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Self-organisation of dodeca-dendronized fullerene into supramolecular discs and helical columns containing a nanowire-like core.

ABSTRACT: Twelve chiral and achiral self-assembling dendrons have been grafted onto a [60]fullerene hexa-adduct core by copper-catalyzed alkyne azide "click" cycloaddition. The structure adopted by these compounds was determined by the self-assembling peripheral dendrons. These twelve dendrons mediate the self-organisation of the dendronized [60]fullerene into a disc-shaped structure containing the [60]fullerene in the centre. The fullerene-containing discs self-organise into helical supramolecular columns with a fullerene nanowire-like core, forming a 2D columnar hexagonal periodic array. These unprecedented supramolecular structures and their assemblies are expected to provide new developments in chiral complex molecular systems and their application to organic electronics and solar cells.

SUBMITTER: Guerra S

PROVIDER: S-EPMC5657094 | biostudies-literature |

REPOSITORIES: biostudies-literature

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1,3,7,10,14,17,21,28,31,42,52,55-Dodeca-kis(trifluoro-meth-yl)- 1,3,7,10,14,17,21,28,31,42,52,55-dodeca-hydro-(C(60)-I)[5,6]fullerene.

Project description:The title compound, C(72)F(36), is one of four isomers of C(60)(CF(3))(12) for which crystal structures have been obtained. The fullerene mol-ecule has an idealized I(h) C(60) core with the 12 CF(3) groups arranged in an asymmetric fashion on two ribbons of edge-sharing C(6)(CF(3))(2) hexa-gons, a para-meta-para-para-para-meta-para ribbon and a para-meta-para ribbon, giving an overall pmp(3)mp,pmp structure. There are no cage Csp(3)-Csp(3) bonds. The F atoms of two CF(3) groups are disordered over two positions; the site occupancy factors are 0.85/0.15 and 0.73/0.27. There are intra-molecular F?F contacts between pairs of CF(3) groups on the same hexa-gon that range from 2.521?(3) to 2.738?(4)?Å.

| S-EPMC2915227 | biostudies-literature

Dual-Responsive Supramolecular Chiral Assemblies from Amphiphilic Dendronized Tetraphenylethylenes.

Project description:Supramolecular assembly of amphiphilic molecules in aqueous solutions to form stimuli-responsive entities is attractive for developing intelligent supramolecular materials for bioapplications. Here we report on the supramolecular chiral assembly of amphiphilic dendronized tetraphenylethylenes (TPEs) in aqueous solutions. Hydrophobic TPE moieties were connected to the hydrophilic three-fold dendritic oligoethylene glycols (OEGs) through a tripeptide proline-hydroxyproline-glycol (POG) to afford the characteristic topological structural effects of dendritic OEGs and the peptide linker. Both ethoxyl- and methoxyl-terminated dendritic OEGs were used to modulate the overall hydrophilicity of the dendronized TPEs. Their supramolecular aggregates exhibited thermoresponsive behavior that originated from the dehydration and collapse of the dendritic OEGs, and their cloud point temperatures (Tcps) were tailored by solution pH conditions. Furthermore, aggregation-induced fluorescent emission (AIE) from TPE moieties was used as an indicator to follow the assembly, which was reversibly tuned by temperature variation at different pH conditions. Supramolecular assemblies from these dendronized amphiphiles exhibited enhanced supramolecular chirality, which was dominated mainly by the interaction balance between TPE with dendritic OEG and TPE with POG moieties and was modulated through different solvation by changing solution temperature or pH conditions. More interestingly, ethoxyl-terminated dendritic OEG provided a much stronger shielding effect than its methoxyl-terminated counterpart to prevent amino groups within the peptide from protonation, even in strong acidic conditions, resulting in different responsive behavior to the solution temperature and pH conditions for these supramolecular aggregates.

| S-EPMC10537776 | biostudies-literature

Supramolecular frameworks based on [60]fullerene hexakisadducts.

Project description:[60]Fullerene hexakisadducts possessing 12 carboxylic acid side chains form crystalline hydrogen-bonding frameworks in the solid state. Depending on the length of the linker between the reactive sites and the malonate units, the distance of the [60]fullerene nodes and thereby the spacing of the frameworks can be controlled and for the most elongated derivative, continuous channels are obtained within the structure. Stability, structural integrity and porosity of the material were investigated by powder X-ray diffraction, thermogravimetry and sorption measurements.

| S-EPMC5238557 | biostudies-literature

Cortical-like mini-columns of neuronal cells on zinc oxide nanowire surfaces.

Project description:A long-standing goal of neuroscience is a theory that explains the formation of the minicolumns in the cerebral cortex. Minicolumns are the elementary computational units of the mature neocortex. Here, we use zinc oxide nanowires with controlled topography as substrates for neural-cell growth. We observe that neuronal cells form networks where the networks characteristics exhibit a high sensitivity to the topography of the nanowires. For certain values of nanowires density and fractal dimension, neuronal networks express small world attributes, with enhanced information flows. We observe that neurons in these networks congregate in superclusters of approximately 200 neurons. We demonstrate that this number is not coincidental: the maximum number of cells in a supercluster is limited by the competition between the binding energy between cells, adhesion to the substrate, and the kinetic energy of the system. Since cortical minicolumns have similar size, similar anatomical and topological characteristics of neuronal superclusters on nanowires surfaces, we conjecture that the formation of cortical minicolumns is likewise guided by the interplay between energy minimization, information optimization and topology. For the first time, we provide a clear account of the mechanisms of formation of the minicolumns in the brain.

| S-EPMC6411964 | biostudies-literature

Fabrication of supramolecular cyclodextrin-fullerene nonwovens by electrospinning.

Project description:Direct electrospinning of small molecules has great potential to fabricate a new class of fiber materials because this approach realizes the creation of various functional materials through the numerous molecular combinations. In this paper, we demonstrate a proof-of-concept to fabricate supramolecular fiber materials composed of cyclodextrin (CD)-fullerene inclusion complexes by electrospinning. Similar to the molecular state of fullerenes in solution, the resulting fibers include molecularly-dispersed fullerenes. We believe such a concept could be expanded to diverse host-guest complexes, opening up supramolecular solid materials science and engineering.

| S-EPMC6334797 | biostudies-literature

Dendronized supramolecular nanocapsules: pH independent, water-soluble, deep-cavity cavitands assemble via the hydrophobic effect.

Project description:At neutral pH, dendronized deep-cavity cavitands were shown to form supramolecular nanocapsules via assembly around a range of guest molecules.

| S-EPMC2744078 | biostudies-literature

Complex Arrangement of Orthogonal Nanoscale Columns via a Supramolecular Orientational Memory Effect.

Project description:Memory effects, including shape, chirality, and liquid-crystallinity, have enabled macroscopic materials with novel functions. However, the generation of complex supramolecular nanosystems via memory effects has not yet been investigated. Here, we report a cyclotriveratrylene-crown (CTV) compound that self-assembles into supramolecular columns and spheres forming, respectively, hexagonal and cubic mesophases. Upon transition from one phase to the other, an epitaxial relationship holds, via an unprecedented supramolecular orientational memory effect. Specifically, the molecular orientation and columnar character of supramolecular packing is preserved in the cubic phase, providing an otherwise inaccessible structure comprising orthogonally oriented domains of supramolecular columns. The continuous columnar character of tetrahedrally distorted supramolecular spheres self-organized from the CTV derivative in the faces of the Pm3?n lattice is the basis of this supramolecular orientational memory, which holds throughout cycling in temperature between the two phases. This concept is expected to be general for other combinations of periodic and quasiperiodic arrays generated from supramolecular spheres upon transition to supramolecular columns.

| S-EPMC5292035 | biostudies-literature

Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography.

Project description:We report on a potential method to separate sugars by using the specific interaction between fullerenes and saccharides in liquid chromatography (LC). Aromatic rings with high electron density are believed to interact strongly with saccharides due to CH-π and/or OH-π interactions. In this study, the fullerene-bonded columns were used to separate saccharides by LC under aqueous conditions. As a result, 2-aminobenzamide-labeled glucose homopolymer (Glcs) was effectively separated by both C60 and C70 columns in the range of Glc-1 to Glc-20 and high blood glucose level being retained in greater quantity. Furthermore, similar separations were identified by LC-mass spectrometry with non-labeled glucose homopolymers. Theoretical study based on molecular dynamics and DFT calculation demonstrated that a supramolecular complex of saccharide-fullerene was formed through CH-π and/or OH-π interactions, and that the interactions between saccharide and fullerene increase with the increase units of the saccharide. Additionally, the C60 column retained disaccharides containing maltose, trehalose, and sucrose. In this case, it was assumed that the retention rates were determined by the difference of the dipole moment in each saccharide. These results suggest that the dipole-induced dipole interaction was dominant, and that maltose-with the higher dipole moment-was more strongly retained compared to other disaccharides having lower dipole moment.

| S-EPMC7429847 | biostudies-literature

Conductance through a helical state in an Indium antimonide nanowire.

Project description:The motion of an electron and its spin are generally not coupled. However in a one-dimensional material with strong spin-orbit interaction (SOI) a helical state may emerge at finite magnetic fields, where electrons of opposite spin will have opposite momentum. The existence of this helical state has applications for spin filtering and cooper pair splitter devices and is an essential ingredient for realizing topologically protected quantum computing using Majorana zero modes. Here, we report measurements of a quantum point contact in an indium antimonide nanowire. At magnetic fields exceeding 3 T, the 2 e 2/h conductance plateau shows a re-entrant feature toward 1 e 2/h which increases linearly in width with magnetic field. Rotating the magnetic field clearly attributes this experimental signature to SOI and by comparing our observations with a numerical model we extract a spin-orbit energy of approximately 6.5 meV, which is stronger than the spin-orbit energy obtained by other methods.Indium antimonide nanowires have large spin-orbit coupling, which can give rise to helical states that are an important part of proposals for topological quantum computing. Here the authors measure conductance through the helical states and extract a larger spin-orbit energy than obtained before.

| S-EPMC5589903 | biostudies-literature

A ?-gel scaffold for assembling fullerene to photoconducting supramolecular rods.

Project description:Nonequilibrium self-assembly of molecules holds a huge prospect as a tool for obtaining new-generation materials for future applications. Crystallization of neutral molecules within a supramolecular gel matrix is one example in which two nonequilibrium processes occur orthogonal to each other. On the other hand, electronically interacting donor-acceptor two-component systems are expected to form phase-miscible hybrid systems. Contrary to the expectation, we report the behavior of a ?-gel, derived from oligo(p-phenylenevinylene), OPVA, as a scaffold for the phase separation and crystallization of fullerene (C60) to supramolecular rods with increased transient photoconductivity (???max = 2.4 × 10-4 cm2 V-1 s-1). The C60 supramolecular rods in the ?-gel medium exhibited high photocurrent in comparison to C60 loaded in a non-?-gel medium. This finding provides an opportunity for large-scale preparation of micrometer-sized photoconducting rods of fullerenes for device application.

| S-EPMC5035126 | biostudies-literature

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