Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

An Approach to Paracyclophane-Based Tetrathiafulvalenes: Synthesis and Characterization of a Pseudo-Geminal [2.2]Paracyclophane 1,3-Dithia-2-Thione.

ABSTRACT: The synthesis of paracyclophane-based tetrathiafulvalene precursors is described in the context of the importance of these compounds in the field of material chemistry. Pseudo-geminal bis(1,3-dithia-2-thione) was synthesized via the corresponding 1,3-dithiol-2-ylium salt. The latter was obtained by a synthetic procedure that involves 4,15-bis(acetyl)[2.2]paracyclophane, a new compound of interest for many researchers.

SUBMITTER: Bahrin LG

PROVIDER: S-EPMC7698277 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

An Approach to Paracyclophane-Based Tetrathiafulvalenes: Synthesis and Characterization of a <i>Pseudo-Geminal</i> [2.2]Paracyclophane 1,3-Dithia-2-Thione.

Bahrin Lucian G LG Hopf Henning H Jones Peter G PG Birsa Mihail L ML Sarbu Laura G LG

Molecules (Basel, Switzerland) 20201111 22

The synthesis of paracyclophane-based tetrathiafulvalene precursors is described in the context of the importance of these compounds in the field of material chemistry. <i>Pseudo-geminal</i> bis(1,3-dithia-2-thione) was synthesized via the corresponding 1,3-dithiol-2-ylium salt. The latter was obtained by a synthetic procedure that involves 4,15-bis(acetyl)[2.2]paracyclophane, a new compound of interest for many researchers. ...[more]

PMID: 33187391

Similar Datasets

π-Stacked Polymer Consisting of a Pseudo⁻meta⁻[2.2]Paracyclophane Skeleton.

Project description:A novel π-stacked polymer based on a pseudo⁻meta⁻linked [2.2]paracyclophane moieties was synthesized by Sonogashira-Hagihara coupling. The UV-vis absorption spectra of the synthesized polymer and model compounds revealed an extension of the conjugation length owing to the through-space conjugation. The optical properties of the π-stacked dimer with the pseudo⁻meta⁻linked [2.2]paracyclophane unit were compared with those of the corresponding dimers with the pseudo⁻ortho⁻ and pseudo⁻para⁻linked [2.2]paracyclophane units.

| S-EPMC6403781 | biostudies-literature

A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane.

Project description:We report a green and convenient protocol to prepare 4,7,12,15-tetrachloro[2.2]paracyclophane, the precursor of parylene D, from 2,5-dichloro-p-xylene. In the first bromination step, with H2O2-HBr as a bromide source, this procedure becomes organic-waste-free and organic-solvent-free and can appropriately replace the existing bromination methods. The Winberg elimination-dimerization step, using aqueous sodium hydroxide solution instead of silver oxide for anion exchange, results in a significant improvement in product yield. Furthermore, four substituted [2.2]paracyclophanes were also prepared in this convenient way.

| S-EPMC5238561 | biostudies-literature

6,7,8,9,10,11,12,13-Octa-hydro-5H-1,3-dithiole[4,5-b][1,4]dithia-cyclo-tridecine-2-thione.

Project description:In the crystal structure of the title compound, C(12)H(18)S(5), no significant inter-molecular π-π inter-actions are found. Weak inter-molecular C-S⋯π [S⋯centroid = 3.787 (1) Å] inter-actions and van der Waals forces may be effective in the stabilization of the structure.

| S-EPMC2960369 | biostudies-literature

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties.

Project description:The synthesis of [2.2]paracyclophane derivatives containing tetrathiafulvalene units has been accomplished by the coupling reaction of 4-([2.2]paracyclophan-4-yl)-1,3-dithiol-2-thione in the presence of trimethylphosphite. The 1,3-dithiol-2-thione derivative was in turn synthesized by the regioselective bromination of 4-acetyl[2.2]paracyclophane, then through the corresponding dithiocarbamates and 1,3-dithiolium salts.

| S-EPMC4660956 | biostudies-literature

Synthesis, aggregation induced emission and through space conjugation of triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene.

Project description:4-Bromo substituted [2.2]paracyclophane-1,9-diene was synthesized from the corresponding dithia[3.3]paracyclophane in three steps through benzyne Steven rearrangement, oxidation, and a thermal elimination reaction. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene was successfully prepared by the Suzuki-Miyaura cross-coupling reaction of 4-bromo substituted [2.2]paracyclophane-1,9-diene and 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1,3,2-dioxaborolane using Pd(OAc)2 as a catalyst, S-Phos as a ligand and K3PO4 as a base. The structures of bromo substituted [2.2] paracyclophane-1,9-diene and triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene were fully characterized by 1H NMR spectroscopy and X-ray crystallography. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene exhibited aggregation-induced emission characteristics when the water fraction was higher than 80% in the THF/water mixtures. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene displays much higher fluorescence when the water fraction is 90% compared to that of model compounds due to both through bond and through space conjugation. To the best for our knowledge, we are the first to synthesize triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene with aggregation-induced emission characteristics.

| S-EPMC9080709 | biostudies-literature

A Luminescent 1D Silver Polymer Containing [2.2]Paracyclophane Ligands.

Project description:[2.2]Paracyclophane scaffolds have seen limited use as building blocks in supramolecular chemistry. Here, we report the synthesis and characterization of a 1D coordination polymer consisting of silver(I) ions bound to a [2.2]paracyclophane scaffold functionalized with two 4-pyridyl units. The structure of the polymer has been determined from single crystal X-ray diffraction analysis and reveals two different silver coordination motifs that alternate along the 1D coordination polymer. The coordination polymer exhibits strong blue and sky-blue fluorescence in solution and in the crystalline solid state, respectively.

| S-EPMC8371969 | biostudies-literature

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane.

Project description:We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner.

| S-EPMC8042488 | biostudies-literature

[2.2]Paracyclophane-Based TCN-201 Analogs as GluN2A-Selective NMDA Receptor Antagonists.

Project description:Recent studies have shown the involvement of GluN2A subunit-containing NMDA receptors in various neurological and pathological disorders. In the X-ray crystal structure, TCN-201 (1) and analogous pyrazine derivatives 2 and 3 adopt a U-shape (hairpin) conformation within the binding site formed by the ligand binding domains of the GluN1 and GluN2A subunits. In order to mimic the resulting π/π-interactions of two aromatic rings in the binding site, a [2.2]paracyclophane system was designed to lock these aromatic rings in a parallel orientation. Acylation of [2.2]paracyclophane (5) with oxalyl chloride and chloroacetyl chloride and subsequent transformations led to the oxalamide 7, triazole 10 and benzamides 12. The GluN2A inhibitory activities of the paracyclophane derivatives were tested with two-electrode voltage clamp electrophysiology using Xenopus laevis oocytes expressing selectively functional NMDA receptors with GluN2A subunit. The o-iodobenzamide 12 b with the highest similarity to TCN-201 showed the highest GuN2A inhibitory activity of this series of compounds. At a concentration of 10 μM, 12 b reached 36 % of the inhibitory activity of TCN-201 (1). This result indicates that the [2.2]paracyclophane system is well accepted by the TCN-201 binding site.

| S-EPMC8596836 | biostudies-literature

Substitution Pattern Controlled Quantum Interference in [2.2]Paracyclophane-Based Single-Molecule Junctions.

Project description:Quantum interference (QI) of electron waves passing through a single-molecule junction provides a powerful means to influence its electrical properties. Here, we investigate the correlation between substitution pattern, conductance, and mechanosensitivity in [2.2]paracyclophane (PCP)-based molecular wires in a mechanically controlled break junction experiment. The effect of the meta versus para connectivity in both the central PCP core and the phenyl ring connecting the terminal anchoring group is studied. We find that the meta-phenyl-anchored PCP yields such low conductance levels that molecular features cannot be resolved; in the case of para-phenyl-coupled anchoring, however, large variations in conductance values for modulations of the electrode separation occur for the pseudo-para-coupled PCP core, while this mechanosensitivity is absent for the pseudo-meta-PCP core. The experimental findings are interpreted in terms of QI effects between molecular frontier orbitals by theoretical calculations based on density functional theory and the Landauer formalism.

| S-EPMC8414552 | biostudies-literature

Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes.

Project description:Substituted [2.2]metaparacyclophanes are amongst the least studied of the simple cyclophanes. This is undoubtedly the result of the lengthy syntheses of these compounds. We report the simple synthesis of a rare example of a non-symmetric [2.2]metaparacyclophane. Treatment of [2.2]paracyclophane under standard nitration conditions gives a mixture of 4-nitro[2.2]paracyclophane, 4-hydroxy-5-nitro[2.2]metaparacyclophane and a cyclohexadienone cyclophane.

| S-EPMC8261525 | 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