Chemistry - A European Journal

Cover image for Vol. 18 Issue 5

January 27, 2012

Volume 18, Issue 5

Pages 1261–1543

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      Cover Picture: Hydrogen-Bonding-Mediated J-Aggregation and White-Light Emission from a Remarkably Simple, Single-Component, Naphthalenediimide Chromophore (Chem. Eur. J. 5/2012) (page 1261)

      Mijanur Rahaman Molla and Dr. Suhrit Ghosh

      Article first published online: 19 JAN 2012 | DOI: 10.1002/chem.201290013

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      A carboxylic acid appended naphthalenediimide (NDI) derivative exhibits hydrogen-bonding-mediated, lamellar-type, self-assembly in the nonpolar solvent methyl cyclohexane (MCH). Such a self-assembled material shows bright and almost pure white-light emission in contrast to the blue-emitting monomeric NDI building block. For more information see the Communication by S. Ghosh and M. R. Molla on page 1290 ff.

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  3. News

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  4. Communications

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    1. Vinylidenecyclopropanes

      Reactions of Vinylidenecyclopropanes with Diphenyl Diselenide in the Presence of AIBN and Thermally-Induced Further Transformations (pages 1280–1285)

      Wei Yuan, Dr. Yin Wei, Prof. Min Shi and Prof. Yuxue Li

      Article first published online: 2 JAN 2012 | DOI: 10.1002/chem.201103461

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      Radical transformers: The chemical transformation of vinylidenecyclopropanes with diphenyl diselenide in the presence of AIBN and upon heating gives the corresponding bicyclo[3.1.0]hexane derivatives in good yields. These compounds undergo thermal-induced radical 1,4-hydrogen shifts through a ring-opening pathway of allylic cyclopropane to give the corresponding cyclohexene derivatives stereoselectively in good yields at 200 °C (see scheme).

    2. Sensors

      Mercury(II) Ion Detection via Pyrene-Mediated Photolysis of Disulfide Bonds (pages 1286–1289)

      Dr. Bin-Cheng Yin, Dr. Mingxu You, Prof. Weihong Tan and Prof. Bang-Ce Ye

      Article first published online: 5 JAN 2012 | DOI: 10.1002/chem.201103348

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      A novel probe design of a pyrene-disulfide molecular assembly has been proposed and its application for the fluorescence turn-on detection of mercury(II) ions (Hg2+) has been demonstrated. By taking advantage of the pyrene-assisted efficient photolysis of disulfide bonds, our proposed sensing system exhibits both high selectivity and sensitivity toward Hg2+ detection with a detection limit of 5 nM (1 ppb) (see figure).

    3. White-Light Emission

      Hydrogen-Bonding-Mediated J-Aggregation and White-Light Emission from a Remarkably Simple, Single-Component, Naphthalenediimide Chromophore (pages 1290–1294)

      Mijanur Rahaman Molla and Dr. Suhrit Ghosh

      Article first published online: 5 JAN 2012 | DOI: 10.1002/chem.201103600

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      Almost pure white-light emission (fluorescence quantum yield=0.70) from a remarkably simple single-component, carboxylic acid appended naphthalenediimide (NDI) derivative has been reported. Aggregation-induced modulation of photophysical properties was attributed to hydrogen-bonding-mediated J-type π stacking among the NDI chromophores.

    4. Electrochemistry

      Photoelectrochemical Hydrogen Generation by an [FeFe] Hydrogenase Active Site Mimic at a p-Type Silicon/Molecular Electrocatalyst Junction (pages 1295–1298)

      Bhupendra Kumar, Dr. Maryline Beyler, Prof. Dr. Clifford P. Kubiak and Dr. Sascha Ott

      Article first published online: 5 JAN 2012 | DOI: 10.1002/chem.201102860

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      Let there be light! A dithiolate-bridged [FeFe] complex with structural features of the [FeFe] hydrogenase active site has been photoelectrochemically reduced by a p-type Si photocathode at a potential 500 mV less negative compared with a glassy carbon electrode (see figure). In the presence of HClO4, hydrogen generation has been achieved at a photovoltage of 600 mV with a (105±5) % Faradaic efficiency.

    5. Energy Transfer

      A “Clickable” Styryl Dye for Fluorescent DNA Labeling by Excitonic and Energy Transfer Interactions (pages 1299–1302)

      Dipl.-Ing. Moritz M. Rubner, Dipl.-Chem. Carolin Holzhauser, Dipl.-Chem. Peggy R. Bohländer and Prof. Hans-Achim Wagenknecht

      Article first published online: 3 JAN 2012 | DOI: 10.1002/chem.201102622

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      Turn on and turn red: The CyIQ dye as an internal DNA label can be combined with itself and thiazole red as intrastrand fluorophore pairs (see figure). Excitonic and energy transfer interactions provide interesting alternatives for fluorescence readouts, which are either fluorescence enhancement or fluorescence color change, respectively.

    6. Forensics

      Dating Bloodstains with Fluorescence Lifetime Measurements (pages 1303–1305)

      Kevin Guo, Prof. Samuel Achilefu and Prof. Mikhail Y. Berezin

      Article first published online: 4 JAN 2012 | DOI: 10.1002/chem.201102935

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      Age of bloodstains: Determining the age of a bloodstain at a crime scene is one of the greatest and oldest challenges in forensic science. The results presented herein, with dog blood as a model, indicate a highly reproducible correlation between the fluorescence lifetime and the age of the bloodstain (see figure). The time-dependent changes in fluorescence lifetime were attributed to the alteration of tryptophan.

    7. Halogen Bonds

      4,4′-Azobis(halopyridinium) Derivatives: Strong Multidentate Halogen-Bond Donors with a Redox-Active Core (pages 1306–1310)

      Dipl.-Chem. Florian Kniep, Sebastian M. Walter, Dr. Eberhardt Herdtweck and Dr. Stefan M. Huber

      Article first published online: 4 JAN 2012 | DOI: 10.1002/chem.201103071

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      Halopyridiniums also do the trick: An easily accessible class of highly potent bis(pyridinium)-based multidentate halogen-bond (XB) donors is introduced, which, in addition to their inherent XB acidity, also include a built-in redox option (see scheme). These XB donors function as activating reagents for the carbon–bromine bond in benzhydryl bromide. During the reaction, bromide is oxidized to elemental bromine, which forms the basis of a parallel activation mechanism.

  5. Full Papers

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    1. Metallogels

      Synthesis and Photophysical Properties of Self-Assembled Metallogels of Platinum(II) Acetylide Complexes with Elaborate Long-Chain Pyridine-2,6-Dicarboxamides (pages 1312–1321)

      Dr. Kai-Chi Chang, Ju-Ling Lin, Yuan-Ting Shen, Chen-Yen Hung, Chan-Yu Chen and Dr. Shih-Sheng Sun

      Article first published online: 5 JAN 2012 | DOI: 10.1002/chem.201103030

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      Hot stuff! A series of platinum(II) acetylide metallogelators with elaborate long-chain pyridine-2,6-dicarboxamides was synthesized and showed unusual emission enhancement at elevated temperatures upon gel-to-sol transition (see figure) due to the higher molecular degree of freedom, which allows rearrangement of molecular aggregates to reach low-energy excimeric assemblies in the excited state.

    2. Helical Structures

      Substituent Effects in Double-Helical Hydrogen-Bonded AAA-DDD Complexes (pages 1322–1327)

      Hong-Bo Wang, Bhanu P. Mudraboyina and Prof. James A. Wisner

      Article first published online: 28 DEC 2011 | DOI: 10.1002/chem.201103001

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      Control from A to D: A series of tri-acceptor (AAA) and tri-donor (DDD) hydrogen-bond arrays were synthesized and the effect of substituents on the stability of their complementary double-helical complexes was investigated. The modifications demonstrate predictable control over complex affinities of more than three orders of magnitude from 102 to >105M−1 (or >20 kJ mol−1) within the same underlying recognition motif (see figure).

    3. Water Solubility

      A Charge-Transfer Challenge: Combining Fullerenes and Metalloporphyrins in Aqueous Environments (pages 1328–1341)

      Evangelos Krokos, Dr. Fabian Spänig, Michaela Ruppert, Prof. Dr. Andreas Hirsch and Prof. Dr. Dirk. M. Guldi

      Article first published online: 30 DEC 2011 | DOI: 10.1002/chem.201102851

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      Like a porphyrin in water: A series of truly water-soluble C60/porphyrin electron donor–acceptor conjugates (see figure) has been synthesized to serve as powerful mimics of photosynthetic reaction centers.

    4. Carbohydrates

      Pre-organization of the Core Structure of E-Selectin Antagonists (pages 1342–1351)

      Dr. Daniel Schwizer, Dr. John T. Patton, Dr. Brian Cutting, Dr. Martin Smieško, Beatrice Wagner, Dr. Ako Kato, Dr. Céline Weckerle, Florian P. C. Binder, Dr. Said Rabbani, Dr. Oliver Schwardt, Dr. John L. Magnani and Prof. Beat Ernst

      Article first published online: 30 DEC 2011 | DOI: 10.1002/chem.201102884

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      The gimmick with the mimic: A new class of N-acetyl-D-glucosamine (GlcNAc) mimics was incorporated into E-selectin antagonists. The test compounds and their 2′-benzoylated analogues exhibit affinities in the low micromolar range. STD-NMR suggests that the increase in affinity does not result from an additional hydrophobic contact of the alkyl substituent, but rather from a steric effect stabilizing the antagonist in its bioactive conformation (see figure).

    5. DNA Recognition

      Interactions of Multicationic Bis(guanidiniocarbonylpyrrole) Receptors with Double-Stranded Nucleic Acids: Syntheses, Binding Studies, and Atomic Force Microscopy Imaging (pages 1352–1363)

      Karsten Klemm, Dr. Marijana Radić Stojković, Gordan Horvat, Prof. Vladislav Tomišić, Dr. Ivo Piantanida and Prof. Dr. Carsten Schmuck

      Article first published online: 23 DEC 2011 | DOI: 10.1002/chem.201101544

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      Groovy binding: Compounds 13 (see scheme, Cbz=carbobenzyloxy) with two guanidiniocarbonylpyrrole moieties linked by oligoamide bridges strongly interact with double-stranded (ds) DNA and dsRNA as determined by UV/Vis and CD spectroscopy and isothermal titration microcalorimetry. The receptors bind into the minor groove in DNA and the major groove in RNA, thereby not only strongly stabilizing the double strands but also leading to a concentration-dependent condensation of the nucleic acid.

    6. Halogen Bonds

      On the Cl⋅⋅⋅N Halogen Bond: A Rotational Study of CF3Cl⋅⋅⋅NH3 (pages 1364–1368)

      Gang Feng, Dr. Luca Evangelisti, Nicola Gasparini and Prof. Dr. Walther Caminati

      Article first published online: 23 DEC 2011 | DOI: 10.1002/chem.201101582

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      My name is bond - halogen bond: The symmetric-top rotational spectra of six isotopologues of the halogen-bonded complex CF3Cl-NH3 have been assigned by Fourier transform microwave spectroscopy. Information on the bond energy and on the structure has been obtained (see figure).

    7. Boron Compounds

      Experimental and Theoretical Studies on Organic D-π-A Systems Containing Three-Coordinate Boron Moieties as both π-Donor and π-Acceptor (pages 1369–1382)

      Prof. Dr. Lothar Weber, Daniel Eickhoff, Prof. Dr. Todd B. Marder, Dr. Mark A. Fox, Prof. Dr. Paul J. Low, Austin D. Dwyer, Prof. Dr. David J. Tozer, Dr. Stefanie Schwedler, Dr. Andreas Brockhinke, Dr. Hans-Georg Stammler and Beate Neumann

      Article first published online: 30 DEC 2011 | DOI: 10.1002/chem.201102059

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      Unusual push–pull systems containing 1,4-phenylene, 4,4′-biphenylene, 2,5-thiophene and 5,5′-dithiophene (shown here) as π-conjugated bridges and different types of three-coordinate boron moieties serving as π-donors (1,3,2-benzodiazaborolyl) and π-acceptors (dimesitylboryl) were prepared. The HOMO in the blue-green fluorescing compounds is mainly diazaborolyl in character; the LUMO is dominated by the empty p orbital at the boron atom of the BMes2 group.

    8. Asymmetric Catalysis

      Rhodium-Catalyzed Asymmetric Hydrogenation of Olefins with PhthalaPhos, a New Class of Chiral Supramolecular Ligands (pages 1383–1400)

      Dr. Luca Pignataro, Michele Boghi, Dr. Monica Civera, Dr. Stefano Carboni, Prof. Dr. Umberto Piarulli and Prof. Dr. Cesare Gennari

      Article first published online: 28 DEC 2011 | DOI: 10.1002/chem.201102018

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      H-bonds for all seasons: Chiral ligands bearing a secondary bis-amide group afford excellent stereoselectivity in the asymmetric hydrogenation of olefins. H-bonding-led substrate orientation is likely to occur during the catalytic cycle (see figure).

    9. Carbon Nanotubes

      Nanographite Impurities in Carbon Nanotubes: Their Influence on the Oxidation of Insulin, Nitric Oxide, and Extracellular Thiols (pages 1401–1407)

      Elaine Lay Khim Chng and Prof. Martin Pumera

      Article first published online: 23 DEC 2011 | DOI: 10.1002/chem.201102080

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      Impure and simple: Nanographite impurities within carbon nanotubes (CNTs) govern the “electrocatalytic” oxidation of biomolecules. The influence of nanographite impurities extends to different types of CNTs; that is, single-walled CNTs, double-walled CNTs, and few-walled CNTs. Therefore, the reason for such “electrocatalytic activity” in CNTs is impurities in the carbon nanotubes that are usually inherently present as a result of their fabrication.

    10. Enzymes

      Lanthanide(III) Complexes That Contain a Self-Immolative Arm: Potential Enzyme Responsive Contrast Agents for Magnetic Resonance Imaging (pages 1408–1418)

      Dr. Thomas Chauvin, Dr. Susana Torres, Dr. Renato Rosseto, Dr. Jan Kotek, Dr. Bernard Badet, Dr. Philippe Durand and Dr. Éva Tóth

      Article first published online: 28 DEC 2011 | DOI: 10.1002/chem.201101779

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      Trial by fire: Enzyme-responsive contrast agents for MRI studies have been designed based on a “self-immolative” mechanism. Enzymatic cleavage of the appropriate substrate moiety on the contrast agent initiates a cascade reaction that is expected to result in structural changes of the LnIII complex with a concomitant response in the T1- or PARACEST-contrast-enhancing properties.

    11. Lanthanides

      Pyridine-Based Lanthanide Complexes Combining MRI and NIR Luminescence Activities (pages 1419–1431)

      Dr. Célia S. Bonnet, Dr. Frédéric Buron, Dr. Fabien Caillé, Dr. Chad M. Shade, Dr. Bohuslav Drahoš, Dr. Laurent Pellegatti, Dr. Jian Zhang, Dr. Sandrine Villette, Prof. Dr. Lothar Helm, Prof. Dr. Chantal Pichon, Dr. Franck Suzenet, Prof. Dr. Stéphane Petoud and Dr. Éva Tóth

      Article first published online: 30 DEC 2011 | DOI: 10.1002/chem.201102310

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      Bimodal application: Pyridine-based polyamino–polycarboxylate ligands (see figure) ensure non-toxicity as well as advantageous magnetic and luminescence properties for the corresponding Gd3+ and near-infrared-emitting lanthanide complexes.

    12. Fluorescent Probes

      Novel Application of Ag Nanoclusters in Fluorescent Imaging of Human Serum Proteins after Native Polyacrylamide Gel Electrophoresis (PAGE) (pages 1432–1437)

      Yanan Wang, Jing Zhang, Lingyun Huang, Dacheng He, Lin Ma, Prof. Dr. Jin Ouyang and Fubin Jiang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/chem.201101310

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      PAGE proof: Direct detection of human serum proteins after native PAGE was accomplished by using DNA oligonucleotide-stabilized Ag nanoclusters as a fluorescent probe (see figure). Compared with staining methods, it is simple, fast, nontoxic, and offers higher sensitivity and resolution.

    13. The Application of Amine-Terminated Silicon Quantum Dots on the Imaging of Human Serum Proteins after Polyacrylamide Gel Electrophoresis (PAGE) (pages 1438–1443)

      Pingping Liu, Dr. Na Na, Dr. Lingyun Huang, Prof. Dr. Dacheng He, Changgang Huang and Prof. Dr. Jin Ouyang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/chem.201102187

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      Tuning PAGE: Photoluminescent imaging of human serum proteins after PAGE by using amine-terminated silicon quantum dots as fluorescent probes, is reported (see scheme). By using this nontoxic, simple method, high sensitivity and resolution can be achieved.

    14. Hypervalent Compounds

      Synthesis of Anionic Hypervalent Cyclic Selenenate Esters: Relevance to the Hypervalent Intermediates in Nucleophilic Substitution Reactions at the Selenium(II) Center (pages 1444–1457)

      Karuthapandi Selvakumar, Prof. Harkesh B. Singh, Nidhi Goel, Prof. Udai P. Singh and Prof. Ray J. Butcher

      Article first published online: 21 DEC 2011 | DOI: 10.1002/chem.201003725

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      Come up and Se me: Aryl selenium(II) species that contain 2,6-di-ortho-carboxylate groups exhibit dynamic behavior in solution. Organic cations, such as adeninium ions, exchange between the two carboxylate groups via the selenuranide anion.

    15. Density Functional Calculations

      Adsorption of Uranyl Species onto the Rutile (110) Surface: A Periodic DFT Study (pages 1458–1466)

      Qing-Jiang Pan, Samuel O. Odoh, Abu Md. Asaduzzaman and Georg Schreckenbach

      Article first published online: 23 DEC 2011 | DOI: 10.1002/chem.201101320

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      Contaminant adsorption: The sorption of uranyl species onto the TiO2 rutile (110) surface was explored in periodic DFT calculations. Adsorbates SASC, with H2O, OH, and CO32− ligands (see figure), represent the most important UVI species in natural aqueous systems. Variations in geometry parameters of surface complexes were rationalized by the coordination competition of equatorial groups. The present calculations indicate an energetic preference for the sorption of aquouranyl species versus other adsorbates.

    16. Magnetic Nanoparticles

      Enhancement of Photoresponse Properties of Conjugated Polymers/Inorganic Semiconductor Nanocomposites by Internal Micro-Magnetic Field (pages 1467–1475)

      Chenglong Hu, Yujie Chen, Prof. Xudong Chen, Bin Zhang, Jin Yang, Juying Zhou and Prof. Ming Qiu Zhang

      Article first published online: 27 DEC 2011 | DOI: 10.1002/chem.201101769

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      Hybrid materials: The internal micro-magnetic field (IMMF) effect in Fe3O4@PANI-CdS photoelectric active hybrid nanocomposites was found to improve their power conversion efficiencies (PCE) by increasing the number of singlet polaron pairs through field-dependent intersystem crossing (ISC). The PCE of as-prepared nanocomposites was improved from 1.135 to 3.563 % with changes in IMMF from 0 to 1.2×10−3 emu g−1 (see figure).

    17. Heterocycles

      A Versatile Thiouronium-Based Solid-Phase Synthesis of 1,3,5-Triazines (pages 1476–1486)

      Kah Hoe Kong, Chong Kiat Tan, Xijie Lin and Prof. Yulin Lam

      Article first published online: 27 DEC 2011 | DOI: 10.1002/chem.201102097

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      Building on a scaffold: A thiouronium-based solid-phase synthesis of 1,3,5-triazine has been developed. The sulfur linker employed is stable under both acidic and basic conditions and is versatile enough to provide access to monocyclic, bicyclic, and spirocyclic compounds with the 1,3,5-triazine scaffold (see scheme).

    18. Nitramines

      N-Bound Primary Nitramines Based on 1,5-Diaminotetrazole (pages 1487–1501)

      Prof. Dr. Thomas M. Klapötke, Dr. Franz A. Martin and Dr. Jörg Stierstorfer

      Article first published online: 27 DEC 2011 | DOI: 10.1002/chem.201102142

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      It's hotting up: 5-Amino-1-nitriminotetrazole and 5-amino-4-methyl-1-nitriminotetrazole (see figure) were synthesized by applying very mild nitration conditions and using nitronium tetrafluoroborate as the nitration reagent. Both compounds are zwitterions and exhibit high positive heats of formation in relation to high sensitivities to outer stimuli.

    19. Solar Cells

      Platinum(II)–Bis(aryleneethynylene) Complexes for Solution-Processible Molecular Bulk Heterojunction Solar Cells (pages 1502–1511)

      Dr. Feng-Rong Dai, Dr. Hong-Mei Zhan, Qian Liu, Ying-Ying Fu, Jin-Hua Li, Dr. Qi-Wei Wang, Prof. Zhiyuan Xie, Prof. Lixiang Wang, Dr. Feng Yan and Prof. Wai-Yeung Wong

      Article first published online: 23 DEC 2011 | DOI: 10.1002/chem.201102598

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      Roll on the sunshine! The synthesis, characterization, field-effect mobilities, and photovoltaic properties of a new series of platinum(II)–bis(aryleneethynylene) small molecules for solution-processed molecular bulk heterojunction solar cells are described (see figure). The best power conversion efficiency of 2.4 % (with a peak external quantum efficiency of up to 49 %) was achieved under illumination with an AM 1.5 solar-cell simulator.

    20. Hydroboration

      Catalytic Non-Conventional trans-Hydroboration: A Theoretical and Experimental Perspective (pages 1512–1521)

      Jessica Cid, Dr. Jorge J. Carbó and Dr. Elena Fernández

      Article first published online: 30 DEC 2011 | DOI: 10.1002/chem.201102729

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      A life less ordinary: Pinacolborane and catecholborane were activated by rhodium complexes for the transfer of boryl and hydride groups onto the same unhindered carbon atom of terminal alkynes, thereby accomplishing a non-conventional trans-hydroboration reaction. The use of bulky phosphine groups on the rhodium complexes favored the Z selectivity.

    21. Nanotubes

      A Strategy for the High Dispersion of PtRu Nanoparticles onto Carbon Nanotubes and Their Electrocatalytic Oxidation of Methanol (pages 1522–1527)

      Dr. Yinjie Kuang, Ying Cui, Yunsong Zhang, Yaming Yu, Xiaohua Zhang and Prof. Jinhua Chen

      Article first published online: 16 JAN 2012 | DOI: 10.1002/chem.201102822

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      NP and tuck: A strategy using the non-covalent functionalization of carbon nanotubes (CNTs) with 1-pyrenecarboxaldehyde (PCA) for the high dispersion of noble-metal nanoparticles (NPs) onto CNTs was developed. The oxidation product of PCA can effectively anchor and stabilize the in situ produced PtRu NPs on the surface of the CNTs. The obtained PtRu-NP/CNT-PCA nanohybrids show excellent electrocatalytic performance for methanol oxidation.

    22. Rotaxanes

      Light-Harvesting in Multichromophoric Rotaxanes (pages 1528–1535)

      Dr. Maria E. Gallina, Dr. Bilge Baytekin, Prof. Dr. Christoph Schalley and Prof. Dr. Paola Ceroni

      Article first published online: 28 DEC 2011 | DOI: 10.1002/chem.201102981

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      A mechanically interlocked antenna: Two rotaxanes consisting of six naphthyl units appended to the stoppers and a pyrene chromophore attached to the wheel perform as light-harvesting antennae (see figure). Upon excitation of the naphthyl units energy transfer to the pyrene acceptor takes place with an efficiency higher than 90 %.

    23. Surfactants

      Morphology-Controlled Synthesis of Poly(oxyethylene)silicone or Alkylsilicone Surfactants with Explicit, Atomically Defined, Branched, Hydrophobic Tails (pages 1536–1541)

      Dr. Ferdinand Gonzaga, John B. Grande and Prof. Dr. Michael A. Brook

      Article first published online: 27 DEC 2011 | DOI: 10.1002/chem.201103093

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      Heads and tails: The synthesis of explicit silicone moieties allows for the preparation of well-defined silicone–poly(ethylene glycol) surfactants by click chemistry (see scheme). This, in turn, allows structure–surface-activity relationships to be explored for the first time.

  6. Preview

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    3. Graphical Abstract
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    1. You have free access to this content
      Preview: Chem. Eur. J. 6/2012 (page 1543)

      Article first published online: 19 JAN 2012 | DOI: 10.1002/chem.201290016

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