Chemistry - A European Journal

Cover image for Vol. 23 Issue 16

Editor: Neville Compton, Deputy Editors: Anne Deveson, Elisabeth Roedern

Impact Factor: 5.771

ISI Journal Citation Reports © Ranking: 2015: 24/163 (Chemistry Multidisciplinary)

Online ISSN: 1521-3765

Associated Title(s): Angewandte Chemie International Edition, Chemistry – An Asian Journal, ChemistryOpen, ChemistrySelect, ChemBioChem, ChemCatChem, ChemElectroChem, ChemMedChem, ChemPhotoChem, ChemPhysChem, ChemPlusChem, ChemSusChem, European Journal of Inorganic Chemistry, European Journal of Organic Chemistry

Board Member Highlights | Most Cited Articles | Most Prolific Authors

Twentieth Anniversary

Chemistry—A European Journal celebrates its 20th anniversary. Born out of discussions between Nobel Laureate Jean-Marie Lehn, Heinrich Nöth, the then President of the Gesellschaft Deutscher Chemiker (German Chemical Society, GDCh), and Peter Gölitz, Editor of Angewandte Chemie at a conference in Munich in 1993, Chemistry—A European Journal opened its doors for business in September 1994, and the first issue appeared in April 1995.

In the anniversary editorial by Editor-in-Chief Dr. Neville Compton, find out more about the history and development of the journal over the past 20 years and a list of the top 20 most prolific authors in the journal since its launch.

Read the Editorial now.

Anniversary Quiz: The Art of Chemistry

Each week, for twenty weeks, we will post a question based on one of the fabulous pieces of cover art that we have received over the past twenty years. Take part now and win.

Most Cited

Discover the most cited articles in Chemistry—A European Journal of the past 20 years:

All Types | Concepts | Reviews | Minireviews | Full Papers | Communications

Board Members' Highlights

As part of our celebration of the 20th volume and anniversary of the journal, starting from the last quarter of 2014 and throughout 2015, published issues will feature special Concept, Review, Minireview, and research articles contributed by our Board Members. This represents an opportunity to highlight some of the developments that have helped make the journal successful in its first 20 years, to reveal remaining challenges in well-trodden areas, and to introduce new concepts that are likely to flourish in the coming years. These articles will be free to read during the anniversary year.

Azafullerene C59N in Donor–Acceptor Dyads: Synthetic Approaches and Properties

Azafullerene C59N in Donor–Acceptor Dyads: Synthetic Approaches and Properties

Georgios Rotas*, Nikos Tagmatarchis*

Energy conversion schemes: Donor–acceptor systems based on the azafullerene C59N are reviewed. While focusing on the synthetic strategies, the properties of systems employing this azafullerene as electron or energy acceptor are also presented, unfolding both the synthetic access as well as the unique electronic properties of these systems. Both in dyads in solution as well as in solar cell devices, C59N is revealed as a promising acceptor for energy conversion schemes.

Chem. Eur. J. 2016, 22, No. 4, 1206–1214 [Minireview]

Solar Electricity and Solar Fuels: Status and Perspectives in the Context of the Energy Transition

Solar Electricity and Solar Fuels: Status and Perspectives in the Context of the Energy Transition

Nicola Armaroli*, Vincenzo Balzani*

On the move: The energy transition to renewables has started and the development of solar electricity is much more consolidated than that of solar fuels. The transition process suffers two key constraints, that is, relatively low net energy gains and the limited availability of mineral resources to manufacture converters and accumulators.

Chem. Eur. J. 2016, 22, No. 1, 32–57 [Review]

Artificial Photosynthesis at Dynamic Self-Assembled Interfaces in Water

Artificial Photosynthesis at Dynamic Self‐Assembled Interfaces in Water

Malte Hansen, Stefan Troppmann, Burkhard König*

The interface makes the difference: Self-assembled dynamic interfaces like micelles and vesicles help solving challenges of homogeneous solar energy conversion systems by self-organization, compartmentation and protection of catalytic units. This Minireview highlights the progress in the utilization and functionalization of micellar and vesicular systems for light-driven oxygen or hydrogen evolution.

Chem. Eur. J. 2016, 22, No. 1, 58–72 [Minireview]

Long, Multicenter Bonding—A New Concept for Supramolecular Materials

Long, Multicenter Bonding—A New Concept for Supramolecular Materials

Joel S. Miller*

The long and the short of it: Supramolecular structures can form from directional, long, multicenter bonding interactions based upon the intermolecular recognition and π-dimerization of radicals (see scheme).

Chem. Eur. J. 2015, 21, No. 26, 9302–9305 [Concept]

Glyconanomaterials for Combating Bacterial Infections

Glyconanomaterials for Combating Bacterial Infections

Olof Ramström*, Mingdi Yan*

Small wonder: Glyconanomaterials (see figure) offer exceptional potential towards combating bacterial infections. These materials can accommodate different effectors and can be tailored in terms of targeting, size, shape, presentation, etc. In this Concept article, the different advantages of glyconanomaterials are described, and their potential in antibiotic “revitalization” is pointed out.

Chem. Eur. J. 2015, 21, No. 46, 16310–16317 [Concept]

Carbocatalysis: The State of “Metal-Free” Catalysis

Carbocatalysis: The State of “Metal‐Free” Catalysis

Chun Kiang Chua, Martin Pumera*

Beyond the C: The application of chemically modified graphene materials as carbocatalysts is reviewed. Emphasis is placed on the impact of trace metallic impurities on the catalytic capabilities and the validity of such proclaimed “metal-free” carbocatalysts.

Chem. Eur. J. 2015, 21, No. 36, 12550–12562 [Minireview]

Peptide δ-Turn: Literature Survey and Recent Progress

Peptide δ‐Turn: Literature Survey and Recent Progress

Claudio Toniolo*, Marco Crisma, Alessandro Moretto, Cristina Peggion, Fernando Formaggio, Carlos Alemán, Carlos Cativiela, Chandrasekharan Ramakrishnan, Padmanabhan Balaram

cis-Peptide turn, turn, turn: Published results on peptide δ-turn conformation, characterized by a cis-amide bond and an intramolecularly H bonded, eight-membered pseudo-cyclic structure, are reviewed. Recent advancements in our laboratories on this rarely investigated, local folded structure are also presented.

Chem. Eur. J. 2015, 21, No. 40, 13866–13877 [Minireview]

Antivitamins B12—A Structure- and Reactivity-Based Concept

Antivitamins B12—A Structure‐ and Reactivity‐Based Concept

Bernhard Kräutler*

′B12-Dummies′ have a structure similar to vitamin B12 but cannot assume the metabolic role of the essential vitamin. In this Concept article novel strategies for the design and synthesis of such ′antivitamins B12′ are described. Studies of their effects are suggested to be helpful for elucidating the molecular mechanisms of still puzzling pathophysiological effects of B12-deficiency.

Chem. Eur. J. 2015, 21, No. 32, 11280–11287 [Concept]

Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine

Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine

Barry M. Trost*, Maksim Osipov

Intriguingly complex: The communesin alkaloids and perophoramidine are complex, structurally related natural products that have intrigued organic chemists for the past twenty years. This review serves to summarize the synthetic strategies that have been developed to access the communesin ring system and the total syntheses of these alkaloids.

Chem. Eur. J. 2015, 21, No. 46, 16318–16343 [Review]

The “Speedy” Synthesis of Atom-Specific 15N Imino/Amido-Labeled RNA

The “Speedy” Synthesis of Atom‐Specific 15N Imino/Amido‐Labeled RNA

Sandro Neuner, Tobias Santner, Christoph Kreutz, Ronald Micura*

Fast syntheses for 15N-labeled nucleoside phosphoramidites are urgently needed to generate access to RNA with selective labeling patterns. These are in turn needed for advanced NMR spectroscopic experiments to explore RNA structure, folding, and dynamics (see scheme). In this concept study, we present our preferred synthetic routes and show applications on riboswitch RNA.

Chem. Eur. J. 2015, 21, No. 33, 11634–11643 [Concept]

How to Make Weak Noncovalent Interactions Stronger

How to Make Weak Noncovalent Interactions Stronger

Jiang-Fei Xu, Linghui Chen, Xi Zhang*

Finding strength in weakness: In this Concept, four strategies are introduced for strengthening weak noncovalent interactions: 1) Preorganization of binding sites; 2) spatial confinement effects; 3) multivalent enhancement; 4) synergistic binding with multiple forces.

Chem. Eur. J. 2015, 21, No. 34, 11938–11946 [Concept]

Pincer-Type Complexes for Catalytic (De)Hydrogenation and Transfer (De)Hydrogenation Reactions: Recent Progress

Pincer‐Type Complexes for Catalytic (De)Hydrogenation and Transfer (De)Hydrogenation Reactions: Recent Progress

Svenja Werkmeister, Jacob Neumann, Kathrin Junge, Matthias Beller*

Pincers of power: This minireview is focused on the recent progress of the application of various precious and non-precious metal pincer-type catalysts. Besides hydrogenation reactions, their utilization for dehydrogenation and transfer (de)hydrogenation reactions is also described. Especially, but not exclusively, the usage of ruthenium and iron pincer complexes is highlighted for C[BOND]C, C[BOND]N, and C[BOND]O bond transformations.

Chem. Eur. J. 2015, 21, No. 35, 12226–12250 [Minireview]

Duplex-Selective Ruthenium-Based DNA Intercalators

Duplex‐Selective Ruthenium‐Based DNA Intercalators

Chad M. Shade, Robert D. Kennedy, Jessica L. Rouge, Mari S. Rosen, Mary X. Wang, Soyoung E. Seo, Daniel J. Clingerman, Chad A. Mirkin*

Enhanced luminescence in the presence of duplex rather than single-stranded DNA was observed for a [Ru(dipyrido[3,2-a:2′,3′-c]phenazine)L2]2+-based DNA intercalator that was specifically modified by functionalizing the bipyridine ligands with esters and carboxylic acids.

Chem. Eur. J. 2015, 21, No. 31, 10983–10987 [Communication]

Directional Dynamic Covalent Motion of a Carbonyl Walker on a Polyamine Track

Directional Dynamic Covalent Motion of a Carbonyl Walker on a Polyamine Track

Petr Kovaříček, Jean-Marie Lehn*

Walking, but in which direction? Carboxybenzaldehyde derivatives are able to form dynamic covalent bonds with both primary and secondary amines. This ability led to the introduction of controlled directional displacement of a small molecule along a non-symmetric polyamine track, which is fuelled by acid/base addition. The carboxybenzaldehyde group thus extends the realm of dynamic covalent chemistry of imines to secondary amines and opens new perspectives in this field.

Chem. Eur. J. 2015, 21, No. 26, 9380–9384 [Full Paper]

On the Extreme Oxidation States of Iridium

On the Extreme Oxidation States of Iridium

Pekka Pyykkö*, Wen-Hua Xu

Room at the bottom: A qualitative 18-electron structure is maintained in [Ir(CO)3]3− and beyond. A good correlation of the oxidation state with the experimental Mössbauer isomer shifts is found for IrIII–IX (see figure). A map of these numerous [M(CO)n]x species was also made.

Chem. Eur. J. 2015, 21, No. 26, 9468–9473 [Full Paper]

Photobiocatalysis: The Power of Combining Photocatalysis and Enzymes

Photobiocatalysis: The Power of Combining Photocatalysis and Enzymes

Juan Antonio Maciá-Agulló, Avelino Corma, Hermenegildo Garcia*

Light the way to biocatalysis! The present review presents the state of the art in the field of photobiocatalysis and has been organized based on the semiconductor and the reaction type including oxidations, hydrogen generation, and CO2 reduction. The possibility of direct enzyme activation by the semiconductor and the influence of the nature of the mediator are also discussed (see scheme).

Chem. Eur. J. 2015, 21, No. 31, 10940–10959 [Minireview]

Recent Developments in Synthetic Carbohydrate-Based Diagnostics, Vaccines, and Therapeutics

Recent Developments in Synthetic Carbohydrate‐Based Diagnostics, Vaccines, and Therapeutics

Alberto Fernández-Tejada*, F. Javier Cañada, Jesús Jiménez-Barbero*

Medicinal chemistry: On the basis of the important progress recently made in glycochemistry, glycobiology, and glycomedicine, a complete overview of successful applications and future perspectives of carbohydrates in the biopharmaceutical and medical fields (see graphic) is provided.

Chem. Eur. J. 2015, 21, No. 30, 10616–10628 [Review]

Hierarchical Assembly of Plasmonic Nanoparticles

Hierarchical Assembly of Plasmonic Nanoparticles

Cyrille Hamon*, Luis M. Liz-Marzán*

Held in suspense: The figure illustrates the assembly of metallic nanoparticles upon drying a colloidal suspension. In this Minireview, the main parameters and methods that can be tuned to achieve such organized networks are defined.

Chem. Eur. J. 2015, 21, No. 28, 9956–9963 [Minireview]

Ln0.5A0.5MnO3 (Ln=Lanthanide, A= Ca, Sr) Perovskites Exhibiting Remarkable Performance in the Thermochemical Generation of CO and H2 from CO2 and H2O

Ln0.5A0.5MnO3 (Ln=Lanthanide, A= Ca, Sr) Perovskites Exhibiting Remarkable Performance in the Thermochemical Generation of CO and H2 from CO2 and H2O

Sunita Dey, B. S. Naidu, C. N. R. Rao*

Y0.5A0.5MnO3 (A= Sr, Ca) perovskites show remarkable oxygen and fuel production activity in the two-step thermochemical splitting of CO2 and H2O (see scheme). The investigation reveals the influence of Ln and A cation size in Ln0.5A0.5MnO3 (Ln=rare earth ion, A= Sr, Ca) perovskites in the thermochemical splitting of CO2 and H2O. Decrease in the rare earth ion size enhances the O2 and fuel production yield and reduces the reaction temperature.

Chem. Eur. J. 2015, 21, No. 19, 7077–7081 [Communication]

Imidazolium Salt Ion Pairs in Solution

Imidazolium Salt Ion Pairs in Solution

Hubert K. Stassen, Ralf Ludwig, Alexander Wulf, Jairton Dupont*

A pair of liquids: The formation, stabilisation, and reactivity of contact ion pairs of non-protic imidazolium ionic liquids dissolved in organic solvents are conceptualized in the light of selected experimental evidence, as well theoretical calculations, reported mainly in the last ten years.

Chem. Eur. J. 2015, 21, No. 23, 8324–8335 [Minireview]

Beyond Stereoselectivity, Switchable Catalysis: Some of the Last Frontier Challenges in Ring-Opening Polymerization of Cyclic Esters

Beyond Stereoselectivity, Switchable Catalysis: Some of the Last Frontier Challenges in Ring‐Opening Polymerization of Cyclic Esters

Sophie M. Guillaume, Evgueni Kirillov, Yann Sarazin, Jean-François Carpentier*

Searching for the switches: Metal-based catalysts and initiators have long been integral to the ring-opening polymerization (ROP) of cyclic esters. However, several challenges remain. This review surveys advances in the development of new metal-based catalysts for the isoselective ROP, as well as that of ROP catalysts that can be switched between two catalytic states by external stimuli.

Chem. Eur. J. 2015, 21, No. 22, 7988–8003 [Review]

Gold Carbene or Carbenoid: Is There a Difference?

Gold Carbene or Carbenoid: Is There a Difference?

Yahui Wang, Michael E. Muratore, Antonio M. Echavarren*

Carbene or carbenoid that is the question? The term gold carbene is proposed to describe gold carbene-like intermediates, regardless of which of the carbene or carbocation extreme resonance dominates.

Chem. Eur. J. 2015, 21, No. 20, 7332–7339 [Concept]

New Phenomena in Organometallic-Mediated Radical Polymerization (OMRP) and Perspectives for Control of Less Active Monomers

New Phenomena in Organometallic‐Mediated Radical Polymerization (OMRP) and Perspectives for Control of Less Active Monomers

Rinaldo Poli*

Challenges facing controlled polymerization: Recent progress in organometallic-mediated radical polymerization (OMRP) is outlined with focus on the achievements and perspectives in the controlled polymerization of “less active monomers” (LAMs).

Chem. Eur. J. 2015, 21, No. 19, 6988–7001 [Concept]

Polyoxometalate-Mediated One-Pot Synthesis of Pd Nanocrystals with Controlled Morphologies for Efficient Chemical and Electrochemical Catalysis

Polyoxometalate‐Mediated One‐Pot Synthesis of Pd Nanocrystals with Controlled Morphologies for Efficient Chemical and Electrochemical Catalysis

Dongheun Kim, Ji Hyun Seog, Minjune Kim, MinHo Yang, Eleanor Gillette, Sang Bok Lee*, Sang Woo Han*

Single-crystalline Pd nanocrystals with controlled shapes and sizes were synthesized by a polyoxometalate-mediated one-pot aqueous synthesis method. The prepared Pd nanocrystals exhibited enhanced catalytic properties toward electrochemical and chemical reactions (see figure).

Chem. Eur. J. 2015, 21, No. 14, 5387–5394 [Full Paper]

Mechanosensitive Membrane Probes

Mechanosensitive Membrane Probes

Marta Dal Molin, Quentin Verolet, Saeideh Soleimanpour, Stefan Matile*

Lobsters, flippers, disorder, tension, and potential: The origins of the concept of mechanosensitive membrane probes—from fishmarket and scuba diving to the chemistry of vision, mechanochromic organic materials, and mechanosensitive channels—are briefly reviewed (see scheme).

Chem. Eur. J. 2015, 21, No. 16, 6012–6021 [Concept]

Intrinsic Organic-Based Synthetic/Artificial Antiferromagnets

Intrinsic Organic‐Based Synthetic/Artificial Antiferromagnets

Joel S. Miller*

Intrinsic multilayered, antiferromagnets based on the antiferromagnetic coupling of sub-nm ferrimagnetic layers with the same motif as that for artificial/synthetic antiferromagnets exhibiting giant magnetoresistance (GMR) have been achieved.

Chem. Eur. J. 2015, 21, No. 12, 4506–4510 [Minireview]

Flow Chemistry Meets Advanced Functional Materials

Flow Chemistry Meets Advanced Functional Materials

Rebecca M. Myers, Daniel E. Fitzpatrick, Richard M. Turner, Steven V. Ley*

Go with the flow: This Review describes the use of flow chemistry methods for the synthesis of advanced functional materials, ranging from quantum dots, nanoparticles and metal–organic frameworks to polymers and dyes, and the improvements that can accrue when delivering in-line high purity and high precision species with superior properties over their batch-mode-prepared congeners. The emphasis is upon the wide variety of devices and reactor configurations that help create these opportunities in many areas of contemporary materials science.

Chem. Eur. J. 2014, 20, No. 39, 12348–12366 [Review]

The syn/anti-Dichotomy in the Palladium-Catalyzed Addition of Nucleophiles to Alkenes

The syn/anti‐Dichotomy in the Palladium‐Catalyzed Addition of Nucleophiles to Alkenes

Pavel Kočovský*, Jan-E. Bäckvall*

The stereochemistry of Pd-catalyzed nucleophilic addition to alkenes is discussed with the focus on oxygen and nitrogen nucleophiles and the Wacker oxidation of ethylene; numerous examples of synthetic applications are presented. From the reviewed material it is clear that anti-addition is strongly favored in intermolecular addition to olefin-palladium complexes even if the nucleophile is coordinated to the metal (see scheme).

Chem. Eur. J. 2015, 21, No. 1, 36–56 [Review]

Chemical Energy Powered Nano/Micro/Macromotors and the Environment

Chemical Energy Powered Nano/Micro/Macromotors and the Environment

James Guo Sheng Moo, Martin Pumera*

First response: Use of synthetic nano/micro/macromotors has demonstrated potential in environmental remediation, both in pollutant removal and contaminant degradation, owing to motion- induced mixing. At the same time, the chemical environment exerts influence on the locomotion of the motors, allowing these sensitized self-powered devices to be deployed as sensors and first responders to chemical leakage.

Chem. Eur. J. 2015, 21, No. 1, 58–72 [Minireview]

Aminocatalysis: Beyond Steric Shielding and Hydrogen-Bonding

Aminocatalysis: Beyond Steric Shielding and Hydrogen‐Bonding

Bruno Matos Paz, Hao Jiang, Karl Anker Jørgensen*

The law of attraction: What determines the stereochemical outcome in aminocatalytic transformations when the steric-shielding or hydrogen-directing approach is not possible? The Concept article will postulate that the stereochemical outcome can be accounted for by electrostatic interactions between the catalytic bound substrate and the reagent in the transition state.

Chem. Eur. J. 2015, 21, No. 5, 1846–1853 [Concept]

Replacement of Water Molecules in a Phosphate Binding Site by Furanoside-Appended lin-Benzoguanine Ligands of tRNA-Guanine Transglycosylase (TGT)

Replacement of Water Molecules in a Phosphate Binding Site by Furanoside‐Appended lin‐Benzoguanine Ligands of tRNA‐Guanine Transglycosylase (TGT)

Luzi J. Barandun, Frederik R. Ehrmann, Daniel Zimmerli, Florian Immekus, Maude Giroud, Claudio Grünenfelder, W. Bernd Schweizer, Bruno Bernet, Michael Betz, Andreas Heine, Gerhard Klebe*, François Diederich*

Phosphate binding sites: Furanoside-appended lin-benzoguanines are investigated as a replacement for a water cluster in the polar ribose-34 pocket of the enzyme tRNA-guanine transglycosylase (see figure), which has been identified as a drug target for the treatment of Shigellosis. Based on X-ray co-crystal structures, it is proposed that furanosides are suitable groups to fill phosphate binding sites.

Chem. Eur. J. 2015, 21, No. 1, 126–135 [Full Paper]

Electrophilic Amination: The Case of Nitrenoids

Electrophilic Amination: The Case of Nitrenoids

Pavel Starkov, Timothy F. Jamison, Ilan Marek*

Nitrenoids at the crossroads: Among the numerous approaches and reagents employed for electrophilic amination, nitrenoids have long stayed out of the limelight. The discovery, structural features and chemical reactivity of these promising reagents are systematically reviewed.

Chem. Eur. J. 2015, 21, No. 14, 5278–5300 [Review]

Construction of a High-Mannose-Type Glycan Library by a Renewed Top-Down Chemo-Enzymatic Approach

Construction of a High‐Mannose‐Type Glycan Library by a Renewed Top‐Down Chemo‐Enzymatic Approach

Kohki Fujikawa, Akihiko Koizumi, Masakazu Hachisu, Akira Seko, Yoichi Takeda, Yukishige Ito*

A comprehensive method for the construction of a high-mannose-type glycan library by systematic chemo-enzymatic trimming of a single Man9-based precursor was developed. After systematic trimming of the precursor, 37 high-mannose-type glycans were obtained (see figure). The power of the methodology was demonstrated by the enzymatic activity of human recombinant N-acetylglucosaminyltransferase-I toward M7–M3 glycans, clarifying the substrate specificity in the context of high-mannose-type glycans.

Chem. Eur. J. 2015, 21, No. 8, 3224–3233 [Full Paper]

Tandem Catalysis Utilizing Olefin Metathesis Reactions

Tandem Catalysis Utilizing Olefin Metathesis Reactions

Grzegorz K. Zieliński*, Karol Grela*

Pedal to the metal: Various examples of tandem catalysis involving olefin metathesis are discussed, with a view to illustrating some interesting synthetic concepts and showing their synthetic value. The differences between tandem processes and other types of one-pot transformation are stressed.

Chem. Eur. J. 10.1002/chem.201505136 [Concept]

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