ChemSusChem

Cover image for Vol. 5 Issue 11

November 2012

Volume 5, Issue 11

Pages 2089–2287

  1. Cover Picture

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      Cover Picture: Biocatalyzed Artificial Photosynthesis by Hydrogen-Terminated Silicon Nanowires (ChemSusChem 11/2012) (page 2089)

      Hwa Young Lee, Dr. Jungki Ryu, Jae Hong Kim, Sahng Ha Lee and Prof. Chan Beum Park

      Article first published online: 14 NOV 2012 | DOI: 10.1002/cssc.201290046

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      Cofactor Regeneration: Second Nature for Silicon Nanowires The cover image illustrates the successful regeneration of NAD(P)H cofactors by using silicon nanowires under visible light, mimicking natural photosynthesis. The efficient light harvesting and utilization of solar energy is a key factor in natural photosynthesis, maintaining the viability of green plants and photosynthetic bacteria by converting solar energy into chemical energy. In natural photosynthesis, photoexcited electrons from photosynthetic reaction centers are passed along to regenerate reducing power in the form of NAD(P)H cofactors from their oxidized form. The Communication by Chan Beum Park and colleagues at the Korea Advanced Institute of Science and Technology and MIT, reported on page 2129, demonstrates that hydrogen-terminated silicon nanowires possess a high photocatalytic ability that is suitable for visible-light-driven regeneration of NAD(P)H and redox enzymatic synthesis towards biocatalyzed artificial photosynthesis.

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    1. Graphical Abstract: ChemSusChem 11/2012 (pages 2091–2099)

      Article first published online: 14 NOV 2012 | DOI: 10.1002/cssc.201290047

  3. News

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  4. Review

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    1. Electrochemical Valorisation of Glycerol (pages 2106–2124)

      Dr. Mário Simões, Dr. Stève Baranton and Prof. Christophe Coutanceau

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cssc.201200335

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      Sweet success of electron: Glycerol from biofuel industries can be valorised through green and sustainable electrochemical processes (fuel or electrolysis cell) for cogenerating energy or hydrogen and value-added chemicals (i.e., dihydroxyacetone, hydroxypyruvate, mesoxalate, etc.). Kinetics, selectivity and reaction mechanism strongly depend on the composition and structure of the catalyst and on the applied potential. Pt-free catalysts as active as Pt have been developed for the controlled oxidation of glycerol.

  5. Highlight

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    1. Deoxygenation of Biomass-Derived Feedstocks: Hurdles and Opportunities (pages 2125–2127)

      Dr. Saikat Dutta

      Article first published online: 24 OCT 2012 | DOI: 10.1002/cssc.201200596

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      Say no to O: The catalytic deoxygenation of biomass-derived feedstocks (sugars, sugar alcohols) is a promising pathway towards a sustainable chemical production economy. The development of efficient synthetic protocols for oxygen removal is highly desirable to derive chemical building blocks and fuels. A major challenge is selection/design of effective catalysts. This Highlight appraises the hurdles and opportunities for deoxygenation of biomass feedstocks.

  6. Communications

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    1. Biocatalyzed Artificial Photosynthesis by Hydrogen-Terminated Silicon Nanowires (pages 2129–2132)

      Hwa Young Lee, Dr. Jungki Ryu, Jae Hong Kim, Sahng Ha Lee and Prof. Chan Beum Park

      Article first published online: 3 SEP 2012 | DOI: 10.1002/cssc.201200251

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      Down to the wires: A highly efficient artificial photosynthetic system employing hydrogen-terminated silicon nanowires is reported. The nanowires enable a cascading electron transfer from electron donor to NAD+ via a rhodium-based electron mediator. Approximately 80 % of NADH is photoregenerated from NAD+ by the nanowires during 2 h of light irradiation, and successfully coupled with the photoenzymatic synthesis of L-glutamate.

    2. Simple Nickel-Based Catalyst Systems Combined With Graphitic Carbon Nitride for Stable Photocatalytic Hydrogen Production in Water (pages 2133–2138)

      Jingfeng Dong, Prof. Mei Wang, Xueqiang Li, Lin Chen, Yu He and Prof. Licheng Sun

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cssc.201200490

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      A molecular catalyst system containing only earth-abundant elements is combined with g-C3N4 as photosensitizer. The in situ generated complexes serve as catalysts for visible-light-driven H2 production in aqueous solution, and do not require organic solvent or a Brønsted acid. H2 evolution from the Ni-based catalyst system can be maintained for over 60 h, demonstrating that the combination is a promising approach to improve the lifetimes of molecular catalysts towards photochemical H2 production.

    3. Copper-Based Catalysts for Efficient Valorization of Cellulose (pages 2139–2142)

      Kameh Tajvidi, Kristina Pupovac, Murhat Kükrek and Prof. Dr. Regina Palkovits

      Article first published online: 11 OCT 2012 | DOI: 10.1002/cssc.201200482

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      Noble causes: Cellulose is effectively converted into methanol, propylene, and ethylene glycol over Cu-based catalysts. Overall yields of above 93 %, together with 63 % yield of C1–C3 compounds, can be reached over simple noble-metal-free systems, opening new opportunities for the sustainable and cost-efficient valorization of cellulose.

    4. DDQ-Catalyzed Oxidative C[BOND]O Coupling Of sp3 C[BOND]H Bonds With Carboxylic Acids (pages 2143–2146)

      Hong Yi, Qiang Liu, Jie Liu, Ziqi Zeng, Yuhong Yang and Prof. Aiwen Lei

      Article first published online: 5 NOV 2012 | DOI: 10.1002/cssc.201200458

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      Da-ddy, DDQ: By using catalytic amounts of DDQ combined with MnO2 as oxidant, an efficient oxidative C[BOND]O coupling of benzylic sp3 C[BOND]H bonds with carboxylic acids affords a series of carboxylic esters in 70–98 % yields. A wide range of functional groups and various carboxylic acids are tolerated. The reaction involves both C[BOND]H functionalization and C[BOND]O bond formation.

    5. Chemical Activation of a Mononuclear Non-Porphyrinic Manganese Complex using Water as Oxygen Source for the Oxygen Atom Transfer Reaction (pages 2147–2150)

      Moulay Youness El Kadiri, Dr. Sanae El Ghachtouli, Dr. Régis Guillot, Laurianne Billon, Dr. Marie-France Charlot, Dr. Eric Framery, Prof. Bruno Andrioletti and Prof. Ally Aukauloo

      Article first published online: 9 OCT 2012 | DOI: 10.1002/cssc.201200440

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      Water, a powerful ally: A MnIII complex with an N4O-coordinating ligand and a deprotonated water molecule as sixth ligand is chemically oxidized by a CeIV one-electron oxidant. The results indicate catalytic oxygen atom transfer to alkenes, with the oxygen atom originating from a water molecule. These findings demonstrate the possibility of using water as oxygen source to perform the oxidation of organic substrates.

    6. Catalytic Oxidative Decarboxylation of Malic Acid into Dimethyl Malonate in Methanol with Dioxygen (pages 2151–2154)

      Junxia Liu, Dr. Zhongtian Du, Yanliang Yang, Tianliang Lu, Dr. Fang Lu and Prof. Dr. Jie Xu

      Article first published online: 10 OCT 2012 | DOI: 10.1002/cssc.201200489

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      If you′ve got it, use it: Malic acid is converted into dimethyl malonate by a direct, one-pot process. The process is cyanide- and halide-free. Phosphovanadomolybdates serve as bifunctional catalysts, effecting the oxidative decarboxylation and esterification in a consecutive manner. Oxidative C[BOND]C bond cleavage first forms hemiacetals. The results serve as example for the production of valuable chemicals by fully utilizing the oxygen atoms and basic structure inherent to biomass products.

    7. Mixed Proton–Electron Conducting Chromite Electrocatalysts as Anode Materials for LWO-Based Solid Oxide Fuel Cells (pages 2155–2158)

      Dr. Cecilia Solís, Dr. Vicente B. Vert, Maria Balaguer, Sonia Escolástico, Dr. Stefan Roitsch and Dr. José M. Serra

      Article first published online: 6 NOV 2012 | DOI: 10.1002/cssc.201200446

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      Chromite anodes in LWO PC-SOFC: Chemically compatible LSCN/LWO symmetric cells show the high protonic conductivity and p-type electronic conductivity of LSCN in reducing atmospheres. This allows to avoid blending with other protonic or electronic materials and enlarges the surface area. An Rp of 2.68 Ω cm2 at 750 °C and performance in LF-limited processes demonstrate the potential of LSCN as anode material.

    8. A 3D Hexaporous Carbon Assembled from Single-Layer Graphene as High Performance Supercapacitor (pages 2159–2164)

      Prasad Yadav, Abhik Banerjee, Sreekuttan Unni, Dr. Jyoti Jog, Dr. Sreekumar Kurungot and Dr. Satishchandra Ogale

      Article first published online: 9 OCT 2012 | DOI: 10.1002/cssc.201200421

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      Thumbs up for porous graphene! Single-layer-graphene-assembled 3D hexaporous carbon is prepared by catalyst-free pyrolysis of poly(4-styrenesulfonic acid-co-maleic acid) sodium salt. The material has a hierarchical structure of mesoporous as well as microporous graphene with hexagonal nanopores of uniform size and shape. The results show that the sample is highly conducting in aqueous electrolyte, with an extremely high surface area of 1720 m2 g−1 and an enhanced capacitance of 154 F g−1.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlight
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    1. Cell-Free Metabolic Engineering: Production of Chemicals by Minimized Reaction Cascades (pages 2165–2172)

      Dr. Jan-Karl Guterl, Dr. Daniel Garbe, Jörg Carsten, Fabian Steffler, Bettina Sommer, Steven Reiße, Anja Philipp, Martina Haack, Broder Rühmann, Prof. Andre Koltermann, Dr. Ulrich Kettling, Prof. Thomas Brück and Prof. Volker Sieber

      Article first published online: 19 OCT 2012 | DOI: 10.1002/cssc.201200365

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      An order of enzymes, hold the cells: For chemical and fuel production from biomass, chemical methods are often supplemented by biological means, such as microbial systems. It is demonstrated here that microbial reaction cascades can be redesigned and simplified to an extent that cell-free bulk production of chemicals and fuels from biomass becomes feasible. Specifically, glucose is converted to ethanol and to isobutanol by using only six and eight enzymes respectively and one cofactor. Larger alcohols such as isobutanol are known to poison microbial systems.

    2. Room Temperature Solid-State Synthesis of a Conductive Polymer for Applications in Stable I2-Free Dye-Sensitized Solar Cells (pages 2173–2180)

      Byeonggwan Kim, Jong Kwan Koh, Dr. Jeonghun Kim, Won Seok Chi, Prof. Jong Hak Kim and Prof. Eunkyoung Kim

      Article first published online: 3 SEP 2012 | DOI: 10.1002/cssc.201200349

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      What a wait for solid state: 2,5-Dibromo-3,4-propylenedioxythiophene (DBProDOT), a new monomer that is a solid at room temperature, has been synthesized to produce poly(3,4-propylenedioxythiophene) (ssPProDOT). I2-free solid-state dye-sensitized solar cells with ssPProDOT exhibit exceptional long-term stability (>1500 h) with an efficiency of 3.5 % at 100 mW cm−2.

    3. The Synthesis and the Chemical and Physical Properties of Non-Aqueous Silylamine Solvents for Carbon Dioxide Capture (pages 2181–2187)

      Amy L. Rohan, Jackson R. Switzer, Kyle M. Flack, Ryan J. Hart, Swetha Sivaswamy, Elizabeth J. Biddinger, Manish Talreja, Manjusha Verma, Sean Faltermeier, Paul T. Nielsen, Pamela Pollet, George F. Schuette, Prof. Charles A. Eckert and Prof. Charles L. Liotta

      Article first published online: 23 AUG 2012 | DOI: 10.1002/cssc.201200393

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      Silylamine molecular liquids reversibly react with CO2 to form the corresponding ammonium carbamates (reversible ionic liquids). The molecular liquid is easily regenerated quantitatively from the reversible ionic liquid upon heating. The ability to tune bulk properties by making structural changes presents an opportunity for optimization by developing a system that balances conversion with viscosity and minimizes the energy required for regeneration.

    4. Changes in Surface Chemistry of Carbon Materials upon Electrochemical Measurements and their Effects on Capacitance in Acidic and Neutral Electrolytes (pages 2188–2199)

      Dr. Denisa Hulicova-Jurcakova, Erika Fiset, Prof. Gao Qing Max Lu and Prof. Teresa J. Bandosz

      Article first published online: 19 OCT 2012 | DOI: 10.1002/cssc.201200376

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      Test boosts performance: The significant increase of the energy storage capacity upon three-eletrode tests observed in oxygen- and nitrogen+oxygen-rich carbons in an acidic electrolyte is attributed to two different mechanisms: For oxygen-rich carbons (CA, CB), the double-layer capacitance is amplified because of the removal of O-I and O-II bulky oxygen-containing functionalities, whereas for nitrogen+oxygen-rich (CAU, CBU) carbons, the pseudocapacitance is enhanced, a result of the increased proportion of pyridone N-5 nitrogen atoms.

    5. Optimizing the Deposition of Hydrogen Evolution Sites on Suspended Semiconductor Particles using On-Line Photocatalytic Reforming of Aqueous Methanol Solutions (pages 2200–2206)

      Dr. G. Wilma Busser, Bastian Mei and Prof. Dr. Martin Muhler

      Article first published online: 22 OCT 2012 | DOI: 10.1002/cssc.201200374

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      Creating gateways for electrons: The number of hydrogen evolution sites on Ga2O3-based photocatalysts is optimized in a continuously flushed water-splitting set-up equipped with on-line gas analysis. A fast sequential photodeposition method is established by monitoring the amount of hydrogen evolved from the sacrificial agent methanol.

    6. From Biomass Wastes to Highly Efficient CO2 Adsorbents: Graphitisation of Chitosan and Alginate Biopolymers (pages 2207–2214)

      Dr. Ana Primo, Amparo Forneli, Prof. Dr. Avelino Corma and Prof. Dr. Hermenegildo García

      Article first published online: 11 SEP 2012 | DOI: 10.1002/cssc.201200366

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      Sphere of influence: We report the valorization of two natural biopolymers as highly efficient, reversible CO2 adsorbents. Pyrolysis leads to graphitic carbons that adsorb amounts of CO2 at 0 °C and atmospheric pressure double that of the currently best CO2 adsorbents (per mass unit). In addition, the materials also exhibit higher adsorption capacity per volume unit, a parameter that is more relevant for industrial applications where the limiting factor is the volume of adsorption towers.

    7. Acid-Catalyzed Dehydration of Fructose into 5-Hydroxymethylfurfural by Cellulose-Derived Amorphous Carbon (pages 2215–2220)

      Prof. Dr. Xinhua Qi, Haixin Guo, Luyang Li and Prof. Dr. Richard L. Smith Jr.

      Article first published online: 27 AUG 2012 | DOI: 10.1002/cssc.201200363

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      Solid improvement: Cellulose-derived carbon catalysts with [BOND]SO3H, [BOND]COOH, and phenolic [BOND]OH groups are used for the efficient catalytic conversion of fructose into 5-hydroxymethylfurfural in an ionic liquid (see picture).

    8. Antibacterial Soybean-Oil-Based Cationic Polyurethane Coatings Prepared from Different Amino Polyols (pages 2221–2227)

      Dr. Ying Xia, Zongyu Zhang, Prof. Michael R. Kessler, Prof. Byron Brehm-Stecher and Prof. Richard C. Larock

      Article first published online: 20 SEP 2012 | DOI: 10.1002/cssc.201200352

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      Plant-oil-based antibacterial coatings: Antibacterial soybean-oil-based cationic polyurethane coatings have been successfully prepared from five different amino polyols. The structure of these amino polyols affects the mechanical properties, thermal stability, and antibacterial properties of the coatings. These coatings exhibit antibacterial properties to both gram-positive and gram-negative bacteria, with best antibacterial activity against a structural mutant of Salmonella minnesota possessing a severely truncated outer membrane structure.

    9. Pyrolytic Sugars from Cellulosic Biomass (pages 2228–2236)

      Najeeb Kuzhiyil, Dustin Dalluge, Prof. Xianglan Bai, Kwang Ho Kim and Prof. Robert C. Brown

      Article first published online: 13 SEP 2012 | DOI: 10.1002/cssc.201200341

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      Thermolytic sugars from biomass: Using a simple acid pretreatment, the catalytic activity of naturally occurring alkali and alkaline earth metals in lignocellulosic biomass is dramatically reduced, allowing the purely thermal production of sugars from biomass. The optimal amount of acid for the thermal depolymerization of biomass to sugars is proportional to the amount of alkali and alkaline earth metals inherently contained in the biomass feedstock.

    10. ZK-5: A CO2-Selective Zeolite with High Working Capacity at Ambient Temperature and Pressure (pages 2237–2242)

      Dr. Qingling Liu, Trong Pham, Marc D. Porosoff and Prof. Raul F. Lobo

      Article first published online: 21 AUG 2012 | DOI: 10.1002/cssc.201200339

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      CO2 selective adsorbent: The 8-membered-ring small-pore zeolite ZK-5, ion-exchanged with different cations, is investigated as a CO2 selective adsorbent. Despite its high Si/Al ratio (4.7) ZK-5 can adsorb CO2 at 10 % v/v in nitrogen with high working capacity as well as high CO2/N2 selectivity. Mg-ZK-5 is identified as an adsorbent with low isosteric heat of adsorption and excellent properties for adsorption-driven pressure swing processes.

    11. Base-Free Direct Oxidation of 1-Octanol to Octanoic Acid and its Octyl Ester over Supported Gold Catalysts (pages 2243–2248)

      Dr. Tamao Ishida, Yuichiro Ogihara, Dr. Hironori Ohashi, Dr. Tomoki Akita, Dr. Tetsuo Honma, Dr. Hiroshi Oji and Prof. Dr. Masatake Haruta

      Article first published online: 12 OCT 2012 | DOI: 10.1002/cssc.201200324

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      Coming up for air: Supported gold nanoparticles enable the aerobic oxidation of a less reactive alcohol, 1-octanol, to directly produce octanoic acid and octyl octanoate under base-free conditions. The product distributions can be tuned by the proper selection of metal oxide supports. The results may enable greener processes for the production of high-value carboxylic acids and esters.

    12. Methyl Ricinoleate as Platform Chemical for Simultaneous Production of Fine Chemicals and Polymer Precursors (pages 2249–2254)

      Antoine Dupé, Dr. Mathieu Achard, Dr. Cédric Fischmeister and Dr. Christian Bruneau

      Article first published online: 25 SEP 2012 | DOI: 10.1002/cssc.201200320

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      The derivatization of methyl ricinoleate followed by ring-closing metathesis (RCM) or sequential RCM/hydrogenation and RCM/cross-metathesis lead to a variety of biosourced compounds of interest for fine chemistry and polymer synthesis. 3,6-Dihydropyran, and α,β-unsaturated lactone derivatives have been prepared with concomitant production of polymer precursors. Tetrahydropyran and lactone derivatives as well as valuable monomers in particular polyamide precursors have also been prepared.

    13. Recovery of Ionic Liquids with Aqueous Two-Phase Systems Induced by Carbon Dioxide (pages 2255–2261)

      Dazhen Xiong, Dr. Huiyong Wang, Zhiyong Li and Prof. Jianji Wang

      Article first published online: 5 SEP 2012 | DOI: 10.1002/cssc.201200307

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      Recovery of Ionic Liquids: Solutions of ionic liquids (ILs) and amines are separated into aqueous two-phase systems in the presence of CO2, in which the upper phase is ammonium-salt-rich and the lower phase is IL-rich. Thus, the ILs in aqueous solutions can be efficiently recovered, and the amines can be regenerated by heating and bubbling Ar or N2 through the salt-rich phase. The recovery efficiency of the ILs is as high as 99 %.

    14. Tailor-Made Anion-Exchange Membranes for Salinity Gradient Power Generation Using Reverse Electrodialysis (pages 2262–2270)

      Enver Guler, Yali Zhang, Dr. Michel Saakes and Dr. Kitty Nijmeijer

      Article first published online: 25 OCT 2012 | DOI: 10.1002/cssc.201200298

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      The other side of membranes: The use of tailor-made anion-exchange membranes in reverse electrodialysis is studied. Membranes with thinner film thickness achieve the highest power density because of their lower area resistance and high permselectivity (see figure). This is, to the best of our knowledge, the first example of a reverse electrodialysis stack using tailor-made anion-exchange membranes prepared in a more environmentally friendly and safer way relative to conventional methods.

    15. Diffusion-Barrier-Free Porous Carbon Monoliths as a New Form of Activated Carbon (pages 2271–2277)

      Takashi Kubo, Dr. Hirotoshi Sakamoto, Dr. Toshihiko Fujimori, Dr. Tsutomu Itoh, Dr. Tomonori Ohba, Prof. Hirofumi Kanoh, Dr. Manuel Martínez-Escandell, Dr. José M. Ramos-Fernández, Mirian Casco, Prof. Francisco Rodríguez-Reinoso, Dr. Koki Urita, Prof. Isamu Moriguchi, Prof. Morinobu Endo and Prof. Katsumi Kaneko

      Article first published online: 28 SEP 2012 | DOI: 10.1002/cssc.201200234

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      Methane storage: Newly developed nanoporous carbon monoliths have superior advantages over traditional activated-carbon powder. In particular, nanoporous carbon monoliths can provide an explicit clue to solve the damping of adsorption and desorption kinetics owing to the diffusion-drive obstacle.

    16. Limitation of Discharge Capacity and Mechanisms of Air-Electrode Deactivation in Silicon–Air Batteries (pages 2278–2285)

      Dr. Peter Jakes , Gil Cohn, Prof. Dr. Yair Ein-Eli, Dr. Frieder Scheiba, Prof. Dr. Helmut Ehrenberg and Dr. Rüdiger-A. Eichel 

      Article first published online: 2 OCT 2012 | DOI: 10.1002/cssc.201200199

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      Mechanism of catalyst deactivation: Electrocatalytic oxygen reduction at the air cathode in silicon–air batteries critically impacts battery performance. We describe a mechanism of air-electrode deactivation: upon discharge, the MnO2 catalyst is modified by the formation of of a MnF2 surface layer formation that is catalytically inactive for the oxygen reduction reaction and limits the discharge capacity. The ability for this deactivation layer to form is greatly impacted by the water content of the electrolyte.

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    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlight
    7. Communications
    8. Full Papers
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    1. You have free access to this content
      Preview: ChemSusChem 12/2012 (page 2287)

      Article first published online: 14 NOV 2012 | DOI: 10.1002/cssc.201290049

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