Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 20

May 12, 2006

Volume 45, Issue 20

Pages 3187–3381

    1. Cover Picture: Silica-Based Mesoporous Organic–Inorganic Hybrid Materials (Angew. Chem. Int. Ed. 20/2006) (page 3187)

      Frank Hoffmann, Maximilian Cornelius, Jürgen Morell and Michael Fröba

      Version of Record online: 5 MAY 2006 | DOI: 10.1002/anie.200690070

      Like Honeycomb is how the pore structures of silica-based mesoporous organic–inorganic hybrid materials often appear. In the Review on page 3216 ff., M. Fröba and co-workers give an overview of their preparation. The cover picture shows hybrids whose pores are functionalized with cyclam (ligand), sulforhodamine B (laser die), and a cinchona derivative (for heterogeneous asymmetric catalysis). Particular attention is given to the class of periodic mesoporous organosilicas (PMOs).

    2. Finding a Chemist in a Haystack (pages 3202–3203)

      Allison Mills

      Version of Record online: 5 MAY 2006 | DOI: 10.1002/anie.200601545

    3. Selective Oxidation of Organic Compounds—Sustainable Catalytic Reactions with Oxygen and without Transition Metals? (pages 3206–3210)

      Dieter Lenoir

      Version of Record online: 5 MAY 2006 | DOI: 10.1002/anie.200502702

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      Going without: Alcohols can be oxidized with oxygen and without transition-metal complexes (see scheme; TEMPO=2,2,6,6-tetramethylpiperidine-N-oxide). Conventional methods are compared with new catalytic variants developed for this reaction and for the complete oxidation of pollutants with regard to sustainability.

    4. Not Unhydrolyzed at pH 8 (pages 3212–3214)

      Xaver Kästele, Peter Klüfers and Reinhold Tacke

      Version of Record online: 26 APR 2006 | DOI: 10.1002/anie.200503534

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      Contrary to a recent claim that the zwitterionic bis(diolato)silicate 1 exhibits remarkable hydrolytic stability at pH 7–8, a closer look at 29Si and 13C NMR spectroscopic data of 1 under various conditions (solvent, pH, concentration) reveals that hydrolysis products are the predominant species in solution.

    5. Silica-Based Mesoporous Organic–Inorganic Hybrid Materials (pages 3216–3251)

      Frank Hoffmann, Maximilian Cornelius, Jürgen Morell and Michael Fröba

      Version of Record online: 5 MAY 2006 | DOI: 10.1002/anie.200503075

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      Pores for thought: The modification of mesoporous silica phases with organic components extends this class of materials and their potential application in areas such as the production of insulators in the chip industry. Periodic mesoporous organosilicas (PMOs) occupy a special position in this respect, as the organic component is an integral part of the framework. The figure shows a PMO with a crystal-like structure of the pore wall.

    6. An Approach To Prepare Membrane Proteins for Single-Molecule Imaging (pages 3252–3256)

      David A. Cisneros, Daniel J. Muller, Sofian M. Daud and Jeremy H. Lakey

      Version of Record online: 24 APR 2006 | DOI: 10.1002/anie.200504506

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      Observed from above: A cysteine mutation in a membrane protein enables it to be fixed in a defined orientation on flat gold surfaces (see picture, left). Subsequent coassembly with thiolipids produces clearly defined, immobilized proteins. Analysis by atomic force microscopy provides topographs of similar quality to those revealed from 2D crystals.

    7. Total Synthesis of Abyssomicin C and atrop-Abyssomicin C (pages 3256–3260)

      K. C. Nicolaou and Scott T. Harrison

      Version of Record online: 24 APR 2006 | DOI: 10.1002/anie.200601116

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      Into the abyss: A total synthesis of abyssomicin C (1) through a metathesis-based strategy offers a highly convergent approach to the construction of analogues. A novel and potent atropisomer of the natural product 1 was thus discovered, namely atrop-abyssomicin C (2), which reveals subtle yet important structural differences to 1 (see structures; O red, C gray, H white).

    8. Evolution of Nano- to Microsized Spherical Assemblies of a Short Oligo(p-phenyleneethynylene) into Superstructured Organogels (pages 3261–3264)

      Ayyppanpillai Ajayaghosh, Reji Varghese, Vakayil K. Praveen and Sankarapillai Mahesh

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200600256

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      Wires to particles: A subtle balance of H-bonding, π-stacking, and van der Waals interactions facilitates the concentration-controlled self-assembly of a short molecular wire (see figure) into nanoparticles and fluorescent microspheres in nonpolar hydrocarbon solvents. Above a critical concentration, a blue-light emitting organogel is formed.

    9. Synthesis of a Rhodaazacyclopropane and Characterization of Its Radical Cation by EPR Spectroscopy (pages 3265–3269)

      Pascal Maire, Anandaram Sreekanth, Torsten Büttner, Jeffrey Harmer, Igor Gromov, Heinz Rüegger, Frank Breher, Arthur Schweiger and Hansjörg Grützmacher

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200504382

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      Rh steps into the ring: The radical cation shown is best described as a rhodaazacyclopropane (A) rather than as a RhI iminium ion complex (B). EPR and DFT data indicate that the delocalization of the unpaired electron into the ligand framework contributes to the stability of A (see plot of the singly occupied molecular orbital).

    10. A (Tetrasilacyclobutadiene)tricarbonyliron Complex [{η4-(tBu2MeSi)4Si4}Fe(CO)3]: The Silicon Cousin of Pettit's (Cyclobutadiene)tricarbonyliron Complex [(η4-H4C4)Fe(CO)3] (pages 3269–3272)

      Kazunori Takanashi, Vladimir Ya. Lee, Masaaki Ichinohe and Akira Sekiguchi

      Version of Record online: 19 APR 2006 | DOI: 10.1002/anie.200600338

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      All in the family: [(η4-R4Si4)Fe(CO)3] 2 (R=SiMetBu2) represents a neutral silicon congener of a (cyclobutadiene)tricarbonyliron complex and was synthesized by the reaction of the dibromocyclotetrasilene R4Si4Br21 with Na2[Fe(CO)4]. The tetrasilacyclobutadiene ligand in 2 has stronger π-donating properties than the cyclobutadiene ligand in the parent complex [(η4-H4C4)Fe(CO)3].

    11. C30H126−: Self-Aggregation, High Charge Density, and Pyramidalization in a Supramolecular Structure of a Supercharged Hemifullerene (pages 3273–3277)

      Noach Treitel, Tuvia Sheradsky, Lingqing Peng, Lawrence T. Scott and Mordecai Rabinovitz

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200503542

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      Charging hemifullerene C30H12 with potassium metal gives the hexaanion C30H126−(16−). The NMR data, which indicate high symmetry, high charge density, and pyramidalization of the C-4 positions, as well as DFT calculations, are consistent with a tetramer [16−]4/24 K+, in which six K+ ions bridge four hexaanions (see picture; red K+, yellow H, blue C; the remaining 18 solvent-separated K+ ions are not shown).

    12. Nonconventional Catalysts for Isotactic Propene Polymerization in Solution Developed by Using High-Throughput-Screening Technologies (pages 3278–3283)

      Thomas R. Boussie, Gary M. Diamond, Christopher Goh, Keith A. Hall, Anne M. LaPointe, Margarete K. Leclerc, Vince Murphy, James A. W. Shoemaker, Howard Turner, Robert K. Rosen, James C. Stevens, Francesca Alfano, Vincenzo Busico, Roberta Cipullo and Giovanni Talarico

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200600240

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      A textbook example of catalyst discovery, optimization, and commercial implementation is provided with the discovery of a class of Hf-based non-metallocene olefin polymerization catalysts (see picture; Hf orange sphere, N blue, C(Me) green, C orange), their advanced high-throughput screening, and their industrial application in a high-temperature solution process for the production of highly isotactic polypropylene based materials.

    13. Total Chemical Synthesis, Folding, and Assay of a Small Protein on a Water-Compatible Solid Support (pages 3283–3287)

      Erik C. B. Johnson, Thomas Durek and Stephen B. H. Kent

      Version of Record online: 5 APR 2006 | DOI: 10.1002/anie.200600381

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      All wrapped up: A protein was assembled inside a beaded polymer, then folded with concomitant formation of disulfide bonds, and assayed for biochemical activity while still bound to the water-compatible polymer.

    14. A Sodalite-like Framework Based on Octacyanomolybdate and Neodymium with Guest Methanol Molecules and Neodymium Octahydrate Ions (pages 3287–3291)

      Zhao-Xi Wang, Xiao-Fei Shen, Jun Wang, Peng Zhang, Yi-Zhi Li, Emmanuel N. Nfor, You Song, Shin-ichi Ohkoshi, Kazuhito Hashimoto and Xiao-Zeng You

      Version of Record online: 11 APR 2006 | DOI: 10.1002/anie.200600455

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      Heavy-metal sodalite: NdIII reacts with [MoV(CN)8]3− in methanol to form a new 3D framework consisting of cyanide-bridged NdIII and MoIV ions. The anionic framework (red and blue in the picture) has a cage structure similar to that of the zeolite sodalite and contains hexagonal channels filled by methanol molecules and [NdIII(H2O)8]3+ ions (green spheres).

    15. A Co2N2 Diamond-Core Resting State of Cobalt(I): A Three-Coordinate CoI Synthon Invoking an Unusual Pincer-Type Rearrangement (pages 3291–3295)

      Alison R. Fout, Falguni Basuli, Hongjun Fan, John Tomaszewski, John C. Huffman, Mu-Hyun Baik and Daniel J. Mindiola

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200504343

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      Unmasking the truth: The dimer [{(μ2-PNP)Co}2] (Co light blue, N dark blue, P green, C gray, only one carbon atom of the isopropyl groups shown; PNP=[N{2-P(CHMe2)2-4-MeC6H3}2]) contains a Co2N2 diamond core and bridging PNP ligands. Upon reaction with ClCPh3, CO, or N2, rearrangement of the PNP ligands to a terminal chelating mode is observed to give four-coordinate Co complexes such as [{(PNP)Co}22-N2)].

    16. Solid-Phase Enzyme Activity Assay Utilizing an Entrapped Fluorescence-Signaling DNA Aptamer (pages 3295–3299)

      Nicholas Rupcich, Razvan Nutiu, Yingfu Li and John D. Brennan

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200504576

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      Layered enzyme assays: The use of a layered sol-gel based material allows for spatial separation of coimmobilized enzyme and fluorescent aptamer reporter species. This provides a route for facile assaying of enzyme activity and inhibition in cases where the aptamer signals the presence of the enzyme substrate. This then results in accurate IC50 determinations.

    17. Towards Clean Fuels: Molecular-Level Sulfur Reactivity in Heavy Oils (pages 3299–3303)

      Tushar V. Choudhary, Jim Malandra, John Green, Stephen Parrott and Byron Johnson

      Version of Record online: 5 APR 2006 | DOI: 10.1002/anie.200503660

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      Heavy-oil desulfurization is an important process for the production of clean (ultra-low sulfur) transportation fuels. The relative reactivities of the sulfur compounds present in heavy oils (the graphic shows retention times for thiophenes (T) and annulated thiophenes on nonpolar and polar columns) are strongly dependent on the conditions of the desulfurization process.

    18. Multiplexed DNA Detection with Biobarcoded Nanoparticle Probes (pages 3303–3306)

      Savka I. Stoeva, Jae-Seung Lee, C. Shad Thaxton and Chad A. Mirkin

      Version of Record online: 7 APR 2006 | DOI: 10.1002/anie.200600124

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      Sorting the mail: A highly selective assay for the detection of multiple DNA targets in solution was developed based on gold nanoparticles with oligonucleotide reporters. Four DNA targets associated with infectious viruses were detected simultaneously without enzymatic amplification at mid-femtomolar concentrations.

    19. Reversible Photocontrol of Deoxyribozyme-Catalyzed RNA Cleavage under Multiple-Turnover Conditions (pages 3306–3309)

      Sonja Keiper and Joseph S. Vyle

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200600164

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      Lights, camera, action! Photoswitchable nucleoside analogues containing o-, m-, or p-azobenzenes can be inserted in the catalytic core of RNA-cleaving 10–23 deoxyribozymes by replacing a nonconserved residue (see picture). Irradiation of the modified deoxyribozymes at 366 nm enhances RNA cleavage rates up to ninefold, thus achieving the rates observed for the unmodified deoxyribozyme.

    20. Crystal Structure of the Homo sapiens Cytoplasmic Ribosomal Decoding Site Complexed with Apramycin (pages 3310–3314)

      Jiro Kondo, Boris François, Alexandre Urzhumtsev and Eric Westhof

      Version of Record online: 5 APR 2006 | DOI: 10.1002/anie.200600354

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      On target: The crystal structure of the complex formed between apramycin and the cytoplasmic ribosomal decoding sites of human cells (see picture; complex in yellow, adenine residues numbered) was studied and compared with that of the analogous bacterial complex. The studies provide insight into apramycin toxicity in humans.

    21. Gold-Catalyzed Intermolecular Hydroamination of Allenes with Arylamines and Resulting High Chirality Transfer (pages 3314–3317)

      Naoko Nishina and Yoshinori Yamamoto

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200600331

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      Au contraire! Contrary to the relatively well-studied metal-catalyzed intramolecular hydroamination of allenes, the intermolecular reaction is rare and is here accomplished with a gold(III) catalyst. Aryl amines 2 react with chiral allenes 1 in the presence of AuBr3 at ambient temperature to produce chiral allylamines 3 (Ar=Ph; o-, m-, p-CH3C6H4) in good yields with high ee values.

    22. Direct Protein Identification from Nonspecific Peptide Pools by High-Accuracy MS Data Filtering (pages 3317–3319)

      Vinh An Thieu, Dieter Kirsch, Thomas Flad, Claudia Müller and Bernhard Spengler

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200503787

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      Validate your results! High-accuracy mass spectrometric analysis and composition-based de novo sequencing (CBS) combined with database(DB)-assisted protein identification allows for the rapid production of validated analytical results in proteome research. A simplified sample preparation scheme is sufficient to provide for reliable identification of proteins even when following nonspecific and unknown degradation processes.

    23. Total Synthesis of Phoslactomycin B and Its Biosynthetic Deamino Precursor (pages 3320–3323)

      Yong-Gang Wang, Ryuichi Takeyama and Yuichi Kobayashi

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200600458

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      The implicated intermediate in the biosynthesis of phospholine (phoslactomycin B, see picture), namely its deamino precursor, as well as phospholine itself are synthesized. The phoslactomycins show antitumor, antibacterial, and antifungal activities, however, it is not yet known which part of the skeleton contributes to the activities.

    24. Lanthanide Complexes of the Monovacant Dawson Polyoxotungstate [α1-P2W17O61]10− as Selective and Recoverable Lewis Acid Catalysts (pages 3324–3327)

      Cécile Boglio, Gilles Lemière, Bernold Hasenknopf, Serge Thorimbert, Emmanuel Lacôte and Max Malacria

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200600364

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      Catalytic cornerstone: Lanthanide(III) complexes of a lacunary Dawson-type polyoxometalate catalyze Lewis acid mediated reactions (see figure, TMS=trimethylsilyl). The compounds (NBu4)5H21-Ln(H2O)4P2W17O61] (Ln=Yb, Sm, Eu, La) are much more chemoselective than the lanthanide triflates. Furthermore, the polyoxotungstic framework can play a role, presumably through H-bonding to the substrates.

    25. Gold–Organic–Inorganic High-Surface-Area Materials as Precursors of Highly Active Catalysts (pages 3328–3331)

      Gerolamo Budroni and Avelino Corma

      Version of Record online: 19 APR 2006 | DOI: 10.1002/anie.200600552

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      Heart of gold: A three-component material composed of 2-nm Au nanoparticles (see picture; blue spheres) capped with alkanethiols that are partially functionalized with alkoxysilane groups and then incorporated into an “open shell” of silica was prepared. Upon calcination, the sample is a highly active catalyst for the oxidation of CO at low temperatures, being an order of magnitude more active than Au on structured mesoporous materials.

      Corrected by:

      Corrigendum: Gold–Organic–Inorganic High-Surface-Area Materials as Precursors of Highly Active Catalysts

      Vol. 45, Issue 38, 6244, Version of Record online: 19 SEP 2006

    26. Are Aluminoxanes Nanotubular? Structural Evidence from a Quantum Chemical Study (pages 3331–3334)

      Mikko Linnolahti, John R. Severn and Tapani A. Pakkanen

      Version of Record online: 7 APR 2006 | DOI: 10.1002/anie.200600197

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      Tubes or cages? Quantum chemical calculations provide new evidence that methylaluminoxanes prefer nanotubular shapes with diameters of approximately 1 nm (see picture). These nanotubes are capable of adopting several structures, of which zigzag (4,0) is energetically favored.

    27. Regulating Supramolecular Function in Membranes: Calixarenes that Enable or Inhibit Transmembrane Cl Transport (pages 3334–3338)

      Jennifer L. Seganish, Paul V. Santacroce, Kevan J. Salimian, James C. Fettinger, Peter Zavalij and Jeffery T. Davis

      Version of Record online: 11 APR 2006 | DOI: 10.1002/anie.200504489

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      Self-assembled transporter: Self-association of a partial-cone calixarene amide provides membrane-active aggregates that enable the transport of chloride anions across phospholipid membranes (see picture). Additionally, a regulatory system is described, wherein an inactive calixarene analogue inhibits the active chloride transporter.

    28. Feature Multiplexing—Improving the Efficiency of Microarray Devices (pages 3338–3341)

      Matthew J. Schmid, Kalpana Manthiram, Scott M. Grayson, James C. Willson, Jason E. Meiring, Kathryn M. Bell, Andrew D. Ellington and C. Grant Willson

      Version of Record online: 11 APR 2006 | DOI: 10.1002/anie.200502151

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      So much information: An exponential increase in information density for sensor microarrays is enabled through the development of a new multiplexed probe distribution approach to form a feature-multiplexed array. The picture shows a fluorescence micrograph of the sensor response during a detection assay.

    29. Surfactant-Modulated Switching of Molecular Transport in Nanometer-Sized Pores of Membrane Gates (pages 3341–3345)

      Riaan Schmuhl, Albert van den Berg, Dave H. A. Blank and Johan E. ten Elshof

      Version of Record online: 10 APR 2006 | DOI: 10.1002/anie.200504579

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      An open-and-shut case: A switchable membrane gate for ionic species that operates by co-addition and removal of surfactant molecules is demonstrated (see picture). The permeability of the gate to specific ions can be manipulated and tuned by changing the nature and concentration of the surfactant.

    30. CaCO3–Poly(methyl methacrylate) Nanoparticles for Fast Enrichment of Low-Abundance Peptides Followed by CaCO3-Core Removal for MALDI-TOF MS Analysis (pages 3345–3349)

      Weitao Jia, Xuehua Chen, Haojie Lu and Pengyuan Yang

      Version of Record online: 7 APR 2006 | DOI: 10.1002/anie.200503485

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      An octopus for observation: A CaCO3–poly(methyl methacrylate) (PMMA) nanoparticle that has a destroyable core of CaCO3 was applied to the enrichment of low-abundance peptides and proteins. The linear chains of PMMA linked on the CaCO3 core spread out into the solution like the tentacles of an octopus, and the resulting nanoparticle-adsorbed peptides or proteins are analyzed by MALDI-TOF MS (see scheme).

    31. Heck Coupling with Nonactivated Alkenyl Tosylates and Phosphates: Examples of Effective 1,2-Migrations of the Alkenyl Palladium(II) Intermediates (pages 3349–3353)

      Anders L. Hansen, Jean-Philippe Ebran, Mårten Ahlquist, Per-Ola Norrby and Troels Skrydstrup

      Version of Record online: 11 APR 2006 | DOI: 10.1002/anie.200600442

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      What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron-deficient olefins. An unexpected 1,2-migration of the alkenyl PdII intermediates (see Scheme) leads to the isomerized Heck coupling product.

    32. Rhodium-Catalyzed Asymmetric Addition of Aryl- and Alkenylboronic Acids to Isatins (pages 3353–3356)

      Ryo Shintani, Mitsunori Inoue and Tamio Hayashi

      Version of Record online: 5 APR 2006 | DOI: 10.1002/anie.200600392

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      Mopping up the rhodium: A rhodium-catalyzed asymmetric addition of arylboronic acids to isatins has been developed to produce biologically relevant 3-aryl-3-hydroxy-2-oxindoles in high yield (see scheme). High enantioselectivity was observed with (R)-MeO-mop as a ligand, and the reaction could be extended to the addition of alkenyl groups.

    33. Highly Diastereoselective Silyl-Modified Sakurai Multicomponent Reaction (pages 3357–3360)

      Jiøí Pospíšil, Takuya Kumamoto and István E. Markó

      Version of Record online: 10 APR 2006 | DOI: 10.1002/anie.200600169

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      The more the merrier: A multicomponent Sakurai reaction has been developed in which an efficient, highly diastereoselective three-component condensation of an aldehyde 1, allyl silane 2, and silylated alcohol 3 is mediated by trimethylsilyl triflate (TMSOTf). Products such as 4 can serve as direct precursors to dihydropyran skeletons, which is demonstrated by the synthesis of a portion of (+)-ambruticin. TBS=tert-butyldimethylsilyl.

    34. Reactive Polymer Coatings that “Click” (pages 3360–3363)

      Himabindu Nandivada, Hsien-Yeh Chen, Lidija Bondarenko and Joerg Lahann

      Version of Record online: 19 APR 2006 | DOI: 10.1002/anie.200600357

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      Everything just clicks into place: Alkyne-group functionalized polymer films that are deposited from the gas phase allow spatially defined immobilization of biomolecules, such as biotin, through the 1,3-dipolar cycloaddition click reaction with azide derivatives (see scheme). Such biofunctional surfaces have applications in diagnostics and biosensors.

    35. Charge Separation at Self-Assembled Nanostructured Bulk Interface in Block Copolymers (pages 3364–3368)

      Stefan M. Lindner, Sven Hüttner, Arnaud Chiche, Mukundan Thelakkat and Georg Krausch

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200503958

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      Proper percolation of charges in solar cells is possible with the self-assembled nanostructure of a block-copolymer film (see the TEM cross section of a solar cell). A photovoltaic device made from such a block copolymer exhibits a ten-times higher short circuit current and a considerably larger photovoltage than its polymer-blend analogue.

    36. σ-Donor and π-Acceptor Stacking Interactions in a trans-2-Linked C60–Cobalt(II) Tetraphenylporphyrin Diad (pages 3368–3372)

      Jörg Dannhäuser, Wolfgang Donaubauer, Frank Hampel, Markus Reiher, Boris Le Guennic, Björn Corzilius, Klaus-Peter Dinse and Andreas Hirsch

      Version of Record online: 19 APR 2006 | DOI: 10.1002/anie.200504383

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      Hold me close: A trans-2-linked molecular diad displays both σ-donor and π-acceptor interations (see picture). The crystal structure reveals linear stacking arrangements in which the fullerene moiety is located directly above the porphyrin moiety of the neighboring molecule.

    37. Structure-Sensitive and Self-Assembled Helical Pyrene Array Based on DNA Architecture (pages 3372–3375)

      Elke Mayer-Enthart and Hans-Achim Wagenknecht

      Version of Record online: 18 APR 2006 | DOI: 10.1002/anie.200504210

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      Five times is more than fivefold: The helical π-stacked array of pyrene-modified uridine shows a strong fluorescence enhancement that is structure sensitive to base mismatches. As the fluorescence is highly sequence dependent, it can serve as a structure-sensitive probe for DNA.

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