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1.
  • Cousins, David L., et al. (author)
  • Pyrimidin-6-yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis
  • 2021
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 133:17, s. 9498-9501
  • Journal article (peer-reviewed)abstract
    • We report a novel and general method to access a highly under‐studied privileged scaffold – pyrimidines bearing a trifluoroborate at C4, and highlight the broad utility of these intermediates in a rich array of downstream functionalization reactions. This chemistry is underpinned by the unique features of the trifluoroborate group; its robustness provides an opportunity to carry out chemoselective reactions at other positions on the pyrimidine while providing a pathway for elaboration at the C‐B bond when suitably activated.
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2.
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3.
  • Goesten, Maarten, et al. (author)
  • Cesium's off-the-map valence orbital
  • 2017
  • In: Angewandte Chemie. - : Wiley. - 1521-3773 .- 1433-7851 .- 0044-8249 .- 1521-3757.
  • Journal article (peer-reviewed)abstract
    • The Td-symmetric [CsO4]+ ion, featuring Cs in an oxidation state of 9, is computed to be a minimum. Cs uses outer core 5s and 5p orbitals to bind the oxygens. The valence Cs 6s orbital lies too high to be involved in bonding, and contributes to Rydberg levels only. From a Molecular Orbital perspective, the bonding scheme reminds of XeO4: an octet of electrons to bind electronegative ligands, and no low-lying acceptor orbitals on the central atom. In this sense, Cs+ resembles hypervalent Xe.
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4.
  • Karlsmo, Martin, 1995, et al. (author)
  • High‐performant all‐organic aqueous sodium‐ion batteries enabled by PTCDA electrodes and a hybrid Na/Mg electrolyte
  • 2021
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 60:46, s. 24709-24715
  • Journal article (peer-reviewed)abstract
    • Aqueous sodium-ion batteries (ASIBs) are aspiring candidates for low environmental impact energy storage, especially when using organic electrodes. In this respect, perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) is a promising anode active material, but it suffers from extensive dissolution in conventional aqueous electrolytes. As a remedy, we here present a novel aqueous electrolyte, which inhibits the PTCDA dissolution and enables their use as all-organic ASIB anodes with high capacity retention and Coulombic efficiencies. Furthermore, the electrolyte is based on two, hence “hybrid”, inexpensive and non-fluorinated Na/Mg-salts, it displays favourable physico-chemical properties and an electrochemical stability window >3 V without resorting to the extreme salt concentrations of water-in-salt electrolytes. Altogether, this paves the way for ASIBs with both relatively high energy densities, inexpensive total cell chemistries, long-term sustainability, and improved safety.
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5.
  • Ma, Le Anh, 1992-, et al. (author)
  • Strategies for Mitigating Dissolution of Solid Electrolyte Interphases in Sodium-Ion Batteries
  • 2021
  • In: Angewandte Chemie International Edition. - : John Wiley & Sons. - 1433-7851 .- 1521-3773. ; 60:9, s. 4855-4863
  • Journal article (peer-reviewed)abstract
    • The interfacial reactions in sodium-ion batteries (SIBs) are not well understood yet. The formation of a stable solid electrolyte interphase (SEI) in SIBs is still challenging due to the higher solubility of the SEI components compared to lithium analogues. This study therefore aims to shed light on the dissolution of SEI influenced by the electrolyte chemistry. By conducting electrochemical tests with extended open circuit pauses, and using surface spectroscopy, we determine the extent of self-discharge due to SEI dissolution. Instead of using a conventional separator, beta-alumina was used as sodium-conductive membrane to avoid crosstalk between the working and sodium-metal counter electrode. The relative capacity loss after a pause of 50 hours in the tested electrolyte systems ranges up to 30 %. The solubility of typical inorganic SEI species like NaF and Na2CO3 was determined. The electrolytes were then saturated by those SEI species in order to oppose ageing due to the dissolution of the SEI.
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6.
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7.
  • Achenbach, Bastian, et al. (author)
  • Porous Salts Containing Cationic Al24-Hydroxide-Acetate Clusters from Scalable, Green and Aqueous Synthesis Routes
  • 2023
  • In: Angewandte Chemie International Edition. - 1433-7851 .- 1521-3773. ; 62:29
  • Journal article (peer-reviewed)abstract
    • The solution chemistry of aluminum is highly complex and various polyoxocations are known. Here we report on the facile synthesis of a cationic Al24 cluster that forms porous salts of composition [Al24(OH)56(CH3COO)12]X4, denoted CAU-55-X, with X=Cl−, Br−, I−, HSO4−. Three-dimensional electron diffraction was employed to determine the crystal structures. Various robust and mild synthesis routes for the chloride salt [Al24(OH)56(CH3COO)12]Cl4 in water were established resulting in high yields (>95 %, 215 g per batch) within minutes. Specific surface areas and H2O capacities with maximum values of up to 930 m2 g−1 and 430 mg g−1 are observed. The particle size of CAU-55-X can be tuned between 140 nm and 1250 nm, permitting its synthesis as stable dispersions or as highly crystalline powders. The positive surface charge of the particles, allow fast and effective adsorption of anionic dye molecules and adsorption of poly- and perfluoroalkyl substances (PFAS). 
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8.
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9.
  • Agarwala, Hemlata, et al. (author)
  • Alternating Metal-Ligand Coordination Improves Electrocatalytic CO2 Reduction by a Mononuclear Ru Catalyst**
  • 2023
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 62:17
  • Journal article (peer-reviewed)abstract
    • Molecular electrocatalysts for CO2-to-CO conversion often operate at large overpotentials, due to the large barrier for C−O bond cleavage. Illustrated with ruthenium polypyridyl catalysts, we herein propose a mechanistic route that involves one metal center that acts as both Lewis base and Lewis acid at different stages of the catalytic cycle, by density functional theory in corroboration with experimental FTIR. The nucleophilic character of the Ru center manifests itself in the initial attack on CO2 to form [Ru-CO2]0, while its electrophilic character allows for the formation of a 5-membered metallacyclic intermediate, [Ru-CO2CO2]0,c, by addition of a second CO2 molecule and intramolecular cyclization. The calculated activation barrier for C−O bond cleavage via the metallacycle is decreased by 34.9 kcal mol−1 as compared to the non-cyclic adduct in the two electron reduced state of complex 1. Such metallacyclic intermediates in electrocatalytic CO2 reduction offer a new design feature that can be implemented consciously in future catalyst designs.
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10.
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11.
  • Agosta, Lorenzo, et al. (author)
  • Origin of the Hydrophobic Behaviour of Hydrophilic CeO2
  • 2023
  • In: Angewandte Chemie International Edition. - : Wiley-VCH Verlagsgesellschaft. - 1433-7851 .- 1521-3773. ; 62:35
  • Journal article (peer-reviewed)abstract
    • The nature of the hydrophobicity found in rare-earth oxides is intriguing. The CeO2 (100) surface, despite its strongly hydrophilic nature, exhibits hydrophobic behaviour when immersed in water. In order to understand this puzzling and counter-intuitive effect we performed a detailed analysis of the water structure and dynamics. We report here an ab-initio molecular dynamics simulation (AIMD) study which demonstrates that the first water layer, in immediate contact with the hydroxylated CeO2 surface, is responsible for the effect behaving as a hydrophobic interface with respect to the rest of the liquid water. The hydrophobicity is manifested in several ways: a considerable diffusion enhancement of the confined liquid water as compared with bulk water at the same thermodynamic condition, a weak adhesion energy and few H-bonds above the hydrophobic water layer, which may also sustain a water droplet. These findings introduce a new concept in water/rare-earth oxide interfaces: hydrophobicity mediated by specific water patterns on a hydrophilic surface.
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12.
  • Ahlquist, Mårten, et al. (author)
  • Dispersion and Back-Donation Gives Tetracoordinate [Pd(PPh3)4]
  • 2011
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 50:49, s. 11794-11797
  • Journal article (peer-reviewed)abstract
    • 18e R.I.P. The apparent compliance of [Pd(PPh3)4] ("tetrakis") with the 18-electron rule is not due to an electronic preference on the central metal. Pd is valence-saturated already by two ligands. Further ligand addition gives a minor energy gain, and is only possible due to strong back-bonding. Dispersion corrections are needed for properly describing the interactions between the ligands.
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14.
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15.
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16.
  • Akkarasamiyo, Sunisa, et al. (author)
  • Intermolecular Stereospecific Substitution of Underivatized Enantioenriched Secondary Alcohols by Organocatalysis
  • 2019
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 58:50, s. 17908-17910
  • Journal article (peer-reviewed)abstract
    • The stereospecific substitution of non-derivatized and non-allylic enantioenriched alcohols with only water as a by-product would enable the use of readily available alcohols as substrates for green and sustainable transformations. However, the poor leaving group ability of the OH group has hampered the development of such a process. Denton and co-workers recently described the use of (2-hydroxybenzyl)diphenylphosphine oxide as a catalyst of a redox-neutral and zero-waste-generating Mitsunobu reaction. This innovative process constitutes the first intermolecular stereospecific substitution of non-allylic alcohols, and might find industrial applications.
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17.
  • Alam, Rauful, et al. (author)
  • Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids : Stereodivergent Synthesis of up to Three Contiguous Stereocenters
  • 2016
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 55:46, s. 14417-14421
  • Journal article (peer-reviewed)abstract
    • The catalytic asymmetric allylboration of cyclic imines with gamma,gamma-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst. 3-Methylindole provided products with three adjacent stereocenters with high stereoselectivity in one synthetic operation.
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18.
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19.
  • Alsufyani, Maryam, et al. (author)
  • Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance
  • 2022
  • In: Angewandte Chemie International Edition. - : WILEY-V C H VERLAG GMBH. - 1433-7851 .- 1521-3773. ; 61:7
  • Journal article (peer-reviewed)abstract
    • Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0 % benzene (P-0), to 50 % (P-50), and 75 % (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S cm and Power factors of 13.2 mu Wm(-1) K-2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.
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20.
  • Andersen, Thomas L., et al. (author)
  • Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-C-11-Acetylation of Peptides
  • 2017
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 56:16, s. 4549-4553
  • Journal article (peer-reviewed)abstract
    • A mild and effective method is described for C-11-labeling of peptides selectively at the N-terminal nitrogen or at internal lysine positions. The presented method relies on the use of specific biphosphine palladium-methyl complexes and their high reactivity towards amino-carbonylation of amine groups in the presence [C-11] carbon monoxide. The protocol facilitates the production of native N-C-11-acetylated peptides, without any structural modifications and has been applied to a selection of bioactive peptides.
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21.
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22.
  • Andreasson, Joakim, 1973, et al. (author)
  • Molecular 2 : 1 digital multiplexer
  • 2007
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 46:6, s. 958-961
  • Journal article (peer-reviewed)abstract
    • (Chemical Equation Presented) Two into one: A porphyrin linked to two photochromic moieties performs as a 2:1 digital multiplexer (MUX). It takes heat and red light as the two inputs (in 1 and in 2), and a third switchable input (green light, sel) selects whether the output (porphyrin fluorescence) reports the state of in 1 or in 2. Each photochromic moiety may be independently photoisomerized to isomers that quench the porphyrin fluorescence. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
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23.
  • Andreasson, Joakim, 1973, et al. (author)
  • Molecular AND logic gate based on electric dichroism of a photochromic dihydroindolizine
  • 2005
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 44:46, s. 7591-7594
  • Journal article (peer-reviewed)abstract
    • (Chemical Equation Presented) Very ANDy: A photochromic molecular switch has been found to act as an AND Boolean logic gate. The switch takes as input both UV light, which causes photo-isomerization of a dihydroindolizine to an open, dipolar form, and an electric field, which aligns this isomer in solution (see scheme). The output of the gate is read as the electric linear dichroism response of the open isomer. The gate can be reset with visible light. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
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26.
  • Antzutkin, Oleg, et al. (author)
  • Hydrogen bonding in Alzheimer’s amyloid-β fibrils probed by 15N{17O} REAPDOR solid-state NMR spectroscopy
  • 2012
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 51:41, s. 10289-10292
  • Journal article (peer-reviewed)abstract
    • An exclusive label: 15N{17O} REAPDOR NMR was used to validate intermolecular C17O⋅⋅⋅H15N hydrogen bonding in Ac-Aβ(16–22)-NH2 (see scheme) and Aβ(11–25) amyloid fibrils, which are associated with Alzheimer’s disease, by selectively labeling them with 17O and 15N. This method was effective for confirming the structure of these fibrils, and could be useful for a number of other biological samples.
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27.
  • Arkhypchuk, Anna I., et al. (author)
  • Cascade Reactions Forming Highly Substituted, Conjugated Phospholes and 1,2-Oxaphospholes
  • 2012
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 51:31, s. 7776-7780
  • Journal article (peer-reviewed)abstract
    • The reaction of a phospha-Wittig–Horner reagent with diacetylenic ketones (see scheme) results in a cascade of reactions that can lead to both an oxaphosphole-terminated cumulene system and an alkene-bridged bis-phosphole. The reaction outcome is determined by the nature of the acetylene termini, with phenyl groups stabilizing a carbene intermediate that dimerizes to give the bis-phosphole product.
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28.
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29.
  • Aslandukov, Andrey, et al. (author)
  • Anionic N18 Macrocycles and a Polynitrogen Double Helix in Novel Yttrium Polynitrides YN6 and Y2N11 at 100 GPa
  • 2022
  • In: Angewandte Chemie International Edition. - Weinheim, Germany : Wiley-VCH Verlagsgesellschaft. - 1433-7851 .- 1521-3773. ; 61:34
  • Journal article (peer-reviewed)abstract
    • Two novel yttrium nitrides, YN6 and Y2N11, were synthesized by direct reaction between yttrium and nitrogen at 100 GPa and 3000 K in a laser-heated diamond anvil cell. High-pressure synchrotron single-crystal X-ray diffraction revealed that the crystal structures of YN6 and Y2N11 feature a unique organization of nitrogen atoms-a previously unknown anionic N-18 macrocycle and a polynitrogen double helix, respectively. Density functional theory calculations, confirming the dynamical stability of the YN6 and Y2N11 compounds, show an anion-driven metallicity, explaining the unusual bond orders in the polynitrogen units. As the charge state of the polynitrogen double helix in Y2N11 is different from that previously found in Hf2N11 and because N-18 macrocycles have never been predicted or observed, their discovery significantly extends the chemistry of polynitrides.
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30.
  • Aslandukov, Andrey, et al. (author)
  • Stabilization Of The CN35− Anion In Recoverable High-pressure Ln3O2(CN3) (Ln=La, Eu, Gd, Tb, Ho, Yb) Oxoguanidinates
  • 2023
  • In: Angewandte Chemie International Edition. - : WILEY-V C H VERLAG GMBH. - 1433-7851 .- 1521-3773. ; 62:47
  • Journal article (peer-reviewed)abstract
    • A series of isostructural Ln(3)O(2)(CN3) (Ln=La, Eu, Gd, Tb, Ho, Yb) oxoguanidinates was synthesized under high-pressure (25-54 GPa) high-temperature (2000-3000 K) conditions in laser-heated diamond anvil cells. The crystal structure of this novel class of compounds was determined via synchrotron single-crystal X-ray diffraction (SCXRD) as well as corroborated by X-ray absorption near edge structure (XANES) measurements and density functional theory (DFT) calculations. The Ln(3)O(2)(CN3) solids are composed of the hitherto unknown CN35- guanidinate anion-deprotonated guanidine. Changes in unit cell volumes and compressibility of Ln(3)O(2)(CN3) (Ln=La, Eu, Gd, Tb, Ho, Yb) compounds are found to be dictated by the lanthanide contraction phenomenon. Decompression experiments show that Ln(3)O(2)(CN3) compounds are recoverable to ambient conditions. The stabilization of the CN35- guanidinate anion at ambient conditions provides new opportunities in inorganic and organic synthetic chemistry.
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31.
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32.
  • Baber, Ashleigh E., et al. (author)
  • Stabilization of Catalytically Active Cu plus Surface Sites on TitaniumCopper Mixed-Oxide Films**
  • 2014
  • In: Angewandte Chemie International Edition. - : Gesellschaft Deutscher Chemiker. - 1433-7851 .- 1521-3773. ; 53:21, s. 5336-5340
  • Journal article (peer-reviewed)abstract
    • The oxidation of CO is the archetypal heterogeneous catalytic reaction and plays a central role in the advancement of fundamental studies, the control of automobile emissions, and industrial oxidation reactions. Copper-based catalysts were the first catalysts that were reported to enable the oxidation of CO at room temperature, but a lack of stability at the elevated reaction temperatures that are used in automobile catalytic converters, in particular the loss of the most reactive Cu+ cations, leads to their deactivation. Using a combined experimental and theoretical approach, it is shown how the incorporation of titanium cations in a Cu2O film leads to the formation of a stable mixed-metal oxide with a Cu+ terminated surface that is highly active for CO oxidation.
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33.
  • Bach, Anders, et al. (author)
  • Design and synthesis of highly potent and plasma-stable dimeric inhibitors of the PSD-95-NMDA receptor interaction
  • 2009
  • In: Angewandte Chemie International Edition. - : Wiley-VCH. - 1433-7851 .- 1521-3773. ; 48:51, s. 9685-9689
  • Journal article (peer-reviewed)abstract
    • On the double: Dimerization of monomeric peptide ligands towards the PDZ domains of the protein PSD-95 (postsynaptic density 95) leads to potent inhibitors of protein-protein interactions with stability in blood plasma. Optimization of the length of the polyethylene glycol linker results in unprecedented affinity for inhibitors of the PDZ1-2 domain.
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34.
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35.
  • Bae, Juna, et al. (author)
  • Phase Transformation Behavior of a Two-Dimensional Zeolite
  • 2019
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 58:30, s. 10230-10235
  • Journal article (peer-reviewed)abstract
    • Understanding the molecular-level mechanisms of phase transformation in solids is of fundamental interest for functional materials such as zeolites. Two-dimensional (2D) zeolites, when used as shape-selective catalysts, can offer improved access to the catalytically active sites and a shortened diffusion length in comparison with their 3D analogues. However, few materials are known to maintain both their intralayer microporosity and structure during calcination for organic structure-directing agent (SDA) removal. Herein we report that PST-9, a new 2D zeolite which has been synthesized via the multiple inorganic cation approach and fulfills the requirements for true layered zeolites, can be transformed into the small-pore zeolite EU-12 under its crystallization conditions through the single-layer folding process, but not through the traditional dissolution/recrystallization route. We also show that zeolite crystal growth pathway can differ according to the type of organic SDAs employed.
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36.
  • Bai, Licheng, et al. (author)
  • Explaining the Size Dependence in Platinum-Nanoparticle-Catalyzed Hydrogenation Reactions
  • 2016
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 55:50, s. 15656-15661
  • Journal article (peer-reviewed)abstract
    • Hydrogenation reactions are industrially important reactions that typically require unfavorably high H-2 pressure and temperature for many functional groups. Herein we reveal surprisingly strong size-dependent activity of Pt nanoparticles (PtNPs) in catalyzing this reaction. Based on unambiguous spectral analyses, the size effect has been rationalized by the size-dependent d-band electron structure of the PtNPs. This understanding enables production of a catalyst with size of 1.2 nm, which shows a sixfold increase in turnover frequency and 28-fold increase in mass activity in the regioselective hydrogenation of quinoline, compared with PtNPs of 5.3 nm, allowing the reaction to proceed under ambient conditions with unprecedentedly high reaction rates. The size effect and the synthesis strategy developed herein may provide a general methodology in the design of metal-nanoparticle-based catalysts for a broad range of organic syntheses.
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37.
  • Bai, Pu, et al. (author)
  • A Layered Cationic Aluminum Oxyhydroxide as a Highly Efficient and Selective Trap for Heavy Metal Oxyanions
  • 2020
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 59:44, s. 19539-19544
  • Journal article (peer-reviewed)abstract
    • Cationic framework materials, especially pure inorganic cationic frameworks that can efficiently and selectively capture harmful heavy metal oxyanions from aqueous solution are highly desired yet scarcely reported. Herein, we report the discovery of a 2D cationic aluminum oxyhydroxide, JU-111, which sets a new benchmark for heavy metal oxyanion sorbents, especially for Cr-VI. Its structure was solved based on 3D electron diffraction tomography data. JU-111 shows fast sorption kinetics (ca. 20 min), high capture capacity (105.4 mg g(-1)), and broad working pH range (3-10) toward Cr(VI)oxyanions. Unlike layered double hydroxides (LDHs), which are poorly selective in the presence of CO32-, JU-111 retains excellent selectivity for Cr(VI)even under a large excess of CO32-. These superior features coupled with the ultra-low cost and environmentally benign nature make JU-111 a promising candidate for toxic metal oxyanion remediation as well as other potential applications.
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38.
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39.
  • Bally, Marta, 1981, et al. (author)
  • Norovirus GII.4 Virus-like Particles Recognize Galactosylceramides in Domains of Planar Supported Lipid Bilayers.
  • 2012
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 51:48, s. 12020-4
  • Journal article (peer-reviewed)abstract
    • A sticky situation: Domain-dependent recognition of the glycosphingolipid galactosylceramide by norovirus-like particles (see picture; red/yellow) is shown using supported lipid bilayers (purple) as model membranes. Optimal ligand presentation is found to promote strong binding to GalCer. This presentation can be found at the edges of the glycosphingolipid-enriched domains (green) and binding is repressed in the absence of these domains.
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40.
  • Barragan, Ana, et al. (author)
  • Design and Manipulation of a Minimalistic Hydrocarbon Nanocar on Au(111)
  • 2023
  • In: Angewandte Chemie International Edition. - : WILEY-V C H VERLAG GMBH. - 1433-7851 .- 1521-3773. ; 62:6
  • Journal article (peer-reviewed)abstract
    • Nanocars are carbon-based single-molecules with a precise design that facilitates their atomic-scale control on a surface. The rational design of these molecules is important in atomic and molecular-scale manipulation to advance the development of molecular machines, as well as for a better understanding of self-assembly, diffusion and desorption processes. Here, we introduce the molecular design and construction of a collection of minimalistic nanocars. They feature an anthracene chassis and four benzene derivatives as wheels. After sublimation and adsorption on an Au(111) surface, we show controlled and fast manipulation of the nanocars along the surface using the tip of a scanning tunneling microscope (STM). The mechanism behind the successful displacement is the induced dipole created over the nanocar by the STM tip. We utilized carbon monoxide functionalized tips both to avoid decomposition and accidentally picking the nanocars up during the manipulation. This strategy allowed thousands of maneuvers to successfully win the Nanocar Race II championship.
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41.
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42.
  • Bartholomeyzik, Teresa, et al. (author)
  • Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes : Control of Selectivity and Role of H2O
  • 2014
  • In: Angewandte Chemie International Edition. - Weinheim : Wiley-VCH Verlag GmbH & Co. KGaA. - 1433-7851 .- 1521-3773. ; 53:33, s. 8696-8699
  • Journal article (peer-reviewed)abstract
    • Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF3 center dot Et2O as an additive, whereas addition of water leads to arylated trienes. These conditions provide the respective products with excellent selectivities (generally > 97:3) for a range of boronic acids and different allenynes. It has been revealed that water plays a crucial role for the product distribution.
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43.
  • Barut, Inci, 1984, et al. (author)
  • Correlative Cellular Mass Spectrometry Imaging and Amperometry Show Dose Dependent Changes in Lipid Composition and Exocytosis
  • 2023
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 62:15
  • Journal article (peer-reviewed)abstract
    • Aberrant functioning of the proteasome has been associated with crucial pathologic conditions including neurodegeneration. Yet, the complex underlying causes at the cellular level remain unclear and there are conflicting reports of neuroprotective to neurodegenerative effects of proteasomal inhibitors such as lactacystin that are utilised as models for neurodegenerative diseases. The conflicting results may be associated with different dose regimes of lactacystin and hence we have performed a dose dependent study of the effects of lactacystin to identify concurrent changes in the cell membrane lipid profile and the dynamics of exocytosis using a combination of surface sensitive mass spectrometry and single cell amperometry. Significant changes of negatively charged lipids were associated with different lactacystin doses that showed a weak correlation with exocytosis while changes in PE and PE−O lipids showed dose dependent changes correlated with initial pore formation and total release of vesicle content respectively.
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44.
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45.
  • Bauer, Brigitte, 1978, et al. (author)
  • Proteomic Analysis of Plasma Membrane Vesicles
  • 2009
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 48:9, s. 1656-1659
  • Journal article (peer-reviewed)abstract
    • (Figure Presented) A simple and scalable method is presented for harvesting, purification, and on-chip processing of mammalian plasma membrane vesicles (PMVs) optimized for downstream proteome analysis. After immobilization on a microfluidic flow-cell of PMVs, the embedded membrane proteins are proteolytically digested, and the peptides harvested and analyzed by LC-MS/MS. Over 93% of the detected proteins are plasma-membrane-derived. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
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46.
  • Beahm, Brendan J, et al. (author)
  • A visualizable chain-terminating inhibitor of glycosaminoglycan biosynthesis in developing zebrafish
  • 2014
  • In: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 53:13, s. 3347-3352
  • Journal article (peer-reviewed)abstract
    • Heparan sulfate (HS) and chondroitin sulfate (CS) glycosaminoglycans (GAG) are proteoglycan-associated polysaccharides with essential functions in animals. They have been studied extensively by genetic manipulation of biosynthetic enzymes, but chemical tools for probing GAG function are limited. HS and CS possess a conserved xylose residue that links the polysaccharide chain to a protein backbone. Here we report that, in zebrafish embryos, the peptide-proximal xylose residue can be metabolically replaced with a chain-terminating 4-azido-4-deoxyxylose (4-XylAz) residue by administration of UDP-4-azido-4-deoxyxylose (UDP-4-XylAz). UDP-4-XylAz disrupted both HS and CS biosynthesis and caused developmental abnormalities reminiscent of GAG biosynthesis and laminin mutants. The azide substituent of protein-bound 4-XylAz allowed for rapid visualization of the organismal sites of chain termination in vivo through bioorthogonal reaction with fluorescent cyclooctyne probes. UDP-4-XylAz therefore complements genetic tools for studies of GAG function in zebrafish embryogenesis.
  •  
47.
  • Behren, Sandra, et al. (author)
  • Fucose binding motifs on mucin core glycopeptides impact bacterial lectin recognition
  • 2023
  • In: Angewandte Chemie International Edition. - 1433-7851 .- 1521-3773. ; 62:32
  • Journal article (peer-reviewed)abstract
    • Mucin glycoproteins are essential components of the mucosal barrier, which protects the host from pathogens. Throughout evolution, bacteria have developed strategies to modulate and penetrate this barrier, and cause virulence by interacting with mucin O-glycans at the epithelial cell-surface. O-fucosylated glycan epitopes on mucins are key ligands of many bacterial lectins. Here, a chemoenzymatic synthesis strategy is described to prepare a library of fucosylated mucin core glycopeptides to enable studies of mucin-interacting and fucose-binding bacterial lectins. Glycan cores with biologically important Lewis and H-antigens were prepared decorating the peptide backbone at different sites and densities. The fucosylated mucin glycopeptides were applied in microarray binding studies to explore the importance of glycan core and peptide backbone presentation of these antigens in binding interactions with the P. aeruginosa lectin LecB and the C. difficile toxin A.
  •  
48.
  • Belanger-Chabot, Guillaume, et al. (author)
  • Ammonia-(Dinitramido)boranes: High-Energy-Density Materials.
  • 2015
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 54, s. 11730-11734
  • Journal article (peer-reviewed)abstract
    • Two ammonia-(dinitramido)boranes were synthesized by the reaction of dinitroamine with ammonia-borane. These compds. are the first reported examples of (dinitramido)boranes. Ammonia-mono(dinitramido)borane is a perfectly oxygen-balanced high-energy-d. material (HEDM) composed of an ammonia-BH2 fuel group and a strongly oxidizing dinitramido ligand. Although it is thermally not stable enough for practical applications, its predicted specific impulse as a solid rocket propellant would be 333 s. Its predicted performance as an explosive matches that of pentaerythtritol tetranitrate (PETN) and significantly exceeds that of trinitrotoluene (TNT). Its structure was established by X-ray crystallog. and vibrational and multinuclear NMR spectroscopy. Addnl., the over-oxidized ammoniabis(dinitramido)borane was detected by NMR spectroscopy. [on SciFinder(R)]
  •  
49.
  • Belanger-Chabot, Guillaume, et al. (author)
  • [BH3C(NO2)3]-: The First Room-Temperature Stable (Trinitromethyl)borate.
  • 2013
  • In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 52:42, s. 11002-11006
  • Journal article (peer-reviewed)abstract
    • The first stable (trinitromethyl)borate anion [BH3C(NO2)3]- was synthesized and structurally characterized. The BH3 group in [BH3C(NO2)3]- provides a significant increase in stability compared to the previously studied BCl3 analog. The [Na(glyme)2]+, PNP+, and PPh4+ salts of [BH3C(NO2)3]- were successfully isolated and characterized by NMR and vibrational spectroscopy. The PNP+ salt was structurally characterized, confirming the theor. predicted B-C connectivity. [on SciFinder(R)]
  •  
50.
  • Belanger-Chabot, Guillaume, et al. (author)
  • Dinitramidoborates, a Fascinating Case of Competing Oxygen and Nitrogen Donors and Tautomerism
  • 2017
  • In: Angewandte Chemie. - : Wiley. - 1521-3773 .- 1433-7851. ; 56:36, s. 10881-10885
  • Journal article (peer-reviewed)abstract
    • Reactions of the BH4- anion with equimolar amounts of HN(NO2)2 or of BH3*THF with K+[N(NO2)2]- produced a mono-substituted [BH3N(NO2)2]- anion which contains a B-N connected dinitramido ligand. The reaction of BH4- with two equivalents of HN(NO2)2 afforded the di-substituted borate anion consisting of two isomers, one with both nitramido ligands attached to B through N and the other one with one ligand attached through N and the other one through O. The disubstituted dinitramidoborates are marginally stable under ambient conditions, and the isomer with two N-connected ligands was characterized by its crystal structure. A tri-substituted borate was tentatively identified by NMR in the reaction of BH4- with a large excess of HN(NO2)2. All anions are highly energetic. Theoretical calculations show that the energy differences between the B-N and B-O tautomers are small, explaining the observed ease of ligand exchange.
  •  
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