Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Nitrogen-embedded buckybowl and its assembly with C60.

ABSTRACT: Curved π-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved π surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved π systems. Here we report the synthesis of a π-extended azacorannulene with nitrogen in its centre. The oxidation of 9-aminophenanthrene provides tetrabenzocarbazole, which is converted to the azabuckybowl through palladium-catalysed intramolecular coupling. The electron-donating nature and curved π surface of the azabuckybowl enable its tight association with C60 in solution and solid states. High charge mobility is observed for the azabuckybowl/C60 assembly. This compound may be of interest in the fields of curved π systems as fullerene hosts, anisotropic π donors and precursors to nitrogen-containing nanocarbon materials.

SUBMITTER: Yokoi H

PROVIDER: S-EPMC4569845 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Nitrogen-embedded buckybowl and its assembly with C60.

Yokoi Hiroki H Hiraoka Yuya Y Hiroto Satoru S Sakamaki Daisuke D Seki Shu S Shinokubo Hiroshi H

Nature communications 20150904

Curved π-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved π surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved π systems. Here we report the synthesis of a π-extended azacorannulene with nitrogen in its centre. The oxidation of 9-aminophenanthrene provides tetrabenzocarbazole, which is converted to the azabuckybowl through palladium- ...[more]

PMID: 26337912

Similar Datasets

Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60.

Project description:A directly connected azabuckybowl dimer was synthesized via a palladium-catalysed C-H/C-Br coupling. The electron-donating nature of the pyrrolic nitrogen atoms of the azabuckybowl enabled a strong complexation with pristine C60. In the presence of two equivalents of C60, the azabuckybowl dimer formed crystals with a 1 : 2 stoichiometry. Conversely, in diluted solution, complexes with a 1 : 1 stoichiometry of the dimer and C60 were detected predominantly, and these precipitated upon increasing the concentration of C60. Scanning electron microscopy images of the precipitate showed fibre-like aggregates, indicating the formation of supramolecular assemblies with 1D chain structures. A variable-temperature 1H NMR analysis revealed that the precipitate consists of the dimer and C60 in a 1 : 1 ratio.

| S-EPMC5872494 | biostudies-literature

On-surface synthesis of a nitrogen-embedded buckybowl with inverse Stone-Thrower-Wales topology.

Project description:Curved π-conjugated polycyclic aromatic hydrocarbons, buckybowls, constitute an important class of materials with wide applications in materials science. Heteroatom doping of buckybowls is a viable route to tune their intrinsic physicochemical properties. However, synthesis of heteroatom-doped buckybowls is a challenging task. We report on a combined in-solution and on-surface synthetic strategy toward the fabrication of a buckybowl containing two fused nitrogen-doped pentagonal rings. We employ ultra-high-resolution scanning tunneling microscopy and spectroscopy, in combination with density functional theory calculations to characterize the final compound. The buckybowl contains a unique combination of non-hexagonal rings at its core, identified as the inverse Stone-Thrower-Wales topology, resulting in a distinctive bowl-opening-down conformation of the buckybowl on the surface. Our controlled design of non-alternant, heteroatom-doped polycyclic aromatic frameworks with established bottom-up fabrication techniques opens new opportunities in the synthesis of carbon nanostructures with the perspective of engineering properties of graphene-based devices.

| S-EPMC5928119 | biostudies-literature

Diffusion and self-assembly of C60 molecules on monolayer graphyne sheets.

Project description:The motion of a fullerene (C60) on 5 different types of graphyne is studied by all-atom molecular dynamics simulations and compared with former studies on the motion of C60 on graphene. The motion shows a diffusive behavior which consists of either a continuous motion or discrete movements between trapping sites depending on the type of the graphyne sheet. For graphyne-4 and graphyne-5, fullerenes could detach from the surface of the graphyne sheet at room temperature which was not reported for similar cases on graphene sheets. Collective motion of a group of fullerenes interacting with a graphyne studied and it is shown that fullerenes exhibit stable assemblies. Depending on the type of graphyne, these assemblies can have either single or double layers. The mobility of the assembled structures is also dependent on the type of the graphyne sheet. The observed properties of the motion suggests novel applications for the complexes of fullerene and monolayer graphynes.

| S-EPMC4766508 | biostudies-literature

Micromirror-Embedded Coverslip Assembly for Bidirectional Microscopic Imaging.

Project description:3D imaging of a biological sample provides information about cellular and subcellular structures that are important in cell biology and related diseases. However, most 3D imaging systems, such as confocal and tomographic microscopy systems, are complex and expensive. Here, we developed a quasi-3D imaging tool that is compatible with most conventional microscopes by integrating micromirrors and microchannel structures on coverslips to provide bidirectional imaging. Microfabricated micromirrors had a precisely 45° reflection angle and optically clean reflective surfaces with high reflectance over 95%. The micromirrors were embedded on coverslips that could be assembled as a microchannel structure. We demonstrated that this simple disposable device allows a conventional microscope to perform bidirectional imaging with simple control of a focal plane. Images of microbeads and cells under bright-field and fluorescent microscopy show that the device can provide a quick analysis of 3D information, such as 3D positions and subcellular structures.

| S-EPMC7345240 | biostudies-literature

Atom-Photon Coupling from Nitrogen-vacancy Centres Embedded in Tellurite Microspheres.

Project description:We have developed a technique for creating high quality tellurite microspheres with embedded nanodiamonds (NDs) containing nitrogen-vacancy (NV) centres. This hybrid method allows fluorescence of the NVs in the NDs to be directly, rather than evanescently, coupled to the whispering gallery modes of the tellurite microspheres at room temperature. As a demonstration of its sensing potential, shifting of the resonance peaks is also demonstrated by coating a sphere surface with a liquid layer. This new approach is a robust way of creating cavities for use in quantum and sensing applications.

| S-EPMC4476097 | biostudies-other

Escherichia coli strain:C60

Project description:Escherichia coli strain:C60 Genome sequencing and assembly

| PRJNA382427 | ENA

Directed block copolymer self-assembly implemented via surface-embedded electrets.

Project description:Block copolymer (BCP) nanolithography is widely recognized as a promising complementary approach to circumvent the feature size limits of conventional photolithography. The directed self-assembly of BCP thin film to form ordered nanostructures with controlled orientation and localized pattern has been the key challenge for practical nanolithography applications. Here we show that BCP nanopatterns can be directed on localized surface electrets defined by electron-beam irradiation to realize diverse features in a simple, effective and non-destructive manner. Charged electrets can generate a built-in electric field in BCP thin film and induce the formation of perpendicularly oriented microdomain of BCP film. The electret-directed orientation control of BCP film can be either integrated with mask-based patterning technique or realized by electron-beam direct-writing method to fabricate microscale arbitrary lateral patterns down to single BCP cylinder nanopattern. The electret-directed BCP self-assembly could provide an alternative means for BCP-based nanolithography, with high resolution.

| S-EPMC4756386 | biostudies-literature

Dynamics of quantum correlation between separated nitrogen-vacancy centers embedded in plasmonic waveguide.

Project description:We investigate the dynamics of quantum correlation between two separated nitrogen vacancy centers (NVCs) placed near a one-dimensional plasmonic waveguide. As a common medium of the radiation field of NVCs propagating, the plasmonic waveguide can dynamically induce quantum correlation between the two NVCs. It is interesting to find that such dynamically induced quantum correlation can be preserved in the long-time steady state by locally applying individual driving on the two NVCs. In particular, we also show that a large degree of quantum correlation can be established by this scheme even when the distance between the NVCs is much larger than their operating wavelength. This feature may open new perspectives for devising active decoherence-immune solid-state optical devices and long-distance NVC-based quantum networks in the context of plasmonic quantum electrodynamics.

| S-EPMC4616030 | biostudies-other

Buckybowl and its chiral hybrids featuring eight-membered rings and helicene units.

Project description:Here we report the synthesis of a novel buckybowl (7) with a high bowl-to-bowl inversion barrier (ΔG‡ = 38 kcal mol-1), which renders the rate of inversion slow enough at room temperature to establish two chiral polycyclic aromatic hydrocarbons (PAHs). By strategic fusion of eight-membered rings to the rim of 7, the chiral hybrids 8 and 9 are synthesized and display helicity and positive and negative curvature, allowing the enantiomers to be configurationally stable and their chiroptical properties are thoroughly examined. Computational and experimental studies reveal the enantiomerization mechanisms for the chiral hybrids and demonstrate that the eight-membered ring strongly affects the conformational stability. Because of its static and doubly curved conformation, 9 shows a high binding affinity towards C60. The OFET performance of 7-9 could be tuned and the hybrids show ambipolar characteristics. Notably, the 9·C60 cocrystal exhibits well-balanced ambipolar performance with electron and hole mobilities of up to 0.19 and 0.11 cm2 V-1 s-1, respectively. This is the first demonstration of a chiral curved PAH and its complex with C60 for organic devices. Our work presents new insight into buckybowl-based design of PAHs with configurational stability and intriguing optoelectronic properties.

| S-EPMC10548505 | biostudies-literature

Hexathioalkyl sumanenes: an electron-donating buckybowl as a building block for supramolecular materials.

Project description:Unlike planar aromatic compounds, bowl-shaped sumanene, which has concave and convex faces with different electrostatic potentials, tends to form a one-dimensional columnar assembly without causing slip-stacking in the crystal. Here we report the first successful synthesis of liquid-crystalline (LC) sumanenes, which was brought about by the incorporation of six thioalkyl groups (R = SC6H13 or SC12H25) into the aromatic part of sumanene. In contrast to the case of the mesophase formation of corannulene, which requires the presence of many dendritic side chains, sumanene derivatives with simple alkyl chains can exhibit a remarkably high-order columnar LC mesophase over a wide temperature range. While non-substituted sumanene inherently behaves as an electron acceptor, hexathioalkyl versions, such as hexathiomethyl sumanene, show electron-donating properties, resulting in complexation with C60. Considering its unique shape, electronic properties, and self-assembly behavior, the electron-donating sumanene may represent a new building block for constructing supramolecular materials, both by itself and in combination with fullerene derivatives.

| S-EPMC5863616 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

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