Browse
Submit Data
Databases
API
Help

Dataset Information

7 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A facile route to old and new cyclophanes via self-assembly and capture.

ABSTRACT: Cyclophanes are a venerable class of macrocyclic and/or cage compounds that often feature high strain, unusual conformations and quite surprising properties, many of which are legendary in physical organic chemistry. However, the discovery of new, diverse cyclophanes and derivatives has been hindered by syntheses that are traditionally low-yielding, requiring long reaction times, laborious purification steps and often extreme conditions. Herein, we demonstrate a new self-assembly route to a variety of discrete cyclic and caged disulfide structures, which can then be kinetically captured upon sulfur extrusion at room temperature to give a diversity of new thioether (hetera)cyclophanes in high yield. In addition to the synthesis of novel macrocycles (dimers through hexamers), this process provides an improved route to a known macrobicyclic trithiacyclophane. This technique also enables the facile isolation of a tetrahedral macrotricyclic tetrathiacyclophane in two steps at an ambient temperature.

SUBMITTER: Collins MS

PROVIDER: S-EPMC4821999 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Facile self-assembly of neutral dendritic metallocycles via oxygen-to-platinum coordination.

Project description:A new approach for the fabrication of neutral dendritic metallocycles is described. By combining rigid 120 degrees dicarboxylate donor linkers funtionalized with [G0]-[G3] Frechet-type dendrons and complementary rigid 60 degrees and 120 degrees di-Pt(II) acceptor subunits, neutral rhomboidal metallodendrimers and hexagonal metallodendrimers, respectively, were prepared under mild conditions in high yields. The assemblies have well-defined shapes and sizes and were characterized by multinuclear NMR ((1)H and (31)P), mass spectrometry (ESI (+)-TOF-MS and APPI(+)-TOF-MS), and elemental analysis. Isotopically resolved mass spectrometry data support the formation of the neutral [2 + 2] rhomboidal, and [3 + 3] hexagonal metallodendrimers, and NMR data are consistent with the formation of all ensembles. The structures of the [G0] and [G1] neutral rhomboidal metallodendrimers (3a and 3b) were unambiguously confirmed via single-crystal X-ray crystallography. The shape and size of [G3] neutral hexagonal metallodendrimer 5d was established with MMFF force-field simulations.

| S-EPMC2749078 | biostudies-literature

A facile approach toward multicomponent supramolecular structures: selective self-assembly via charge separation.

Project description:A novel approach toward the construction of multicomponent two-dimensional (2-D) and three-dimensional (3-D) metallosupramolecules is reported. Simply by mixing carboxylate and pyridyl ligands with cis-Pt(PEt(3))(2)(OTf)(2) in a proper ratio, coordination-driven self-assembly occurs, allowing for the selective generation of discrete multicomponent structures via charge separation on the metal centers. Using this method, a variety of 2-D rectangles and 3-D prisms were prepared under mild conditions. Moreover, multicomponent self-assembly can also be achieved by supramolecule-to-supramolecule transformations. The products were characterized by (31)P and (1)H multinuclear NMR spectroscopy, electrospray ionization mass spectrometry, and pulsed-field-gradient spin echo NMR techniques together with computational simulations.

| S-EPMC3016897 | biostudies-literature

Facile self-assembly of colloidal diamond from tetrahedral patchy particles via ring selection.

Project description:Diamond-structured crystals, particularly those with cubic symmetry, have long been attractive targets for the programmed self-assembly of colloidal particles, due to their applications as photonic crystals that can control the flow of visible light. While spherical particles decorated with four patches in a tetrahedral arrangement-tetrahedral patchy particles-should be an ideal building block for this endeavor, their self-assembly into colloidal diamond has proved elusive. The kinetics of self-assembly pose a major challenge, with competition from an amorphous glassy phase, as well as clathrate crystals, leaving a narrow widow of patch widths where tetrahedral patchy particles can self-assemble into diamond crystals. Here we demonstrate that a two-component system of tetrahedral patchy particles, where bonding is allowed only between particles of different types to select even-member rings, undergoes crystallization into diamond crystals over a significantly wider range of patch widths conducive for experimental fabrication. We show that the crystallization in the two-component system is both thermodynamically and kinetically enhanced, as compared to the one-component system. Although our bottom-up route does not lead to the selection of the cubic polytype exclusively, we find that the cubicity of the self-assembled crystals increases with increasing patch width. Our designer system not only promises a scalable bottom-up route for colloidal diamond but also offers fundamental insight into crystallization into open lattices.

| S-EPMC8640719 | biostudies-literature

Fabrication of PPy Nanosphere/rGO Composites via a Facile Self-Assembly Strategy for Durable Microwave Absorption.

Project description:Traditional magnetic metal and alloy materials suffer from easy oxidation and high density, which hinders their practical application as high-performance microwave absorbers. Lightweight and durability have become new goals in the fabrication of the next generation of microwave absorbers. Herein, we report the synthesis of polypyrrole (PPy) nanosphere/reduced graphene oxide (rGO) composites through chemical reduction of self-assembly PPy nanosphere/GO hybrids. PPy nanospheres and GO are integrated effectively by π⁻π interaction of dual conjugated systems. When the mass ratio of PPy nanospheres to rGO is 0.6:1, the resultant composite, PPy/rGO-0.6, presents comparable/superior reflection loss characteristics to those magnetic metals and their related graphene-based composites in previous studies. Electromagnetic analysis reveals that well-matched characteristic impedance, multiple polarization loss, and good conductivity loss are, together, responsible for the excellent microwave absorption performance of PPy/rGO-0.6. More importantly, PPy/rGO-0.6 also exhibits good microwave absorption after being treated at 423 K for a long time. This work provides a new idea for designing and preparing a high-performance microwave absorber with lightweight and durable features.

| S-EPMC6403787 | biostudies-literature

Facile Synthesis and Self-Assembly of Amphiphilic Polyether-Octafunctionalized Polyhedral Oligomeric Silsesquioxane via Thiol-Ene Click Reaction.

Project description:We demonstrated here a facile and efficient synthesis of polyhedral oligomeric silsesquioxane-based amphiphilic polymer by thiol-ene click chemistry. The properties of polyhedral oligomeric silsesquioxane (POSS)?PEG amphiphilic polymers were studied in detail by a combination of ¹H NMR, 13C NMR, 29Si NMR FT-IR, GPC, and TG analysis. The newly-designed thiol-ene protocol obtains only anti-Markovnikov addition POSS-based amphiphilic polymers when compared with platinum-catalysed hydrosilylation method. The critical micelle concentration (CMC) of the resulting polymers are in the range of 0.011 to 0.050 mg/mL, and dynamic light scattering (DLS) results revealed that the obtained amphiphilic polymers can self-assemble into nanoparticles in aqueous solutions with a bimodal (two peaks) distribution. Furthermore, the specific polymer showed obvious thermo-sensitive behaviour at 45.5 °C.

| S-EPMC6432379 | biostudies-literature

Synthetic ion channels via self-assembly: a route for embedding porous polyoxometalate nanocapsules in lipid bilayer membranes.

Project description:Porous polyoxometalate nanocapsules of Keplerate type are known to exhibit the functionality of biological ion channels; however, their use as an artificial ion channel is tempered by the high negative charge of the capsules, which renders their spontaneous incorporation into a lipid bilayer membrane unlikely. In this Letter we report coarse-grained molecular dynamics simulations that demonstrate a route for embedding negatively charged nanocapsules into lipid bilayer membranes via self-assembly. A homogeneous mixture of water, cationic detergent, and phospholipid was observed to spontaneously self-assemble around the nanocapsule into a layered, liposome-like structure, where the nanocapsule was enveloped by a layer of cationic detergent followed by a layer of phospholipid. Fusion of such a layered liposome with a lipid bilayer membrane was observed to embed the nanocapsule into the lipid bilayer. The resulting assembly was found to remain stable even after the surface of the capsule was exposed to electrolyte. In the latter conformation, water was observed to flow into and out of the capsule as Na(+) cations entered, suggesting that a polyoxometalate nanocapsule can form a functional synthetic ion channel in a lipid bilayer membrane.

| S-EPMC2885702 | biostudies-literature

New route for self-assembly of ?-lactalbumin nanotubes and their use as templates to grow silver nanotubes.

Project description:Nanotubes are formed by self-assembly of ?-lactalbumin milk protein following a different route than established for the hydrolysis which involves V8 enzyme, phosphate buffer and appropriate amounts of calcium at neutral pH. The resulting nanotubes are used as templates for the growth of conductive silver nanotubes. TEM, SEM-EDS, AFM and FTIR are used for characterization.

| S-EPMC5389836 | biostudies-literature

Glutamate Receptors and Glioblastoma Multiforme: An Old "Route" for New Perspectives.

Project description:Glioblastoma multiforme (GBM) is the most aggressive malignant tumor of the central nervous system, with poor survival in both treated and untreated patients. Recent studies began to explain the molecular pathway, comprising the dynamic structural and mechanical changes involved in GBM. In this context, some studies showed that the human glioblastoma cells release high levels of glutamate, which regulates the proliferation and survival of neuronal progenitor cells. Considering that cancer cells possess properties in common with neural progenitor cells, it is likely that the functions of glutamate receptors may affect the growth of cancer cells and, therefore, open the road to new and more targeted therapies.

| S-EPMC6479730 | biostudies-literature

Facile synthesis of hierarchical CNF/SnO2/Ni nanostructures via self-assembly process as anode materials for lithium ion batteries.

Project description:Hierarchical carbon nanofibre (CNF)/SnO2/Ni nanostructures of graphitized carbon nanofibres and SnO2 nanocrystallines and Ni nanocrystallines have been prepared via divalent tin-alginate assembly on polyacrylonitrile (PAN) fibres, controlled pyrolysis and ball milling. Fabrication is implemented in three steps: (1) formation of a tin-alginate layer on PAN fibres by coating sodium alginate on PAN in a water medium followed by polycondensation in SnCl2 solution; (2) heat treatment at 450°C in a nitrogen atmosphere; (3) ball milling the mixture of CNF/SnO2 fibres and Ni powder. The CNF/SnO2/Ni nanocomposite exhibits good lithium ion storage capacity and cyclability, providing a facile and low-cost approach for the large-scale preparation of anode materials for lithium ion batteries.

| S-EPMC6030287 | biostudies-literature

A Facile Route to Synthesize Nanographene Reinforced PBO Composites Fiber via in Situ Polymerization.

Project description:The polymer matrix with introduced carbon-based nanofiber displays fascinating properties. They have inspired extensive research on the synthesis of polymer composites, which have been applied in catalysis, electronics, and energy storage. In this report, we reported a facile and efficient method to prepare poly(p-phenylene benzobisoxazole) (PBO)/nanographene (PNG) composites fibers via in-situ polymerization, accompanied by the reduction from (nanographene oxide) NGO to (nanographene) NG. By tuning the ratio of feeding PBO monomer to NGO, various composites fibers with 0.1⁻1 wt % contents of NG were obtained. The efficient PBO chains grafting made NG uniformly disperse in the PBO matrix, and it also increased the uniformity of the packing orientation of PBO chains. Consequently, the tensile strength, tensile modulus, and thermal stability of the obtained PNG composites fibers had been improved significantly. In addition, the composites fibers with 0.5 wt % NG exhibited a 25% increment in tensile strength, and a 41% enhancement in tensile modulus compared with neat PBO fibers. It reveals an excellent reinforcement to PBO composites fibers with NG.

| S-EPMC6432332 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data