ChemSusChem

Cover image for Vol. 6 Issue 2

February 2013

Volume 6, Issue 2

Pages 211–388

  1. Cover Picture

    1. Top of page
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    5. Mastheads
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      Cover Picture: Enamine Catalysis in Flow with an Immobilized Peptidic Catalyst (ChemSusChem 2/2013) (page 211)

      Dr. Yukihiro Arakawa and Prof. Dr. Helma Wennemers

      Article first published online: 6 FEB 2013 | DOI: 10.1002/cssc.201390006

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      The front cover shows a flow system that operates with a highly effective immobilized peptidic catalyst, reported by Helma Wennemers and co-workers from the ETH Zürich, Switzerland on page 242. More than 600 turnovers and high stereoselectivities are achieved on a scale of >450 mmol (>100 g), without a significant drop of the activity or stereoselectivity of the immobilized peptidic catalyst. This high efficiency and sustainability of a flow system is unprecedented in the very active field of enamine catalysis and opens the way for more practical applications.

  2. Cover Profile

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    2. Cover Picture
    3. Cover Profile
    4. Graphical Abstract
    5. Mastheads
    6. News
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    1. You have free access to this content
      Enamine Catalysis in Flow with an Immobilized Peptidic Catalyst (page 212)

      Dr. Yukihiro Arakawa and Prof. Dr. Helma Wennemers

      Article first published online: 6 FEB 2013 | DOI: 10.1002/cssc.201300054

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      “This is the first example of highly stereo- and chemoselective enamine catalysis in a continuous flow reactor on a scale of >100 g (>450 mmol).” This and more about the story behind the front cover research can be found on p. 212.

  3. Graphical Abstract

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    1. Graphical Abstract: ChemSusChem 2/2013 (pages 213–220)

      Article first published online: 6 FEB 2013 | DOI: 10.1002/cssc.201390007

  4. Mastheads

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    1. Masthead: ChemSusChem 2/2013 (page 214)

      Article first published online: 6 FEB 2013 | DOI: 10.1002/cssc.201390008

    2. Masthead: ChemSusChem 2/2013 (page 223)

      Article first published online: 6 FEB 2013 | DOI: 10.1002/cssc.201390009

  5. News

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    1. Spotlights on our sister journals: ChemSusChem 2/2013 (pages 224–227)

      Article first published online: 6 FEB 2013 | DOI: 10.1002/cssc.201390010

  6. Minireview

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    1. Palladium-Catalyzed Oxidative Carbonylation Reactions (pages 229–241)

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

      Article first published online: 10 JAN 2013 | DOI: 10.1002/cssc.201200683

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      The truth about carbonylations: Palladium-catalyzed oxidative carbonylation reactions have undergone a rapid development during recent years. Nowadays, a plethora of palladium catalysts and reaction protocols are available for the synthesis of carbonyl-containing products, which are important intermediates in the manufacture of dyes, pharmaceuticals, agrochemicals, and other industrial products. Herein, we summarize the developments of oxidative carbonylation transformations of alkenes, alkynes, arenes, and organometalic reagents.

  7. Communications

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    1. Enamine Catalysis in Flow with an Immobilized Peptidic Catalyst (pages 242–245)

      Dr. Yukihiro Arakawa and Prof. Dr. Helma Wennemers

      Article first published online: 19 NOV 2012 | DOI: 10.1002/cssc.201200740

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      Pep talk: An immobilized peptidic catalyst achieves more than 600 turnovers in a continuous-flow system, allowing the production of chiral γ-nitroaldehydes with excellent stereoselectivities on a scale of >450 mmol (>100 g). Such a high efficiency opens the way for more practical applications of enamine catalysis.

    2. Gold Nanoparticles Produced In Situ Mediate Bioelectricity and Hydrogen Production in a Microbial Fuel Cell by Quantized Capacitance Charging (pages 246–250)

      Dr. Shafeer Kalathil, Prof. Dr. Jintae Lee and Prof. Dr. Moo Hwan Cho

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cssc.201200747

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      Oppan quantized style: By adding a gold precursor at its cathode, a microbial fuel cell (MFC) is demonstrated to form gold nanoparticles that can be used to simultaneously produce bioelectricity and hydrogen. By exploiting the quantized capacitance charging effect, the gold nanoparticles mediate the production of hydrogen without requiring an external power supply, while the MFC produces a stable power density.

    3. Lipase-Mediated Oxidative Delignification in Non-Aqueous Media: Formation of De-Aromatized Lignin-Oil and Cellulase-Accessible Polysaccharides (pages 251–255)

      Lotte Wiermans, Dr. María Pérez-Sánchez and Dr. Pablo Domínguez de María

      Article first published online: 9 JAN 2013 | DOI: 10.1002/cssc.201200704

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      Pulp & Oil: We report the unprecedented formation of de-aromatized lignin oil together with a white polysaccharide fraction when lignocellulose is treated with peracids, which are formed in situ by enzymes. A preliminary characterization of the lignin oil is provided, together with the evidence that the delignified lignocellulose is accessible to cellulases to afford fermentable sugars. As a first proof-of-concept, the reported approach may bring promising new research lines in the future.

    4. Cyanomethylbenzoic Acid: An Acceptor for Donor–π–Acceptor Chromophores Used in Dye-Sensitized Solar Cells (pages 256–260)

      Dr. Wanchun Xiang, Akhil Gupta, Muhammad Kalim Kashif, Dr. Noel Duffy, Dr. Ante Bilic, Prof. Dr. Richard A. Evans, Prof. Dr. Leone Spiccia and Prof. Dr. Udo Bach

      Article first published online: 23 JAN 2013 | DOI: 10.1002/cssc.201200636

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      Sensing the sun: Incorporation of a cyanomethyl benzoic acid electron acceptor into donor–π–acceptor sensitizers for dye-sensitized-solar cell is shown to lead to devices with improved conversion efficiency when compared with more widely used cyanoacetic acid acceptor.

  8. Full Papers

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    1. TiN Nanoparticles on CNT–Graphene Hybrid Support as Noble-Metal-Free Counter Electrode for Quantum-Dot-Sensitized Solar Cells (pages 261–267)

      Duck Hyun Youn, Minsu Seol, Jae Young Kim, Dr. Ji-Wook Jang, Youngwoo Choi, Prof. Kijung Yong and Prof. Jae Sung Lee

      Article first published online: 9 JAN 2013 | DOI: 10.1002/cssc.201200775

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      Titanium nitride electrocatalyst: TiN nanoparticles on a carbon nanotube–graphene hybrid support are fabricated and utilized as a new counter electrode material for quantum-dot-sensitized solar-cell applications. The new material exhibits enhanced power-conversion efficiency (relative to the state-of-the-art Au electrode), which is ascribed to a reduced charge-transfer resistance and a larger surface area relative to the Au electrode.

    2. Capacity Decay and Remediation of Nafion-based All-Vanadium Redox Flow Batteries (pages 268–274)

      Dr. Qingtao Luo, Dr. Liyu Li, Dr. Wei Wang, Zimin Nie, Dr. Xiaoliang Wei, Dr. Bin Li, Dr. Baowei Chen, Dr. Zhenguo Yang and Dr. Vincent Sprenkle

      Article first published online: 3 DEC 2012 | DOI: 10.1002/cssc.201200730

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      All-vanadium redox flow batteries are considered to be one of the most promising technologies for large-scale stationary energy storage. Nevertheless, constant capacity decay severely jeopardizes their long-term stability. The capacity-decay mechanism of vanadium flow batteries using a Nafion membrane is investigated and elucidated. Capacity-restoration methods are proposed and experimentally validated.

    3. Covalently Cross-Linked Sulfone Polybenzimidazole Membranes with Poly(Vinylbenzyl Chloride) for Fuel Cell Applications (pages 275–282)

      Jingshuai Yang, Dr. David Aili, Dr. Qingfeng Li, Dr. Lars N. Cleemann, Dr. Jens Oluf Jensen, Prof. Niels J. Bjerrum and Prof. Ronghuan He

      Article first published online: 9 JAN 2013 | DOI: 10.1002/cssc.201200716

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      Cross my heart: New cross-linked high-temperature electrolytes based on sulfone polybenzimidazole and poly(vinylbenzyl chloride) are developed. The cross-linked membranes exhibit excellent stability towards radical oxidation, high resistance to acid swelling, and improved mechanical strength, which allows higher acid doping levels, increased proton conductivity, and significantly improved fuel cell performance and durability.

    4. Synthesis of Nanovoid Bi2WO6 2D Ordered Arrays as Photoanodes for Photoelectrochemical Water Splitting (pages 283–290)

      Dr. Liwu Zhang and Prof. Dr. Detlef Bahnemann

      Article first published online: 16 JAN 2013 | DOI: 10.1002/cssc.201200708

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      Nanovoid photoanode: A facile method to improve the efficiency of solar energy conversion systems by minimizing the charge-carrier diffusion length and increasing the light absorption is proposed. The Bi2WO6 nanovoid array photoanode shows a much higher photocurrent density and photon-to-H2 conversion efficiency than planar Bi2WO6 photoanodes.

    5. Understanding Self-Photorechargeability of WO3 for H2 Generation without Light Illumination (pages 291–298)

      Dr. Charlene Ng, Dr. Akihide Iwase, Dr. Yun Hau Ng and Prof. Rose Amal

      Article first published online: 15 JAN 2013 | DOI: 10.1002/cssc.201200702

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      Photorechargeability in the dark! Insights into the self-photorechargeability phenomenon of WO3 is covered in this work. The proposed mechanism is studied by investigating the intercalation and de-intercalation of alkali cations through cyclic voltammetry studies. Maximum charge capacity is also monitored to optimise the charge storage ability. The stored electrons are also successfully utilised for H2 generation in the absence of light illumination.

    6. Ordered Mesoporous Tungsten Suboxide Counter Electrode for Highly Efficient Iodine-Free Electrolyte-Based Dye-Sensitized Solar Cells (pages 299–307)

      Inyoung Jeong, Changshin Jo, Dr. Arockiam Anthonysamy, Jung-Min Kim, Dr. Eunae Kang, Jongkook Hwang, Dr. Easwaramoorthi Ramasamy, Prof. Shi-Woo Rhee, Prof. Jin Kon Kim, Dr. Kyoung-Su Ha, Dr. Ki-Won Jun and Prof. Jinwoo Lee

      Article first published online: 23 DEC 2012 | DOI: 10.1002/cssc.201200647

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      WOx before Pt: Ordered mesoporous tungsten suboxide (m-WO3−x) is synthesized by using a hard template and a partial reduction process. The m-WO3−x is used as an alternative catalyst for a counter electrode (CE) instead of Pt for iodine-free electrolyte (T2/T)-based dye-sensitized solar cells. The catalytic activity of m-WO3−x CE is superior to that of conventional Pt CEs.

    7. Segmented Tetrasulfonated Copoly(Arylene Ether Sulfone)s: Improving Proton Transport Properties by Extending the Ionic Sequence (pages 308–319)

      Shogo Takamuku, E. Annika Weiber and Prof. Patric Jannasch

      Article first published online: 10 JAN 2013 | DOI: 10.1002/cssc.201200601

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      Membrane power: The use of a new tetrasulfonated monomer to prepare segmented sulfonated aromatic polysulfones, instead of traditional disulfonated ones, facilitates ionic cluster formation in proton-exchange membranes. This results in durable fuel-cell membranes with improved water-uptake characteristics and significantly enhanced proton conductivity.

    8. Single-Walled Carbon Nanotube/Polyaniline/n-Silicon Solar Cells: Fabrication, Characterization, and Performance Measurements (pages 320–327)

      Daniel D. Tune, Dr. Benjamin S. Flavel, Prof. Jamie S. Quinton, Prof. Amanda V. Ellis and Prof. Joseph G. Shapter

      Article first published online: 15 JAN 2013 | DOI: 10.1002/cssc.201200600

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      Nanotube films help capture the sun: Carbon nanotube–silicon solar cells are a recently investigated photovoltaic architecture with demonstrated high efficiencies. Hybrid solar-cell devices with an efficiency of approximately 9.7 %, and comprising a thin film of polyaniline deposited on silicon and covered by a single-walled carbon nanotube film are fabricated and characterized.

    9. Anion-Conductive Membranes with Ultralow Vanadium Permeability and Excellent Performance in Vanadium Flow Batteries (pages 328–335)

      Dr. Zhensheng Mai, Prof. Dr. Huamin Zhang, Hongzhang Zhang, Wanxing Xu, Wenping Wei, Prof. Dr. Hui Na and Prof. Dr. Xianfeng Li

      Article first published online: 22 JAN 2013 | DOI: 10.1002/cssc.201200561

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      Breakthrough barrier: Quaternized poly(tetramethyl diphenyl ether sulfone) membranes synthesized through a bromination route are introduced into a vanadium flow battery (VFB) as an anion-conductive membrane separator (see picture), with a higher battery efficiency than commercial Nafion 115 owing to outstanding selectivity between proton and vanadium ions.

    10. Debinding Mechanisms in Thermoplastic processing of a Ba0.5Sr0.5Co0.8Fe0.2O3−δ- Stearic Acid–Polystyrene Mixture (pages 336–344)

      Mehdi Salehi, Dr. Frank Clemens, Prof. Dr. Eugenio H. Otal, Dr. Davide Ferri, Prof. Dr. Thomas Graule and Prof. Dr. Bernard Grobéty

      Article first published online: 23 DEC 2012 | DOI: 10.1002/cssc.201200540

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      Unusually active ceramics: This study analyses the role of a reactive ceramic powder during the thermal treatment of the thermoplastic feedstock. BSCF (Ba0.5Sr0.5Co0.8Fe0.2O3−δ) in contrast to other ceramics, clearly participates in the decomposition reaction of polystyrene (PS). Owing to the release of oxygen by BSCF, the decomposition mechanism of PS in contact with the powder is changed from a pyrolytic to a thermoxidative mechanism.

    11. Catalytic Synthesis of Hydroxymethyl-2-oxazolidinones from Glycerol or Glycerol Carbonate and Urea (pages 345–352)

      Prof. Angela Dibenedetto, Dr. Francesco Nocito, Dr. Antonella Angelini, Dr. Imre Papai, Prof. Michele Aresta and Dr. Raffaella Mancuso

      Article first published online: 7 DEC 2012 | DOI: 10.1002/cssc.201200524

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      ZrPped up! Oxazolidinones are synthesized by treating glycerol carbonate or glycerol with urea in the presence of γ-Zr phosphate as the catalyst. Increasing the temperature increases the conversion yield, but the selectivity decreases, making the separation process more difficult. Two isomers, 6 and 6′, are formed from glycerol carbonate with a quasi-molar ratio, whereas the formation of 6′ is preferred when starting from glycerol.

    12. Micro/Milliflow Processing with Selective Catalyst Microwave Heating in the Cu-Catalyzed Ullmann Etherification Reaction: A μ2-Process (pages 353–366)

      Dr. Faysal Benaskar, Dr. Narendra G. Patil, Prof. Dr. Evgeny V. Rebrov, Alladin Ben-Abdelmoumen, Prof. Dr. Jan Meuldijk, Prof. Dr. Lumbertus A. Hulshof, Prof. Dr. Volker Hessel and Prof. Dr. Jaap C. Schouten

      Article first published online: 27 NOV 2012 | DOI: 10.1002/cssc.201200504

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      Hot catalyst with microwaves: An alternative way to supply thermal energy to liquids is by microwave heating. However, the combination of well-defined, structured nanoparticles with microwaves allows even more promising catalyst heating without arcing effects and bulk liquid heating. Ullmann-type C[BOND]O coupling has been performed in a microwave flow process with high yields.

    13. Magnetic Poly(vinylpyridine)-Coated Carbon Nanotubes: An Efficient Supramolecular Tool for Wastewater Purification (pages 367–373)

      Dr. Laura Maggini, Dr. Jean-Marie Raquez, Dr. Riccardo Marega, Jennifer Jensen Ahrens, Florent Pineux, Dr. Franck Meyer, Prof. Philippe Dubois and Prof. Davide Bonifazi

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cssc.201200413

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      Magnetic carbon-nanotube-based M2+ scavenger: An enhanced supramolecular material based on magnetic carbon nanotubes able to exert M2+-depolluting action in water solutions is described. Its strong decontamination activity, combined with easy recyclability, makes this material an appropriate candidate for efficient bulk wastewater treatment.

    14. Hydrothermal Carbons from Hemicellulose-Derived Aqueous Hydrolysis Products as Electrode Materials for Supercapacitors (pages 374–382)

      Dr. Camillo Falco, Dr. Juan Manuel Sieben, Dr. Nicolas Brun, Dr. Marta Sevilla, Dr. Torbjorn van der Mauelen, Prof. Emilia Morallón, Prof. Diego Cazorla-Amorós and Dr. Maria-Magdalena Titirici

      Article first published online: 14 JAN 2013 | DOI: 10.1002/cssc.201200817

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      Turn waste into value: A low value by-product of the bioethanol production from lignocellulosic biomass is successfully employed as precursor for the synthesis of porous nanostructured carbon materials through hydrothermal carbonization (HTC). Silica-nanoparticle templates and chemical activation are used to introduce tailored porosity within the HTC carbon structure, which is beneficial to their performance as electrode in supercapacitors.

    15. Production of Hybrid Diesel Fuel Precursors from Carbohydrates and Petrochemicals Using Formic Acid as a Reactive Solvent (pages 383–388)

      Dr. Xiaoyuan Zhou and Prof. Thomas B. Rauchfuss

      Article first published online: 23 DEC 2012 | DOI: 10.1002/cssc.201200718

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      Formic acid for fuel: 5-(Hydroxymethyl)furfural (HMF) produced from the dehydration of sugars is coupled with petrochemically derived arenes. The resulting materials are approximately equal by mass of bio- and petro-derived precursors, which are suitable precursors to C12–C14 fuels by subsequent hydrodeoxygenation.

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