Browse
Submit Data
Databases
API
Help

Dataset Information

18 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Contorted Polycyclic Aromatic Hydrocarbons with Two Embedded Azulene Units.

ABSTRACT: Polycyclic aromatic hydrocarbons (PAHs) that contain both five- and seven-membered rings are rare, and those where these rings are annulated to each other and build azulene units have, to date, mainly been generated in minute amounts on surfaces. Herein, a rational approach to synthesize soluble contorted PAHs containing two embedded azulene units in the bulk is presented. By stepwise detachment of tert-butyl groups, a series of three azulene embedded PAHs with different degrees of contortion has been made to study the impact of curvature on aromaticity and conjugation. Furthermore, the azulene PAHs showed high fluorescence quantum yields in the NIR regime.

SUBMITTER: Yang X

PROVIDER: S-EPMC6899884 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Contorted Polycyclic Aromatic Hydrocarbons with Two Embedded Azulene Units.

Yang Xuan X Rominger Frank F Mastalerz Michael M

Angewandte Chemie (International ed. in English) 20191023 49

Polycyclic aromatic hydrocarbons (PAHs) that contain both five- and seven-membered rings are rare, and those where these rings are annulated to each other and build azulene units have, to date, mainly been generated in minute amounts on surfaces. Herein, a rational approach to synthesize soluble contorted PAHs containing two embedded azulene units in the bulk is presented. By stepwise detachment of tert-butyl groups, a series of three azulene embedded PAHs with different degrees of contortion ha ...[more]

PMID: 31550407

Similar Datasets

Visualizing electron delocalization in contorted polycyclic aromatic hydrocarbons.

Project description:Electron delocalization in contorted polycyclic aromatic hydrocarbon (PAH) molecules was examined through 3D isotropic magnetic shielding (IMS) contour maps built around the molecules using pseudo-van der Waals surfaces. The resulting maps of electron delocalization provided an intuitive, yet detailed and quantitative evaluation of the aromatic, non aromatic, and antiaromatic character of the local and global conjugated cyclic circuits distributed over the molecules. An attractive pictural feature of the 3D IMS contour maps is that they are reminiscent of the Clar π-sextet model of aromaticity. The difference in delocalization patterns between the two faces of the electron circuits in contorted PAHs was clearly visualized. For π-extended contorted PAHs, some splits of the π system resulted in recognizable patterns typical of smaller PAHs. The differences between the delocalization patterns of diastereomeric chiral PAHs could also be visualized. Mapping IMS on pseudo-van der Waals surfaces around contorted PAHs allowed visualization of their superimposed preferred circuits for electron delocalization and hence their local and global aromaticity patterns.

| S-EPMC8513938 | biostudies-literature

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 two Polycyclic Aromatic Hydrocarbons (benzo[a]anthracene & benzo[k]fluoranthene)

Project description:To gain deeper insight into the mechanism of toxicity, it is important to identify and characterize miRNAs profiles involved in responses to specific classes of toxicants in conjunction with their impact on gene expression levels. However, few reports have described the effects of toxicants on miRNA expression profiles. Taking into account the prominent role of miRNAs in cancer development, progression, cell cycle control, and proliferation-related processes, it is likely that miRNAs are involved in the toxic response induced by carcinogens. Polycyclic aromatic hydrocarbons (PAHs) are a well-characterized class of human carcinogens. In the present study, we documented the different expression profiles of miRNAs in environmental carcinogen-exposed HepG2 cells by miRNA microarray analysis.

2013-07-22 | GSE49068 | GEO

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

HepG2 treated with two Polycyclic Aromatic Hydrocarbons (benzo[a]anthracene & benzo[k]fluoranthene)

2013-07-22 | E-GEOD-49068 | biostudies-arrayexpress

?-CD Dimer-immobilized Ag Assembly Embedded Silica Nanoparticles for Sensitive Detection of Polycyclic Aromatic Hydrocarbons.

Project description:We designed a ?-CD dimer on silver nanoparticles embedded with silica nanoparticles (Ag@SiO2 NPs) structure to detect polycyclic aromatic hydrocarbons (PAHs). Silica NPs were utilized as a template for embedding silver NPs to create hot spot structures and enhance the surface-enhanced Raman scattering (SERS) signal, and a thioether-bridged dimeric ?-CD was immobilized on Ag NPs to capture PAHs. The assembled Ag NPs on silica NPs were confirmed by TEM and the presence of ?-CD dimer on Ag@SiO2 was confirmed by UV-vis and attenuated total reflection-Fourier transform infrared spectroscopy. The ?-CD dimer@Ag@SiO2 NPs were used as SERS substrate for detecting perylene, a PAH, directly and in a wide linearity range of 10(-7)?M to 10(-2)?M with a low detection limit of 10(-8)?M. Also, the ?-CD dimer@Ag@SiO2 NPs exhibited 1000-fold greater sensitivity than Ag@SiO2 NPs in terms of their perylene detection limit. Furthermore, we demonstrated the possibility of detecting various PAH compounds using the ?-CD dimer@Ag@SiO2 NPs as a multiplex detection tool. Various PAH compounds with the NPs exhibited their distinct SERS bands by the ratio of each PAHs. This approach of utilizing the assembled structure and the ligands to recognize target has potential for use in sensitive analytical sensors.

| S-EPMC4869113 | 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

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