Chemistry - A European Journal

Cover image for Vol. 23 Issue 18

March 28, 2017

Volume 23, Issue 18

Pages 4230–4461

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Cover Profile
    5. Reviews
    6. Communications
    7. Full Papers
    1. You have free access to this content
      Cover Picture: Selective Reductions of N,N-Bis{chloro(aryl)-phosphino}-amines Yielding Three-, Five-, Six-, and Eight-Membered Cyclic Azaphosphanes (Chem. Eur. J. 18/2017) (page 4230)

      Martha Höhne, Markus Joksch, Katharina Konieczny, Dr. Bernd H. Müller, Dr. Anke Spannenberg, Dr. Normen Peulecke and Prof. Uwe Rosenthal

      Version of Record online: 14 FEB 2017 | DOI: 10.1002/chem.201700397

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      The finding of the cyclic structure of PNP-containing compounds is compared to the discovery of the cyclic structure of benzene in 1865 by Kekulé. He told of dreaming of dancing atoms, moving snake-like resulting in an ouroboros—the serpent eating its own tail. This brought him to the idea of the cyclic structure of benzene. In 1886 the German Chemical Society humorously adopted his idea and published a cyclic structure consisting of six monkeys holding hands. The formation of cyclic compounds is the quintessence of this publication and is illustrated in this abstract way. More information can be found in the Full Paper by U. Rosenthal et al. on page 4298 ff.

    2. You have free access to this content
      Inside Cover: Robust Colloidal Nanoparticles of Pyrrolopyrrole Cyanine J-Aggregates with Bright Near-Infrared Fluorescence in Aqueous Media: From Spectral Tailoring to Bioimaging Applications (Chem. Eur. J. 18/2017) (page 4231)

      Cangjie Yang, Dr. Xiaochen Wang, Prof. Dr. Mingfeng Wang, Dr. Keming Xu and Prof. Dr. Chenjie Xu

      Version of Record online: 25 JAN 2017 | DOI: 10.1002/chem.201700125

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      Near-infrared fluorescent J-aggregates were discovered in colloidal nanoparticles of pyrrolopyrrole cyanines stabilized by amphiphilic block co-polymers in aqueous media. The formation of such colloidal-state J-aggregates can be tuned by the chemical structure and the concentration of the chromophores inside the polymeric nanoparticles, and can be further enhanced by ultrasonic treatment. These J-aggregate nanoparticles with an average diameter of 30 nm, exhibit a narrow emission band at 773 nm, a fluorescence quantum yield comparable to that of indocyanine green, and significantly enhanced photostability that is ideal for long-term bioimaging. More information can be found in the Full Paper by M. Wang et al. on page 4310 ff.

    3. You have free access to this content
      Inside Back Cover: Photoantimicrobial Biohybrids by Supramolecular Immobilization of Cationic Phthalocyanines onto Cellulose Nanocrystals (Chem. Eur. J. 18/2017) (page 4462)

      Dr. Eduardo Anaya-Plaza, Eveline van de Winckel, Joona Mikkilä, Dr. Jani-Markus Malho, Prof. Olli Ikkala, Oscar Gulías, Roger Bresolí-Obach, Prof. Montserrat Agut, Prof. Santi Nonell, Prof. Tomás Torres, Prof. Mauri A. Kostiainen and Dr. Andrés de la Escosura

      Version of Record online: 1 FEB 2017 | DOI: 10.1002/chem.201700350

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      Cellulose, a cheap and abundant biomaterial, leads to photosensitizing biohybrids through the immobilization of cationic phthalocyanine dyes onto the surface of cellulose nanocrystals. These biohybrids are efficient and broad-spectrum photoantimicrobial agents against opportunistic fungal pathogens, Gram-positive, and Gram-negative bacteria. More information can be found in the Full Paper by T. Torres, M. A. Kostiainen, et al. on page 4320 ff.

    4. You have free access to this content
      Back Cover: A Tryptoline Ring-Distortion Strategy Leads to Complex and Diverse Biologically Active Molecules from the Indole Alkaloid Yohimbine (Chem. Eur. J. 18/2017) (page 4463)

      Nicholas G. Paciaroni, Dr. Ranjala Ratnayake, Dr. James H. Matthews, Verrill M. Norwood IV, Austin C. Arnold, Prof. Long H. Dang, Prof. Hendrik Luesch and Prof. Robert W. Huigens III

      Version of Record online: 3 FEB 2017 | DOI: 10.1002/chem.201605731

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      A tryptoline-based ring distortion strategy enabled rapid access to an array of complex and diverse molecular scaffolds synthesized from the indole alkaloid, yohimbine. During these investigations, 70 complex and diverse small molecules were synthesized and subjected to a panel phenotype screen. These efforts led to the identification of several biologically active hit compounds, including one compound that demonstrates HIF-dependent antiproliferative activity in HCT116 (colorectal cancer) cells. More information can be found in the Full Paper by R. W. Huigens III et al. on page 4327 ff.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Cover Profile
    5. Reviews
    6. Communications
    7. Full Papers
    1. Frontispiece: An Overview of Structural Features of Antibacterial Glycoconjugate Vaccines That Influence Their Immunogenicity

      Farjana Khatun, Dr. Rachel J. Stephenson and Prof. Istvan Toth

      Version of Record online: 29 MAR 2017 | DOI: 10.1002/chem.201781861

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      Glycoconjugate Vaccines Immunogenic carbohydrate chains derived from the bacterial capsular polysaccharides, lipoteichoic acid and lipopolysaccharides are used as B cell antigens to develop glycoconjugate vaccines. To boost the immune activity of these antigens, immunogenic carrier proteins (T cell antigens) are covalently conjugated with/without the help of spacer molecule(s) by using appropriate conjugation chemistry. Structurally defined neoglycoconjuagtes consist of short-chain carbohydrates attached to single carrier protein, whereas structurally complex cross-linked glycoconjugates composed of multiple active sites containing long-chain carbohydrates conjugated to single/multiple protein(s). Both of these vaccines are effective against bacterial infectious diseases. For more details, see the Review article by I. Toth et al. on page 4233 ff.

    2. Frontispiece: Enhanced Structural Organization in Covalent Organic Frameworks Through Fluorination

      Sampath B. Alahakoon, Dr. Gregory T. McCandless, Arosha A. K. Karunathilake, Dr. Christina M. Thompson and Prof. Ronald A. Smaldone

      Version of Record online: 29 MAR 2017 | DOI: 10.1002/chem.201781862

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      2D covalent organic frameworks (COFs) are a class of crystalline, porous, polymeric materials that have demonstrated promise in a variety of energy storage applications. The use of fluorine-containing monomers produces 2D-COFs with not only greatly improved surface areas (over 2000 m2 g−1 compared to 760 m2 g−1 for the non-fluorinated analogue), but also with improved crystallinity and larger, better defined pore diameters. In their Communication on page 4255 ff., R. A. Smaldone et al. report on the formation of these COFs under varying reaction times and temperatures to obtain a greater insight into their mechanism of formation.

    3. Frontispiece: Structurally Stable Attractive Nanoscale Emulsions with Dipole–Dipole Interaction-Driven Interdrop Percolation

      Kyounghee Shin, Gyeonghyeon Gong, Jonas Cuadrado, Serim Jeon, Mintae Seo, Hong Sung Choi, Prof. Jae Sung Hwang, Prof. Youngbok Lee, Prof. Alberto Fernandez-Nieves and Prof. Jin Woong Kim

      Version of Record online: 29 MAR 2017 | DOI: 10.1002/chem.201781863

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      An attractive nanoemulsion fluid system with a drop-percolated network is depicted in the image, in which dipole–dipole interaction between phosphorylcholine groups of lecithin and methoxy end groups of poly(ethylene oxide)-block-poly(ϵ-caprolactone) leads to a gel-like rheological behavior. This intriguing emulsion system significantly enhances transdermal delivery efficiency due to its favorable attraction to the skin as well as high diffusivity of the nanoscale emulsion drops. More information can be found in the Full Paper by Y. Lee, A. Fernandez-Nieves, J. W. Kim et al. on page 4292 ff.

  3. Cover Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Cover Profile
    5. Reviews
    6. Communications
    7. Full Papers
    1. You have free access to this content
      Selective Reductions of N,N-Bis{chloro(aryl)-phosphino}-amines Yielding Three-, Five-, Six-, and Eight-Membered Cyclic Azaphosphanes (page 4232)

      Martha Höhne, Markus Joksch, Katharina Konieczny, Dr. Bernd H. Müller, Dr. Anke Spannenberg, Dr. Normen Peulecke and Prof. Uwe Rosenthal

      Version of Record online: 6 FEB 2017 | DOI: 10.1002/chem.201700398

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      We consider the formation of new PN rings as the essence of this paper.” Read more about the story behind the cover in the Cover Profile and about the research itself on page 4298 ff. (DOI: 10.1002/chem.201605836).

  4. Reviews

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Cover Profile
    5. Reviews
    6. Communications
    7. Full Papers
    1. Medicinal Chemistry

      An Overview of Structural Features of Antibacterial Glycoconjugate Vaccines That Influence Their Immunogenicity (pages 4233–4254)

      Farjana Khatun, Dr. Rachel J. Stephenson and Prof. Istvan Toth

      Version of Record online: 18 JAN 2017 | DOI: 10.1002/chem.201603599

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      Design for life: The avidity and selectivity of glycoconjugate vaccines (see scheme) is dependent on key factors, such as the choice of carbohydrate antigen, immunogenic carrier molecule, conjugation strategy, ratio of carbohydrate to carrier protein, and the spacer used for the conjugation process. This Review article presents the importance of the variables governing the development of antibacterial glycoconjugate vaccines and their effects on immune efficacy.

  5. Communications

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Cover Profile
    5. Reviews
    6. Communications
    7. Full Papers
    1. Organic Frameworks

      Enhanced Structural Organization in Covalent Organic Frameworks Through Fluorination (pages 4255–4259)

      Sampath B. Alahakoon, Dr. Gregory T. McCandless, Arosha A. K. Karunathilake, Dr. Christina M. Thompson and Prof. Ronald A. Smaldone

      Version of Record online: 3 MAR 2017 | DOI: 10.1002/chem.201700412

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      Stack ‘em up: A strategy to significantly improve the crystallinity and the surface area of 2D covalent organic frameworks (COFs), by simple variation in the electronic structure of non-planar precursors through fluorination, is presented (see figure).

    2. Ring-Opening Polymerization

      Zinc versus Magnesium: Orthogonal Catalyst Reactivity in Selective Polymerizations of Epoxides, Bio-derived Anhydrides and Carbon Dioxide (pages 4260–4265)

      Dr. Prabhjot K. Saini, Dr. Giulia Fiorani, Prof. Robert T. Mathers and Prof. Charlotte K. Williams

      Version of Record online: 15 MAR 2017 | DOI: 10.1002/chem.201605690

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      Take your pick! Mixtures of epoxide, bio-derived anhydride and carbon dioxide were selectively enchained using Mg and Zn catalysts. Surprisingly both catalysts show high but exactly opposite selectivities leading to block sequence controlled copolymers.

    3. Heterogeneous Catalysis

      Metal–Organic-Framework-Derived Carbons: Applications as Solid-Base Catalyst and Support for Pd Nanoparticles in Tandem Catalysis (pages 4266–4270)

      Xinle Li, Biying Zhang, Yuhui Fang, Weijun Sun, Zhiyuan Qi, Yuchen Pei, Shuyan Qi, Pengyu Yuan, Xuechen Luan, Tian Wei Goh and Prof. Wenyu Huang

      Version of Record online: 24 MAR 2017 | DOI: 10.1002/chem.201605852

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      Double duty: MOF-derived carbons with high nitrogen contents are used as solid-base catalysts and as the support for Pd nanoparticles in tandem catalysis.

    4. Carbenes | Hot Paper

      Rearrangement of a Transient Gold Vinylidene into Gold Carbenes (pages 4271–4275)

      Dr. Wouter Debrouwer and Prof. Alois Fürstner

      Version of Record online: 13 MAR 2017 | DOI: 10.1002/chem.201700326

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      Metamorphosis: An aldehyde is not electrophilic enough per se to be attacked by a gold acetylide, but activation with a Lewis acid triggers spontaneous formation of a gold vinylidene, which evolves into a Fischer gold carbene; the recorded data suggest that this product might actually be better viewed as an acylgold complex protonated by triflic acid.

    5. Nanotechnology

      Enzyme-Controlled Nanodevice for Acetylcholine-Triggered Cargo Delivery Based on Janus Au–Mesoporous Silica Nanoparticles (pages 4276–4281)

      Antoni Llopis-Lorente, Paula Díez, Cristina de la Torre, Dr. Alfredo Sánchez, Dr. Félix Sancenón, Dr. Elena Aznar, Dr. María D. Marcos, Dr. Paloma Martínez-Ruíz, Prof. Ramón Martínez-Máñez and Dr. Reynaldo Villalonga

      Version of Record online: 15 MAR 2017 | DOI: 10.1002/chem.201700603

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      Janus Au–mesoporous silica nanoparticles functionalized with acetylcholinesterase on the Au face and with supramolecular β-cyclodextrin:benzimidazole inclusion complexes as caps on the mesoporous silica face were made and characterized. The nanodevice is able to selectively deliver cargo in the presence of acetylcholine via enzyme-mediated acetylcholine hydrolysis, locally lowering pH and opening the supramolecular gate.

    6. Photoredox Catalysis

      Generation of the SCF3 Radical by Photoredox Catalysis: Intra- and Intermolecular Carbotrifluoromethylthiolation of Alkenes (pages 4282–4286)

      Dr. Guillaume Dagousset, Dr. Cédric Simon, Dr. Elsa Anselmi, Dr. Béatrice Tuccio, Dr. Thierry Billard and Dr. Emmanuel Magnier

      Version of Record online: 13 MAR 2017 | DOI: 10.1002/chem.201700734

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      Electrophilic N-trifluoromethylthiosaccharin was used for the first time as the source of the SCF3 radical. The formation of this radical, as well as other key intermediates, was highlighted by using spin trapping/EPR spectroscopy. Visible-light-promoted intra- and intermolecular carbotrifluoromethylthiolation of alkenes has been successfully developed.

    7. Heavier Tetrylenes

      First Insertions of Carbene Ligands into Ge−N and Si−N Bonds (pages 4287–4291)

      Lucía Álvarez-Rodríguez, Prof. Dr. Javier A. Cabeza, Dr. Pablo García-Álvarez, Prof. Dr. Mar Gómez-Gallego, Alba D. Merinero and Prof. Dr. Miguel A. Sierra

      Version of Record online: 15 MAR 2017 | DOI: 10.1002/chem.201700828

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      Caught with a ring: The 4-membered ring of amidinatotetrylenes has been expanded with Fischer carbene complexes. These reactions, which afford complexes containing a novel type of 5-membered ring tetrylene ligand, proceed through unprecedented insertions of carbene ligands into Ge−N and Si−N bonds.

  6. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Cover Profile
    5. Reviews
    6. Communications
    7. Full Papers
    1. Drug Delivery | Hot Paper

      Structurally Stable Attractive Nanoscale Emulsions with Dipole–Dipole Interaction-Driven Interdrop Percolation (pages 4292–4297)

      Kyounghee Shin, Gyeonghyeon Gong, Jonas Cuadrado, Serim Jeon, Mintae Seo, Hong Sung Choi, Prof. Jae Sung Hwang, Prof. Youngbok Lee, Prof. Alberto Fernandez-Nieves and Prof. Jin Woong Kim

      Version of Record online: 14 FEB 2017 | DOI: 10.1002/chem.201604722

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      Attractive nanoemulsions: Extremely stable attractive nanoemulsion fluids are fabricated by engineering a resilient PEO-b-PCL/lecithin thin-film at the interface. Dipole–dipole attraction between drops leads to formation of a drop-percolated emulsion network, thus exhibiting a gel-like rheological behavior as well as excellent transdermal delivery performance.

    2. Coordination Chemistry | Very Important Paper

      Selective Reductions of N,N-Bis{chloro(aryl)-phosphino}-amines Yielding Three-, Five-, Six-, and Eight-Membered Cyclic Azaphosphanes (pages 4298–4309)

      Martha Höhne, Markus Joksch, Katharina Konieczny, Dr. Bernd H. Müller, Dr. Anke Spannenberg, Dr. Normen Peulecke and Prof. Uwe Rosenthal

      Version of Record online: 14 FEB 2017 | DOI: 10.1002/chem.201605836

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      The wheel of fortune: Different dehalogenation reactions of N,N-bis{chloro(aryl)-phosphino}-amines are developed to synthesize various P-N-P-containing cyclic compounds. Their coordination behavior to group VI transition metal carbonyls was determined.

    3. Bioorganic Chemistry | Hot Paper

      Robust Colloidal Nanoparticles of Pyrrolopyrrole Cyanine J-Aggregates with Bright Near-Infrared Fluorescence in Aqueous Media: From Spectral Tailoring to Bioimaging Applications (pages 4310–4319)

      Cangjie Yang, Dr. Xiaochen Wang, Prof. Dr. Mingfeng Wang, Dr. Keming Xu and Prof. Dr. Chenjie Xu

      Version of Record online: 20 JAN 2017 | DOI: 10.1002/chem.201604741

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      JAGG versus HAGG: Colloidal nanoparticles (NPs) containing near-infrared-fluorescent J-aggregates (JAGGs) of pyrrolopyrrole cyanines stabilized by amphiphilic block co-polymers were prepared in aqueous medium. The JAGG NPs exhibit a narrow emission band at 773 nm, a fluorescence quantum yield comparable to that of indocyanine green, and significantly enhanced photostability, ideal for long-term bioimaging (see figure). Analogues with extended conjugation form weakly fluorescent H-aggregates (HAGGs).

    4. Functional Materials

      Photoantimicrobial Biohybrids by Supramolecular Immobilization of Cationic Phthalocyanines onto Cellulose Nanocrystals (pages 4320–4326)

      Dr. Eduardo Anaya-Plaza, Eveline van de Winckel, Joona Mikkilä, Dr. Jani-Markus Malho, Prof. Olli Ikkala, Oscar Gulías, Roger Bresolí-Obach, Prof. Montserrat Agut, Prof. Santi Nonell, Prof. Tomás Torres, Prof. Mauri A. Kostiainen and Dr. Andrés de la Escosura

      Version of Record online: 18 JAN 2017 | DOI: 10.1002/chem.201605285

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      Photoantimicrobial biohybrids are easily produced by the non-covalent immobilization of cationic phthalocyanines onto the surface of sulfated cellulose nanocrystals through electrostatic interactions, resulting in a well-defined and highly efficient nanostructured photosensitizing system.

    5. Diversity-Oriented Synthesis

      A Tryptoline Ring-Distortion Strategy Leads to Complex and Diverse Biologically Active Molecules from the Indole Alkaloid Yohimbine (pages 4327–4335)

      Nicholas G. Paciaroni, Dr. Ranjala Ratnayake, Dr. James H. Matthews, Verrill M. Norwood IV, Austin C. Arnold, Prof. Long H. Dang, Prof. Hendrik Luesch and Prof. Robert W. Huigens III

      Version of Record online: 3 FEB 2017 | DOI: 10.1002/chem.201604795

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      Generating diversity: A tryptoline ring-distortion strategy is described that enables the rapid synthesis of 70 complex and diverse compounds from yohimbine; an indole alkaloid. The compounds synthesized had architecturally complex and unique scaffolds, unlike that of yohimbine and other scaffolds.

    6. Nanostructures

      Double-Shelled TiO2 Hollow Spheres Assembled with TiO2 Nanosheets (pages 4336–4343)

      Dr. Chao Zhang, Prof. Yuming Zhou, Prof. Yiwei Zhang, Dr. Shuo Zhao, Dr. Jiasheng Fang, Prof. Xiaoli Sheng, Dr. Tao Zhang and Hongxing Zhang

      Version of Record online: 6 MAR 2017 | DOI: 10.1002/chem.201602654

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      Spot the ball: Double-shelled hollow spheres of TiO2 were synthesized by hydrothermal treatment of TiO2-coated solid SiO2 spheres. The spheres are comprised of TiO2 nanosheets and can be converted without structural collapse to anatase spheres by calcination. The synthesis method can be readily adapted to form hollow structures with different shapes and compositions

    7. Mesoporous Materials | Hot Paper

      Highly Ordered Mesostructured Vanadium Phosphonate toward Electrode Materials for Lithium-Ion Batteries (pages 4344–4352)

      Peng Mei, Dr. Malay Pramanik, Jaewoo Lee, Dr. Yusuke Ide, Prof. Zeid Abdullah Alothman, Prof. Jung Ho Kim and Prof. Yusuke Yamauchi

      Version of Record online: 7 MAR 2017 | DOI: 10.1002/chem.201604159

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      Cationic surfactants: Highly ordered mesostructured vanadium phosphonates (VP; see figure) have been synthesized in the presence of cetyltrimethylammonium bromide (CTAB) as a structure directing agent. Nitrilotris(methylene)triphosphonic acid (NMPA) and (ammonium/sodium) metavanadate (NH4VO3/NaVO3) have been used for the construction of pore walls.

    8. Radiolabeling

      Crystal Structures of Diaryliodonium Fluorides and Their Implications for Fluorination Mechanisms (pages 4353–4363)

      Dr. Yong-Sok Lee, Dr. Joong-Hyun Chun, Dr. Milan Hodošček and Dr. Victor W. Pike

      Version of Record online: 2 MAR 2017 | DOI: 10.1002/chem.201604803

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      Origin of the ortho effect: The “ortho effect” imparted by an o-alkyl group in the reaction of diaryliodonium salts with a fluoride ion is attributed to a favorable electrostatic interaction between the incoming fluoride and the o-methyl group in the transition state (TSB).

    9. Hydrogenase Models

      Influence of the Dithiolate Bridge on the Oxidative Processes of Diiron Models Related to the Active Site of [FeFe] Hydrogenases (pages 4364–4372)

      Federica Arrigoni, Salma Mohamed Bouh, Prof. Luca De Gioia, Dr. Catherine Elleouet, Prof. François Y. Pétillon, Prof. Philippe Schollhammer and Dr. Giuseppe Zampella

      Version of Record online: 2 MAR 2017 | DOI: 10.1002/chem.201605060

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      Nitrogen in the bridge: Electrochemical studies and density functional theory calculations reveal the striking influence of the pendant amine in the dithiolate bridge on the oxidative processes of diiron models of the active site of [FeFe] hydrogenases (see figure).

    10. Solar Cells

      High-Efficiency Perovskite Solar Cells Based on New TPE Compounds as Hole Transport Materials: The Role of 2,7- and 3,6-Substituted Carbazole Derivatives (pages 4373–4379)

      Dr. Linna Zhu, Yahan Shan, Rui Wang, Debei Liu, Dr. Cheng Zhong, Prof. Qunliang Song and Dr. Fei Wu

      Version of Record online: 7 MAR 2017 | DOI: 10.1002/chem.201605187

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      Outperforming the star: Four tetraphenylethylene-centered hole transport materials (HTMs) with 2,7- or 3,6-substituted carbazole derivatives are synthesized and applied in perovskite solar cells. The 2,7-carbazole-based HTMs show higher performance than the 3,6-carbazole-based HTMs (see figure; FTO= fluorine tin oxide, FF=fill factor).

    11. Magnetic Properties

      Pentagonal Bipyramid FeII Complexes: Robust Ising-Spin Units towards Heteropolynuclear Nanomagnets (pages 4380–4396)

      Dr. Arun Kumar Bar, Dr. Nayanmoni Gogoi, Dr. Céline Pichon, Dr. V. M. L. Durga Prasad Goli, Mehrez Thlijeni, Dr. Carine Duhayon, Dr. Nicolas Suaud, Prof. Nathalie Guihéry, Dr. Anne-Laure Barra, Prof. S. Ramasesha and Dr. Jean-Pascal Sutter

      Version of Record online: 6 MAR 2017 | DOI: 10.1002/chem.201605549

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      Take five: Pentagonal bipyramid FeII complexes have been investigated to evaluate their potential as Ising-spin building units for the preparation of heteropolynuclear complexes that are likely to behave as single-molecule magnets (see figure).

    12. Chalcogens

      Oxidation of Substituted Phosphanylboranes with Chalcogens (pages 4397–4404)

      Christian Marquardt, Oliver Hegen, Tobias Kahoun and Prof. Dr. Manfred Scheer

      Version of Record online: 8 MAR 2017 | DOI: 10.1002/chem.201605625

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      Oxidation time! Stoichiometric reaction of the phosphanylboranes Ph2P-BH2⋅NMe3 and tBuHP-BH2⋅NMe3 with elemental chalcogens or peroxides leads to the mono-oxidized species. Thus, first derivatives of neutral B-P-Te-containing compounds have been isolated. In the case of the secondary phosphanylborane, further oxidation is also possible.

    13. Asymmetric Reactions

      Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles (pages 4405–4414)

      Prof. Dr. Barry M. Trost, Dr. Walter H. Chan and Dr. Sushant Malhotra

      Version of Record online: 6 MAR 2017 | DOI: 10.1002/chem.201605810

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      An orthogonal set of reaction conditions has been developed for the asymmetric Pd-catalyzed prenylation of 3-alkyl- and 3-aryloxindoles, allowing for selective formation of both the prenyl and reverse-prenyl oxindoles. The subtle factors that guide regioselectivity are applied to reactions using hemi- and monoterpenoid electrophiles. The absolute stereochemistry of the products was determined through the asymmetric synthesis of flustramines A and B.

    14. Organic Light-Emitting Diodes

      Dibenzobarrelene-Based Azaacenes: Emitters in Organic Light-Emitting Diodes (pages 4415–4421)

      Michael Ganschow, Silke Koser, Sebastian Hahn, Dr. Frank Rominger, Dr. Jan Freudenberg and Prof. Dr. Uwe H. F. Bunz

      Version of Record online: 3 MAR 2017 | DOI: 10.1002/chem.201605820

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      Milled to perfection: Direct fusion of dibenzobarrelene moieties to azacenes cores (see figure), either through classic condensation reactions or by solvent-free ball-milling, leads to soluble solid-state emitters that exhibit improved performance with respect to their iptycene analogues.

    15. Quantum Chemistry

      You have full text access to this OnlineOpen article
      The Bonding Situation in Metalated Ylides (pages 4422–4434)

      M. Sc. Lennart T. Scharf, Dr. Diego M. Andrada, Prof. Dr. Gernot Frenking and Prof. Dr. Viktoria H. Gessner

      Version of Record online: 7 MAR 2017 | DOI: 10.1002/chem.201605997

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      Dative or not? The bonding situation in metalated ylides (L=anionic, see scheme) and their related bisylides was examined by DFT calculations. Dative, ylidic, and double bonds can be formed depending on the substitution pattern and the total charge of the compounds. In general, several resonance structures contribute to the “real” bonding situation, which in turn can be tailored by careful selection of L.

    16. Electrochemistry

      NiCoP Nanoarray: A Superior Pseudocapacitor Electrode with High Areal Capacitance (pages 4435–4441)

      Menglai Kong, Zao Wang, Weiyi Wang, Min Ma, Danni Liu, Shuai Hao, Prof. Rongmei Kong, Prof. Gu Du, Prof. Abdullah M. Asiri, Prof. Yadong Yao and Prof. Xuping Sun

      Version of Record online: 15 MAR 2017 | DOI: 10.1002/chem.201700017

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      NiCoP nanoarray on nickel foam behaves as a superior 3D pseudocapacitor electrode, delivering a high areal capacitance of 9.2 F cm−2 at a current density of 2 mA cm−2 with good rate capability and cycling stability. Its combination with AC leads to an asymmetric supercapacitor with an energy density of 1.16 mWh cm−2 at a power density of 1.6 mW cm−2. This device can light six LED bulbs and split water to hydrogen and oxygen using a NiCoP nanoarray-based two-electrode alkaline water electrolyzer.

    17. Macrocyclic Polymers

      Cyclodextrin Nanoparticles Bearing 8-Hydroxyquinoline Ligands as Multifunctional Biomaterials (pages 4442–4449)

      Dr. Valentina Oliveri, Dr. Francesco Bellia and Prof. Graziella Vecchio

      Version of Record online: 8 MAR 2017 | DOI: 10.1002/chem.201700031

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      Going metallic: The metal ions (Cu2+ or Zn2+) can modulate the assembly of the novel metal-chelating β-cyclodextrin polymer bearing 8-hydroxyquinoline ligands. The synergistic effect of cyclodextrins and quinolines determines the high inhibitory modulation toward self- and metal-induced Aβ aggregation.

    18. Supramolecular Chemistry | Hot Paper

      Directly Attached Bisdonor-BF2 Chelated Azadipyrromethene-Fullerene Tetrads for Promoting Ground and Excited State Charge Transfer (pages 4450–4461)

      Melissa A. Collini, Michael B. Thomas, Dr. Venugopal Bandi, Prof. Dr. Paul A. Karr and Prof. Dr. Francis D'Souza

      Version of Record online: 3 MAR 2017 | DOI: 10.1002/chem.201700200

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      Close encounters of the charge transfer kind: Directly connected supramolecular triads and tetrads featuring bisphenothiazine or bisferrocene, azaBODIPY, and C60 have been newly synthesized to demonstrate ground and excited state intramolecular charge transfer.

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