Browse
Submit Data
Databases
API
Help

Dataset Information

7 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles.

ABSTRACT: The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels-Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels-Alder reaction of tetrazines with p-quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.

SUBMITTER: Kocak R

PROVIDER: S-EPMC7991620 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents.

Project description:Pyrroles and its fused forms possess antimicrobial activities, they can easily interact with biomolecules of living systems. A series of substituted pyrroles, and its fused pyrimidines and triazines forms have been synthesised, all newly synthesised compound structures were confirmed by spectroscopic analysis. Generally, the compounds inhibited growth of some important human pathogens, the best effect was given by: 2a, 3c, 4d on Gram-positive bacteria and was higher on yeast (C. albicans), by 5c on Gram-negative bacteria and by 5a then 3c on filamentous fungi (A. fumigatus and F. oxysporum). Such results present good antibacterial and antifungal potential candidates to help overcome the global problem of antibiotic resistance and opportunistic infections outbreak. Compound 3c gave the best anti-phytopathogenic effect at a 50-fold lower concentration than Kocide 2000, introducing a safe commercial candidate for agricultural use. The effect of the compounds on DNA was monitored to detect the mode of action.

| S-EPMC8491725 | biostudies-literature

Synthesis and Characterization of Vanillin-Based π-Conjugated Polyazomethines and Their Oligomer Model Compounds.

Project description:The synthesis of π-conjugated polymers via an environmentally friendly procedure is generally challenging. Herein, we describe the synthesis of divanillin-based polyazomethines, which are derived from a potentially bio-based monomer. The polymerization is performed in 5 min under microwave irradiation without any metallic catalyst, with water as the only by-product. The vanillin-based polyazomethines were characterized by SEC, TGA, and UV-Vis spectroscopy. Model compounds were designed and characterized by X-ray diffraction and UV-Vis spectroscopy. The structure/properties study of vanillin-based azomethines used as models allowed us to unequivocally confirm the E configuration and to highlight the cross-conjugated nature of divanillin-based polymers.

| S-EPMC9268122 | biostudies-literature

Surface-Assisted Synthesis of N-Containing π-Conjugated Polymers.

Project description:On-surface synthesis has recently emerged as a powerful strategy to design conjugated polymers previously precluded in conventional solution chemistry. Here, an N-containing pentacene-based precursor (tetraazapentacene) is ex-professo synthesized endowed with terminal dibromomethylene (:CBr2 ) groups to steer homocoupling via dehalogenation on metallic supports. Combined scanning probe microscopy investigations complemented by theoretical calculations reveal how the substrate selection drives different reaction mechanisms. On Ag(111) the dissociation of bromine atoms at room temperature triggers the homocoupling of tetraazapentacene units together with the binding of silver adatoms to the nitrogen atoms of the monomers giving rise to a N-containing conjugated coordination polymer (P1). Subsequently, P1 undergoes ladderization at 200 °C, affording a pyrrolopyrrole-bridged conjugated polymer (P2). On Au(111) the formation of the intermediate polymer P1 is not observed and, instead, after annealing at 100 °C, the conjugated ladder polymer P2 is obtained, revealing the crucial role of metal adatoms on Ag(111) as compared to Au(111). Finally, on Ag(100) the loss of :CBr2 groups affords the formation of tetraazapentacene monomers, which coexist with polymer P1. Our results contribute to introduce protocols for the synthesis of N-containing conjugated polymers, illustrating the selective role of the metallic support in the underlying reaction mechanisms.

| S-EPMC9259725 | biostudies-literature

Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides.

Project description:We present a completely solid-phase synthetic strategy to create three- and four-fold peptide-appended π-electron molecules, where the multivalent oligopeptide presentation is dictated by the symmetries of reactive handles placed on discotic π-conjugated cores. Carboxylic acid and anhydride groups were viable amidation and imidation partners, respectively, and oligomeric π-electron discotic cores were prepared through Pd-catalyzed cross-couplings. Due to intermolecular hydrogen bonding between the three or four peptide axes, these π-peptide hybrids self-assemble into robust one-dimensional nanostructures with high aspect ratios in aqueous solution. The preparation of these systems via solid-phase methods will be detailed along with their self-assembly properties, as revealed by steady-state spectroscopy and transmission electron microscopy and electrical characterization using field-effect transistor measurements.

| S-EPMC6640940 | biostudies-literature

Synthesis and liquid crystalline properties of new triazine-based π-conjugated macromolecules with chiral side groups.

Project description:In this study, we reported the synthesis of a new tribranched macromolecule liquid crystal with triazine in the centre. The central triazine core is bonded via sequences of Sonigashira coupling to 3 triazine unites through acetylenic bridges. The triazines at the periphery are substituted with 2 chiral citronellyloxy side groups. The salt of the resulting star-shaped macromolecule, which was oily at room temperature, with 4-dodecyloxybenzoic acid at 1:1 ratio exhibited a Smectic C (SmC) mesophase. The liquid crystalline properties of organic salt were investigated using DSC (differential scanning calorimetry) and POM (polarizing optical microscopy).

| S-EPMC7671215 | biostudies-literature

Nanoscale π-conjugated ladders.

Project description:It is challenging to increase the rigidity of a macromolecule while maintaining solubility. Established strategies rely on templating by dendrons, or by encapsulation in macrocycles, and exploit supramolecular arrangements with limited robustness. Covalently bonded structures have entailed intramolecular coupling of units to resemble the structure of an alternating tread ladder with rungs composed of a covalent bond. We introduce a versatile concept of rigidification in which two rigid-rod polymer chains are repeatedly covalently associated along their contour by stiff molecular connectors. This approach yields almost perfect ladder structures with two well-defined π-conjugated rails and discretely spaced nanoscale rungs, easily visualized by scanning tunnelling microscopy. The enhancement of molecular rigidity is confirmed by the fluorescence depolarization dynamics and complemented by molecular-dynamics simulations. The covalent templating of the rods leads to self-rigidification that gives rise to intramolecular electronic coupling, enhancing excitonic coherence. The molecules are characterized by unprecedented excitonic mobility, giving rise to excitonic interactions on length scales exceeding 100 nm. Such interactions lead to deterministic single-photon emission from these giant rigid macromolecules, with potential implications for energy conversion in optoelectronic devices.

| S-EPMC8595307 | biostudies-literature

On-surface synthesis of π-conjugated ladder-type polymers comprising nonbenzenoid moieties.

Project description:On-surface synthesis provides a powerful approach toward the atomically precise fabrication of π-conjugated ladder polymers (CLPs). We report herein the surface-assisted synthesis of nonbenzenoid CLPs from cyclopenta-annulated anthracene monomers on Au(111) under ultrahigh vacuum conditions. Successive thermal annealing steps reveal the dehalogenative homocoupling to yield an intermediate 1D polymer and the subsequent cyclodehydrogenation to form the fully conjugated ladder polymer. Notably, neighbouring monomers may fuse in two different ways, resulting in six- and five-membered rings, respectively. The structure and electronic properties of the reaction products have been investigated via low-temperature scanning tunneling microscopy and spectroscopy, complemented by density-functional theory calculations. Our results provide perspectives for the on-surface synthesis of nonbenzenoid CLPs with the potential to be used for organic electronic devices.

| S-EPMC8251514 | biostudies-literature

Heptazine-Based <i>π</i>-Conjugated Materials for Light-Emitting.

Project description:On the basis of planar and relatively rigid nitrogen-rich heterocyclic system of the heptazine core, heptazine-based π-conjugated materials have aroused widespread attention over the past decade by virtue of the fascinating electronic, optical, thermal, and mechanical properties in the fields of light-emitting, photocatalysis, sensors, environmental remediation, and so forth. However, there are still several obstacles to be solved before practical applications, such as low photoluminescence quantum efficiencies for light-emitting and weak visible absorption for photocatalysis. To further enhance various properties of heptazine-based π-conjugated materials, a series of strategies have been developed, including ingenious molecular design and modification, novel synthetic, and preparation methods. In this review, the significant progress of monomeric and polymeric heptazine-based π-conjugated materials and their applications typically in light-emitting are reviewed, which is beneficial for the acceleration of practical applications of heptazine-based materials and devices.

| S-EPMC8249734 | biostudies-literature

Annulative ?-extension of indoles and pyrroles with diiodobiaryls by Pd catalysis: rapid synthesis of nitrogen-containing polycyclic aromatic compounds.

Project description:A palladium-catalyzed one-step annulative ?-extension (APEX) reaction of indoles and pyrroles that allows rapid access to nitrogen-containing polycyclic aromatic compounds is described. In the presence of palladium pivalate and silver carbonate, diverse indoles or pyrroles coupled with diiodobiaryls in a double direct C-H arylation manner to be transformed into the corresponding ?-extended compounds in a single step. The newly developed catalytic system enables the use of various pyrroles and indoles as templates with a series of diiodobiaryls to provide structurally complicated and largely ?-extended nitrogen-containing polycyclic aromatic compounds that are otherwise difficult to synthesize.

| S-EPMC6180308 | biostudies-literature

Efficient Colorimetric Fluoride Anion Sensor Based on π-Conjugated Carbazole Small Molecule.

Project description:The ability to detect fluoride anions with high selectivity and sensitivity by using the naked eye is crucial yet challenging. In this study, a novel, simple conjugated organic dye, N-tert-butyldimethylsilyl-3,6-diiodocarbazole (CA-TBMDS) was developed and used for the first time as a colorimetric sensor for fluoride. CA-TBMDS was found to be a highly sensitive fluoride chemosensor, with a detection limit as low as 3 × 10-5 M. The reaction of CA-TBMDS with fluoride anions in a tetrahydrofuran solution resulted in a color change from colorless to yellow under ambient light, which can be discriminated by the naked eye. The sensor operated via intermolecular proton transfer between the amide units and the fluoride anion, as confirmed by proton nuclear magnetic resonance titration. CA-TBMDS is not only highly sensitive to fluoride anions, but also exhibits high sensitivity in the presence of various ions. This work demonstrates that N-butyldimethylchlorosilane-based organic dyes have prospective utility as a type of fluoride anion chemosensor.

| S-EPMC8423907 | 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