Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations.

ABSTRACT: Nitrogen-doped polycyclic aromatic hydrocarbons (aza-PAHs) have found broad applications in material sciences. Herein, a modular electrochemical synthesis of aza-PAHs was developed via a rhodium-catalyzed cascade C-H activation and alkyne annulation. A multifunctional O-methylamidoxime enabled the high chemo- and regioselectivity. The isolation of two key rhodacyclic intermediates made it possible to delineate the exact order of three C-H activation steps. In addition, the metalla-electrocatalyzed multiple C-H transformation is characterized by unique functional group tolerance, including highly reactive iodo and azido groups.

SUBMITTER: Kong WJ

PROVIDER: S-EPMC7155118 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations.

Kong Wei-Jun WJ Shen Zhigao Z Finger Lars H LH Ackermann Lutz L

Angewandte Chemie (International ed. in English) 20200128 14

Nitrogen-doped polycyclic aromatic hydrocarbons (aza-PAHs) have found broad applications in material sciences. Herein, a modular electrochemical synthesis of aza-PAHs was developed via a rhodium-catalyzed cascade C-H activation and alkyne annulation. A multifunctional O-methylamidoxime enabled the high chemo- and regioselectivity. The isolation of two key rhodacyclic intermediates made it possible to delineate the exact order of three C-H activation steps. In addition, the metalla-electrocatalyz ...[more]

PMID: 31793169

Similar Datasets

HepG2 treated with Polycyclic Aromatic Hydrocarbons (PAHs)

2012-04-18 | GSE37326 | GEO

Polycyclic aromatic hydrocarbons degraders

Project description:Polycyclic aromatic hydrocarbons degraders Raw sequence reads

| PRJNA590550 | ENA

HepG2 treated with Polycyclic Aromatic Hydrocarbons (PAHs)

Project description:Assessing the potential carcinogenicity of human toxins represents an ongoing challenge. Chronic rodent bioassays predict human cancer risk with limited reliability, and are expensive and time-consuming. To identify alternative prediction methods, we evaluated a transcriptomics-based human in vitro model to classify carcinogens by their modes of action. The aim of this study was to determine the transcriptomic response and identify specific molecular signatures of polycyclic aromatic hydrocarbons (PAHs), which can be used as predictors of carcinogenicity of environmental toxins in human in vitro systems. We found that characteristic molecular signatures facilitate identification and prediction of carcinogens. To evaluate the change in gene expression levels, human hepatocellular carcinoma (HepG2) cells were exposed to nine different PAHs (benzo[a]pyrene, dibenzo[a,h]anthracene, 3-methylcholanthrene, naphthalene, chrysene, phenanthrene, benzo[a]anthracene, benzo[k]fluoranthene, and indeno[1,2,3-c,d]pyrene) for 48 h. Gene expression analysis was conducted using a 44K whole human genome microarray (Agilent Technologies, USA).

2012-04-17 | E-GEOD-37326 | biostudies-arrayexpress

Polycyclic aromatic hydrocarbons-Polluted Soil

Project description:Polycyclic aromatic hydrocarbons-Polluted Soil Metagenome

| PRJNA656884 | ENA

Zirconacyclopentadiene-Annulated Polycyclic Aromatic Hydrocarbons.

Project description:Syntheses of large polycyclic aromatic hydrocarbons (PAHs) and graphene nanostructures demand methods that are capable of selectively and efficiently fusing large numbers of aromatic rings, yet such methods remain scarce. Herein, we report a new approach that is based on the quantitative intramolecular reductive cyclization of an oligo(diyne) with a low-valent zirconocene reagent, which gives a PAH with one or more annulated zirconacyclopentadienes (ZrPAHs). The efficiency of this process is demonstrated by a high-yielding fivefold intramolecular coupling to form a helical ZrPAH with 16?fused rings (from a precursor with no fused rings). Several other PAH topologies are also reported. Protodemetalation of the ZrPAHs allowed full characterization (including by X-ray crystallography) of PAHs containing one or more appended dienes with the ortho-quinodimethane (o-QDM) structure, which are usually too reactive for isolation and are potentially valuable for the fusion of additional rings by Diels-Alder reactions.

| S-EPMC5671771 | biostudies-literature

Rhoda-Electrocatalyzed C-H Methylation and Paired Electrocatalyzed C-H Ethylation and Propylation.

Project description:The use of electricity over traditional stoichiometric oxidants is a promising strategy for sustainable molecular assembly. Herein, we describe the rhoda-electrocatalyzed C-H activation/alkylation of several N-heteroarenes. This catalytic approach has been successfully applied to several arenes, including biologically relevant purines, diazepam, and amino acids. The versatile C-H alkylation featured water as a co-solvent and user-friendly trifluoroborates as alkylating agents. Finally, the rhoda-electrocatalysis with unsaturated organotrifluoroborates proceeded by paired electrolysis.

| S-EPMC9299020 | biostudies-literature

Extended O-Doped Polycyclic Aromatic Hydrocarbons.

Project description:The synthesis of O-doped benzorylenes, in which peripheral carbon atoms have been replaced by oxygen atoms, has been achieved for the first time. This includes key high-yielding ring-closure steps which, through intramolecular C-O bond formation, allow stepwise planarization of oligonaphthalenes. Single-crystal X-ray diffraction showed that the tetraoxa derivative forms remarkable face-to-face ?-? stacks in the solid state, a favorable solid-state arrangement for organic electronics.

| S-EPMC5071652 | biostudies-literature

Classifying polycyclic aromatic hydrocarbons by carcinogenic potency using in vitro biosignatures

Project description:In this study, we compare genomic signature safter treatment ofprimary human bronchial epithelial cells (HBEC) cultured in 3D with polycyclic aromatic hydrocarbons (PAHs) and identify genesets predictive of cancer risk.

2020-10-28 | GSE156147 | GEO

Proteinaceous Nano container Encapsulate Polycyclic Aromatic Hydrocarbons.

Project description:Polycyclic aromatic hydrocarbons (PAHs) are toxic, mutagenic and among the most damaging chemical compounds with regard to living organisms. Because of their persistence and wide distribution removal from the environment is an important challenge. Here we report a new Nano container matrix based on the deep sea archaea-derived RHCC-Nanotube (RHCC-NT), which rapidly and preferentially binds low molecular weight PAHs. Under controlled-laboratory conditions and using fluorescence spectroscopy in combination with X-ray crystallography and MD simulations, we quantified the real-time binding of low molecular weight PAHs (2-4 rings) to our substrate. Binding coefficients ranged from 5.4?±?1.6 (fluorene) to 32?±?7.0??M (acenaphthylene) and a binding capacity of 85 pmoles PAH per mg RHCC-NT, or 2.12 ?moles in a standard 25?mg sampler. The uptake rate of pyrene was calculated to be 1.59 nmol/hr?mol RHCC-NT (at 10? C). Our results clearly show that RHCC-NT is uniquely suited as a monitoring matrix for low molecular weight PAHs.

| S-EPMC6355809 | biostudies-literature

Anharmonic vibrational spectroscopy of polycyclic aromatic hydrocarbons (PAHs).

Project description:While powerful techniques exist to accurately account for anharmonicity in vibrational molecular spectroscopy, they are computationally very expensive and cannot be routinely employed for large species and/or at non-zero vibrational temperatures. Motivated by the study of Polycyclic Aromatic Hydrocarbon (PAH) emission in space, we developed a new code, which takes into account all modes and can describe all infrared transitions including bands becoming active due to resonances as well as overtone, combination, and difference bands. In this article, we describe the methodology that was implemented and discuss how the main difficulties were overcome, so as to keep the problem tractable. Benchmarking with high-level calculations was performed on a small molecule. We carried out specific convergence tests on two prototypical PAHs, pyrene (C16H10) and coronene (C24H12), aiming at optimising tunable parameters to achieve both acceptable accuracy and computational costs for this class of molecules. We then report the results obtained at 0 K for pyrene and coronene, comparing the calculated spectra with available experimental data. The theoretical band positions were found to be significantly improved compared to harmonic density functional theory calculations. The band intensities are in reasonable agreement with experiments, the main limitation being the accuracy of the underlying calculations of the quartic force field. This is a first step toward calculating moderately high-temperature spectra of PAHs and other similarly rigid molecules using Monte Carlo sampling.

| S-EPMC6214506 | biostudies-other

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