Chemistry – An Asian Journal

Cover image for Vol. 11 Issue 24

December 19, 2016

Volume 11, Issue 24

Pages 3466–3605

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Focus Reviews
    4. Communications
    5. Full Papers
    1. You have free access to this content
      Cover Picture: Size-Dependent Surface Migration of Au Alloys on Si Nanowires at Different Cooling Rates (Chem. Asian J. 24/2016) (page 3466)

      Yi-Seul Park, Hyun Ji Kim and Prof. Jin Seok Lee

      Version of Record online: 12 DEC 2016 | DOI: 10.1002/asia.201601530

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      The surface migration behavior of Au alloys was investigated through the variation of cooling conditions after growth of vertically aligned Si nanowires (SiNWs) by an Au catalyst-assisted vapor–liquid–solid mechanism. The Au alloy showed a size-dependent surface migration behavior at the top of the SiNWs with varying cooling rate. During fast cooling, the Au alloy stayed at the top of the SiNWs regardless of the Au alloy diameter. In contrast, during slow cooling, the small Au alloys migrated from the top to the sidewalls of the SiNWs, whereas the large Au alloys did not migrate from the top of the SiNWs caused by Au–Si eutectic stability. More information can be found in the Communication by Jin Seok Lee et al. on page 3487 in Issue 24, 2016 (DOI: 10.1002/asia.201601325).

    2. You have free access to this content
      Inside Cover: Mechanistic Studies of TiO2 Photocatalysis and Fenton Degradation of Hydrophobic Aromatic Pollutants in Water (Chem. Asian J. 24/2016) (page 3467)

      Dr. Yuanzheng Gong, Dr. Chun Yang, Prof. Hongwei Ji, Prof. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Version of Record online: 14 DEC 2016 | DOI: 10.1002/asia.201601513

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      The substitution and direct departure of the ipso-H by OH radicals has long been considered as the main route for the hydroxylation of aromatic compounds in water. Detailed isotope-labelled experiments showed that part of the ipso-H shifted to the adjacent carbon in the aromatic ring and was retained in the final phenols (1,2-NIH shift). The results indicated that besides the common ipso-substitution, a Wagner–Meerwein rearrangement of the carbocation intermediates also exists during the hydroxylation of aromatic compounds in H2O via advanced oxidation technologies. More information can be found in the Full Paper by Wanhong Ma, Jincai Zhao et al. on page 3568 in Issue 24, 2016 (DOI: 10.1002/asia.201601299).

  2. Focus Reviews

    1. Top of page
    2. Cover Pictures
    3. Focus Reviews
    4. Communications
    5. Full Papers
    1. Chitin/Chitosan Modification

      Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides (pages 3468–3481)

      Dr. Luísa C. R. Carvalho, Fausto Queda, Cátia V. Almeida Santos and Dr. M. Manuel B. Marques

      Version of Record online: 23 NOV 2016 | DOI: 10.1002/asia.201601041

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      Chitin and chitosan are attractive biopolymers with enormous structural possibilities for chemical modification, creating platforms for new chemical entities with a broad scope of applications, ranging from material science to medicine. Regioselective modification of these biopolymers paves the way for improved properties and tailored activities. Thus, the most recent advances in chitin/chitosan regioselective modification, reaction conditions, selectivity, and the impact on applications are reviewed.

  3. Communications

    1. Top of page
    2. Cover Pictures
    3. Focus Reviews
    4. Communications
    5. Full Papers
    1. Antitumor Agents

      Three-Arm, Biotin-Tagged Carbazole–Dicyanovinyl–Chlorambucil Conjugate: Simultaneous Tumor Targeting, Sensing, and Photoresponsive Anticancer Drug Delivery (pages 3482–3486)

      Yarra Venkatesh, Dr. S. Karthik, Y. Rajesh, Prof. Mahitosh Mandal, Dr. Avijit Jana and Prof. N. D. Pradeep Singh

      Version of Record online: 18 NOV 2016 | DOI: 10.1002/asia.201601264

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      On target: The design, synthesis, and in vitro biological studies of a biotin–carbazole–dicyanovinyl–chlorambucil conjugate are reported. One bond undergoes a thiol–ene click reaction with intracellular thiols, thereby shutting down internal charge transfer and resulting in a change of the fluorescence color from green to blue, and thus, sensing the tumor microenvironment. Subsequent photoirradiation results in release of the anticancer drug in a controlled manner (see figure).

    2. Si Nanowires

      Size-Dependent Surface Migration of Au Alloys on Si Nanowires at Different Cooling Rates (pages 3487–3492)

      Yi-Seul Park, Hyun Ji Kim and Prof. Jin Seok Lee

      Version of Record online: 11 NOV 2016 | DOI: 10.1002/asia.201601325

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      Size-dependent migration: The size-dependent migration mechanism of Au alloys was investigated at different cooling rates, which is related to different Au-Si eutectics. The diameters of Au alloys were varied by controlling the thickness of the Au film as a catalyst for SiNW growth.

    3. Fluorogenic Probes

      A Self-Immobilizing and Fluorogenic Probe for β-Lactamase Detection (pages 3493–3497)

      Wuyu Mao, Lingying Xia, Yaqun Wang and Prof. Dr. Hexin Xie

      Version of Record online: 16 NOV 2016 | DOI: 10.1002/asia.201601344

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      Bacteria are not irresistible: A self-immobilizing and fluorogenic probe for the detection of β-lactamase activity has been developed. This fluorogenic reagent, upon activation by β-lactamases, turns on a fluorescence signal and, more importantly, generates a covalent linkage to the target enzymes or the nearby proteins.

    4. Nanorods

      Unprecedented Charge-Transfer Complex of Fused Diporphyrin as Near-Infrared Absorption-Induced High-Aspect-Ratio Nanorods (pages 3498–3502)

      B. Shivaprasad Achary, Dr. Sabapathi Gokulnath, Samrat Ghosh, Madoori Mrinalini, Dr. Seelam Prasanthkumar and Dr. Lingamallu Giribabu

      Version of Record online: 17 NOV 2016 | DOI: 10.1002/asia.201601363

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      CT complex induced nanorods: Structural similarities of perylene in fused diporphyrin and perylene diimide result in charge-transfer complex in chloroform. Subsequent diffusion of methanol vapors lead to hierarchical self-assembled high aspect ratio nanorods via coalesced nanospheres.

    5. Sulfenylation

      Synthesis of Thioethers and Thioesters with Alkyl Arylsulfinates as the Sulfenylation Agent under Metal-Free Conditions (pages 3503–3507)

      Yahui Li, Fengxiang Zhu, Zechao Wang and Prof. Dr. Xiao-Feng Wu

      Version of Record online: 22 NOV 2016 | DOI: 10.1002/asia.201601376

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      Smell-free sulfenylation! A study on the coupling of cycloalkanes with alkyl arylsulfinates has been performed. Using iodine as the catalyst, through Csp3−H bond activation and sulfinates reduction, a wide range of thioethers were produced in moderate to high yields. Additionally, various thiocarboxylic esters can also be produced by simply performing the reaction under CO pressure. Notably, this is the first report in which alkyl arylsulfinates were used as sulfenylation agents in a cross-coupling transformation.

    6. Aminocarbonylation

      Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides (pages 3508–3512)

      Yong-Sik Seo, Dr. Dong-Su Kim and Prof. Dr. Chul-Ho Jun

      Version of Record online: 25 NOV 2016 | DOI: 10.1002/asia.201601421

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      Good ol′ carbon monoxide… A novel method for the preparation of amides and phthalimides has been developed. The process involves a palladium catalyzed aminocarbonylation of an aryl halide, using a carbodiimide and formic acid as the carbonyl source. Experimental data suggest that the mechanistic pathway for this process involves an in situ generation of carbon monoxide from the reaction of formic acid with a carbodiimide in the presence of a palladium catalyst.

  4. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Focus Reviews
    4. Communications
    5. Full Papers
    1. Chiral Selectors

      6-TIPS-β-Cyclodextrin-Modified Fe3O4 for Facile Enantioseparation of 1-(1-Naphthyl)ethylamine (pages 3513–3519)

      Lu Wang, Xiang-Yong Liang, Prof. Dr. Li-Sheng Ding, Prof. Dr. Sheng Zhang and Prof. Dr. Bang-Jing Li

      Version of Record online: 15 NOV 2016 | DOI: 10.1002/asia.201601151

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      A great fit: A new kind of chiral magnetic nanoparticle (MNPs) with high magnetic saturation and high chiral recognition ability was successfully fabricated by using heptakis-(6-O-triisopropylsilyl)-β-cyclodextrin (6-TIPS-β-CD; see figure) as a chiral selector. Stereoselective absorption experiments by using 1-(1-naphthyl)ethylamine as a model for aromatic amines indicated that these TIPS-β-CD-MNPs showed high chiral recognition ability.

    2. Core–Shell Hybrids

      Basil Seed Inspired Design for a Monodisperse Core–Shell Sn@C Hybrid Confined in a Carbon Matrix for Enhanced Lithium-Storage Performance (pages 3520–3527)

      Dr. Jinwen Qin, Dr. Bing Liu and Prof. Minhua Cao

      Version of Record online: 28 NOV 2016 | DOI: 10.1002/asia.201601180

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      It's a seedy deal: A Sn@C hybrid from a basil seed inspired design shows superior electrochemical performance. Structural and morphological evolution can explain the gradual increase in capacity for lithium-ion batteries.

    3. Hypergolic Fuels

      Towards N-Alkylimidazole Borane-based Hypergolic Fuels (pages 3528–3533)

      Dr. Shi Huang, Dr. Wenquan Zhang, Dr. Tianlin Liu, Dr. Kangcai Wang, Dr. Xiujuan Qi, Prof. Jiaheng Zhang and Prof. Qinghua Zhang

      Version of Record online: 25 NOV 2016 | DOI: 10.1002/asia.201601194

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      Greener rocket fuels: A series of N-alkylimidazole borane compounds has been synthesized, which display hypergolic reactivity with the oxidizer of white fuming nitric acid. Compared with popular hypergolic ionic liquids, these fuels have the advantages of low viscosity and cost-effectiveness, and easily scaled-up production.

    4. Nickel Nanoparticles

      In Situ Confined Growth Based on a Self-Templating Reduction Strategy of Highly Dispersed Ni Nanoparticles in Hierarchical Yolk–Shell Fe@SiO2 Structures as Efficient Catalysts (pages 3534–3540)

      Jiao Jiao, Prof. Haiyan Wang, Wanchun Guo, Ruifei Li, Kesong Tian, Prof. Zhaopeng Xu, Yin Jia, Yuehao Wu and Ling Cao

      Version of Record online: 23 NOV 2016 | DOI: 10.1002/asia.201601196

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      Get the yolk! A hierarchical yolk–shell Fe@SiO2/Ni catalyst with an inner movable Fe core and an ultrathin SiO2/Ni shell assembled from nanosheets was synthesized by a self-templating reduction strategy (see figure). The spatial confinement of 4 nm Ni nanoparticles in ultrathin SiO2 nanosheets (2.6 nm thick) could prevent their agglomeration during catalytic reductions and expose the abundant active Ni sites to reactants, to provide high activity and stability.

    5. Hydrogen Storage Materials

      Preparation and Catalytic Activity of a Novel Nanocrystalline ZrO2@C Composite for Hydrogen Storage in NaAlH4 (pages 3541–3549)

      Xin Zhang, Ruyan Wu, Zeyi Wang, Prof. Mingxia Gao, Prof. Hongge Pan and Prof. Yongfeng Liu

      Version of Record online: 23 NOV 2016 | DOI: 10.1002/asia.201601204

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      Boosting hydrogen storage: In situ-synthesized nanocrystalline ZrO2@C exhibits good catalytic activity for hydrogen storage in NaAlH4. The NaAlH4–7 wt % ZrO2@C sample releases hydrogen starting from 126 °C and reabsorbs hydrogen starting from 54 °C, and these temperatures are lower by 71 and 36 °C, respectively, than those for pristine NaAlH4 (see figure).

    6. Heterogenized Homogeneous Catalysts

      Triazole-Containing Dendrimer-like Core Cross-Linked Micelles that Stabilize Pd Nanoparticles as Heterogenized Homogeneous Catalysts for Room-Temperature Suzuki–Miyaura Reactions in Water (pages 3550–3556)

      Bing Li, Yangyang Yu, Prof. Pengxiang Zhao and Prof. Shiyong Zhang

      Version of Record online: 22 NOV 2016 | DOI: 10.1002/asia.201601248

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      Simple and efficient! Facile-to-prepare triazole-containing dendrimer-like core cross-linked micelle stabilized palladium nanoparticles (Pd@triazole-DCCMs) has been established as an excellent heterogenized homogeneous catalyst for room-temperature Suzuki–Miyaura reaction in water.

    7. Building Blocks for Organic Solar Cells

      Conjugated Oligothiophene Derivatives Based on Bithiophene with Unsaturated Bonds as Building Blocks for Solution-Processed Bulk Heterojunction Organic Solar Cells (pages 3557–3567)

      Dr. Chaohua Cui, Yue Wu, Dr. Man-Sing Cheung, Dr. Cheuk-Lam Ho, Dr. Qingchen Dong, Prof. Dr. Zhenyang Lin, Prof. Dr. Yongfang Li and Prof. Dr. Wai-Yeung Wong

      Version of Record online: 25 NOV 2016 | DOI: 10.1002/asia.201601281

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      Conjugation rules! A new building block ATVTA that uses stiff carbon–carbon triple bonds (A) as the linkages on a 1,2-di(2-thienyl)-ethene (TVT) unit has been developed. The effects of three building blocks (TVT, AT2 and ATVTA units) and the nature of the terminal electron acceptors in several conjugated oligothiophene derivatives were studied systematically.

    8. Isotopic Tracing | Very Important Paper

      Mechanistic Studies of TiO2 Photocatalysis and Fenton Degradation of Hydrophobic Aromatic Pollutants in Water (pages 3568–3574)

      Dr. Yuanzheng Gong, Dr. Chun Yang, Prof. Hongwei Ji, Prof. Chuncheng Chen, Prof. Wanhong Ma and Prof. Jincai Zhao

      Version of Record online: 22 NOV 2016 | DOI: 10.1002/asia.201601299

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      Radical influences: NIH shift phenomena were observed during the evolution of HO–adduct radicals in TiO2 photocatalysis and Fenton degradations of water-insoluble aromatics. Results indicate that a mixed mechanism of both the carbocation intermediate pathway and oxygen-capturing pathway occurs in both reactions (see figure).

    9. Fluorescent Probes

      A Selective Near-Infrared Fluorescent Probe for In Vivo Imaging of Thiophenols from a Focused Library (pages 3575–3582)

      Yue Pan, Tian-Bing Ren, Dan Cheng, Dr. Ze-Bing Zeng, Dr. Lin Yuan and Dr. Xiao-Bing Zhang

      Version of Record online: 22 NOV 2016 | DOI: 10.1002/asia.201601309

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      Bright idea! Owing to its many desirable properties, such as excitation/emission in the near-IR region, good cell-membrane permeability, intracellular stability, and low cytotoxicity, CCP-1 is a potential candidate for thiophenol detection both in vitro and in vivo. In a model study, thiophenol was successfully visualized in living animals for the first time (see scheme).

    10. Hypervalent Iodine

      Preparation of Heteroaromatic (Aryl)iodonium Imides as I−N Bond-Containing Hypervalent Iodine (pages 3583–3588)

      Kazuma Ishida, Prof. Dr. Hideo Togo and Prof. Dr. Katsuhiko Moriyama

      Version of Record online: 23 NOV 2016 | DOI: 10.1002/asia.201601349

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      When N and I get along… Heteroaromatic (aryl)iodonium imides containing an iodine–nitrogen bond and a hypervalent iodine(III) atom were prepared from heteroarenes, bis(sulfon)imides and (diacetoxyiodo)arenes under mild conditions. The compounds were stable under air and in organic solvents, and could be easily purified by precipitation. The introduction of substituents to the iodoarenes facilitated the purification of some of the products.

    11. Polycycles

      π-Extended Star-Shaped Polycyclic Aromatic Hydrocarbons based on Fused Truxenes: Synthesis, Self-Assembly, and Facilely Tunable Emission Properties (pages 3589–3597)

      Cheng Cheng, Yi Jiang, Dr. Cheng-Fang Liu, Jian-Dong Zhang, Prof. Dr. Wen-Yong Lai and Prof. Dr. Wei Huang

      Version of Record online: 11 NOV 2016 | DOI: 10.1002/asia.201601355

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      A star is born: A new set of star-shaped polycyclic aromatic hydrocarbons (PAHs) with unique self-assembly behavior and facilely tunable emission properties has been synthesized through a stepwise oxidative cyclodehydrogenation procedure.

    12. Substituent Effects

      Substituent Effects in BODIPY in Live Cell Imaging (pages 3598–3605)

      Dr. Sandip V. Mulay, Tesla Yudhistira, Dr. Minsuk Choi, Youngsam Kim, Jinjoo Kim, Yoon Jeong Jang, Prof. Dr. Sangyong Jon and Prof. Dr. David G. Churchill

      Version of Record online: 23 NOV 2016 | DOI: 10.1002/asia.201601400

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      Body? Pie? No, it′s BODIPY! Substituents on boron-dipyrromethene (BODIPY) have been shown to play significant roles for the detection of biologically important analytes under in vitro conditions and in live cell imaging studies. The probe shows a selective and sensitive turn-on response with NaOCl over other reactive oxygen/nitrogen species (ROS/RNS) in vitro. Surprisingly, in live cell experiments, the probe specifically accumulates in lipid droplets and shows fluorescence turn-on responses because of aggregation-induced emission (AIE) owing to the lipophilic mesityl group at the meso position of the BODIPY.

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