Chemistry – An Asian Journal

Cover image for Vol. 5 Issue 9

September 3, 2010

Volume 5, Issue 9

Pages 1937–2127

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Communications
    7. Full Papers
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    1. Cover Picture: Synthesis, Spectroscopy, Crystal Structure Determination, and Quantum Chemical Calculations of BODIPY Dyes with Increasing Conformational Restriction and Concomitant Red-Shifted Visible Absorption and Fluorescence Spectra (Chem. Asian J. 9/2010) (page 1937)

      Volker Leen, Wenwu Qin, Wensheng Yang, Jie Cui, Chan Xu, Xiaoliang Tang, Weisheng Liu, Koen Robeyns, Luc Van Meervelt, David Beljonne, Roberto Lazzaroni, Claire Tonnelé, Noël Boens and Wim Dehaen

      Version of Record online: 30 AUG 2010 | DOI: 10.1002/asia.201090028

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      Two BODIPY dyes with increasingly rigid conformations were synthesized from the conformationally unconstrained 3,5-di-(2-bromophenoxy)-4,4-difluoro-8-(4-methylphenyl)-4-bora-3a,4a-diaza-s-indacene through palladium-catalyzed intramolecular benzofuran formation. In their Full Paper on page 2016 ff., W. Qin, W. Dehaen et al. report how restricted bond rotation of the phenoxy fragments led to more-intense absorption and fluorescence signals at longer wavelengths relative to the unconstrained dye. X-ray diffraction analysis showed progressively more-extended planarity of the chromophore with increasing conformational restriction. These conclusions were confirmed by quantum chemical calculations of the lowest electronic excitations.

  2. Graphical Abstract

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

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

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

      Peering into Biological Nanopore: A Practical Technology to Single-Molecule Analysis (pages 1952–1961)

      Hai-Yan Wang, Yi-Lun Ying, Yang Li and Yi-Tao Long

      Version of Record online: 28 JUL 2010 | DOI: 10.1002/asia.201000279

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      The magical nanopore: This Focus Review highlights the technical details of biological nanopores, especially α-hemolysin, in the detection of peptides or proteins from the technique point of view. The set-up, interference, and data analysis of biological nanopores by different methods are discussed briefly.

  5. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Communications
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    1. Hydrogenase Models

      An Iron(II) Carbonyl Thiolato Complex Bearing 2-Methoxy-Pyridine: A Structural Model of the Active Site of [Fe] Hydrogenase (pages 1962–1964)

      Soichiro Tanino, Yasuhiro Ohki and Kazuyuki Tatsumi

      Version of Record online: 21 JUL 2010 | DOI: 10.1002/asia.201000408

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      Model complex: An FeII complex bearing a thiolate, 2-methoxy-pyridine, and three facially arranged CO ligands was synthesized as a structural analogue of the active site of a CO-inhibited form of [Fe] hydrogenase, from the reaction of [FeBr2(CO)4] with NaS{2,6-(mesityl)2C6H3} and the successive treatment with 2-methoxy-pyridine.

    2. Ruthenium Complexes

      Ruthenium(III) Complexes of Macrocyclic Tertiary Amines Mediated NO Release from S-Nitrosothiols under in vitro and in vivo Conditions (pages 1965–1969)

      Chi-Ming Ho, Hiu-Chi Leung, Chun-Nam Lok and Chi-Ming Che

      Version of Record online: 28 JUL 2010 | DOI: 10.1002/asia.201000368

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      There′s just NO SNAP! RuIII complexes of macrocyclic tertiary amines, especially trans-[Ru(14-TMC)Cl2]Cl (1), could mediate nitric oxide (NO) release from S-nitrosothiols in the presence of biological reductants. Interestingly, complex 1 was found to enhance rat aorta relaxation in the presence of S-nitroso-N-acetylpenicillamine (SNAP) under in vivo conditions.

    3. Ionic Liquids

      Manganese Acetate in Pyrrolidinium Ionic Liquid as a Robust and Efficient Catalytic System for Epoxidation of Aliphatic Terminal Alkenes (pages 1970–1973)

      Kam-Piu Ho, Wing-Leung Wong, Lawrence Yoon Suk Lee, Kin-Ming Lam, Tak Hang Chan and Kwok-Yin Wong

      Version of Record online: 24 JUN 2010 | DOI: 10.1002/asia.201000109

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      Green epoxides! A novel and simple ionic liquid/manganese acetate catalytic system has been developed for the rapid and selective oxidation of aliphatic terminal alkenes to epoxides. It provides an efficient, reusable, and scalable protocol for the green synthesis of epoxides from various aliphatic terminal alkenes.

    4. Asymmetric Catalysis

      Highly Enantioselective Friedel–Crafts–type Alkylation Reactions of Indoles with Chalcone Derivatives using a Chiral Barium Catalyst (pages 1974–1977)

      Tetsu Tsubogo, Yuichiro Kano, Yasuhiro Yamashita and Shū Kobayashi

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/asia.201000347

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      Ba Ba black sheep: We have developed novel barium/binol catalysts prepared from alkaline earth metal amides and chiral binaphthol ligands. These catalysts effectively promoted the asymmetric Friedel–Crafts–type alkylation reactions of indoles with chalcone derivatives. This is the first example of asymmetric Friedel–Crafts–type alkylation reactions using chiral Brønsted bases.

    5. Antibacterial Materials

      Unusual Antibacterial Property of Mesoporous Titania Films: Drastic Improvement by Controlling Surface Area and Crystallinity (pages 1978–1983)

      Hamid Oveisi, Simin Rahighi, Xiangfen Jiang, Yoshihiro Nemoto, Ali Beitollahi, Soichi Wakatsuki and Yusuke Yamauchi

      Version of Record online: 21 JUL 2010 | DOI: 10.1002/asia.201000351

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      Keep it clean! The extraordinary antibacterial property of mesoporous titania films is discovered. The inactivation effect of bacteria is determined by several significant factors such as surface area, titania phase, anatase crystallinity, and surface morphology, which can be controlled by the applied calcination temperatures.

    6. Polyoxometalates

      En Route to Nanodevices of Polyoxometalate: Incorporating the Giant Nanoporous Molybdenum-Oxide based Wheels and Balls into Nanotubular Arrays (pages 1984–1987)

      Lijuan Zhang, Tian Xiong, Yunshan Zhou and Lihui Zhang

      Version of Record online: 7 JUL 2010 | DOI: 10.1002/asia.201000220

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      Layered tubes: The giant nanoporous molybdenum-oxide based polyoxometalates of the wheel and Keplerate type with unique features, which can be considered as the basis of a new type of nanochemistry and nanomaterials science and find a variety of applications, can be easily incorporated into nanotubular arrays with well defined wall thickness and aperture.

    7. Nanomaterials

      Photochemical Behavior of High Quantum Yield SWNTs Functionalized with Anthracene Salts (pages 1988–1991)

      Lingjie Meng, Chuanlong Fu, Zhaofu Fei, Qinghua Lu and Paul J. Dyson

      Version of Record online: 14 JUL 2010 | DOI: 10.1002/asia.201000236

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      I hope you like bamim too: Anthracene derivatives attached to functionalized single-walled carbon nanotubes through Coulombic interactions undergo a partial (and reversible) photodimerization process upon irradiation with UV light of appropriate wavelengths.

  6. Full Papers

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

      Linear Poly(methyl glycerol) and Linear Polyglycerol as Potent Protein and Cell Resistant Alternatives to Poly(ethylene glycol) (pages 1992–2000)

      Marie Weinhart, Ingo Grunwald, Monika Wyszogrodzka, Linda Gaetjen, Andreas Hartwig and Rainer Haag

      Version of Record online: 2 JUL 2010 | DOI: 10.1002/asia.201000127

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      A coat with arms! A fast and efficient approach to terminal-functionalized linear polyglycerols for subsequent surface modification is described. The resulting biocompatibility of the functionalized surfaces in comparison to a PEG-functionalized surface is demonstrated by protein adsorption and cell-adhesion testing.

    2. Mesoporous Materials

      Redox Active Mesoporous Hybrid Materials by In situ Syntheses with Urea-linked Triethoxysilylated Phenothiazines (pages 2001–2015)

      Zhou Zhou, Adam W. Franz, Sarah Bay, Biprajit Sarkar, Andreas Seifert, Piaoping Yang, Alex Wagener, Stefan Ernst, Markus Pagels, Thomas J. J. Müller and Werner R. Thiel

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/asia.201000098

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      Making hybrids: Mesoporous hybrid materials containing covalently grafted phenothiazines have been synthesized by the direct condensation of TEOS and appropriate silicon derivatives. Upon oxidation with (NO)BF4 or SbCl5, stable phenothiazine radical cations are generated in the pores of the materials, which can be detected by means of UV/Vis, emission, and EPR spectroscopies. The electron transfer into and out of these materials has been investigated by cyclic voltammetry.

    3. BODIPY Dyes

      Synthesis, Spectroscopy, Crystal Structure Determination, and Quantum Chemical Calculations of BODIPY Dyes with Increasing Conformational Restriction and Concomitant Red-Shifted Visible Absorption and Fluorescence Spectra (pages 2016–2026)

      Volker Leen, Wenwu Qin, Wensheng Yang, Jie Cui, Chan Xu, Xiaoliang Tang, Weisheng Liu, Koen Robeyns, Luc Van Meervelt, David Beljonne, Roberto Lazzaroni, Claire Tonnelé, Noël Boens and Wim Dehaen

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/asia.201000248

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      To close to color: A sequence of nucleophilic aromatic substitution and palladium catalyzed ring formation yields conformationally restricted BODIPY dyes with large red shifts of the absorption and emission spectra (see figure).

    4. Hydrosilylation

      Facile and Efficient Reduction of Ketones in the Presence of Zinc Catalysts Modified by Phenol Ligands (pages 2027–2035)

      Stephan Enthaler, Björn Eckhardt, Shigeyoshi Inoue, Elisabeth Irran and Matthias Driess

      Version of Record online: 15 JUL 2010 | DOI: 10.1002/asia.201000317

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      Sizzling silylation! Simple zinc complexes generated in situ catalyze the hydrosilylation of aliphatic and aromatic ketones with silanes as the hydride source with excellent turnover frequencies (>999 h−1) and broad group tolerance.

    5. Excited-State Dynamics

      Strongly Absorbing π–π* States in Heteroleptic Dipyrrin/2,2′-Bipyridine Ruthenium Complexes: Excited-State Dynamics from Resonance Raman Spectroscopy (pages 2036–2046)

      Tracey M. McLean, Deidre M. Cleland, Samuel J. Lind, Keith C. Gordon, Shane G. Telfer and Mark R. Waterland

      Version of Record online: 27 JUL 2010 | DOI: 10.1002/asia.201000033

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      Sensitivity issue: Emission from dipyrrin complexes displays a remarkable sensitivity on the structure of the 5-aryl substituent. The first resonance Raman study of a novel nonemissive heteroleptic ruthenium(II) dipyrrin species demonstrates that this sensitivity arises from the large scale torsional motion of the phenyl substituent in the Frank–Condon region. DFT calculations reveal the origin of these dynamics in the delocalization of charge onto the phenyl ring.

    6. Organocatalysis

      Organocatalytic Stereoselective α-Alkylation of Aldehydes with Stable Carbocations (pages 2047–2052)

      Fides Benfatti, Elena Benedetto and Pier Giorgio Cozzi

      Version of Record online: 6 JUL 2010 | DOI: 10.1002/asia.201000160

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      Go organic! Organocatalytic alkylation of aldehydes is realized with relatively stable isolated carbocations (see scheme; TFA=trifluoroacetic acid). Moderate to good enantioselectivities (up to 92 % ee) are observed. Reaction with stereogenic carbocation (flavilium fluoroborate) shows a moderate diastereoselectivity (up to 9:1).

    7. Bioluminescence

      Development of Luciferin Analogues Bearing an Amino Group and Their Application as BRET Donors (pages 2053–2061)

      Hideo Takakura, Kiyoshi Sasakura, Tasuku Ueno, Yasuteru Urano, Takuya Terai, Kenjiro Hanaoka, Takashi Tsuboi and Tetsuo Nagano

      Version of Record online: 26 JUL 2010 | DOI: 10.1002/asia.201000219

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      Following fireflies: We systematically synthesized novel bioluminogenic substrates bearing an amino group on benzothiazole, quinoline, naphthalene, and coumarin scaffolds. They emitted bioluminescence in various colors. The coumarylluciferin derivative was applied as an energy donor substrate for a bioluminescence resonance energy transfer system system utilizing firefly luciferin–luciferase reaction with yellow fluorescent protein.

    8. Polymers

      Homoleptic Platinum(II) and Palladium(II) Organothiolates and Phenylselenolates: Solvothermal Synthesis, Structural Determination, Optical Properties, and Single-Source Precursors for PdSe and PdS Nanocrystals (pages 2062–2074)

      Stephen Sin-Yin Chui, Kam-Hung Low, Jun Lu, V. A. L. Roy, Sharon Lai-Fung Chan and Chi-Ming Che

      Version of Record online: 27 JUL 2010 | DOI: 10.1002/asia.201000233

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      The power of powder! Powder X-ray diffraction was used to characterize intractable polymeric solids, chain-like metal coordination polymers with tuneable optical band gaps perturbed by d8 transition metal(II) ions and Group 6 donor atoms.

    9. Photochemistry

      The N-Arylamino Conjugation Effect in the Photochemistry of Fluorescent Protein Chromophores and Aminostilbenes (pages 2075–2085)

      Guan-Jhih Huang and Jye-Shane Yang

      Version of Record online: 15 JUL 2010 | DOI: 10.1002/asia.201000209

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      Show me the way: The analogies and differences in the solvent-dependent fluorescence and E–Z isomerization quantum yields between the N-arylamino-derived fluorescent protein chromophores and trans-aminostilbenes reveal the relative efficiencies of the three nonradiative decay pathways, the τ and ω torsions, and hydrogen-bonding-induced internal conversion (see scheme).

    10. Oxidants

      Tuning the Stability and Reactivity of Metal-bound Alkylperoxide by Remote Site Substitution of the Ligand (pages 2086–2092)

      Shiro Hikichi, Chiho Kobayashi, Michito Yoshizawa and Munetaka Akita

      Version of Record online: 29 JUN 2010 | DOI: 10.1002/asia.201000183

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      Gaining control: Thermal stability and oxidizing reactivity of nickel(II)–alkylperoxo species can be controlled by tuning the electronic property of the ligand without changing the coordination structure. Thermal stability of the brominated ligand complex is higher than that of the prototype non-brominated ligand complex.

    11. Electroluminescence

      Versatile Benzimidazole/Triphenylamine Hybrids: Efficient Nondoped Deep-Blue Electroluminescence and Good Host Materials for Phosphorescent Emitters (pages 2093–2099)

      Shaolong Gong, Yongbiao Zhao, Meng Wang, Chuluo Yang, Cheng Zhong, Jingui Qin and Dongge Ma

      Version of Record online: 22 JUL 2010 | DOI: 10.1002/asia.201000206

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      See deep blue: Two new bipolar compounds that combine triphenylamine and benzimidazole moieties have been synthesized and characterized. The results reveal that the bipolar compound 1 can be a potential multifunctional material as both deep-blue emitter and host for the phosphorescent dopant in organic light-emitting diodes (OLEDs; see image).

    12. Mesoporous Materials

      Prototype of Low Thermal Expansion Materials: Fabrication of Mesoporous Silica/Polymer Composites with Densely Filled Polymer inside Mesopore Space (pages 2100–2105)

      Shosuke Kiba, Norihiro Suzuki, Yoshinori Okawauchi and Yusuke Yamauchi

      Version of Record online: 21 JUL 2010 | DOI: 10.1002/asia.201000202

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      Framing polymers: A new model of polymer mobility restriction using mesoporous silica with a large pore space is proposed. The mesopores are easily penetrated by polymer chains owing to the capillary force during mechanical composite processing. The robust inorganic frameworks covering the polymer effectively restrict polymer mobility against thermal energy, which should contribute to low thermal expansion properties.

    13. Amino Alcohols

      Using a Combination of Magnetic Anisotropic Effects for the Configurational Assignment of Amino Alcohols (pages 2106–2112)

      Victoria Leiro, José Manuel Seco, Emilio Quiñoá and Ricardo Riguera

      Version of Record online: 2 JUL 2010 | DOI: 10.1002/asia.201000229

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      Prim and proper: The combined magnetic anisotropic effects generated by two auxiliary moieties of 2-methoxy-2-phenylacetic acid (MPA) allows the establishment of a methodology for the determination of the absolute configuration of terminal prim/sec and sec/prim 1,2-amino alcohols (see image).

    14. Lactams

      Synthesis and Biological Activities of Azalamellarins (pages 2113–2123)

      Sasiwadee Boonya-udtayan, Nattawut Yotapan, Christina Woo, Carson J. Bruns, Somsak Ruchirawat and Nopporn Thasana

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/asia.201000237

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      From lactone to lactam: The synthesis of azalamellarins (see scheme), a new series of lactam analogue of biologically active lamellarins, was studied using CuI-mediated, microwave-assisted C[BOND]Namide bond formation. Seventeen azalamellarins were synthesized and evaluated for their cytotoxicity against a panel of four human tumor cell lines.

  7. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Focus Review
    6. Communications
    7. Full Papers
    8. Preview
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      Preview: Chem. Asian J. 10/2010 (page 2127)

      Version of Record online: 30 AUG 2010 | DOI: 10.1002/asia.201090031

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