Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of reactive 1,3-diphenyl-6-aryl-substituted fulvene chromophores.

ABSTRACT: This data article describes a detailed synthetic strategy and experimental data for the synthesis of brominated fulvene chromophores as reactive precursors/monomers for conjugated organic materials. Metal-mediated coupling reactions of brominated fulvenes would result in conjugated small molecules or polymers that would find application as organic light emitting diodes (OLEDs) and photovoltaic (PV) applications.

SUBMITTER: Budy SM

PROVIDER: S-EPMC6141161 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of reactive 1,3-diphenyl-6-aryl-substituted fulvene chromophores.

Budy Stephen M SM Son David Y DY Balaich Gary J GJ Iacono Scott T ST

Data in brief 20180622

This data article describes a detailed synthetic strategy and experimental data for the synthesis of brominated fulvene chromophores as reactive precursors/monomers for conjugated organic materials. Metal-mediated coupling reactions of brominated fulvenes would result in conjugated small molecules or polymers that would find application as organic light emitting diodes (OLEDs) and photovoltaic (PV) applications. ...[more]

PMID: 30229036

Similar Datasets

Crystal structures of a series of 6-aryl-1,3-diphenyl-fulvenes.

Project description:The synthesis and crystal structures of a series of 6-aryl-fuvlenes (fulvene is 5-methyl-idene-cyclo-penta-1,3-diene) with varying methyl-ation patterns on the 6-phenyl substituent are reported, namely 6-(3-methyl-phen-yl)-1,3-di-phenyl-fulvene (C25H20), 6-(4-methyl-phen-yl)-1,3-di-phenyl-fulvene (C25H20), 6-mesityl-3-di-phenyl-fulvene (C27H24) and 6-(2,3,4,5,6-penta-methyl-phen-yl)-1,3-di-phenyl-fulvene (C29H28). The bond lengths are typical of those observed in related fulvenes. A network of C-H⋯π ring inter-actions consolidates the packing in each structure.

| S-EPMC6658983 | biostudies-literature

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes.

Project description:Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl-4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at -75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2 at -60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. -45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3-dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.

| S-EPMC5629374 | biostudies-literature

Coordination complexes of chromium(0) with a series of 1,3-diphenyl-6-aryl-fulvenes.

Project description:The synthesis and structural properties of a series of chromium tricarbonyl 'piano-stool' complexes bearing substituted penta-fulvene ligands were studied. The complexes, tricarbon-yl(1,3,6-tri-phenyl-fulvene)chromium(0) benz-ene hemisolvate, [Cr(C24H18)(CO)3]·0.5C6H6 (I), tricarbon-yl[1,3-di-phen-yl-6-(3-vinyl-phen-yl)fulvene]chromium(0), [Cr(C26H20)(CO)3] (II), and tricarbon-yl[1,3-diphenyl-6-(pyren-1-yl)fulvene]chromium(0), [Cr(C34H22)(CO)3] (III), each have a distorted octa-hedral geometry, with the fulvene coordinated in a π-η2:π-η2:π-η2 fashion. Significant deviation of the exocyclic fulvene double bond from the cyclo-penta-diene plane accompanies coordination. Evidence of non-covalent π-π inter-actions was observed in both (I) and (III), with centroid-to-centroid distances ranging from 3.330 (8) to 3.494 (8) Å.

| S-EPMC6127717 | biostudies-literature

1,3-Diethyl-1,3-diphenyl-urea.

Project description:The mol-ecule of the title compound, C(17)H(20)N(2)O, a symmetrical derivative of urea, shows non-crystallographic C(2) symmetry. Inter-action with the aromatic system of the phenyl substituents as well as amide-type resonance is responsible for the marked planarization of the coordination environments of the N atoms. C-H?O contacts give rise to the formation of centrosymmetric dimers in the crystal structure. The closest distance between the centroids of two adjacent rings is 3.8938?(11)?Å.

| S-EPMC3100078 | biostudies-literature

Boron-substituted 1,3-dihydro-1,3-azaborines: synthesis, structure, and evaluation of aromaticity.

Project description:Getting the family together: A general synthetic strategy based on nucleophilic substitution provided B-substituted 1,3-dihydro-1,3-azaborines (see scheme), BN isosteres of arenes with potential for application in biomedicine and materials science. Experimental structural analysis and calculations suggest that the aromaticity of the 1,3-dihydro-1,3-azaborine heterocycle is intermediate between that of benzene and that of 1,2-dihydro-1,2-azaborine.

| S-EPMC3813462 | biostudies-literature

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins.

Project description:Novel dihydro-1,3-oxazinoporphyrins and naphtho[e]bis(dihydro-1,3-oxazinoporphyrin) derivatives, in which the porphyrin macrocycle is covalently linked to the dihydro-1,3-oxazine ring system were successfully synthesized from 5-(4-aminophenyl)-10,15,20-triphenylporphyrin in good yields. The structures of the target products were established on the basis of spectral data and elemental analyses.

| S-EPMC3628549 | biostudies-other

Metal-Free Synthesis of 1,3-Disiloxanediols and Aryl Siloxanols.

Project description:The first example of metal-free oxidative hydrolysis of hydrido-siloxanes is reported. Both base-catalyzed and organocatalytic hydrolysis methods are demonstrated to transform 1,3-dihydrido-disiloxanes into 1,3-disiloxanediols. The first example of a chemoselective silane hydrolysis is demonstrated.

| S-EPMC6648610 | biostudies-literature

An efficient catalytic method for fulvene synthesis.

Project description:The effects of the nature and amount of base, substrate structure, amount of added water and solvent on the condensation of carbonyl compounds with cyclopentadiene in the presence of secondary amines were investigated. Based on these studies, a new efficient and green synthesis of fulvenes was developed.

| S-EPMC3196336 | biostudies-literature

Synthesis, structure, and antibiotic activity of aryl-substituted LpxC inhibitors.

Project description:The zinc-dependent deacetylase LpxC catalyzes the committed step of lipid A biosynthesis in Gram-negative bacteria and is a validated target for the development of novel antibiotics to combat multidrug-resistant Gram-negative infections. Many potent LpxC inhibitors contain an essential threonyl-hydroxamate headgroup for high-affinity interaction with LpxC. We report the synthesis, antibiotic activity, and structural and enzymatic characterization of novel LpxC inhibitors containing an additional aryl group in the threonyl-hydroxamate moiety, which expands the inhibitor-binding surface in LpxC. These compounds display enhanced potency against LpxC in enzymatic assays and superior antibiotic activity against Francisella novicida in cell culture. The comparison of the antibiotic activities of these compounds against a leaky Escherichia coli strain and the wild-type strain reveals the contribution of the formidable outer-membrane permeability barrier that reduces the compounds efficacy in cell culture and emphasizes the importance of maintaining a balanced hydrophobicity and hydrophilicity profile in developing effective LpxC-targeting antibiotics.

| S-EPMC3941642 | biostudies-literature

An Effective Synthesis of Previously Unknown 7-Aryl Substituted Paullones.

Project description:A straightforward three-step procedure affording a wide range of novel 7-aryl substituted paullone derivatives was developed. This scaffold is structurally similar to 2-(1H-indol-3-yl)acetamides-promising antitumor agents-hence, could be useful for the development of a new class of anticancer drugs.

| S-EPMC10005103 | 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