiral Ligands (pages 1184–1195)

      Sanzhong Luo, Long Zhang and Jin-Pei Cheng

      Article first published online: 16 JUN 2009 | DOI: 10.1002/asia.200900080

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      Combining the principles of chiral catalysts with the unique properties of ionic liquids, functionalized chiral ionic liquids (FCILs) have demonstrated promising applications in asymmetric catalysis as a new type of asymmetric organocatalysts and nonclassical chiral ligands.

    3. Drug Screening

      Conjugated Polyelectrolytes as New Platforms for Drug Screening (pages 1196–1206)

      Lingling An and Shu Wang

      Article first published online: 13 JUL 2009 | DOI: 10.1002/asia.200900148

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      Putting a charge into drug discovery: This Focus Review highlights recent research efforts in the development of water-soluble conjugated polyelectrolytes (CPEs) as a new class of optical platforms for the screening of potential drugs. Three types of biological targets for the search of small-molecule active drugs are described: nucleic acid, enzyme, and RNA-protein complex. Future research directions for drug screening based on CPEs are also presented.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
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    1. Self-Assembled Monolayers

      Efficient Bidirectional Photocurrent Generation by Self-Assembled Monolayer of Penta(aryl)[60]fullerene Phosphonic Acid (pages 1208–1212)

      Aiko Sakamoto, Yutaka Matsuo, Keiko Matsuo and Eiichi Nakamura

      Article first published online: 17 JUN 2009 | DOI: 10.1002/asia.200900155

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      Photocurrent-generating fullerenes: New fullerene derivatives bearing a phosphonic acid linker (e.g., C60(C6H4-Ph-4)5(CH2)6PO(OH)2) form self-assembled monolayers (SAMs) on indium tin oxide (ITO) and SnO2 surfaces, and generate both anodic and cathodic photocurrent in the presence of sacrificing reagents.

    2. Bromination

      Vanadium-Catalyzed Oxidative Bromination under Atmospheric Oxygen (pages 1213–1216)

      Kotaro Kikushima, Toshiyuki Moriuchi and Toshikazu Hirao

      Article first published online: 23 JUN 2009 | DOI: 10.1002/asia.200900142

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      A versatile method for a catalytic bromination reaction: The oxidative bromination reaction of arenes, alkenes, and alkynes proceeded under atmospheric oxygen in the presence of a catalytic amount of NH4VO3, a bromide source, and an acid. A bromonium cation-like species is proposed to be involved.

    3. Palladium Catalysis

      Palladium-Catalyzed (N-Oxido-2-pyridinyl)methyl Transfer from 2-(2-Hydroxyalkyl)pyridine N-Oxide to Aryl Halides by β-Carbon Elimination (pages 1217–1220)

      Takafumi Suehiro, Takashi Niwa, Hideki Yorimitsu and Koichiro Oshima

      Article first published online: 5 JUN 2009 | DOI: 10.1002/asia.200900151

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      Successful transfer application: (N-Oxido-2-pyridinyl)methyl transfer from (2-hydroxyalkyl)pyridine N-oxide derivatives to aryl bromides proceeds under palladium catalysis through β-carbon elimination involving cleavage of an unstrained C(sp3)[BOND]C(sp3) bond, yielding 2-benzylpyridine N-oxide derivatives.

    4. Asymmetric Hydrogenation

      NH/π Attraction: A Role in Asymmetric Hydrogenation of Aromatic Ketones with Binap/1,2-Diamine-Ruthenium(II) Complexes (pages 1221–1224)

      Christian A. Sandoval, Qixun Shi, Shasha Liu and Ryoji Noyori

      Article first published online: 24 JUN 2009 | DOI: 10.1002/asia.200900171

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      Role model: Electrostatic NHeq/π attraction plays an important role in asymmetric hydrogenation of acetophenones catalyzed by chiral [RuX2(diphosphine)(1,2-diamine)] complexes. The relative rate of p-substituted ketones bears a Hammett linear relationship with ρ=1.03 but with a notable exception for the p-fluoro ketone. The enantioselectivity is enhanced by an electron-donating p substituent and is decreased by an electron donor.

    5. Phosphinidene Complexes

      Umpolung of Electrophilic Terminal Phosphinidene Complexes by Interaction with Nucleophilic Carbenes (pages 1225–1228)

      Ngoc Hoa Tran Huy, Bruno Donnadieu, Guy Bertrand and François Mathey

      Article first published online: 25 JUN 2009 | DOI: 10.1002/asia.200900177

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      Reaction of the electrophilic terminal phosphinidene complex 2 with the stable nucleophilic carbene 1 leads to an adduct with inversion of polarity at the phosphorus atom. Zwitterionic 3 exhibits nucleophilic character at the phosphorus atom through protonation and alkylation reactions, and can be converted back into its original two components by reactions with electron-poor heterodienes.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
    1. Gold Catalysis

      Reactions of Cationic Gold(I) with Allenoates: Synthesis of Stable Organogold(I) Complexes and Mechanistic Investigations on Gold-Catalyzed Cyclizations (pages 1230–1236)

      Le-Ping Liu and Gerald B. Hammond

      Article first published online: 26 MAY 2009 | DOI: 10.1002/asia.200900091

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      Reactions of gold: A room temperature stable vinyl gold complex was obtained from the reaction of cationic gold(I) with an allenoate. A plausible mechanism for its formation was proposed. The cleavage of the gold–carbon bond by electrophiles indicates that this vinyl gold complex is the likely intermediate in the gold-catalyzed reaction of carbon–carbon multiple bonds.

    2. Oxidative Cyclization

      Osmium-Mediated Oxidative Cyclizations: A Study into the Range of Initiators That Facilitate Cyclization (pages 1237–1247)

      Timothy J. Donohoe, Katherine M. P. Wheelhouse (née Gosby), Peter J. Lindsay-Scott, Gwydion H. Churchill, Matthew J. Connolly, Sam Butterworth and Paul A. Glossop

      Article first published online: 3 JUL 2009 | DOI: 10.1002/asia.200900168

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      Tying up loose ends: A general route to prepare substituted, saturated five-membered heterocycles has been developed. Diols, hydroxy-amides, hydroxy-sulfonamides, and carbamates all cyclize in moderate to excellent yields to give cis-tetrahydrofurans and pyrrolidines, depending upon the position of the heteroatoms in the starting materials.

    3. Porphyrin Tapes

      Synthesis of Extremely π-Extended Porphyrin Tapes from Hybrid meso-meso Linked Porphyrin Arrays: An Approach Towards the Conjugation Length (pages 1248–1256)

      Toshiaki Ikeda, Naoki Aratani and Atsuhiro Osuka

      Article first published online: 30 JUN 2009 | DOI: 10.1002/asia.200900125

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      The longest porphyrin tape! Triply linked porphyrin tapes, up to 24-mer, were synthesized by a hybrid strategy. The effective conjugated length (ECL) has been estimated to be 14–16 on the basis of their absorption spectra. The alternatively introduced meso-aryl substituents considerably enhance the chemical stability and the solubility.

    4. Polymerization

      Electronic and Steric Ligand Effects in the Radical Polymerization of Vinyl Acetate Mediated by β-Ketoiminate Complexes of Cobalt(II) (pages 1257–1265)

      Santhosh Kumar K. S., Yugang Li, Yves Gnanou, Ulrich Baisch, Yohan Champouret, Rinaldo Poli, Kiyoshi C. D. Robson and W. Stephen McNeil

      Article first published online: 16 JUN 2009 | DOI: 10.1002/asia.200900084

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      Setting a trap: Bis(β-ketoiminato) complexes of cobalt(II) display a controlling ability in the radical polymerization of vinyl acetate. While an increased steric encumbrance of the ligand coordination sphere labilizes the CoIII[BOND]PVAc bond, it also makes the CoII complex a poorer trap for the active radical chain.

    5. Clathrate Hydrates

      Tuning the Composition of Guest Molecules in Clathrate Hydrates: NMR Identification and Its Significance to Gas Storage (pages 1266–1274)

      Yutaek Seo, Jong-Won Lee, Rajnish Kumar, Igor L. Moudrakovski, Huen Lee and John A. Ripmeester

      Article first published online: 13 JUL 2009 | DOI: 10.1002/asia.200900087

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      Filling in all the blanks: Structure II (sII) double hydrates can be tuned to optimize gas storage conditions by adjusting the concentration of the water-soluble hydrate former, THF in this study. In situ high-pressure NMR experiments were used to measure the kinetics of reaction between frozen THF solutions and methane gas, and 13C MAS NMR experiments were used to measure the distribution of the guests over the cage sites.

    6. Ruthenium Catalysts

      Isocyanate- and Isothiocyanate-Derived RuIV-Based Alkylidenes: Synthesis, Structure, and Activity (pages 1275–1283)

      P. Santhosh Kumar, Klaus Wurst and Michael R. Buchmeiser

      Article first published online: 29 JUN 2009 | DOI: 10.1002/asia.200900099

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      ROMP it in! Novel isocyanate- and isothiocyanate-derived ruthenium-alkylidene complexes have been prepared and their catalytic activity in various metathesis reactions is described. These compounds are found to be excellent catalysts for the ring-opening metathesis polymerization of cis-cycloocta-1,5-diene and in the regioselective cyclopolymerization of 1,6-heptadiynes yielding polyenes almost entirely based on five-membered repeat units.

    7. Thin Films

      Platinum Films with Controlled 3-Dimensional Nanoscopic Morphologies and Their Effects on Surface Enhanced Raman Scattering (pages 1284–1288)

      Hyun-Ju Lee, U-Hwang Lee, Jin-Young Park, Sang-Hoon Yoo, Sungho Park and Young-Uk Kwon

      Article first published online: 2 JUL 2009 | DOI: 10.1002/asia.200900109

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      SERSed to perfection! Nanostructured films, composed of ∼9 nm thick Pt nanorods with ∼3 nm gaps between them, can absorb visible light and provide many hot junctions that can support the SERS effect. SERS studies of rhodamine 6G and benzenethiol on such Pt films as substrates reveal that the control of the nanostructure is critical for the SERS effect.

    8. Fluorescent Compounds

      Synthesis, Crystal Structure, and Photophysical Properties of (1E,3E,5E)-1,3,4,6-Tetraarylhexa-1,3,5-trienes: A New Class of Fluorophores Exhibiting Aggregation-Induced Emission (pages 1289–1297)

      Masaki Shimizu, Hironori Tatsumi, Kenji Mochida, Katsuhiro Shimono and Tamejiro Hiyama

      Article first published online: 17 JUN 2009 | DOI: 10.1002/asia.200900110

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      Emissive in powder: (1E,3E,5E)-1,3,4,6-Tetraarylhexa-1,3,5-trienes that are nonemissive in CHCl3 are demonstrated to exhibit fluorescence in powder form with good quantum yields of up to 0.44. The emission color ranges from blue to green depending on the substituents at the para position of the phenyl groups.

    9. Cyclopropanation

      Nucleophilic Cyclopropanation Reaction with Bis(iodozincio)methane by 1,4-Addition to α,β-Unsaturated Carbonyl Compounds (pages 1298–1303)

      Kenichi Nomura, Takaharu Hirayama and Seijiro Matsubara

      Article first published online: 16 JUN 2009 | DOI: 10.1002/asia.200900123

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      Being a good neighbor! Treatment of α,β-unsaturated ketones with an electrophilic site at the γ-position in the presence of trimethylsilyl cyanide with bis(iodozincio)methane afforded the (Z)-silyl enol ether of the β-cyclopropyl substituted ketone in good yield. The reaction proceeds by 1,4-addition to form an enolate, and its sequential intramolecular nucleophilic attack to an adjacent electrophilic site.

    10. Photoelectrochemistry

      A Photoelectrochemical Method for Determining the Kinematics of Moving Particles Using an Array of Individually Addressable Electrodes (pages 1304–1308)

      Neil V. Rees and Richard G. Compton

      Article first published online: 16 JUN 2009 | DOI: 10.1002/asia.200900126

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      Collision course: Photoelectrochemistry is used to detect and monitor the trajectory of moving spheres, using an array of individually addressable electrodes. The motion of a sphere is detected by the “dark” transients recorded as the shadow cast by the moving sphere passes over each electrode. The method can be used to determine the size and velocity of a single ball, or simultaneously track two spheres in collision.

    11. Bimetallic Complexes

      Metal–π Interactions Dominate in the Solid-State Structures of Molecular Heterobimetallic Alkali-Metal–Europium(II) Aryloxo Complexes (pages 1309–1317)

      Glen B. Deacon, Peter C. Junk and Graeme J. Moxey

      Article first published online: 7 JUL 2009 | DOI: 10.1002/asia.200900176

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      Two of a (different) kind: Treatment of Eu metal and 2,6-diphenylphenol (HOdpp) with MOdpp (M=Na, K) at 210 °C affords molecular heterobimetallic aryloxo complexes [MEu(Odpp)3] (see picture for M=Na), which were crystallographically characterized as their toluene solvates.

    12. Cancer Therapy

      Improvement of Targeted Gene Delivery to Human Cancer Cells by a Novel Trifunctional Crosslinker (pages 1318–1322)

      Maki Shiota, Lahman Shamsur, Shun-ichi Kawahara, Renu Wadhwa and Yutaka Ikeda

      Article first published online: 3 JUL 2009 | DOI: 10.1002/asia.200900129

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      The more ligands, the better! A facile method for the construction of an immunoconjugate is reported. A novel trifunctional crosslinking reagent is synthesized. By the use of this reagent, ligands targeting the specific cell can be displayed on the surface of the drug carrier with a high density. The increased density of ligands contributes to the high affinity to the target and the improved transfection efficiency.

    13. Silylenes

      A Zwitterionic Silylene as Reactive Intermediate and Its Unusual Dimerization to an N-Heterobicyclic Disilane (pages 1323–1328)

      Yun Xiong, Shenglai Yao and Matthias Driess

      Article first published online: 24 JUN 2009 | DOI: 10.1002/asia.200900127

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      The silylene precursor L′SiBr2 (1) is readily accessible by cyclocondensation of the respective N-lithiated ß-diketiminate with SiBr4. Among the unusual reactivity of 1, its reductive debromination with KC8 furnishes the novel N-heterobicyclic disilane 22, which results from the unexpected dimerization of the transient zwitterionic silylene 2.

    14. Cyclotrimerization

      Preparation of C3-Symmetric Homochiral syn-Trisnorbornabenzenes through Regioselective Cyclotrimerization of Enantiopure Iodonorbornenes (pages 1329–1337)

      A. F. G. Masud Reza, Shuhei Higashibayashi and Hidehiro Sakurai

      Article first published online: 3 JUL 2009 | DOI: 10.1002/asia.200900132

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      Going for the cup: C3-symmetric homochiral syn-trisoxonorbornabenzene possessing a rigid cup-shaped structure was synthesized through a novel regioselective cyclotrimerization of enantiopure iodonorbornenes using palladium nanoclusters. Cup-shaped molecules with a variety of substituents in a helical arrangement on the rigid cup shape were prepared from the common intermediate.

    15. Nanostructures

      Gold-Loaded Carbon Nanoparticles from Poly(vinyl alcohol)-b-poly(acrylonitrile) Non-Shell-Cross-Linked Micelles (pages 1338–1345)

      Rayna Bryaskova, Nicolas Willet, Anne-Sophie Duwez, Antoine Debuigne, Laurent Lepot, Bernard Gilbert, Christine Jérôme, Robert Jérôme and Christophe Detrembleur

      Article first published online: 25 JUN 2009 | DOI: 10.1002/asia.200900130

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      Blocked and loaded: The self-assembly of a novel poly(vinyl alcohol)-b-poly(acrylonitrile) (PVOH-b-PAN) block copolymer in water and the high affinity of gold salts for the poly(acrylonitrile) block were used for the preparation of gold-loaded carbon nanoparticles by the deposition of the gold-loaded PVOH-b-PAN spherical micelles onto silicon wafers, followed by controlled pyrolysis.

    16. Polyhedral Boranes

      Relative Stability of closo-closo, closo-nido, and nido-nido Macropolyhedral Boranes: The Role of Orbital Compatibility (pages 1346–1353)

      Oottikkal Shameema and Eluvathingal D. Jemmis

      Article first published online: 25 JUN 2009 | DOI: 10.1002/asia.200900153

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      A large polyhedron condenses preferentially with a smaller polyhedron owing to orbital compatibility. Calculations at the B3LYP/6-31G* level show that the relative energy of various macropolyhedra is in accordance with the difference in the number of vertices of the individual polyhedra.

    17. Cyclodextrin

      Ester Hydrolysis by a Cyclodextrin Dimer Catalyst with a Tridentate N,N′,N′′-Zinc Linking Group (pages 1354–1360)

      Si-Ping Tang, Ying-Hua Zhou, Huo-Yan Chen, Cun-Yuan Zhao, Zong-Wan Mao and Liang-Nian Ji

      Article first published online: 3 JUL 2009 | DOI: 10.1002/asia.200900108

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      The zinc complex of a novel 2,6-bis(aminomethyl)pyridine-linked β-cyclodextrin dimer was synthesized, characterized, and demonstrated as a potent catalyst for diester hydrolysis. The zinc complex is shown to exhibit a good catalytic ability for bis(4-nitrophenyl) substrates in the hydrolysis of carboxylic acid ester and phosphate esters. The hydrophobic interaction between catalyst and substrate is observed to play an important role.

    18. Electron Transport

      Superior Electron-Transport Ability of π-Conjugated Redox Molecular Wires Prepared by the Stepwise Coordination Method on a Surface (pages 1361–1367)

      Yoshihiko Nishimori, Katsuhiko Kanaizuka, Tomochika Kurita, Toshiaki Nagatsu, Yu Segawa, Fumiyuki Toshimitsu, Satoshi Muratsugu, Mitsuya Utsuno, Shoko Kume, Masaki Murata and Hiroshi Nishihara

      Article first published online: 18 JUN 2009 | DOI: 10.1002/asia.200900072

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      Hop around the block: π-Conjugated redox complex molecular wires that have been constructed on a gold surface through a convenient stepwise ligand–metal coordination method have been shown to exhibit high long-range electron-transport abilities. This transport is caused by facile sequential electron hopping between neighboring metal–complex units within the wire.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
    8. Full Papers
    9. Preview
    1. You have free access to this content
      Preview: Chem. Asian J. 9/2009 (page 1371)

      Article first published online: 29 JUL 2009 | DOI: 10.1002/asia.200990028

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