Chemistry – An Asian Journal

Cover image for Vol. 7 Issue 8

August 2012

Volume 7, Issue 8

Pages 1725–1958

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
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    9. Communications
    10. Full Papers
    1. You have free access to this content
      Cover Picture: C[BOND]C Cross-Coupling Reactions of O6-Alkyl-2-Haloinosine Derivatives and a One-Pot Cross-Coupling/O6-Deprotection Procedure (Chem. Asian J. 8/2012) (page 1725)

      Venkateshwarlu Gurram, Dr. Narender Pottabathini, Ramesh Garlapati, Dr. Avinash B. Chaudhary, Dr. Balaram Patro and Prof. Mahesh K. Lakshman

      Version of Record online: 12 JUL 2012 | DOI: 10.1002/asia.201290030

      Thumbnail image of graphical abstract

      C[BOND]C cross-coupling reactions of O6-alkyl-2-bromoinosine and O6-alkyl-2-chloroinosine derivatives are generally equally efficient, although the former is more rapidly consumed. In their Full paper on page 1853 ff., Narender Pottabathini and Mahesh K. Lakshman et al. show that with an O6-allyl group, cross coupling and deallylation can be conducted in a single step (the cover picture was designed by Satish Lakshman, Pixie Dust Design).

  2. Inside Cover

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    3. Inside Cover
    4. Graphical Abstract
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    7. Communications
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      Inside Cover: Spontaneous Formation of Giant Polymer Vesicles through a Nucleation and Growth Pathway (Chem. Asian J. 8/2012) (page 1726)

      Hanqing Qian, Wei Yao, Shuling Yu, Dr. Ying Chen, Dr. Wei Wu and Prof. Xiqun Jiang

      Version of Record online: 12 JUL 2012 | DOI: 10.1002/asia.201290031

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      Polymer vesicles are one of the important self-assembled structures of macromolecular amphiphiles. Besides the traditional membrane-closing mechanism, an alternative nucleation and growth pathway of vesicle formation has been proposed theoretically based on block copolymers. In their Full paper on page 1875 ff., Xiqun Jiang et al. designed a thermal sensitive amphiphilic hydrogen-bonded interpolymer complex to obtain experimental evidence of the suggested mechanism. They show that small aggregates nucleated from a hydroxypropyl cellulose–acrylic acid (HPC–AA) complex coalesce and grow into large solid spheres, which eventually transform into vesicles.

  3. Graphical Abstract

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Focus Reviews
    7. Communications
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  4. News

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    4. Graphical Abstract
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  5. Focus Reviews

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    1. Trifluoromethylation

      Recent Developments on the Trifluoromethylation of (Hetero)Arenes (pages 1744–1754)

      Dr. Xiao-Feng Wu, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Version of Record online: 19 JUN 2012 | DOI: 10.1002/asia.201200211

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      The road to trifluoromethylation is getting easier: Advances in the synthesis of trifluoromethylated arenes through electrophilic or nucleophilic strategies have been reviewed. Recent breakthroughs allow trifluoromethylation of (hetero)arenes under mild conditions and tolerance of a wide range of functionalities.

  6. Communications

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    1. Cross-Coupling

      Oxidative Trifluoromethylthiolations of Aryl Boronic Acids Using a Copper/O2-Based Protocol (pages 1756–1758)

      Cheng-Pan Zhang and David A. Vicic

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/asia.201200347

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      All you need is air: A new protocol has been developed which can mediate the coupling of aryl and vinyl boronic acids at room temperature in high yields (see scheme, dtbpy=4,4′-di-tert-butyl-2,2′-bipyridine). The reactions take place using simple copper(II) salts under aerobic conditions and do not require the use of expensive silver oxidants.

    2. C[BOND]C Coupling

      Ethylene Glycol: A Powerful Catalyst-Free Medium for C[BOND]C Bond-Forming Reactions (pages 1759–1763)

      Yun-Lin Liu, Xing-Ping Zeng and Prof. Dr. Jian Zhou

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/asia.201200289

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      A good EG: Ethylene glycol (EG) is a catalyst-free medium that can promote the highly efficient Strecker reaction of α-CF2H or α-CF3 ketoimines and TMSCN. EG was used in several reactions, including the catalyst-free Morita–Baylis–Hillman reaction.

  7. Preview

    1. Top of page
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    4. Graphical Abstract
    5. News
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    7. Communications
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    1. You have free access to this content
      Preview: Chem. Asian J. 9/2012 (page 1959)

      Version of Record online: 12 JUL 2012 | DOI: 10.1002/asia.201290034

  8. Communications

    1. Top of page
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    4. Graphical Abstract
    5. News
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    1. Immunosensors

      Label-Free Homogeneous Immunosensor Based on FRET for the Detection of Virus Antibody in Serum (pages 1764–1767)

      Cuiling Zhang, Ding Gao, Guohua Zhou, Lu Chen, Prof. Xian-an Zhang, Prof. Zongqiang Cui and Prof. Zhike He

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/asia.201200221

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      All lit up: A new label-free immunosensor detects SV40 antibody (Ab). It is based on resonance energy transfer (FRET) from quantum dots (QDs) encapsulated in simian vacuolating virus 40 (SV40) virus-like particles to graphene oxide. This method is rapid, inexpensive, and easy to perform.

    2. Hydrogels

      Ionic Surfactants Induce Amphiphilic Tris(Urea) Hydrogel Formation (pages 1768–1771)

      Yuki Jinno and Dr. Masamichi Yamanaka

      Version of Record online: 16 MAY 2012 | DOI: 10.1002/asia.201200152

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      All bundled up: A tris(urea)benzene hydrogelator first self-assembles into fibrous aggregates, which come together to form bundles (see scheme). The bundling process can be controlled by the concentration of ionic surfactant additive. The right concentration leads to supramolecular hydrogel formation.

  9. Full Papers

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

      Hierarchical Nitrogen-Doped Flowerlike ZnO Nanostructure and Its Multifunctional Environmental Applications (pages 1772–1780)

      Hongwei Bai, Dr. Zhaoyang Liu and Prof. Darren Delai Sun

      Version of Record online: 6 JUN 2012 | DOI: 10.1002/asia.201200260

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      Where have all the flowers gone? Flowerlike nanostructures of ZnO demonstrated an array of environmental applications, such as photodegradation of organic pollutants, antibacterial activity, and membrane filtration. These properties are related to the large specific surface area, the good light absorption ability, the suppression of the recombination of electrons and holes, and the creation of porous functional layers.

    2. Nanomaterials

      Polymer-Supported Bimetallic Ag@AgAu Nanocomposites: Synthesis and Catalytic Properties (pages 1781–1788)

      Shaofeng Zhang, Dr. Wei Wu, Prof. Xiangheng Xiao, Juan Zhou, Jinxia Xu, Prof. Feng Ren and Prof. Changzhong Jiang

      Version of Record online: 14 JUN 2012 | DOI: 10.1002/asia.201200348

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      Silver surfer: Polymer-supported bimetallic nanocomposites (PS-Ag@AuAg) were synthesized by using a seed-growth process. The LSPR of these composites could be tailored over a large scale. The catalytic activity of the nanocomposites was remarkably superior to that of the supported monometallic nanocomposites.

    3. Fluorosphores

      Extended Fluorochromism of Anthracene Trimers with a meta-Substituted Triphenylamine or Triphenylphosphine Core (pages 1789–1794)

      Zhiou Li, Hiromi Ishizuka, Yoshihisa Sei, Prof. Dr. Munetaka Akita and Dr. Michito Yoshizawa

      Version of Record online: 11 JUN 2012 | DOI: 10.1002/asia.201200310

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      Fluorescent Triskelions: Combining meta-triphenylamine or triphenylphosphine with three anthracene fluorophores gives rise to fluorescent non-planar triskelions and . The emissive properties of are highly solvatochromic, yielding blue to pale green and even pale yellow fluorescence, whereas the blue emission of is solvent-insensitive. Anthracene trimers and are both emissive in the solid state, displaying yellow and pale green fluorescence, respectively, with moderate quantum yields.

    4. Electrochemistry

      Highly Catalytic Carbon Nanotube/Pt Nanohybrid-Based Transparent Counter Electrode for Efficient Dye-Sensitized Solar Cells (pages 1795–1802)

      Dr. Hong-Yan Chen, Jin-Yun Liao, Dr. Bing-Xin Lei, Prof. Dai-Bin Kuang, Prof. Yueping Fang and Prof. Cheng-Yong Su

      Version of Record online: 8 MAY 2012 | DOI: 10.1002/asia.201200144

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      Bending the rules: An efficient carbon nanotube/platinum nanohybrid-based transparent counter electrode has been fabricated by a facile electrospray method and exhibits excellent electrochemical performances in dye-sensitized solar cells (DSSCs; see picture). Moreover, the as-prepared flexible counter electrode exhibits a conversion efficiency of 8.43 %, which shows great potential in developing low-cost flexible DSSCs.

    5. DNA Binders

      The Fluorophore 4′,6-Diamidino-2-phenylindole (DAPI) Induces DNA Folding in Long Double-Stranded DNA (pages 1803–1810)

      Dr. Maria Rosa Beccia, Dr. Tarita Biver, Alberto Pardini, Jacopo Spinelli, Prof. Fernando Secco, Prof. Marcella Venturini, Dr. Natalia Busto Vázquez, Prof. Maria Pilar Lopez Cornejo, Victoria Isabel Martin Herrera and Prof. Rafael Prado Gotor

      Version of Record online: 21 MAY 2012 | DOI: 10.1002/asia.201200177

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      Building bridges: DAPI is a widely used fluorescent dye, whose complicated binding features to DNAs and RNAs are still not fully understood. In this study, T-jump kinetic analyses, melting experiments, as well as viscometric, binding equilibria, and circular dichroism measurements concur in shedding light on the complex DAPI/DNA interactions, which can change from groove binding to intercalation. Moreover, it is observed for the first time that DAPI is able to induce the formation of a rather compact polymer–dye adduct stabilized by DAPI bridges.

    6. Porphyrinoids

      An Electron-Deficient Porphyrin Tape (pages 1811–1816)

      Hirotaka Mori, Dr. Takayuki Tanaka, Dr. Naoki Aratani, Byung Sun Lee, Pyosang Kim, Prof. Dr. Dongho Kim and Prof. Dr. Atsuhiro Osuka

      Version of Record online: 21 MAY 2012 | DOI: 10.1002/asia.201200247

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      Mix tape: A hexakis(pentafluorophenyl)-substituted mesomeso,β-β,β-β triply linked ZnII–diporphyrin exhibited considerably improved chemical stability, owing to a lowered HOMO, and good solubility in common organic solvents.

    7. Solar Cells

      Influence of Solvent and Bridge Structure in Alkylthio-Substituted Triphenylamine Dyes on the Photovoltaic Properties of Dye-Sensitized Solar Cells (pages 1817–1826)

      Chun Sakong, Se Hun Kim, Sim Bum Yuk, Jin Woong Namgoong, Se Woong Park, Dr. Min Jae Ko, Dong Hoe Kim, Prof. Kug Sun Hong and Prof. Jae Pil Kim

      Version of Record online: 23 MAY 2012 | DOI: 10.1002/asia.201100814

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      Structure and solvent effects: Three novel triphenylamine dyes with different alkylthio-substituted thiophene bridges were synthesized for dye-sensitized solar cells (DSSCs). The photovoltaic performances of the DSSCs showed a marked dependence on the bridge structure and solvent system due to the different amounts of dye adsorbed (see scheme).

    8. Perovskites

      Y:BaZrO3 Perovskite Compounds I: DFT Study on the Unprotonated and Protonated Local Structures (pages 1827–1837)

      Dr. Antonio Cammarata, Prof. Pablo Ordejón, Prof. Antonio Emanuele and Prof. Dario Duca

      Version of Record online: 8 MAY 2012 | DOI: 10.1002/asia.201100974

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      What a dope! Y-doped BaZrO3 derivatives were studied by DFT calculations. Yttrium centers induced topological differences in neighboring oxygen sites, according to the local arrangement of yttrium in the host matrix. Proton-hopping activation energies were reproduced in the structures in which two yttrium atoms formed Y-O-Y moieties. In such systems, the existence of proton-trapping was inferred.

    9. Y:BaZrO3 Perovskite Compounds II: Designing Protonic Conduction by using MD Models (pages 1838–1844)

      Dr. Antonio Cammarata, Prof. Antonio Emanuele and Prof. Dario Duca

      Version of Record online: 8 MAY 2012 | DOI: 10.1002/asia.201100975

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      Why oh Y-O-Y? Y-doped BaZrO3 derivatives were studied by using MD simulations. Previous DFT results were confirmed and, at the same time, an explanation of the close relationship between the local structure and the proton-diffusion dynamics at different temperatures and local Y concentrations is highlighted.

    10. Semiconductor Materials

      Optoelectronic Properties of Dicyanofluorene-Based n-Type Polymers (pages 1845–1852)

      Dr. Chakkooth Vijayakumar, Dr. Akinori Saeki and Prof. Shu Seki

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/asia.201200082

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      Hop to it! The design and synthesis of three dicyanofluorene-based conjugated polymers and their optoelectronic properties including their electron-accepting and conducting properties are described (see scheme). Use of these polymers as n-type materials in all-polymer organic solar cells is explored in combination with poly(3-hexylthiophene).

    11. Cross-Coupling

      C[BOND]C Cross-Coupling Reactions of O6-Alkyl-2-Haloinosine Derivatives and a One-Pot Cross-Coupling/O6-Deprotection Procedure (pages 1853–1861)

      Venkateshwarlu Gurram, Dr. Narender Pottabathini, Ramesh Garlapati, Dr. Avinash B. Chaudhary, Dr. Balaram Patro and Prof. Mahesh K. Lakshman

      Version of Record online: 8 MAY 2012 | DOI: 10.1002/asia.201200093

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      Cross-training: The Pd-catalyzed C[BOND]C cross-coupling of silyl-protected 2-bromo- and 2-chloro-O6-methylinosines were broadly comparable. The C[BOND]C cross-coupling of O6-allyl-2-chloroinosine afforded C-2 aryl- and alkyl-substituted inosine derivatives (see scheme).

    12. Cyclization Reactions

      Synthesis of 3,4-Dihalogenated Furan-2-(5 H)-ones by Electrophilic Cyclization of 4-Hydroxy-2-alkynoates (pages 1862–1866)

      Dr. Hai-Tao Zhu, Li-Jing Wang, Dr. Ke-Gong Ji, Prof. Dr. Xue-Yuan Liu and Prof. Dr. Yong-Min Liang

      Version of Record online: 15 MAY 2012 | DOI: 10.1002/asia.201200137

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      Three amigos: Functionalized 3,4-dihalogenated furan-2(5 H)-ones can be readily prepared in moderate to good yields by treating 4-hydroxy-4-arylbut-2-ynoate derivatives with ICl, IBr, and I2. Both halogen atoms of the electrophile are incorporated in the product (see scheme).

    13. Biosensors

      Sensitive Detection of Small Molecule–Protein Interactions on a Metal–Insulator–Metal Label-Free Biosensing Platform (pages 1867–1874)

      Dr. Amir Syahir, Prof. Kotaro Kajikawa and Prof. Hisakazu Mihara

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/asia.201200138

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      Don′t label me: A simple metal–insulator–metal (MIM) geometry was used for fabricating a highly sensitive detection platform for label-free biosensing. The MIM substrate consists of an Au–PMMA–Ag nanolayer (Ag-MIM), and was studied both theoretically and experimentally. By monitoring reflectivity changes on the surface, the biolayer thickness of various proteins (Mw=6–150 kD) and the interaction between small molecules (Mw≤2 kD) and immobilized proteins was effectively detected as compared with the Au-only substrate.

    14. Polymer Vesicles

      Spontaneous Formation of Giant Polymer Vesicles through a Nucleation and Growth Pathway (pages 1875–1880)

      Hanqing Qian, Wei Yao, Shuling Yu, Dr. Ying Chen, Dr. Wei Wu and Prof. Xiqun Jiang

      Version of Record online: 3 MAY 2012 | DOI: 10.1002/asia.201200155

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      Big friendly giants: A nucleation and growth mechanism for vesicle formation that involved the creation of hydrogen-bonded complexes between thermo-responsive cellulose (HPC) and poly(acrylic acid) (PAA) was demonstrated experimentally. The dynamic formation of HPC-PAA vesicles, rather than a commonly believed membrane-closing mechanism, was observed through a nucleation and growth pathway.

    15. Terpenoids

      Simple Analogues of Qinghaosu (Artemisinin) (pages 1881–1886)

      Dr. Yun Li, Dr. Hong-Dong Hao, Dr. Sergio Wittlin and Prof. Dr. Yikang Wu

      Version of Record online: 15 MAY 2012 | DOI: 10.1002/asia.201200166

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      The temple of artemisinin: The key peroxy bonds in a series of 1,2,4-trioxanes were installed by molybdenum-catalyzed perhydrolysis of the epoxy rings. A novel core structure with potent antimalarial activity was identified.

    16. Porphyrins

      Selective Cycloaddition of Tetracyanoethene (TCNE) and 7,7,8,8-Tetracyano-p-quinodimethane (TCNQ) to Afford meso-Substituted Phenylethynyl Porphyrins (pages 1887–1894)

      Dr. Dominik Koszelewski, Agnieszka Nowak-Król and Prof. Daniel T. Gryko

      Version of Record online: 23 MAY 2012 | DOI: 10.1002/asia.201200179

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      1,1,4,4-Tetracyanobuta-1,3-dienyl porphyrins were prepared by the efficient [2+2] cycloaddition of tetracyanoethene (TCNE) or 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) with meso-substituted trans-A2B2-porphyrins that contained two phenylethynyl groups, followed by a retro-electrocyclization reaction. Depending on the electronic properties of the arylethynyl groups, cycloaddition took place exclusively on either one or two ethynyl moieties.

    17. Heterogeneous Catalysis

      Effect of Calcination Temperature and Pretreatment with Reaction Gas on Properties of Co/γ-Al2O3 Catalysts for Partial Oxidation of Methane (pages 1895–1901)

      Dr. Nuo-Wei Zhang, Prof. Chuan-Jing Huang, Xiao-Quan Zhu, Jing-Dong Xu, Prof. Wei-Zheng Weng and Prof. Hui-Lin Wan

      Version of Record online: 15 MAY 2012 | DOI: 10.1002/asia.201200180

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      A pretreatment by reaction gas! A simple but efficient approach improves the catalytic performance of Al2O3-supported Co catalysts for partial oxidation of methane to syngas. Catalysts pretreated with feedstock showed higher activity and higher stability for the reaction than those without this pretreatment. For the sake of comparison, the effect of calcination temperature was also investigated.

    18. Photocatalysis

      Visible-Light Photocatalytic Activity and Deactivation Mechanism of Ag3PO4 Spherical Particles (pages 1902–1908)

      Dr. Wenguang Wang, Prof. Bei Cheng, Prof. Jiaguo Yu, Prof. Gang Liu and Prof. Wenhong Fan

      Version of Record online: 8 JUN 2012 | DOI: 10.1002/asia.201200197

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      Jumping up and down: Changes in the photocatalytic activity of Ag3PO4 spherical particles under recycling conditions were investigated. It was found that the activity first increased but subsequently decreased with reuse of the particles, the color of which changed from golden yellow (as-prepared sample) to dark yellow to dark gray (recycled for 4 and 7 times, respectively). A possible mechanism is proposed that explains these changes in photocatalytic performance.

    19. Polyfluorinated Compounds

      Generation of Polyfluoroaryl-Fused H-Pyrazolo[5,1-a]isoquinolines through a Reaction of N′-(2-Alkynylbenzylidene)hydrazide with Polyfluoroarene (pages 1909–1914)

      Dr. Ling Zhang, Qian Xiao, Shengqing Ye and Prof. Dr. Jie Wu

      Version of Record online: 6 JUN 2012 | DOI: 10.1002/asia.201200227

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      Catalysis: Polyfluoroarene reacts with N′-(2-alkynylbenzylidene)hydrazide catalyzed by silver triflate in the presence of cesium carbonate, thus leading to polyfluoroaryl-fused H-pyrazolo[5,1-a]isoquinolines in good yields (see scheme).

    20. Metallacycles

      Interconversion of Metallabenzenes and Cyclic η2-Allene-Coordinated Complexes (pages 1915–1924)

      Ran Lin, Jing Zhao, Hanyu Chen, Dr. Hong Zhang and Prof. Dr. Haiping Xia

      Version of Record online: 29 MAY 2012 | DOI: 10.1002/asia.201200231

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      The interconversion of metallabenzenes and cyclic η2-allene-coordinated complexes can be achieved by the introduction of 8-hydroxyquinoline substitution. Studies on the reactivity of the allene-coordinated complex with nucleophiles demonstrate that this type of reaction constitutes a new facile way to prepare unsaturated metallacylces.

    21. Synthetic Methods

      Preparation of THP-Ester-Derived Pyridinium-Type Salts and their Reactions with Various Nucleophiles (pages 1925–1933)

      Prof. Dr. Hiromichi Fujioka, Yutaka Minamitsuji, Takahiro Moriya, Kazuhisa Okamoto, Ozora Kubo, Tomoyo Matsushita and Dr. Kenichi Murai

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/asia.201200234

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      Salty but sweet: Nucleophilic substitution at the anomeric position of tetrahydropyranyl esters via pyridinium-type salt intermediates proceeded without affecting acid-labile protecting groups owing to the use of mild reaction conditions (see scheme).

    22. Fluorescence

      Synthesis and Self-Assembly of Dihydroxyperylene Bisimides for the Tuning of Photophysical Properties (pages 1934–1939)

      Dr. Yongjun Li, Zhihong Qing, Yanwen Yu, Taifeng Liu, Runsheng Jiang and Prof. Yuliang Li

      Version of Record online: 8 JUN 2012 | DOI: 10.1002/asia.201200243

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      Group mentality: 1,10-Dihydroxyperylene bisimides formed J aggregates in nonpolar solvents with a clearly redshifted absorption band. The solvent polarity also influenced hydrogen bonds to the hydroxy group, and thus, altered the photophysical properties of the perylene bisimide (see picture). The photophysical properties could also be tuned by introducing metal ions.

    23. Hybrid Materials

      Wintersweet-Flower-Like CoFe2O4/MWCNTs Hybrid Material for High-Capacity Reversible Lithium Storage (pages 1940–1946)

      Ying Wang, Jinsoo Park, Bing Sun, Prof. Hyojun Ahn and Prof. Guoxiu Wang

      Version of Record online: 16 MAY 2012 | DOI: 10.1002/asia.201200257

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      Stop and smell the flowers: A new hybrid material resembles wintersweet flower buds on branches, in which CoFe2O4 nanoclusters are anchored along carbon nanotubes. The hybrid material shows a high performance for reversible lithium storage, especially a high rate capability. This strategy could also be applied to synthesize other metal oxide/carbon nanotube hybrid materials as high-capacity anode materials for lithium ion batteries.

    24. Cycloaddition

      Intramolecular [2+2] Photocycloaddition Reactions as an Entry to the 2-Oxatricyclo[4.2.1.04, 9]nonan-3-one Skeleton of Lactiflorin (pages 1947–1958)

      Dr. Ping Lu, Dr. Eberhardt Herdtweck and Prof. Dr. Thorsten Bach

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/asia.201200295

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      Substitution matters in the [2+2] photocycloaddition of butenolides : For X,Y=H and X=OTBS, Y=H the crossed products were formed as major regioisomers (r.r.=89:11 to 65:35), whereas the straight products prevailed in the case of X=H, Y=OTBS in particular for R=CH2OBn (r.r.=70:30). The latter product (X=H, Y=OTBS, R=CH2OBn) was successfully converted into the monoterpene glycoside lactiflorin.

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