Cover Picture: Achieving Strong Positive Cooperativity through Activating Weak Non‐Covalent Interactions (Angew. Chem. Int. Ed. 3/2018)

Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H⋅⋅⋅π interactions

Abstract Molecular recognition of aromatic hydrocarbons by four endo -functionalized molecular tubes has been studied by 1 H NMR spectroscopy, computational methods, and single crystal X-ray crystallography. The binding selectivity is rationalized by invoking shape complementarity and dipole alignment. The non-covalent interactions are proved to predominantly be C/N-H⋅⋅⋅ π interactions.

A conformationally adaptive macrocycle : conformational complexity and host–guest chemistry of zorb[4]arene

Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 foll…

Titelbild: Achieving Strong Positive Cooperativity through Activating Weak Non‐Covalent Interactions (Angew. Chem. 3/2018)

endo-Functionalized molecular tubes : selective encapsulation of neutral molecules in non-polar media

Four endo-functionalized molecular tubes with urea/thiourea groups in the deep cavities have been synthesized, and their binding ability to neutral molecules studied. Very high binding affinity and selectivity have been achieved, which are rationalized by invoking the shape and electrostatic complementarity and dipole alignment.

The on-orbit calibration of DArk Matter Particle Explorer

Abstract The DArk Matter Particle Explorer (DAMPE), a satellite-based cosmic ray and gamma-ray detector, was launched on December 17, 2015, and began its on-orbit operation on December 24, 2015. In this work we document the on-orbit calibration procedures used by DAMPE and report the calibration results of the Plastic Scintillator strip Detector (PSD), the Silicon-Tungsten tracKer-converter (STK), the BGO imaging calorimeter (BGO), and the Neutron Detector (NUD). The results are obtained using Galactic cosmic rays, bright known GeV gamma-ray sources, and charge injection into the front-end electronics of each sub-detector. The determination of the boundary of the South Atlantic Anomaly (SAA…

Search for gamma-ray spectral lines with the DArk Matter Particle Explorer

The DArk Matter Particle Explorer (DAMPE) is well suitable for searching for monochromatic and sharp $\gamma$-ray structures in the GeV$-$TeV range thanks to its unprecedented high energy resolution. In this work, we search for $\gamma$-ray line structures using five years of DAMPE data. To improve the sensitivity, we develop two types of dedicated data sets (including the BgoOnly data which is the first time to be used in the data analysis for the calorimeter-based gamma-ray observatories) and adopt the signal-to-noise ratio optimized regions of interest (ROIs) for different DM density profiles. No line signals or candidates are found between 10 and 300 GeV in the Galaxy. The constraints o…

Probing the guest-binding preference of three structurally similar and conformationally adaptive macrocycles.

A hybrid macrocycle was synthesized by combining the repeat units in oxatub[4]arene and zorb[4]arene, and its recognition behavior and conformational analysis were studied. Three structurally similar and conformationally adaptive macrocycles show different guest-binding selectivities and preferences even in a complex mixture containing three macrocycles and three guests.

Direct detection of a break in the teraelectronvolt cosmic-ray spectrum of electrons and positrons

High energy cosmic ray electrons plus positrons (CREs), which lose energy quickly during their propagation, provide an ideal probe of Galactic high-energy processes and may enable the observation of phenomena such as dark-matter particle annihilation or decay. The CRE spectrum has been directly measured up to $\sim 2$ TeV in previous balloon- or space-borne experiments, and indirectly up to $\sim 5$ TeV by ground-based Cherenkov $\gamma$-ray telescope arrays. Evidence for a spectral break in the TeV energy range has been provided by indirect measurements of H.E.S.S., although the results were qualified by sizeable systematic uncertainties. Here we report a direct measurement of CREs in the …

Selective Recognition of Phenazine by 2,6‐Dibutoxylnaphthalene‐Based Tetralactam Macrocycle

A 2,6‐dibutoxylnaphthalene‐based tetralactam macrocycle was designed and synthesized. This macrocycle shows highly selective recognition to phenazine ‐‐ a well‐known secondary metabolite in bacteria and an emerging disinfection byproduct in drinking water. In contrast, the macrocycle shows no binding to the structurally similar dibenzo‐1,4‐dioxin. It was revealed that hydrogen bonding, π‐π and σ‐π interactions are the major driving forces between phenazine and the new tetralactam macrocycle. A perfect complementarity in electrostatic potential surfaces may explain the high selectivity. In addition, the macrocycle shows fluorescent response to phenazine, demonstrating its potential in fluore…

Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H⋅⋅⋅π interactions

Molecular recognition of aromatic hydrocarbons by four endo-functionalized molecular tubes has been studied by 1H NMR spectroscopy, computational methods, and single crystal X-ray crystallography. The binding selectivity is rationalized by invoking shape complementarity and dipole alignment. The non-covalent interactions are proved to predominantly be C/N-H⋅⋅⋅π interactions. peerReviewed

Effects of side chains of oxatub[4]arene on its conformational interconversion, molecular recognition and macroscopic self-assembly.

A series of oxatub[4]arenes with different alkyl side chains have been synthesized. The conformational interconversion, molecular recognition and macroscopic self-assembly behaviour of oxatub[4]arene derivatives were investigated. The difference in side chains slightly changes the binding affinities, but results in different self-assembly morphologies at the solid state.

Measurement of the cosmic ray proton spectrum from 40 GeV to 100 TeV with the DAMPE satellite

DAMPE satellite has directly measured the cosmic ray proton spectrum from 40 GeV to 100 TeV and revealed a new feature at about 13.6 TeV.

A supramolecular system that strictly follows the binding mechanism of conformational selection

Induced fit and conformational selection are two dominant binding mechanisms in biology. Although induced fit has been widely accepted by supramolecular chemists, conformational selection is rarely studied with synthetic systems. In the present research, we report a macrocyclic host whose binding mechanism is unambiguously assigned to conformational selection. The kinetic and thermodynamic aspects of this system are studied in great detail. It reveals that the kinetic equation commonly used for conformational selection is strictly followed here. In addition, two mathematical models are developed to determine the association constants of the same guest to the two host conformations. A “confo…

Achieving Strong Positive Cooperativity through Activating Weak Non-Covalent Interactions

Positive cooperativity achieved through activating weak non-covalent interactions is common in biological assemblies but is rarely observed in synthetic complexes. Two new molecular tubes have been synthesized and the syn isomer binds DABCO-based organic cations with high orientational selectivity. Surprisingly, the ternary complex with two hosts and one guest shows a high cooperativity factor (α=580), which is the highest reported for synthetic systems without involving ion-pairing interactions. The X-ray single-crystal structure revealed that the strong positive cooperativity likely originates from eight C-H⋅⋅⋅O hydrogen bonds between the two head-to-head-arranged syn tube molecules. Thes…

Comparison of proton shower developments in the BGO calorimeter of the Dark Matter Particle Explorer between GEANT4 and FLUKA simulations

The DArk Matter Particle Explorer (DAMPE) is a satellite-borne detector for high-energy cosmic rays and $\gamma$-rays. To fully understand the detector performance and obtain reliable physical results, extensive simulations of the detector are necessary. The simulations are particularly important for the data analysis of cosmic ray nuclei, which relies closely on the hadronic and nuclear interactions of particles in the detector material. Widely adopted simulation softwares include the GEANT4 and FLUKA, both of which have been implemented for the DAMPE simulation tool. Here we describe the simulation tool of DAMPE and compare the results of proton shower properties in the calorimeter from t…

Bis-urea macrocycles with a deep cavity

Redox-Responsive Host-Guest Chemistry of a Flexible Cage with Naphthalene Walls

“Naphthocage”, a naphthalene-based organic cage, reveals very strong binding (up to 1010 M–1) to aromatic (di)cationic guests, i.e., the tetrathiafulvalene mono- and dication and methyl viologen. Intercalation of the guests between two naphthalene walls is mediated by C–H···O, C–H···π, and cation···π interactions. The guests can be switched into and out of the cage by redox processes with high binding selectivity. Oxidation of the flexible cage itself in the absence of a guest leads to a stable radical cation with the oxidized naphthalene intercalated between and stabilized by the other two. Encapsulated guest cations are released from the cavity upon cage oxidation, paving the way to futur…

Abnormal pressure dependence of the phase boundaries in TL/PEO/P(EO-b-DMS) ternary mixtures

The cloud-point temperatures (T-cl's) of both binary poly(ethylene oxide) (PEO)-poly(ethylene oxide-b-dimethylsiloxane) [P(EO-b-DMS)] and ternary[toluene/PEO/P(EO-b-DMS)] systems were determined by light scattering measurements at atmospheric pressure. The phase separation behavior upon cooling in the ternary system has been investigated at atmospheric pressure and under high pressure and compared to the phase behavior in the binary system. The phase transition temperatures have been obtained for all of the samples. As a result, the pressure induces compatibility in the binary mixtures, but for the ternary system, pressure not only can induce mixing but also can induce phase separation.

Redox-Responsive Host–Guest Chemistry of a Flexible Cage with Naphthalene Walls

"Naphthocage", a naphthalene-based organic cage, reveals very strong binding (up to 1010 M-1) to aromatic (di)cationic guests, i.e., the tetrathiafulvalene mono- and dication and methyl viologen. Intercalation of the guests between two naphthalene walls is mediated by C-H···O, C-H···π, and cation···π interactions. The guests can be switched into and out of the cage by redox processes with high binding selectivity. Oxidation of the flexible cage itself in the absence of a guest leads to a stable radical cation with the oxidized naphthalene intercalated between and stabilized by the other two. Encapsulated guest cations are released from the cavity upon cage oxidation, paving the way to futur…

Chelate Cooperativity and Spacer Length Effects on the Assembly Thermodynamics and Kinetics of Divalent Pseudorotaxanes

Homo- and heterodivalent crown-ammonium pseudorotaxanes with different spacers connecting the two axle ammonium binding sites have been synthesized and characterized by NMR spectroscopy and ESI mass spectrometry. The homodivalent pseudorotaxanes are investigated with respect to the thermodynamics of divalent binding and to chelate cooperativity. The shortest spacer exhibits a chelate cooperativity much stronger than that of the longer spacers. On the basis of crystal structure, this can be explained by a noninnocent spacer, which contributes to the binding strength in addition to the two binding sites. Already very subtle changes in the spacer length, i.e., the introduction of an additional…

Using 81Kr and Noble Gases to Characterize and Date Groundwater and Brines in the Baltic Artesian Basin on the One-Million-Year Timescale

Analyses for $^{81}$Kr and noble gases on groundwater from the deepest aquifer system of the Baltic Artesian Basin (BAB) were performed to determine groundwater ages and uncover the flow dynamics of the system on a timescale of several hundred thousand years. We find that the system is controlled by mixing of three distinct water masses: Interglacial or recent meteoric water $(\delta^{18}\text{O} \approx -10.4\unicode{x2030})$ with a poorly evolved chemical and noble gas signature, glacial meltwater $(\delta^{18}\text{O} \leq -18\unicode{x2030})$ with elevated noble gas concentrations, and an old, high-salinity brine component $(\delta^{18}\text{O} \geq -4.5\unicode{x2030}, \geq 90 \text{g …

The DArk Matter Particle Explorer mission

The DArk Matter Particle Explorer (DAMPE), one of the four scientific space science missions within the framework of the Strategic Pioneer Program on Space Science of the Chinese Academy of Sciences, is a general purpose high energy cosmic-ray and gamma-ray observatory, which was successfully launched on December 17th, 2015 from the Jiuquan Satellite Launch Center. The DAMPE scientific objectives include the study of galactic cosmic rays up to $\sim 10$ TeV and hundreds of TeV for electrons/gammas and nuclei respectively, and the search for dark matter signatures in their spectra. In this paper we illustrate the layout of the DAMPE instrument, and discuss the results of beam tests and calib…

A 2,3-dialkoxynaphthalene-based naphthocage

A 2,3-dialkoxynaphthalene-based naphthocage has been synthesized. This naphthocage prefers to bind small organic cations with its low-symmetry conformation, which is in contrast to 2,6-dialkoxynaphthalene-based naphthocages. Self-sorting of these two naphthocages with two structurally similar guests tetramethylammonium and tetraethylammonium was achieved as well. peerReviewed

Directional Shuttling of a Stimuli-Responsive Cone-Like Macrocycle on a Single-State Symmetric Dumbbell Axle

Rotaxane-based molecular shuttles are often operated using low-symmetry axles and changing the states of the binding stations. A molecular shuttle capable of directional shuttling of an acid-responsive cone-like macrocycle on a single-state symmetric dumbbell axle is now presented. The axle contains three binding stations: one symmetric di(quaternary ammonium) station and two nonsymmetric phenyl triazole stations arranged in opposite orientations. Upon addition of an acid, the protonated macrocycle shuttles from the di(quaternary ammonium) station to the phenyl triazole binding station closer to its butyl groups. This directional shuttling presumably originates from charge repulsion and an …

Guest-Induced Folding and Self-Assembly of Conformationally Adaptive Macrocycles into Nanosheets and Nanotubes

A conformationally adaptive macrocycle is presented, namely zorb[4]arene, which exists in multiple conformations in the uncomplexed state. The binding cavity of zorb[4]arene is concealed, either due to a collapsed conformation or by self-inclusion. The zorb[4]arene with long alkyl chains manifests itself with surprisingly low melting point and thus exist as an oil at room temperature. Binding of a guest molecule induces the folding and conformational rigidity of zorb[4]arene and leads to well-defined three-dimensional structures, which can further self-assemble into nanosheets or nanotubes upon solvent evaporation, depending on guest molecules and the conformations they can induce.

Bis-urea macrocycles with a deep cavity.

Two configurational isomers of bis-urea macrocycles have been synthesized, and their neutral molecule recognition was studied by X-ray crystallography and (1)H NMR experiments. Cooperative action between the deep cavity and the urea groups and the influence of dipole alignments on molecular recognition are discussed.

CCDC 1913149: Experimental Crystal Structure Determination

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CCDC 1417789: Experimental Crystal Structure Determination

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CCDC 1577841: Experimental Crystal Structure Determination

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CCDC 1575263: Experimental Crystal Structure Determination

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CCDC 1577176: Experimental Crystal Structure Determination

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CCDC 853183: Experimental Crystal Structure Determination

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CCDC 1443004: Experimental Crystal Structure Determination

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A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 foll…

CCDC 1957981: Experimental Crystal Structure Determination

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Bis-urea macrocycles with a deep cavity

Two bis-urea macrocycles with a deep cavity demonstrate an enzyme-like binding, and the influence of dipole alignments on molecular recognition.

CCDC 1532334: Experimental Crystal Structure Determination

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CCDC 1575262: Experimental Crystal Structure Determination

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CCDC 1417790: Experimental Crystal Structure Determination

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Achieving Strong Positive Cooperativity through Activating Weak Non‐Covalent Interactions

endo-Functionalized molecular tubes: selective encapsulation of neutral molecules in non-polar media

Four endo-functionalized molecular tubes show high binding affinity and selectivity to neutral molecules.

CCDC 1826426: Experimental Crystal Structure Determination

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CCDC 1918923: Experimental Crystal Structure Determination

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CCDC 1838266: Experimental Crystal Structure Determination

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CCDC 1913150: Experimental Crystal Structure Determination

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CCDC 1950443: Experimental Crystal Structure Determination

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CCDC 1417788: Experimental Crystal Structure Determination

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CCDC 1836247: Experimental Crystal Structure Determination

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CCDC 1836509: Experimental Crystal Structure Determination

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CCDC 1828064: Experimental Crystal Structure Determination

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CCDC 1577842: Experimental Crystal Structure Determination

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CCDC 1482002: Experimental Crystal Structure Determination

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CCDC 1838268: Experimental Crystal Structure Determination

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CCDC 1482001: Experimental Crystal Structure Determination

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CCDC 1417791: Experimental Crystal Structure Determination

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CCDC 1971100: Experimental Crystal Structure Determination

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CCDC 1826427: Experimental Crystal Structure Determination

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CCDC 1838267: Experimental Crystal Structure Determination

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CCDC 1838270: Experimental Crystal Structure Determination

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CCDC 1913148: Experimental Crystal Structure Determination

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CCDC 1838269: Experimental Crystal Structure Determination

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