Chemistry - A European Journal

Cover image for Vol. 19 Issue 13

March 25, 2013

Volume 19, Issue 13

Pages 4081–4368

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: Reactions of Group 4 Metallocene Complexes with Mono- and Diphenylacetonitrile: Formation of Unusual Four- and Six-Membered Metallacycles (Chem. Eur. J. 13/2013) (page 4081)

      Lisanne Becker, Dr. Vladimir V. Burlakov, Dr. Perdita Arndt, Dr. Anke Spannenberg, Dr. Wolfgang Baumann, Dr. Haijun Jiao and Prof. Dr. Uwe Rosenthal

      Article first published online: 15 MAR 2013 | DOI: 10.1002/chem.201390041

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      The route taken depends on the metals and Cp′ ligands chosen, as illustrated by reactions of Group 4 metallocene complexes and diphenylated acetonitrile, Ph2CHCN, which undergo coupling, coordination, or H-shifts. Additionally, for zirconocene, an unexpected six-membered fused zirconaheterocycle was formed by changing the substrates to monophenylated acetonitrile, PhCH2CN, and bis(trimethylsilyl)butadiyne. More details of this fascinating chemistry are reported in the Full Paper by U. Rosenthal and co-workers on page 4230 ff. The background of the cover shows different destinations in Rostock and Warnemünde.

    2. You have free access to this content
      Back Cover: A Simple Link between Hydrocarbon and Borohydride Chemistries (Chem. Eur. J. 13/2013) (page 4372)

      Dr. Jordi Poater, Prof. Dr. Miquel Solà, Prof. Dr. Clara Viñas and Prof. Dr. Francesc Teixidor

      Article first published online: 15 MAR 2013 | DOI: 10.1002/chem.201390044

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      Not so different! Hydrocarbons and borohydrides have a common root regulated by the number of valence electrons in a confined space. In their Full Paper on page 4169 ff., M. Solà, F. Teixidor et al. show how the connection between B and C chemistries can aid in the rational design of a certain number of interesting boron-containing molecules and materials. Their results will be also be useful to rationalize the molecular structure of novel compounds that containing boron[BOND]boron and boron[BOND]hydrogen bonds.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
    1. Graphical Abstract: Chem. Eur. J. 13/2013 (pages 4084–4092)

      Article first published online: 15 MAR 2013 | DOI: 10.1002/chem.201390042

  3. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Corrigendum: A Disulfide Bridge Allows for Site-Selective Binding in Liver Bile Acid Binding Protein Thereby Stabilising the Orientation of Key Amino Acid Side Chains (page 4092)

      Dr. Simona Tomaselli, Dr. Michael Assfalg, Dr. Katiuscia Pagano, Dr. Clelia Cogliati, Dr. Serena Zanzoni, Prof. Henriette Molinari and Dr. Laura Ragona

      Article first published online: 15 MAR 2013 | DOI: 10.1002/chem.201300867

  4. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
  5. Concept

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
    1. Nanocomposites

      Hierarchical Structures Based on Functionalized Magnetic Cores and Layered Double-Hydroxide Shells: Concept, Controlled Synthesis, and Applications (pages 4100–4108)

      Mingfei Shao, Prof. Min Wei, Prof. David G. Evans and Prof. Xue Duan

      Article first published online: 19 FEB 2013 | DOI: 10.1002/chem.201204205

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      The core of the matter: The fabrication and application of magnetic-core/layered-double-hydroxide (LDH)-shell composites with hierarchical structure represent a new direction in the development of LDH-based multifunctional materials, which will contribute to the progress of chemistry and material science (see scheme).

  6. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
    1. Nonplanar π Systems

      Solvent-Induced Crystalline-State Emission and Multichromism of a Bent π-Surface System Composed of Dibenzocyclooctatetraene Units (pages 4110–4116)

      Dr. Tomohiko Nishiuchi, Keita Tanaka, Dr. Yoshiyuki Kuwatani, Jooyoung Sung, Prof. Dr. Tohru Nishinaga, Prof. Dr. Dongho Kim and Prof. Dr. Masahiko Iyoda

      Article first published online: 4 MAR 2013 | DOI: 10.1002/chem.201203952

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      All bent out of shape: The solvent of crystallization effectively enhances the emission of flexible, bent, π-conjugated molecules in the crystalline state owing to control of the packing of the molecules in the structure. Multichromism such as thermochromism and vapochromism also arises from the solvent-controlled packing. This crystalline-state emission is attributable to the flexibility of cyclooctatetraene units of the bent π-conjugated molecules in the solid state (see figure).

    2. Immunoassays

      Selective, Sensitive, and Rapid Analysis with Lateral-Flow Assays Based on Antibody-Gated Dye-Delivery Systems: The Example of Triacetone Triperoxide (pages 4117–4122)

      Dr. Estela Climent, Delia Gröninger, Mandy Hecht, Dr. M. Astrid Walter, Prof. Ramón Martínez-Máñez, Dr. Michael G. Weller, Dr. Félix Sancenón, Prof. Pedro Amorós and Dr. Knut Rurack

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201300031

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      Set them free: Brightly fluorescent indicators that are loaded into mesoporous silica nanoparticle carriers, capped with bulky antibodies, are released into the lateral flow of a test strip upon analyte arrival. Integration of the system into a rapid, simple flow test with fluorescence readout is applied for the selective and sensitive determination of the presence of triacetone triperoxide (TATP) as a prototype small-molecule analyte (see figure).

    3. Hydrogen Evolution

      Disordered Co1.28Mn1.71O4 as a Visible-Light-Responsive Photocatalyst for Hydrogen Evolution (pages 4123–4127)

      Zu Peng Chen, Dr. Jun Xing, Dr. Hai Bo Jiang and Prof. Dr. Hua Gui Yang

      Article first published online: 20 FEB 2013 | DOI: 10.1002/chem.201203683

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      Catching the sunlight: The disordered Co1.28Mn1.71O4 was synthesized by a facile reduction method in the presence of amorphous MnO2 precursors and Co2+. It exhibits relatively high hydrogen-production activity under visible-light irradiation (see figure). The larger number of active sites in the bulk catalyst endow nanoparticles with improved water-reduction activity. This is the first demonstration of disordered ternary oxides for visible-light-driven hydrogen evolution in the absence of a cocatalyst.

    4. Asymmetric Synthesis

      Catalytic Enantioselective Decarboxylative Cyanoalkylation of Imines by Using Palladium Pincer Complexes with C2-Symmetric Chiral Bis(imidazoline)s (pages 4128–4134)

      Kengo Hyodo, Masaru Kondo, Prof. Yasuhiro Funahashi and Prof. Shuichi Nakamura

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201203782

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      Manifold products: The enantioselective decarboxylative Mannich-type reaction of cyanoacetic acid with N- (2-pyridinesulfonyl)imines catalyzed by chiral 1,3-bis(imidazolin-2-yl)benzene (Phebim)–PdII complexes afforded products with good enantioselectivity (see scheme). The reaction was applied to a wide range of imines with good yield and enantioselectivity. The obtained products can be converted into various compounds without the loss of enantiopurity.

    5. Air-Stable Bifunctional Allylation Reagents for the Asymmetric Synthesis of Differentiated syn- and anti-1,3-Diols (pages 4135–4139)

      Dr. Jae Seung Lee, Dr. Dongeun Kim, Prof. Suk Bin Kong and Prof. Hyunsoo Han

      Article first published online: 21 FEB 2013 | DOI: 10.1002/chem.201204148

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      Turning the diols: Enantiomerically pure bifunctional reagents I and ent-I undergo asymmetric aldehyde allylation followed by IrI-catalyzed enantioselective decarboxylative allylic etherification to give differentiated syn- and anti-1,3-diols with complete control of the absolute and relative stereochemistry (see scheme; PMP=para-methoxyphenyl, dbcot=dibenzo[a,e]cyclooctatetraene, DBU=1,8-diazabicyclo[5.4.0]undec-7-ene).

    6. C[BOND]H Activation

      Aerobic Oxidative Coupling of Arenes and Olefins through a Biomimetic Approach (pages 4140–4145)

      Dr. Beneesh P. Babu, Xu Meng and Prof. Jan-E. Bäckvall

      Article first published online: 28 FEB 2013 | DOI: 10.1002/chem.201300100

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      Arenes and electron-deficient olefins can be oxidatively coupled through a biomimetic Pd(OAc)2-catalyzed transformation. C[BOND]H activation of the arene partner is effected under reaction conditions of low catalyst loading, normal oxygen pressure, and using p-benzoquinone and iron phthalocyanine as electron-transfer mediators (ETMs). By controlling catalyst loading, the reaction can be made selective for either mono- or diarylation.

    7. Allenolate Addition

      N-Heterocyclic Carbene (NHC)-Catalyzed/Lewis Acid Mediated Conjugate Umpolung of Alkynyl Aldehydes for the Synthesis of Butenolides: A Formal [3+2] Annulation (pages 4146–4150)

      Jing Qi, Dr. Xingang Xie, Runfeng Han, Donghui Ma, Juan Yang and Prof. Dr. Xuegong She

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201204386

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      Reverse to success! A new formal [3+2] annulation reaction combining alkynyl aldehydes and β,γ-unsaturated α-ketoesters has been disclosed by using a NHC-catalyzed/Lewis acid mediated strategy. This cooperative catalysis strategy first allows the “allenolate” intermediate as a nucleophilic synthon at the β-position to react with activated electrophilic reagents by an addition reaction as the key C[BOND]C bond-forming step.

    8. Asymmetric Synthesis

      Kinetic Resolution of Planar-Chiral 1,2-Disubstituted Ferrocenes by Molybdenum-Catalyzed Asymmetric Intraannular Ring-Closing Metathesis (pages 4151–4154)

      Prof. Dr. Masamichi Ogasawara, Sachie Arae, Dr. Susumu Watanabe, Prof. Dr. Kiyohiko Nakajima and Prof. Dr. Tamotsu Takahashi

      Article first published online: 20 FEB 2013 | DOI: 10.1002/chem.201300116

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      Planar chirality: Ring-closing metathesis of 1,2-diallylmetallocenes afforded the corresponding 4,7-dihydroindenyl species in high yields. The metallocenes are planar chiral with two different allylic substituents, and kinetic resolution of the racemic 1,2-diallylmetallocene derivatives was realized by molybdenum-catalyzed asymmetric ring-closing metathesis with excellent enantioselectivity (see scheme).

  7. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Concept
    7. Communications
    8. Full Papers
    1. Multicomponent Reactions

      The Biginelli Reaction with an Imidazolium–Tagged Recyclable Iron Catalyst: Kinetics, Mechanism, and Antitumoral Activity (pages 4156–4168)

      Dr. Luciana M. Ramos, Bruna C. Guido, Catharine C. Nobrega, Dr. José R. Corrêa, Dr. Rafael G. Silva, Dr. Heibbe C. B. de Oliveira, Alexandre F. Gomes, Prof. Fábio C. Gozzo and Prof. Brenno A. D. Neto

      Article first published online: 4 MAR 2013 | DOI: 10.1002/chem.201204314

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      Ion/Iron will: The use of a new imidazolium-tagged iron catalyst as the promoter of the Biginelli reaction allowed the synthesis of several dihydropyrimidinones with attractive biological activity (see scheme). The mechanism of this interesting transformation was evaluated by means of kinetics, NMR spectroscopy, ESI-MS(/MS), and theoretical calculations.

    2. Borohydrides

      A Simple Link between Hydrocarbon and Borohydride Chemistries (pages 4169–4175)

      Dr. Jordi Poater, Prof. Dr. Miquel Solà, Prof. Dr. Clara Viñas and Prof. Dr. Francesc Teixidor

      Article first published online: 18 FEB 2013 | DOI: 10.1002/chem.201204397

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      The missing link: Hydrocarbons and borohydrides have a common root regulated by the number of valence electrons in a confined space (see figure), which has led to the design of new interesting boron-containing molecules.

    3. Supramolecular Systems

      Evidence for Kinetic Nucleation in Helical Nanofiber Formation Directed by Chiral Solvent for a Perylene Bisimide Organogelator (pages 4176–4183)

      Dr. Vladimir Stepanenko, Dr. Xue-Qing Li, Jana Gershberg and Prof. Dr. Frank Würthner

      Article first published online: 11 FEB 2013 | DOI: 10.1002/chem.201204146

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      The self-assembly behavior of a perylene bisimide organogelator has been investigated in chiral solvents by circular dichroism spectroscopy and atomic force microscopy, revealing induction of homochirality in dilute solution under thermodynamic conditions. Furthermore, the observed low helical bias (ee=20 %) of nanofibers formed at high concentration by gelation process is an outcome of kinetic control (see figure).

    4. Structure Elucidation

      Binary Compounds of Boron and Beryllium: A Rich Structural Arena with Space for Predictions (pages 4184–4197)

      Dr. Andreas Hermann, Prof. Dr. N. W. Ashcroft and Prof. Dr. Roald Hoffmann

      Article first published online: 11 FEB 2013 | DOI: 10.1002/chem.201203890

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      Building B[BOND]Be Binaries: Possible compounds of beryllium and boron have been explored theoretically, with a focus on the role of external pressure in the (de)stabilization of various phases. Several compositions (Be2B3, BeB4) are known experimentally; for these we predict specific structures (see figure). Other phases, as yet unknown, with interesting electronic properties, emerge as stable at higher pressures.

    5. Synthetic Methods

      Synthesis, Bonding and Reactivity of a Terminal Titanium Alkylidene Hydrazido Compound (pages 4198–4216)

      Dr. Pei Jen Tiong, Laura R. Groom, Dr. Eric Clot and Prof. Dr. Philip Mountford

      Article first published online: 11 FEB 2013 | DOI: 10.1002/chem.201203905

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      Treatment for terminal titanium: The synthesis, DFT bonding analysis and reactivity of a new terminal titanium alkylidene hydrazido complex are reported (see figure). Single and multiple addition or insertion reactions of the Ti[DOUBLE BOND]Nα bond are reported with CO2, CS2, ArNCO, ArNCS, RCCH, RCN and RSiH2X (X=H, halogen).

    6. Contrast Agents

      Cleaved Iron Oxide Nanoparticles as T2 Contrast Agents for Magnetic Resonance Imaging (pages 4217–4222)

      Dr. Sung Lan Jeon, Dr. Min Kyung Chae, Eun Ju Jang and Dr. Chulhyun Lee

      Article first published online: 23 JAN 2013 | DOI: 10.1002/chem.201201031

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      Nanoparticle contrast agents: Cleaved iron oxide nanoparticles (CIONPs) were prepared from monodisperse hydrophobic iron oxide (FeO) nanoparticles in three steps: surface coating with poly(ethylene glycol)-phospholipid, oxidation under water, and removal of the residual FeO phase with acidic buffer. The CIONPs showed good relaxivities and, because of their empty inner spaces, have potential applications as vectors for drug delivery and chemicals storage.

    7. Stereochemistry

      E/Z Oxime Isomerism in PhC(NOH)CN (pages 4223–4229)

      Prof. D. Scott Bohle, Zhijie Chua, Dr. Inna Perepichka and Kristopher Rosadiuk

      Article first published online: 10 FEB 2013 | DOI: 10.1002/chem.201203357

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      Spin catalysis: The reaction of nitric oxide with benzyl cyanide in the presence of potassium methoxide at low temperature gave the dipotassium salt of bis-diazeniumdiolate 2 in excellent yield (see scheme). Evidence of catalysis by NO of E/Z oxime isomerization has been observed.

    8. Metallacycles

      Reactions of Group 4 Metallocene Complexes with Mono- and Diphenylacetonitrile: Formation of Unusual Four- and Six-Membered Metallacycles (pages 4230–4237)

      Lisanne Becker, Dr. Vladimir V. Burlakov, Dr. Perdita Arndt, Dr. Anke Spannenberg, Dr. Wolfgang Baumann, Dr. Haijun Jiao and Prof. Dr. Uwe Rosenthal

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201204211

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      Metal made modes: [Cp′M2] complexes with different metals and Cp′ ligands react differently with Ph2CHCN (see scheme). M=Zr gives keteniminate and imine ligands as [Cp*2Zr(NC2Ph2)(NCHCHPh2)], M=Ti forms two keteniminates as [Cp*2Ti(NC2Ph2)2]. If Cp′2=rac-(ebthi)=rac-1,2-ethylene-1,1′-bis(η5-tetrahydroindenyl) and M=Ti, an unusual four-membered titanacycle is formed. [Cp2Zr(η2-Me3SiC4SiMe3)] reacts with PhCH2CN to give an unexpected six-membered fused zirconaheterocycle.

    9. Doped Gold Nanoparticles

      Atomic-Level Alloying and De-alloying in Doped Gold Nanoparticles (pages 4238–4243)

      Eric Gottlieb, Dr. Huifeng Qian and Prof. Dr. Rongchao Jin

      Article first published online: 12 FEB 2013 | DOI: 10.1002/chem.201203158

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      Doped! Homogold Au25(SR)18 nanoparticles can be doped with Cu and Ag. The resulting kinetically formed CuxAu25−x(SR)18 alloy nanoparticles show spontaneous de-alloying to Au25(SR)18 over time, whereas no de-alloying was observed in alloyed AgxAu25−x(SR)18 nanoparticles (see scheme).

    10. tRNA Modifications

      Total Synthesis of the Hypermodified RNA Bases Wybutosine and Hydroxywybutosine and Their Quantification Together with Other Modified RNA Bases in Plant Materials (pages 4244–4248)

      Dr. Antje Hienzsch, Christian Deiml, Veronika Reiter and Prof. Dr. Thomas Carell

      Article first published online: 18 FEB 2013 | DOI: 10.1002/chem.201204209

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      Chemical plant: An efficient synthesis of the hypermodified natural tRNA modifications wybutosine (yW) and hydroxywybutosine (OHyW) is reported (see scheme). The preparation of isotope-labeled analogues of yW and OHyW is described, which are used for precise quantification of yW and OHyW in the plant species Arabidopsis thaliana.

    11. Anisotropic Effects

      Magnetic Anisotropy of the C[BOND]C Single Bond (pages 4249–4254)

      Prof. Dr. Marija Baranac-Stojanović and Dr. Milovan Stojanović

      Article first published online: 11 FEB 2013 | DOI: 10.1002/chem.201204267

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      Raising the shield! The classical anisotropy cone for the C[BOND]C single bond should be revised: shielding along its end and deshielding at its side are observed (see figure). This anisotropic effect is dependent on the environment and care should be taken when drawing conclusions based on it. For example, it differs for the staggered and eclipsed conformations of ethane in HCCH planes, as well as for cyclohexane.

    12. Natural Products

      Synthesis of the Carbon Framework of Scholarisine A by Intramolecular Oxidative Coupling (pages 4255–4261)

      Tsugunori Watanabe, Dr. Naoki Umezawa, Dr. Nobuki Kato and Prof. Dr. Tsunehiko Higuchi

      Article first published online: 11 FEB 2013 | DOI: 10.1002/chem.201203454

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      Core skills: The core carbon framework of a highly complex natural product core, scholarisine A, was prepared. The 10-oxa-tricyclo[5.3.1.03, 8]undecan-9-one structure fused with indolenine was constructed by linking C7 and C16 by intramolecular oxidative coupling of non-activated lactone with indole C3 as the key reaction (see scheme; HMDS=hexamethyldisilazide).

    13. Conformational Selection

      Escherichia coli β-Galactosidase Inhibitors through Modifications at the Aglyconic Moiety: Experimental Evidence of Conformational Distortion in the Molecular Recognition Process (pages 4262–4270)

      Luis Calle, Dr. Virginia Roldós, Prof. Dr. F. Javier Cañada, María Laura Uhrig, Alejandro J. Cagnoni, Verónica E. Manzano, Oscar Varela and Prof. Dr. Jesus Jiménez-Barbero

      Article first published online: 19 FEB 2013 | DOI: 10.1002/chem.201203673

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      Unrecognizable: The molecular basis of galactosidase inhibition by novel glycomimetics has been studied by using a combination of NMR spectroscopy and molecular modeling techniques (see figure). It is demonstrated that these molecules are not recognized by Escherichia coli β-galactosidase in their ground-state conformation, with a conformational selection process taking place.

    14. Synthetic Methods

      Copper-Catalyzed Aerobic Oxidative C[BOND]H and C[BOND]C Functionalization of 1-[2-(Arylamino)aryl]ethanones Leading to Acridone Derivatives (pages 4271–4277)

      Jipan Yu, Dr. Haijun Yang, Prof. Dr. Yuyang Jiang and Prof. Dr. Hua Fu 

      Article first published online: 10 FEB 2013 | DOI: 10.1002/chem.201204169

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      Acridone synthesis: Efficient copper-catalyzed aerobic oxidative C[BOND]H and C[BOND]C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C[BOND]H and acetyl C[BOND]C bonds with intramolecular formation of a diarylketone bond (see scheme). The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as oxidant. The corresponding acridones with various functional groups were obtained in moderate to good yields.

    15. Rhenium Complexes

      Solid-State Thermolysis of a fac-Rhenium(I) Carbonyl Complex with a Redox Non-Innocent Pincer Ligand (pages 4278–4286)

      Dr. Titel Jurca, Dr. Wen-Ching Chen, Sheila Michel, Dr. Ilia Korobkov, Dr. Tiow-Gan Ong and Dr. Darrin S. Richeson

      Article first published online: 1 FEB 2013 | DOI: 10.1002/chem.201203045

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      Putting on a brave fac: The solid-state synthesis of low-valent rhenium pincer complexes addresses a major deficiency in the chemistry of imine-coordinated ReI carbonyl compounds. The family of compounds formed possesses a redox-active tridentate bis(imino)pyridine chelate. These new pincer complexes display enhanced metal-to-ligand d–π* electronic transitions, which were analyzed by DFT calculations.

    16. N-Heterocyclic Carbenes

      A New Class of Remote N-Heterocyclic Carbenes with Exceptionally Strong σ-Donor Properties: Introducing Benzo[c]quinolin-6-ylidene (pages 4287–4299)

      Dr. Ulrich F. J. Mayer, Elliot Murphy, Dr. Mairi F. Haddow, Prof. Michael Green, Prof. Roger W. Alder and Prof. Duncan F. Wass

      Article first published online: 1 FEB 2013 | DOI: 10.1002/chem.201203294

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      Classy ligand: Benzo[c]quinolin-6-ylidene is introduced as a new, strongly electron-donating, carbene ligand. Synthetic routes to metal complexes of this ligand and experimental evidence for its strong donor properties are outlined (see figure).

    17. Diacetylenes

      A Diacetylene-Containing Wedge-Shaped Compound: Synthesis, Morphology, and Photopolymerization (pages 4300–4307)

      Dr. Martin Rosenthal , Lei Li , Jaime J. Hernandez, Dr. Xiaomin Zhu, Dr. Dimitri A. Ivanov and Prof. Dr. Martin Möller

      Article first published online: 24 JAN 2013 | DOI: 10.1002/chem.201203240

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      Tails of two diacetylenes: A wedge-shaped compound containing two diacetylene tails can be polymerized under UV irradiation. Detailed analysis of the crystalline structure of this compound revealed that the diacetylene units are oriented along a defined lattice direction (see picture) with a packing period of 4.85 Å, which fulfills the requirements for topochemical polymerization. Importantly, UV polymerization does not affect the phase behavior of the compound, but mainly alters its optical properties.

    18. Anticancer Agents

      Am(m)ines Make the Difference: Organoruthenium Am(m)ine Complexes and Their Chemistry in Anticancer Drug Development (pages 4308–4318)

      Maria V. Babak, Samuel M. Meier , Anton A. Legin, Mahsa S. Adib Razavi, Alexander Roller, Dr. Michael A. Jakupec , Prof. Dr. Bernhard K. Keppler  and Prof. Dr. Christian G. Hartinger 

      Article first published online: 22 JAN 2013 | DOI: 10.1002/chem.201202657

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      Ruthenium(II) arene complexes bearing ammine, ethylenediamine (en), or diethylenetriamine (dien) ligands, such as the depicted [(η6-p-cymene)RuII(dien)]2+, were studied. For this class of compounds, activity in anticancer assays is found when they are stable in aqueous solution and have low rates of hydrolysis and binding to proteins. Mass spectrometric studies revealed formation of mono- and bis-adducts between Ru biphenyl (bip) complexes and ubiquitin (see figure).

    19. Mesoporous Materials

      CuO Quantum-Dot-Sensitized Mesoporous ZnO for Visible-Light Photocatalysis (pages 4319–4326)

      Dr. Yunxin Liu, Jianxin Shi, Dr. Qing Peng and Prof. Dr. Yadong Li

      Article first published online: 27 FEB 2013 | DOI: 10.1002/chem.201203316

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      Into the light! Ultraviolet mesoporous (MP) ZnO photocatalysts can be extended into the visible-light region (see figure) through coupling to CuO quantum dots (QDs). Theoretical analysis demonstrates that the quantum size effect plays a key role in the photoactivity of CuO/ZnO composites.

    20. Photochemistry

      Enantiospecific Photochemical Transformations under Elevated Pressure (pages 4327–4334)

      Anoklase J.-L. Ayitou, Dr. Gaku Fukuhara, Elango Kumarasamy, Prof. Dr. Yoshihisa Inoue and Prof. Dr. J. Sivaguru

      Article first published online: 30 JAN 2013 | DOI: 10.1002/chem.201203665

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      Under pressure: Enantiospecific axial-to-point chiral transfer in light-induced transformations was efficient under elevated pressure at high temperatures. Photoreactions with atropisomeric compounds showed higher enantioselectivity in the photoproducts under elevated pressure, which was rationalized by the increased stability of optically pure atropisomeric compounds at elevated pressure, even at high temperatures (see scheme).

    21. Heterocycles

      Preparation of Highly Functionalised Benzofurans from ortho-Hydroxyphenones and Dichloroethylene: Applications and Mechanistic Investigations (pages 4335–4343)

      Florian Schevenels, Prof. Dr. Bernard Tinant, Prof. Dr. Jean-Paul Declercq and Prof. Dr. István E. Markó

      Article first published online: 18 JAN 2013 | DOI: 10.1002/chem.201201505

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      Smooth operator: A unique, efficient and connective reaction leads to highly functionalised benzofurans in good to excellent yields (see scheme). The key intermediate, a chloromethylene furan, smoothly rearranged into the corresponding benzofuran carbaldehyde under acidic conditions. Mechanistic investigations have been performed and several biologically active benzofurans have been synthesised.

    22. Furan synthesis

      An Efficient Friedel–Crafts/Oxa-Michael/Aromatic Annulation: Rapid Access to Substituted Naphtho[2,1-b]furan, Naphtho[1,2-b]furan, and Benzofuran Derivatives (pages 4344–4351)

      Dr. Shaik Anwar, Wan-Yun Huang, Chih-Hao Chen, You-Song Cheng and Prof. Dr. Kwunmin Chen

      Article first published online: 5 FEB 2013 | DOI: 10.1002/chem.201204221

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      All furans! Functionalized benzo- and naphthofurans were easily prepared in a single step by treating naphthols/substituted phenols with various aromatic/heteroaromatic nitroallylic acetates in good to excellent chemical yields (14–97 %; 32 examples) under mild reaction conditions (see scheme). The reactions proceeded smoothly through an interesting Friedel–Crafts/oxa-Michael/aromatic annulation process.

    23. Dendrimers

      Dendron to Central Core S1–S1 and S2–Sn (n>1) Energy Transfers in Artificial Special Pairs Containing Dendrimers with Limited Numbers of Conformations (pages 4352–4368)

      Prof. Pierre D. Harvey, Dr. Frédérique Brégier, Prof. Shawkat M. Aly, Prof. Jędrzej Szmytkowski, Prof. Matthew F. Paige and Prof. Ronald P. Steer

      Article first published online: 1 FEB 2013 | DOI: 10.1002/chem.201203033

      Thumbnail image of graphical abstract

      Cofacial: Two dendrimers consisting of a cofacial free-base bisporphyrin held by a biphenylene spacer and functionalized with 4-benzeneoxomethane (5-(4-benzene)tri-10,15,20-(4-n-octylbenzene)zinc(II)porphyrin) using either five or six of the six available meso-positions, have been synthesized and characterized as models for the antenna effect in Photosystems I and II.

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