Chemistry – An Asian Journal

Cover image for Vol. 7 Issue 4

April 2012

Volume 7, Issue 4

Pages 625–839

  1. Cover Picture

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      Cover Picture: Catalysis of Gold Nanoparticles within Lysozyme Single Crystals (Chem. Asian J. 4/2012) (page 625)

      Dr. Hui Wei and Prof. Yi Lu

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/asia.201290010

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      While gold nanoparticles (AuNPs) have been widely used in catalysis, a detailed understanding concerning the control of their activity has been lacking. In their Communication on page 680 ff., Hui Wei and Yi Lu report that AuNPs (shown in gold in the image) grown within the single crystals of the protein lysozyme catalyze the reduction of para-nitrophenol (in orange) by NaBH4 to para-aminophenol (in green) in a size-dependent manner. Because the size of the AuNPs can be precisely tuned by the growth period for the protein crystals, a correlation between the size of AuNPs within the protein crystals and their catalytic activity has now been established. The use of chemicals to either accelerate or inhibit the activity of AuNPs is also demonstrated (Image design: Li Huey Tan, Hui Wei, and Yi Lu).

  2. Inside Cover

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      Inside Cover: The Radiative Decay Rates Tune the Emissive Properties of Ruthenium(II) Polypyridyl Complexes: A Computational Study (Chem. Asian J. 4/2012) (page 626)

      Dr. Daniel Escudero, Bobby Happ, Andreas Winter, Martin D. Hager, Prof. Dr. Ulrich S. Schubert and Prof. Dr. Leticia González

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/asia.201290011

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      Tuning the excited-state lifetimes of Ru(II) polypyridyl complexes is the key to their potential applicabilities, for example, as photosensitizers. In their Communication on page 667 ff., Leticia González et al. demonstrate, with the help of quantum chemical calculations, that the different emissive properties of two similar Ru(II) polypyridyl complexes bearing peripheral ligand substitution are governed by the radiative decay rates and not the energy gap law, oppositely to what it is generally believed. This change of paradigm might be transferable to understand the fine tuning on the emissive properties of other Ru(II) polypyridyl complexes.

  3. Graphical Abstract

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  4. News

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  5. Focus Review

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    1. Photocatalysis

      Inorganic Photocatalysts for Overall Water Splitting (pages 642–657)

      Jun Xing, Wen Qi Fang, Prof. Dr. Hui Jun Zhao and Prof. Dr. Hua Gui Yang

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/asia.201100772

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      A split personality: Water splitting to produce H2 and O2 using solar energy in the presence of photocatalysts has been considered for the supply of clean, recyclable energy. Over the past few decades, a number of inorganic photocatalytic materials for overall water splitting have been developed. This review aims to sum up these research efforts, whilst providing a comprehensive understanding of this field.

  6. Communications

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    1. Fluorescent Probes

      An Imidazolium-Based Fluorescent Cyclophane for the Selective Recognition of Iodide (pages 658–663)

      Dr. Vangaru Suresh, Nisar Ahmed, Il Seung Youn and Prof. Dr. Kwang S. Kim

      Version of Record online: 8 FEB 2012 | DOI: 10.1002/asia.201100941

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      For your I's only: A new imidazolium-based fluorescent cyclophane 1 was designed and synthesized that was quenched selectively in the presence of iodide but not other anions, as assessed by fluorimetry. In addition, fluorescence titration experiments, 1H NMR spectroscopic data, and theoretical calculations provide evidence that 1 encapsulates two iodides inside its cavity.

    2. Dehydrogenation

      N[BOND]C Coupling of NO Ligands with β-Carbon Atoms in Aliphatic Tertiary Amines on Nitrosylruthenium Complexes Accompanying Oxidative Dehydrogenation of Amines and C[BOND]H Activation (pages 664–666)

      Dr. Taiki Asayama, Dr. Yasuhiro Arikawa, Takerou Murabe, Shoko Agari, Prof. Keisuke Umakoshi and Prof. Masayoshi Onishi

      Version of Record online: 19 JAN 2012 | DOI: 10.1002/asia.201100816

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      Doctor NO: Unprecedented β-carbon nitrosation of aliphatic tertiary amines on nitrosylruthenium complexes was revealed, where aerobic oxidative dehydrogenation of amines, C[BOND]H bond activation, N[BOND]C coupling, and enamine hydrolysis were involved.

    3. Light Harvesting

      The Radiative Decay Rates Tune the Emissive Properties of Ruthenium(II) Polypyridyl Complexes: A Computational Study (pages 667–671)

      Dr. Daniel Escudero, Bobby Happ, Andreas Winter, Martin D. Hager, Prof. Dr. Ulrich S. Schubert and Prof. Dr. Leticia González

      Version of Record online: 8 FEB 2012 | DOI: 10.1002/asia.201100864

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      Stay tuned: Tuning the excited state lifetimes of RuII polypyridyl complexes is the key to their potential applicabilities, for example, as photosensitizers. This work demonstrates that the different emissive properties of two similar RuII polypyridyl complexes bearing peripheral ligand substitution are governed by the radiative decay rates and not the energy gap law.

    4. Acenes

      “Clean Reaction” Strategy to Approach a Stable, Green Heptatwistacene Containing a Single Terminal Pyrene Unit (pages 672–675)

      Dr. Jinchong Xiao, Dr. Christos D. Malliakas, Yi Liu, Feng Zhou, Gang Li, Prof. Haibin Su, Prof. Mercouri G. Kanatzidis, Prof. Fred Wudl and Prof. Qichun Zhang

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/asia.201100910

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      Let's twist again: A “clean reaction” strategy based on thermally eliminating lactam bridges from a soluble acene precursor through a retro-Diels–Alder reaction gives a new, stable, green heptatwistacene (see structure). The molecule has a twist angle of 23.49°, is very stable even in air, and has an optical band gap of 1.82 eV.

    5. Total Synthesis

      Approaches to the Neurotrophically Active Natural Product 11-O-Debenzoyltashironin: A Chemoenzymatic Total Synthesis of the Structurally Related Sesquiterpene Khusiol (pages 676–679)

      Mukesh K. Sharma, Prof. Martin G. Banwell, Dr. Anthony C. Willis and Prof. A. David Rae

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/asia.201100913

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      Soothes your nerves: The enantiomerically enriched cis-1,2-dihydrocatechol has been converted, over 16 steps including one involving an intramolecular Diels–Alder reaction, into the sesquiterpenoid natural product khusiol (), which is structurally related to the neurite outgrowth-promoting natural product 11-O-debenzoyltashironin ().

    6. Nanoparticles

      Catalysis of Gold Nanoparticles within Lysozyme Single Crystals (pages 680–683)

      Dr. Hui Wei and Prof. Yi Lu

      Version of Record online: 31 JAN 2012 | DOI: 10.1002/asia.201100942

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      Hidden treasure: Gold nanoparticles (AuNPs) within a single protein crystal of lysozyme (see scheme, pink) are shown to efficiently catalyze the reduction of p-nitrophenol by NaBH4, and the catalytic activity initially increased with increased size of AuNPs until the size reached 7.4 nm, after which the activity decreased with increasing size of the AuNPs. The use of chemicals to either accelerate or inhibit the activity is also demonstrated.

    7. Hydrogen Spillover

      Hydrogen Spillover in Pd-doped V2O5 Nanowires at Room Temperature (pages 684–687)

      Prof. Byung Hoon Kim, Dr. Han Young Yu, Won G. Hong, Dr. Jonghyurk Park, Dr. Sung Chul Jung, Youngwoo Nam, Prof. Hu Young Jeong, Prof. Yung Woo Park, Prof. Yongseok Jun and Dr. Hae Jin Kim

      Version of Record online: 24 JAN 2012 | DOI: 10.1002/asia.201100947

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      In the black: a chromic change of Pd-doped V2O5 nanowires from orange to black occurred after exposure to molecular hydrogen at room temperature. The change in color is irreversible and attributed to a hydrogen spillover effect.

    8. Furans

      Efficient Synthesis of Tetrasubstituted Furans from Nitroallylic Acetates and 1,3-Dicarbonyl/α-Activating Ketones by Feist–Bénary Addition–Elimination (pages 688–691)

      Wan-Yun Huang, Yi-Chieh Chen and Kwunmin Chen

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/asia.201100988

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      Pure organic: The synthesis of tetrasubstituted furans often involves transition-metal catalysis or metal–halogen exchange reactions. A new approach to these heterocycles employs the Feist–Bénary addition–elimination process using nitroallylic acetates and 1,3-dicarbonyls (see scheme; X=C, O).

    9. Nanostructures

      Gold Double-Ring Structures Synthesized from Block Copolymer Corpuscle Templates (pages 692–695)

      Seungmin Yoo, Heesook Cho, Dr. Jung-Pil Lee, Prof. Kyoung Taek Kim and Prof. Soojin Park

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/asia.201101032

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      Golden donuts: Polystyrene-block-poly(2-vinylpyridine) block copolymer (BCP) corpuscle templates were prepared on PS-modified substrates. Subsequent metal–polymer complexation and reduction resulted in the formation of gold double-ring structures.

    10. Solar Cells

      New 2, 6-Modified Bodipy Sensitizers for Dye-Sensitized Solar Cells (pages 696–700)

      Jian-Bo Wang, Xia-Qin Fang, Dr. Xu Pan, Prof. Song-Yuan Dai and Prof. Qin-Hua Song

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/asia.201100779

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      Three novel 2,6-modified Bodipy sensitizers were synthesized and evaluated for their use in dye-sensitized solar cells (DSSCs). Among them, dye B3, which carries a n-pentyl group at position 8, exhibits the best solar energy conversion efficiency (1.83 %). The results of this study provide a new strategy for the design of Bodipy derivatives as sensitizers for DSSCs.

  7. Full Papers

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

      The Inherent Electrochemistry of Nickel/Nickel-Oxide Nanoparticles (pages 702–706)

      Marcella Giovanni, Dr. Adriano Ambrosi and Prof. Martin Pumera

      Version of Record online: 13 FEB 2012 | DOI: 10.1002/asia.201101024

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      Down on one Ni: The direct detection of nanoparticles is at the forefront of research owing to its environmental and toxicological applications. A simple and direct electrochemical method is proposed for the determination of the concentration of both nickel (Ni) and nickel oxide (NiO) nanoparticles in alkaline solution.

    2. Energetic Salts

      Nitrogen-Rich Energetic Monoanionic Salts of 3,4-Bis(1 H-5-tetrazolyl)furoxan (pages 707–714)

      Haifeng Huang, Prof. Dr. Zhiming Zhou, Lixuan Liang, Jinhong Song, Kai Wang, Dan Cao, Wenwen Sun, Chengming Bian and Dr. Min Xue

      Version of Record online: 20 JAN 2012 | DOI: 10.1002/asia.201100702

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      Ready for an energy boost? Nitrogen-rich salts in which the anion bears a furoxan ring connected with two tetrazole rings exhibit reasonable physical properties, such as high densities (1.63–1.79 g cm−3) and good thermal stabilities (182–258 °C), and possess high positive heats of formation (859.8–1063.5 kJ mol−1). Their detonation velocities and detonation pressures were calculated to be 7740–8790 m s−1 and 23.1–32.5 GPa, respectively.

    3. Energetic Materials

      Synthesis and Characterization of Two Formyl 2-Tetrazenes (pages 715–724)

      Dr. Henri Delalu and Dr. Carlos Miró Sabaté

      Version of Record online: 20 JAN 2012 | DOI: 10.1002/asia.201100769

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      The synthesis and characterization of two formyl 2-tetrazenes (see figure) is presented. These compounds may have applications as useful building blocks for the synthesis of materials with interesting energetic properties.

    4. Molecular Recognition

      The Interactions of Spore-Coat Morphogenetic Proteins Studied by Single-Molecule Recognition Force Spectroscopy (pages 725–731)

      Haiyan Qiao, Dr. Daniela Krajcikova, Caisheng Liu, Dr. Yongjun Li, Prof. Hongda Wang, Prof. Imrich Barak and Prof. Jilin Tang

      Version of Record online: 19 JAN 2012 | DOI: 10.1002/asia.201100795

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      Spontaneous spores: Spore-coat morphogenetic proteins are chemically bound to an AFM tip and silicon substrate, respectively, through a flexible cross-linker, and by using single-molecule recognition force spectroscopy (SMRFS) the piconewton forces and a series of dynamic kinetic data related to spore-coat morphogenetic proteins are obtained (see picture).

    5. Electrochemical Sensors

      β-Cyclodextrin-Platinum Nanoparticles/Graphene Nanohybrids: Enhanced Sensitivity for Electrochemical Detection of Naphthol Isomers (pages 732–737)

      Gangbing Zhu, Pengbo Gai, Liang Wu, Jianhui Zhang, Xiaohua Zhang and Prof. Dr. Jinhua Chen

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/asia.201100839

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      A new hybrid unveiled: β-Cyclodextrin (β-CD)-platinum nanoparticles (Pt NPs)/graphene nanosheets (GNs) nanohybrids (β-CD-PtNPs/GNs) were prepared for the first time by a simple wet chemical method and used to detect naphthol isomers. Due to the excellent properties of GNs, Pt NPs, and β-CDs, electrodes modified with β-CD-PtNPs/GNs resulted in improved detection limits compared to other electrochemical sensors developed for the detection of naphthol isomers.

    6. Dye-Sensitized Solar Cells

      Organic Dyes Containing Pyrenylamine-Based Cascade Donor Systems with Different Aromatic π Linkers for Dye-Sensitized Solar Cells: Optical, Electrochemical, and Device Characteristics (pages 738–750)

      Dr. K. R. Justin Thomas, Neha Kapoor, Chuan-Pei Lee and Prof. Kuo-Chuan Ho

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/asia.201100849

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      New organic dyes containing pyrenylamine-based cascade donors have been synthesized and characterized by their optical and electrochemical properties. They showed interesting modulation in electronic properties, which are attributable to the changes in the electronic interaction between the donor segments arising from the nature of the linker.

    7. Phthalocyanine Conjugates

      Synthesis and Spectroscopic Properties of Phthalocyanine–[60]Fullerene Conjugates Connected Directly by Means of a Four-Membered Ring (pages 751–758)

      Prof. Takamitsu Fukuda, Yuu Kikukawa, Shiori Takaishi and Prof. Nagao Kobayashi

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/asia.201100850

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      Wedding ring: Covalently C60-conjugated phthalocyanine (Pc) analogues in which the Pc and C60 components are joined by a four-membered ring have been synthesized by taking advantage of a [2+2] cycloaddition reaction of C60 with benzyne units generated from either a Pc derivative or its precursor (see figure). The presence of the C60 moiety affects the electronic structure of the conjugates.

    8. Modified Graphenes

      Inherent Electrochemistry and Activation of Chemically Modified Graphenes for Electrochemical Applications (pages 759–770)

      James Guo Sheng Moo, Dr. Adriano Ambrosi, Dr. Alessandra Bonanni and Prof. Martin Pumera

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/asia.201100852

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      Electrochemical treatment of chemically modified graphenes (CMGs) represents an easy approach to alter surface functionalities and consequently tune electrochemical performance.

    9. Tandem Reactions

      Catalytic Diastereoselective Tandem Conjugate Addition–Elimination Reaction of Morita–Baylis–Hillman C Adducts by C[BOND]C Bond Cleavage (pages 771–777)

      Wenguo Yang, Davin Tan, Richmond Lee, Lixin Li, Dr. Yuanhang Pan, Prof. Kuo-Wei Huang, Prof. Choon-Hong Tan and Prof. Zhiyong Jiang

      Version of Record online: 8 FEB 2012 | DOI: 10.1002/asia.201100863

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      Competitive choice: Through the cleavage of the C[BOND]C bond, the catalytic tandem conjugate addition–elimination reaction of Morita–Baylis–Hillman C adducts has been disclosed. Various SN2′-like C-, S-, and P-allylic compounds are prepared with exclusive E configuration in good to excellent yield. The origin of the selectivity was strongly supported by DFT methods (see scheme).

    10. Quinolines

      InCl3-Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope and Limitations (pages 778–787)

      Tanmoy Chanda, Rajiv Kumar Verma and Dr. Maya Shankar Singh

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/asia.201100872

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      In it to wIn it: The regioselective synthesis of functionalized/annulated quinolines involved the coupling of 2-aminoaryl/alkyl ketones with alkynes/activated-methylenes/α-oxoketene-dithioacetals promoted by InCl3 in MeCN as well as under solvent-free conditions. Simple reductive and oxidative cyclization of 2-nitrobenzaldehyde and 2-aminobenzyl alcohol, respectively, has also been performed to give substituted quinolines.

    11. Ruthenium Complexes

      Preparation of Organometallic Ruthenium–Arene–Diaminotriazine Complexes as Binding Agents to DNA (pages 788–801)

      Dr. Natalia Busto, Jesús Valladolid, Cristina Aliende, Prof. Félix A. Jalón, Prof. Blanca R. Manzano, Dr. Ana M. Rodríguez, Prof. Jorge F. Gaspar, Celia Martins, Dr. Tarita Biver, Dr. Gustavo Espino, Prof. José María Leal and Prof. Begoña García

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/asia.201100883

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      Ru lonesome tonight? A new family of RuII-arene complexes with two different diaminotriazine ligands were synthesized. Bifunctional interactions of complex with DNA through two concurrent binding modes were considered: groove binding (mode 1) concurred with a quenching effect, whereas electrostatic binding (mode 2) implicated the p-cymene ring and promoted an increase in fluorescence.

    12. Mesoporous Materials

      Synthesis of Olive-Shaped Mesoporous Platinum Nanoparticles (MPNs) with a Hard-Templating Method Using Mesoporous Silica (SBA-15) (pages 802–808)

      Hongjing Wang, Dr. Masataka Imura, Dr. Yoshihiro Nemoto, Prof. Dr. Sang-Eon Park and Prof. Dr. Yusuke Yamauchi

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/asia.201100949

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      Antipasti, anyone? Well-ordered olive-shaped mesoporous Pt nanoparticles (see picture) can be prepared by using two-dimensional (2D) hexagonal mesoporous silica (SBA-15) as a hard template. The average particle sizes are controllable in the range of 150 nm to 230 nm by changing the deposition time.

    13. Host–Guest Systems

      Resorcinarene Bis-Thiacrowns: Prospective Host Molecules for Silver Encapsulation (pages 809–817)

      Dr. Kirsi Salorinne, Dr. Elisa Nauha and Prof. Maija Nissinen

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/asia.201100969

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      Binding it soft but strong: Resorcinarene bis-thiacrowns containing soft sulfur donor atoms are shown to be ideal host molecules for high-affinity encapsulation of silver inside the resorcinarene cavity. A 1:2 host–guest binding was observed both in solution and in the solid state.

    14. Organic Photovoltaics

      Dithienocyclopentathieno[3,2-b]thiophene Hexacyclic Arene for Solution-Processed Organic Field-Effect Transistors and Photovoltaic Applications (pages 818–825)

      Prof. Dr. Yen-Ju Cheng, Chiu-Hsiang Chen, Tai-Yen Lin and Prof. Dr. Chain-Shu Hsu

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/asia.201100979

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      Snakes and ladders: Donor–acceptor polymers based on the ladder-type dithienocyclopentathieno[3,2-b]thiophene (DTCTT) unit has promising performance for solution-processed organic transistors and photovoltaics.

    15. Host–Guest Systems

      Unusual Photoreaction of Triquinacene within Self-Assembled Hosts (pages 826–829)

      Dr. Takashi Murase, Yuki Nishijima and Prof. Dr. Makoto Fujita

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/asia.201101005

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      Electron-withdrawing cage: A self-assembled coordination cage accommodates triquinacene (1) to allow a specific photooxidation of the peripheral allylic position via guest-to-host electron transfer. The host cage consists of electron-deficient triazine panels and thus serves as a photochemically active molecular container.

    16. Nanoparticles

      Multifunctional Core–Shell Upconverting Nanoparticles for Imaging and Photodynamic Therapy of Liver Cancer Cells (pages 830–837)

      Zengxia Zhao, Yuning Han, Chenghong Lin, Dong Hu, Fang Wang, Prof. Xiaolan Chen, Prof. Zhong Chen and Prof. Nanfeng Zheng

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/asia.201100879

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      Go on, liver little: NaGdF4:Yb,Er/NaGdF4 nanoparticles with a carboxy aluminum phthalocyanine (AlC4Pc) photosensitizer incorporated inside silica shells were used in photodynamic therapy and magnetic resonance imaging (MRI) of liver cancer cells. In vitro studies indicated that these nanoparticles effectively killed cancer cells upon near-infrared excitation. This work has potential applications in imaging-guided therapy.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
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    1. You have free access to this content
      Preview: Chem. Asian J. 5/2012 (page 839)

      Version of Record online: 29 MAR 2012 | DOI: 10.1002/asia.201290014

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