Chemistry - An Asian Journal v.6 n.3 2011

CURRENT CONTENTS/Chemistry

Chemistry - An Asian Journal v.6 n.3 2011

seoulfric 2011. 3. 21. 11:17

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  Cover Picture: Lamellar-Structured Nanoflakes Comprised of Stacked Oligoaniline Nanosheets (Chem. Asian J. 3/2011) (page 701)
  Zoran D. Zujovic, Cosmin Laslau and Jadranka Travas-Sejdic
  
  Article first published online: 22 FEB 2011 | DOI: 10.1002/asia.201190005
  
  Sheets that stack and curl, a key step in the self-assembly of polyaniline nanostructures, is shown on the Cover Picture, symbolically depicted as proceeding through the intricacies of the Yasukuni Shrine gate in Tokyo. These polyaniline nanostructures have important applications in sensors and electronic devices, but understanding their self-assembly remains a problem. In their Communication on page 791 ff.,Z. D. Zujovic, C. Laslau, and J. Travas-Sejdic describe how this “self-assembly” is strongly dependent on single oligoanilinic nanosheets that undergo subsequent interactions, such as stacking and rolling. These nanosheets stack to become thicker nanoflakes and subsequently serve as nucleation sites for polyaniline synthesis (Photographer: Agustin Rafael Reyes).
Inside Cover
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  Inside Cover: Nanographite Impurities of Single-Walled and Double-Walled Carbon Nanotubes Are Responsible for the Observed “Electrocatalytic” Effect towards the Reduction of Azo Groups (Chem. Asian J. 3/2011) (page 702)
  Emma J. E. Stuart and Martin Pumera
  
  Article first published online: 22 FEB 2011 | DOI: 10.1002/asia.201190006
  
  Carbon nanotubes (CNTs) … … are very important materials in the field of electrochemistry, with great promise for sensors and energy-storage devices. In their Communication on page 804 ff., E. J. E. Stuart and M. Pumera report that nanographite impurities contained within the nanotubes have a profound influence on their electrochemistry. The above picture shows nanographitic impurities reducing the azo group with the contrasting background of the Japanese symbol of purity, the Sakura blossom.
  - Abstract
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Editorial
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  The Hong Kong Chemical Society (pages 704–705)
  Wai-Yeung Wong
  
  Article first published online: 22 FEB 2011 | DOI: 10.1002/asia.201100059
Graphical Abstract
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  Graphical Abstract: Chem. Asian J. 3/2011 (pages 707–714)
  Article first published online: 22 FEB 2011 | DOI: 10.1002/asia.201190007
  - Abstract
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News
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  Spotlights on our sister journals: Chem. Asian J. 3/2011 (pages 716–718)
  Article first published online: 22 FEB 2011 | DOI: 10.1002/asia.201190008
  - Abstract
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Focus Reviews
1. Organocatalysis
  
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  Oxazolones in Organocatalysis, New Tricks for an Old Reagent (pages 720–734)
  Andrea-Nekane R. Alba and Ramon Rios
  
  Article first published online: 11 JAN 2011 | DOI: 10.1002/asia.201000636
  
  Trick and treat: Oxazolones or azlactones are among the most-common starting materials for the synthesis of quaternary amino acids. With the “renaissance” of organocatalysis, oxalactones have emerged as important starting materials for a range of new organocatalytic asymmetric methodologies. EWG=electron-withdrawing group.
2. Nanoparticles
  
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  Aerobic Oxidations Catalyzed by Colloidal Nanogold (pages 736–748)
  Tatsuya Tsukuda, Hironori Tsunoyama and Hidehiro Sakurai
  
  Article first published online: 16 FEB 2011 | DOI: 10.1002/asia.201000611
  
  Gold meets polymers: This Review describes recent progress in colloidal nanogold used as quasi-homogeneous catalysts (see picture) with a focus on our comprehensive studies on poly(N-vinyl-2-pyrrolidone) (PVP)-stabilized gold clusters, and their participation in aerobic oxidation reactions as well as formal Lewis acidic reactions.
3. Logic Gates
  
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  Molecular Logic Gate Arrays (pages 750–766)
  A. Prasanna de Silva
  
  Article first published online: 3 FEB 2011 | DOI: 10.1002/asia.201000603
  
  The pearly gates: Boolean gate arrays of increasing complexity are emerging in laboratories around the world. Some of these can be applied to important problems in sensing, therapy, and object identification.
Essay
1. Energy Sources
  
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  The Legacy of Fossil Fuels (pages 768–784)
  Nicola Armaroli and Vincenzo Balzani
  
  Article first published online: 3 FEB 2011 | DOI: 10.1002/asia.201000797
  
  Let′s move: Fossil fuels have powered the grand achievements of modern society, but the burden that they are imposing on present and future generations is so heavy that the need to phase them out is becoming imperative.
Communications
1. Total Synthesis
  
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  A Practical Synthesis of Cephalostatin 1 (pages 786–790)
  Yong Shi, Lanqi Jia, Qing Xiao, Quan Lan, Xiaohu Tang, Dahai Wang, Min Li, Yu Ji, Tao Zhou and Weisheng Tian
  
  Article first published online: 16 FEB 2011 | DOI: 10.1002/asia.201000882
  
  Let′s get practical: A new practical synthetic strategy for natural sterols starting from pregnan-(16S,20S)-diols and steroid-(16S),22-lactones is presented. A tandem double oxymercuration–demercuration and a substitution–ketalization cascade are considered as the key reactions for the construction of the spiroketal rings.
2. Nanosheets
  
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  Lamellar-Structured Nanoflakes Comprised of Stacked Oligoaniline Nanosheets(pages 791–796)
  Zoran D. Zujovic, Cosmin Laslau and Jadranka Travas-Sejdic
  
  Article first published online: 30 NOV 2010 | DOI: 10.1002/asia.201000703
  
  Three sheets to the wind: The self-assembly of polyaniline nanostructures is strongly dependent on single oligoanilinic nanosheets that undergo subsequent interactions, such as stacking and rolling. Imaging and spectroscopy tools detailed the stacking of nanosheets to form thicker nanoflakes and subsequently serve as nucleation sites for polyaniline synthesis.
3. Domino Reactions
  
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  Fused Phenanthridines: Domino Cyclization of 1,6-Diynes with Bromo(iso)quinoline(pages 797–800)
  Yimin Hu, Yongjie Sun, Jiping Hu, Tao Zhu, Tao Yu and Quansheng Zhao
  
  Article first published online: 11 JAN 2011 | DOI: 10.1002/asia.201000692
  
  An offer you can′t re-fused: The first examples of a convenient domino synthesis of 7,11-diphenyl-9,10-dihydro-8H-cyclopentaphenanthridine derivatives, such as 3, by the domino palladium-catalyzed cyclization reactions of simple 1,6-diynes with bromo(iso)quinoline in a single operation are described.
4. Polymerization
  
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  Postchemistry of Organic Microrods: Thermopolymerization in Aqueous Solution(pages 801–803)
  Jinchong Xiao, Damar Yoga Kusuma, Yuechao Wu, Freddy Boey, Hua Zhang, Pooi See Lee and Qichun Zhang
  
  Article first published online: 4 JAN 2011 | DOI: 10.1002/asia.201000684
  
  Hot Rod: Using the reprecipitation method, microrods of 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) were prepared in aqueous solution. The as-synthesized microrods were found to polymerize in aqueous solution after heated at 75 °C for 4 hours.
5. Nanotubes
  
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  Nanographite Impurities of Single-Walled and Double-Walled Carbon Nanotubes Are Responsible for the Observed “Electrocatalytic” Effect towards the Reduction of Azo Groups (pages 804–807)
  Emma J. E. Stuart and Martin Pumera
  
  Article first published online: 16 NOV 2010 | DOI: 10.1002/asia.201000656
  
  Not all impurities are evil: We demonstrate here that the electrochemistry of single-walled carbon nanotubes (SWCNTs) and double-walled carbon nanotubes (DWCNTs) towards the reduction of azo groups is actually driven by the nanographite impurities within these CNTs. Put differently, most of the electrochemical activity of SWCNTs and DWCNTs towards the reduction of azo groups is due to the presence of the nanographite impurities contained within them.
6. Piezofluorochromism
  
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  Piezofluorochromism of an Aggregation-Induced Emission Compound Derived from Tetraphenylethylene (pages 808–811)
  Xiqi Zhang, Zhenguo Chi, Haiyin Li, Bingjia Xu, Xiaofang Li, Wei Zhou, Siwei Liu, Yi Zhang and Jiarui Xu
  
  Article first published online: 11 JAN 2011 | DOI: 10.1002/asia.201000802
  
  Easy piezy: A new piezofluorochromic-aggregation-induced emission compound is described. The spectroscopic properties and morphological structures were reversibly exhibited upon pressing and annealing. The piezofluorochromic nature is believed to be generated through phase transformation.
Full Papers
1. Gold Catalysis
  
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  Gold(I)-Catalyzed Enantioselective Intermolecular Hydroarylation of Allenes with Indoles and Reaction Mechanism by Density Functional Theory Calculations (pages 812–824)
  Ming-Zhong Wang, Cong-Ying Zhou, Zhen Guo, Ella Lai-Ming Wong, Man-Kin Wong and Chi-Ming Che
  
  Article first published online: 14 DEC 2010 | DOI: 10.1002/asia.201000651
  
  It has a certain aura about it: An enantioselective intermolecular hydroarylation of allenes with indole, catalyzed by a chiral binuclear gold(I) phosphine complex, was developed. DFT calculations revealed that the reaction proceeds through nucleophilic addition of free indole to monoaurated allene intermediate rather than diaurated species, and the intramolecular Au^IAu^I interaction plays a key role in affecting the enatioselectivity of the reaction.
2. Bioinorganic Chemistry
  
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  Gold Nanoparticles Carrying Diatomic Molecules (O₂ and CO) in Aqueous Solution(pages 825–833)
  Keiichi Karasugi, Hiroaki Kitagishi and Koji Kano
  
  Article first published online: 24 JAN 2011 | DOI: 10.1002/asia.201000756
  
  Let′s stick together: Gold nanoparticles functionalized by an artificial hemoglobin/myoglobin (Hb/Mb) model (hemoCD)—composed of an iron(II)–porphyrin and a per-O-methylated β-cyclodextrin dimer with a pyridine linker—and poly(ethylene glycol) were found to bind O₂and CO in aqueous solution (see picture). The functionalized nanoparticles were mainly accumulated in the liver and spleen of a rat.
3. Nanoparticles
  
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  Iron Oxide Nanoparticles Embedded onto 3D Mesochannels of KIT-6 with Different Pore Diameters and Their Excellent Magnetic Properties (pages 834–841)
  Sher Alam, Chokkalingam Anand, S. M. J. Zaidi, Talapaneni Siddulu Naidu, Salem S. Al-Deyab and Ajayan Vinu
  
  Article first published online: 7 JAN 2011 | DOI: 10.1002/asia.201000456
  
  An iron will: Preparation of pore-directed growth of iron oxide nanoparticles inside the mesochannels of 3D mesoporous silica with different pore diameters has been demonstrated (see picture). The obtained materials have high magnetic moments and coercivity relative to those of pure iron oxide nanoparticles and iron oxide supported over other mesoporous samples.
4. Tandem Reactions
  
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  Nickel(0) Complexes with Fluorinated Alkyne Ligands and their Reactivity towards Semihydrogenation and Hydrodefluorination with Water (pages 842–849)
  Rigoberto Barrios-Francisco, Tania Benítez-Páez, Marcos Flores-Alamo, Alma Arévalo and Juventino J. García
  
  Article first published online: 24 NOV 2010 | DOI: 10.1002/asia.201000601
  
  A complex made for two: A series of zerovalent nickel complexes containing a fluorinated alkyne ligand are synthesized and their reactivity towards semihydrogenation and hydrodefluorination in a tandem process is presented (see scheme).
5. Germanium Nanoparticles
  
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  Treatment of TiO₂ with COOH-Functionalized Germanium Nanoparticles to Enhance the Photocurrent of Dye-Sensitized Solar Cells (pages 850–855)
  Chang-Ho Kim, Eun-Sung Ha, Hionsuck Baik and Kang-Jin Kim
  
  Article first published online: 11 JAN 2011 | DOI: 10.1002/asia.201000646
  
  A dye-sensitized solar cell (DSSC) containing a TiO₂ film treated with COOH-functionalized germanium nanoparticles (GeCOOH Nps) exhibited a higher short-circuit photocurrent density (J_sc) than the untreated DSSC using ruthenium complex N719. The enhancement of the J_sc value was attributed mostly to an intramolecular charge transfer from N719 attached to the GeCOOH Nps to the TiO₂ conduction band through the GeCOOH Nps.
6. Photovoltaics
  
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  Synthesis, Characterization, and Physical Properties of a Conjugated Heteroacene: 2-Methyl-1,4,6,7,8,9-hexaphenylbenz(g)isoquinolin-3(2H)-one (BIQ) (pages 856–862)
  Qichun Zhang, Jinchong Xiao, Zongyou Yin, Hieu M. Duong, Fen Qiao, Freddy Boey, Xiao Hu, Hua Zhang and Fred Wudl
  
  Article first published online: 14 DEC 2010 | DOI: 10.1002/asia.201000659
  
  Taking the BIQ: The synthesis and characterization of a stable and blue heteroacene, 2-methyl-1,4,6,7,8,9-hexaphenylbenz(g)isoquinolin-3(2H)-one (BIQ) is described. With its relatively small π framework, BIQ has an absorption λ_max at 620 nm (see figure), which is larger than that of pentacene (λ_max=582 nm), but more stable.
7. Ionic Liquids
  
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  Electronic Effects of para-Substitution on the Melting Points of TAAILs (pages 863–867)
  Tobias Schulz, Sebastian Ahrens, Dirk Meyer, Christoph Allolio, Anke Peritz and Thomas Strassner
  
  Article first published online: 19 JAN 2011 | DOI: 10.1002/asia.201000744
  
  Spotlight on TAAILs: This article describes the influence of electron-donating- and electron-withdrawing substituents in the para-position of the aromatic ring on the melting points of tunable aryl alkyl ionic liquids (TAAILs).
8. Gold Complexes
  
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  Gold Behaves as Hydrogen in the Intermolecular Self-Interaction of Metal Aurides MAu₄ (M=Ti, Zr, and Hf) (pages 868–872)
  Jaehoon Jung, Hyemi Kim, Jong Chan Kim, Min Hee Park and Young-Kyu Han
  
  Article first published online: 11 JAN 2011 | DOI: 10.1002/asia.201000742
  
  Peculiar behavior of gold: Metal tetraaurides MAu₄ (M=Ti, Zr, and Hf) are so named because gold behaves as a halogen. However, gold behaves as hydrogen in their corresponding dimeric system. Similarly to (MH₄)₂, the (μ-Au)₃C_s structures with three three-center two-electron (3c–2e) bonds are found to be the most stable.
9. Self-Assembly
  
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  Self-Assembly of 3,6-Bis(4-triazolyl)pyridazine Ligands with Copper(I) and Silver(I) Ions: Time-Dependant 2D-NOESY and Ultracentrifuge Measurements (pages 873–880)
  Bobby Happ, Georges M. Pavlov, Esra Altuntas, Christian Friebe, Martin D. Hager, Andreas Winter, Helmar Görls, Wolfgang Günther and Ulrich S. Schubert
  
  Article first published online: 29 DEC 2010 | DOI: 10.1002/asia.201000737
  
  Metals that rock: The Sonogashira coupling and the copper(I) catalyzed azide–alkyne cycloaddition provided direct access to 3,6-bis(triazol-4-yl)pyridazine systems, which can be regarded as analogs to 3,6-bis(pyridyl)pyridazine. The introduction of an oligomeric moiety led to a stable copper(I) complex, which is expected to have a [2×2] grid-like structure.
10. Mesoporous Materials
  
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  A Rational Repeating Template Method for Synthesis of 2 D Hexagonally Ordered Mesoporous Precious Metals (pages 881–887)
  Azusa Takai, Yoji Doi, Yusuke Yamauchi and Kazuyuki Kuroda
  
  Article first published online: 14 DEC 2010 | DOI: 10.1002/asia.201000674
  
  Can I take your order please? A repeating template method is presented for the synthesis of mesoporous metals with 2D hexagonal mesostructures. Ordered mesoporous ruthenium and palladium are not easily attainable by soft-template methods.
11. Radical Migrations
  
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  Arginine-Facilitated α- and π-Radical Migrations in Glycylarginyltryptophan Radical Cations (pages 888–898)
  Tao Song, Dominic C. M. Ng, Quan Quan, Chi-Kit Siu and Ivan K. Chu
  
  Article first published online: 26 JAN 2011 | DOI: 10.1002/asia.201000677
  
  Basic instinct: Model tripeptides GXW (X=amino acid residues glycine (G), alanine (A), leucine (L), phenylalanine (F), glutamic acid (E), histidine (H), lysine (K), or arginine (R)) have been used to study the effects of the basicity of the amino acid residue on the radical migrations and dissociations of odd-electron molecular peptide radical cations M^.+ in the gas phase (see picture).
12. Asymmetric Hydrogenation
  
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  Chiral Iridium Spiro Aminophosphine Complexes: Asymmetric Hydrogenation of Simple Ketones, Structure, and Plausible Mechanism (pages 899–908)
  Jian-Bo Xie, Jian-Hua Xie, Xiao-Yan Liu, Qian-Qian Zhang and Qi-Lin Zhou
  
  Article first published online: 15 DEC 2010 | DOI: 10.1002/asia.201000716
  
  The chiral iridium complexes of spiro aminophosphine ligands were demonstrated to be highly efficient catalysts for the hydrogenation of aromatic ketones, providing chiral alcohols in high enantioselectivities (up to 97 % ee) with high turnover number (TON up to 10 000) and turnover frequency (TOF up to 3.7×10⁴ h⁻¹).
13. Dendritic Nanoparticles
  
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  One-Pot Synthesis of Carbon-Supported Dendritic Pd-Au Nanoalloys for Electrocatalytic Ethanol Oxidation (pages 909–913)
  Shin Wook Kang, Young Wook Lee, Minjung Kim, Jong Wook Hong and Sang Woo Han
  
  Article first published online: 7 DEC 2010 | DOI: 10.1002/asia.201000715
  
  Two in one: Carbon-supported bimetallic alloy Pd-Au nanoparticles with dendritic shape have been prepared by a facile one-pot synthesis method. The synthesized catalysts exhibited much higher electrocatalytic activity and durability for ethanol oxidation than those of the commercial Pd catalyst.
14. Hybrid Materials
  
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  Organic–Inorganic Hybrid Saponites Obtained by Intercalation of Titano-Silsesquioxane (pages 914–921)
  Fabio Carniato, Chiara Bisio, Giorgio Gatti, Matteo Guidotti, Laura Sordelli and Leonardo Marchese
  
  Article first published online: 30 NOV 2010 | DOI: 10.1002/asia.201000664
  
  Two hybrid materials, Ti-NHM-1 and Ti-NHM-2, were prepared by the intercalation of a bifunctional titanium-containing silsesquioxane Ti-NH₃POSS in the interlayer spaces of synthetic sodium and protonic saponites, respectively. The bifunctional character (acid and redox) of Ti-NHM-2 was also investigated in detail.
15. Total Synthesis
  
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  Synthetic Studies of the Zoanthamine Alkaloids: Total Synthesis of Zoanthenol Based on an Isoaromatization Strategy (pages 922–931)
  Fumihiko Yoshimura, Yu Takahashi, Keiji Tanino and Masaaki Miyashita
  
  Article first published online: 23 DEC 2010 | DOI: 10.1002/asia.201000552
  
  The mask of zoanthenol: The total synthesis of zoanthenol is described in full detail. Zoanthenol is an aromatic member of the zoanthamine alkaloids and it has potent anti-platelet activity for human aggregation. The key step involves a Brønsted acid-promoted isoaromatization in the AB ring system to install the crucial aromatic ring (see scheme).
16. Asymmetric Additions
  
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  Rhodium-Catalyzed 1,4-Addition of Lithium 2-Furyltriolborates to Unsaturated Ketones and Esters for Enantioselective Synthesis of γ-Oxo-Carboxylic Acids By Oxidation of the Furyl Ring with Ozone (pages 932–937)
  Xiao-Qiang Yu, Tomohiko Shirai, Yasunori Yamamoto and Norio Miyaura
  
  Article first published online: 4 JAN 2011 | DOI: 10.1002/asia.201000589
  
  Get enantioselective! Rhodium-catalyzed 1,4-addition of lithium 5-methyl-2-furyltriolborate to unsaturated ketones to give β-furyl ketones was followed by ozonolysis of the furyl ring for enantioselective synthesis of γ-oxo-carboxylic acids (see scheme; nbd=2,5-norbornadiene).
17. Addition Reactions
  
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  Electrophilic Addition Reaction of Ethene with Hydrogen Chloride on Cold Molecular Films: Evidence of Ethyl Cationic Intermediate (pages 938–944)
  Poong-Ryul Lee, Chang-Woo Lee, Joon-Ki Kim, Eui-Seong Moon and Heon Kang
  
  Article first published online: 24 NOV 2010 | DOI: 10.1002/asia.201000631
  
  A cold ice surface can halt a reaction at an intermediate stage. An ethyl cationic intermediate is kinetically trapped on the ice surface in the course of the electrophilic addition reaction of ethene with hydrogen chloride, as revealed by reactive ion scattering and thermal desorption mass spectrometry.