Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Edge-Decorated Polycyclic Aromatic Hydrocarbons by an Oxidative Coupling Approach.

ABSTRACT: Oxidative phenol coupling reduces reliance on halo/metalated substrates used in conventional redox neutral couplings. A new strategy for constructing polycyclic aromatic hydrocarbons (PAHs) that incorporates oxidative phenol coupling is outlined in a three-stage approach: oxidative fragment coupling, linking of the two resultant units, and oxidative cyclization. The protocol allows rapid assembly of both planar and helical systems with a high degree of edge functionalization. The incorporation of 12 alkoxy groups on systems with 12 rings gave rise to lower optical gaps compared to systems with a lesser degree of edge functionalization.

SUBMITTER: Gilmartin P

PROVIDER: S-EPMC9957926 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Edge-Decorated Polycyclic Aromatic Hydrocarbons by an Oxidative Coupling Approach.

Gilmartin Philip P Vu Cassandra C Rotella Madeline M Kaur Jasjit J Kozlowski Marisa M

Chemistry (Weinheim an der Bergstrasse, Germany) 20221229 10

Oxidative phenol coupling reduces reliance on halo/metalated substrates used in conventional redox neutral couplings. A new strategy for constructing polycyclic aromatic hydrocarbons (PAHs) that incorporates oxidative phenol coupling is outlined in a three-stage approach: oxidative fragment coupling, linking of the two resultant units, and oxidative cyclization. The protocol allows rapid assembly of both planar and helical systems with a high degree of edge functionalization. The incorporation o ...[more]

PMID: 36332182

Similar Datasets

Polycyclic aromatic hydrocarbons degraders

Project description:Polycyclic aromatic hydrocarbons degraders Raw sequence reads

| PRJNA590550 | ENA

HepG2 treated with Polycyclic Aromatic Hydrocarbons (PAHs)

2012-04-18 | GSE37326 | GEO

Polycyclic aromatic hydrocarbons-Polluted Soil

Project description:Polycyclic aromatic hydrocarbons-Polluted Soil Metagenome

| PRJNA656884 | 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

An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons.

Project description:The application of a new benzannulation reaction for the regiocontrolled synthesis of functionalized chrysenes is reported. The initial benzannulation and the subsequent halogen displacement reactions are both highly regiospecific, which thereby enables the regiocontrolled synthesis of a variety of 4,10-disubstituted chrysenes from commercially available 1,5-dihydroxynaphthalene.

| S-EPMC4068280 | biostudies-literature

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

Photoredox Annulation of Polycyclic Aromatic Hydrocarbons.

Project description:The rise of interest in using polycyclic aromatic hydrocarbons (PAHs) and molecular graphenoids in optoelectronics has recently stimulated the growth of modern synthetic methodologies giving access to intramolecular aryl-aryl couplings. Here, we show that a radical-based annulation protocol allows expansion of the planarization approaches to prepare functionalized molecular graphenoids. The enabler of this reaction is peri-xanthenoxanthene, the photocatalyst which undergoes photoinduced single electron transfer with an ortho-oligoarylenyl precursor bearing electron-withdrawing and nucleofuge groups. Dissociative electron transfer enables the formation of persistent aryl radical intermediates, the latter undergoing intramolecular C-C bond formation, allowing the planarization reaction to occur. The reaction conditions are mild and compatible with various electron-withdrawing and -donating substituents on the aryl rings as well as heterocycles and PAHs. The method could be applied to induce double annulation reactions, allowing the synthesis of π-extended scaffolds with different edge peripheries.

| S-EPMC10685425 | 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 π-π stacks in the solid state, a favorable solid-state arrangement for organic electronics.

| S-EPMC5071652 | biostudies-literature

Association of mixed polycyclic aromatic hydrocarbons exposure with oxidative stress in Korean adults.

Project description:Polycyclic aromatic hydrocarbons (PAHs) are widespread pollutants associated with several adverse health effects and PAH-induced oxidative stress has been proposed as a potential mechanism. This study evaluated the associations of single and multiple PAHs exposure with oxidative stress within the Korean adult population, using serum gamma glutamyltransferase (GGT) as an oxidative stress marker. Data from the Second Korean National Environmental Health Survey (2012-2014) were analyzed. For analysis, 5225 individuals were included. PAH exposure was assessed with four urinary PAH metabolites: 1-hydroxyphenanthrene, 1-hydroxypyrene, 2-hydroxyfluorene, and 2-naphthol. After adjusting for age, sex, body mass index, drinking, passive smoking, and current smoking (model 1), as well as the presence of diabetes and hepatobiliary diseases (model 2), complex samples general linear model regression analyses for each metabolite revealed a significant positive association between Ln(1-hydroxyphenanthrene) and Ln(GGT) (model 1: β = 0.040, p < 0.01 and model 2: β = 0.044, p < 0.05). For the complete dataset (n = 4378), a significant positive association was observed between mixture of four urinary PAH metabolites and serum GGT in both the quantile g-computation and the Bayesian kernel machine regression analysis. Our study provides evidence for the association between mixed PAH exposure and oxidative stress.

| S-EPMC10980696 | 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

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