Sigma-Aldrich

Aldrich - 287822; Tri(o-tolyl)phosphine 97%; CAS No. 6163-58-2; P(o-tol)3 | Tris(o-tolyl)phosphine; ligand suitable for Silylation, Suzuki-Miyaura coupling, Stille coupling, Negishi coupling and Buchwald-Hartwig cross coupling reaction| Find related products, papers, technical documents, MSDS & more at Sigma-Aldrich

Tri(o-tolyl)phosphine 97 6163-58-2

Tri(<I>o</I>-tolyl)phosphine

Hybrid nanostructures with switchable and reversible "blue-red-green" emission were efficiently synthesized. These nanostructures comprise polyhedral oligomeric silsesquioxanes (POSS) that behave as a nanocage that can be functionalized with terpyridine-based organic ligands, which can be easily complexed with europium (III) ions. The complexes were characterized by UV-Vis and fluorescence spectroscopy and their stoichiometry was also confirmed by 1 H NMR spectroscopy. In the presence of the Eu(III) ions, the octafunctionalized nanocages self-assemble to form 3D architectures that display an intense red-emission, especially in the solid state. The presence of an alkenyl group bridging the inorganic core to the organic moiety was employed to tune the emission properties by trans-cis isomerization of the double bond. In the case of the octafunctionalized nanocages (O-POSS), this isomerization was monitored in the presence of Eu(III) cations and was accompanied by an evident colour change from blue (trans-O-POSS) to red (Eu@trans-O-POSS) and finally to green (cis-O-POSS) as consequence of the release of the metal cations. This behaviour, together with the easy dispersion of the dry powder and the possibility of coating as a film in presence of small amounts of solvent, makes the emissive solid promising for applications in materials science.

Tuneable Emission of Polyhedral Oligomeric Silsesquioxane Based Nanostructures that Self-Assemble in the Presence of Europium(III) Ions: Reversible trans-to-cis Isomerization.

Polymer dielectrics are ubiquitous in advanced electric energy storage systems. However, the relatively low operating temperature significantly menaces their widespread application at high temperatures, such as for hybrid vehicles and aerospace power electronics. Spider silk, a natural nanocomposite comprised of biopolymer chains and crystal protein nanosheets combined by multiple interfacial interactions, exhibits excellent mechanical properties even at elevated temperatures. Inspired by the hierarchical nanostructure of spider silk, poly(aryl ether sulfone) is anchored to the surface of wide bandgap artificial nanosheets to prepare the nanocomposites with nanoconfinement effect. The bioinspired strategy successfully improves the mechanical and electrical performances of the nanocomposite. Owing to the structural-enabled enhancements, the nanocomposites exhibit excellent breakdown strength and electrical energy storage performance at high temperatures. In detail, giant discharged energy density (2.7 J cm-3 ) and high charge-discharge efficiency (>90%) are simultaneously achieved at 150 °C and 400 MV m-1 . Notably, under 500 MV m-1 , the discharged energy density reaches 4.2 J cm-3 , which is the record high discharged energy density among polymer-based dielectrics at 150 °C. This work demonstrates a viable strategy to design high-temperature polymer dielectrics by constructing nanoconfinement in the nanocomposites.

Bioinspired Polymer Nanocomposites Exhibit Giant Energy Density and High Efficiency at High Temperature.

We have demonstrated two novel donor-acceptor-donor (D-A-D) hole-transport material (HTM) with spiro[fluorene-9,9'-phenanthren-10'-one] as the core structure, which can be synthesized through a low-cost process in high yield. Compared to the incorporation of the conventional HTM of commonly used 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (Spiro-OMeTAD), the synthesis process is greatly simplified for the presented D-A-D materials, including a minimum number of purification processes. This results in an increased production yield (>55 %) and suppressed production cost (<30 $ g-1 ), in addition to high power conversion efficiency (PCE) in perovskite solar cells (PSCs). The PCE of a PSC using our D-A-D HTM reaches 16.06 %, similar to that of Spiro-OMeTAD (16.08 %), which is attributed to comparable hole mobility and charge-transfer efficiency. D-A-D HTMs also provide better moisture resistivity to prolong the lifetime of PSCs under ambient conditions relative to their Spiro-OMeTAD counterparts. The proposed new type of D-A-D HTM has shown promising performance as an alternative HTM for PSCs and can be synthesized with high production throughput.

Facilely Synthesized spiro[fluorene-9,9'-phenanthren-10'-one] in Donor-Acceptor-Donor Hole-Transporting Materials for Perovskite Solar Cells.

The objective of the present PET study was to compare the effect of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on serotonergic neuronal systems and mitochondrial complex I (MC-I) activity with that of dopamine in conscious rhesus monkeys (

Effect of MPTP on Serotonergic Neuronal Systems and Mitochondrial Complex I Activity in the Living Brain: A PET Study on Conscious Rhesus Monkeys.

The molecular structure of polymers has a great influence on their thermoelectric properties; however, the relationship between the molecular structure of a polymer and its thermoelectric properties remains unclear. In this work, two benzo[1,2-b:4,5-b']dithiophene (BDT)-based conjugated polymers are designed and synthesized, which contain alkyl side chains or polar side chains. The effects of the polymer side chain on the physicochemical properties are systematically investigated, especially the thermoelectric performance of the polymers after doping with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane. It is found that the BDT-based conjugated polymer with polar side chains exhibits good miscibility with the dopants, leading to higher thermoelectric properties than those of the polymer with alkyl side chains. This work can serve as a reference for the future design of high-performance organic thermoelectric polymers.

Polar Side Chain Effects on the Thermoelectric Properties of Benzo[1,2-b:4,5-b']Dithiophene-Based Conjugated Polymers.

The spectroscopic and photophysical properties of silicon-containing styryl-carbazole were investigated in various solvents, and the results were analyzed with reference to its carbon derivatives. In n-hexane, both the silicon- and the carbon-containing compounds had very similar emission properties. In acetonitrile, the emission properties remained the same for the C-compound but changed significantly for the Si-compounds. In particular, the fluorescence spectra of the latter were red-shifted, and their radiative rate constants were even 7 times larger than in n-hexane, which suggested that the emissive states of the silicon-containing compounds were different in these two solvents. DFT calculations using the CAM-B3LYP functional showed that the emissive state of the C-compound involves the LUMO+1 orbital regardless of the medium. In contrast, for the Si-compound, changing the medium from n-hexane to acetonitrile resulted in the inversion of the emissive states from an excited state involving the LUMO+1 orbital (the dipole moment μ = 4.2 D) to an excited state involving the LUMO orbital (μ = 8.9 D).

Unusual emission properties of the selected organosilicon compounds containing a styryl-carbazole chromophore: inversion of the singlet excited states.

Deuterium labeled aromatic and heteroaromatic compounds are synthesized in good to excellent yields with >98% deuterium purity via palladium catalyzed deuterodehalogenation reaction using commercially available and inexpensive reagents. Selective deuteration of bromoaniline is also demonstrated without H/D exchange in an amino N-H group.

Catalytic selective deuteration of halo(hetero)arenes.

Proton exchange membrane fuel cells (PEMFCs) are promising devices for clean power generation in automotive, stationary, and portable applications. Perfluorosulfonic acid (PFSA) ionomers (for example, Nafion) have been the benchmark PEMs; however, several problems, including high gas permeability, low thermal stability, high production cost, and environmental incompatibility, limit the widespread dissemination of PEMFCs. It is believed that fluorine-free PEMs can potentially address all of these issues; however, none of these membranes have simultaneously met the criteria for both high performance (for example, proton conductivity) and durability (for example, mechanical and chemical stability). We present a polyphenylene-based PEM (SPP-QP) that fulfills the required properties for fuel cell applications. The newly designed PEM exhibits very high proton conductivity, excellent membrane flexibility, low gas permeability, and extremely high stability, with negligible degradation even under accelerated degradation conditions, which has never been achieved with existing fluorine-free PEMs. The polyphenylene PEM also exhibits reasonably high fuel cell performance, with excellent durability under practical conditions. This new PEM extends the limits of existing fluorine-free proton-conductive materials and will help to realize the next generation of PEMFCs via cost reduction as well as the performance improvement compared to the present PFSA-based PEMFC systems.

Design of flexible polyphenylene proton-conducting membrane for next-generation fuel cells.

This study examined the solution-phase exchange reactions of triphenylphosphine (PPh3) ligands on Au8L72+ (L = PPh3) gold clusters with three different tolyl ligands using electrospray ionization mass spectrometry to provide insight into how steric differences in the phosphines influence the extent of ligand exchange and the stability of the resulting mixed-phosphine clusters. The size distributions of tolyl-exchanged gold clusters were found to depend on the position of the methyl group in the tri(tolyl)phosphine ligands (-ortho, -meta, and -para). Due to different sterics, the tri(m-tolyl)phosphine (TMTP) and tri(p-tolyl)phosphine (TPTP) ligands exchanged efficiently onto the Au8L72+ (L = PPh3) clusters while the tri(o-tolyl)phosphine ligands did not exchange. In addition, while TPTP fully exchanged with all seven PPh3 on the Au8L72+ cluster, TMTP exchanged with only six PPh3 ligands. Employing collision-induced dissociation, the tolyl-exchanged mixed-ligand clusters were demonstrated to fragment through loss of neutral ligands and AuL2+. Comparison of the relative fragmentation yields of PPh3vs. TMTP and TPTP from the mixed-ligand clusters indicated that these tolyl ligands are more strongly bonded to the Au82+ gold core than PPh3. To provide molecular-level insight into the experimental results we also performed complementary electronic structure calculations using density functional theory at the B3LYP-D3/SDD level of theory on representative model systems. These computations revealed that steric interactions of the CH3 group on the tri(o-tolyl)phosphine ligand are responsible for the lack of ligand exchange in solution with PPh3. Our joint experimental and theoretical findings demonstrate the subtle interplay of steric and electronic factors that determine the size distribution, stability, and dissociation pathways of phosphine ligated gold clusters.

Role of sterics in phosphine-ligated gold clusters.

The potential of colloidal crystals for applications in optics and photonics has been recognized since the description of spontaneous self-assembly of monodisperse colloids into periodic opaline geometries. Provided with a laser gain medium, these direct assemblies generate optical feedback and have prospective use as lasers or frequency converters; however, problems associated with the colloidal crystal integrity and low loading fractions of the gain medium in the self-assembled resonator structure have prevented their realization to date. Here, we circumvent these problems by synthesizing monodisperse conjugated polymer colloids, which consist entirely of gain medium. We coassemble these colloids together with a sol-gel precursor to achieve encapsulated photonic crystals, which can be applied via inkjet printing. These conjugated polymer photonic crystals exhibit single line laser emission upon optical pumping. This technique circumvents time-consuming micro- and nanofabrication steps as well as error-prone backfilling and etching procedures, providing an effortless way to generate laser geometries.

Colloidal Crystal Lasers from Monodisperse Conjugated Polymer Particles via Bottom-Up Coassembly in a Sol-Gel Matrix.

We report the synthesis and photophysical properties of Cu(i) complexes with 1,10-phenanthroline (phen) and monodentate phosphine ligands. Single crystal X-ray structural analysis revealed that these have three-coordinated trigonal planar geometries. We also found that one of them, [Cu(phen)(Johnphos)]BF

Photophysical properties of three coordinated copper(i) complexes bearing 1,10-phenanthroline and a monodentate phosphine ligand.

Two novel low band gap donor-acceptor (D-A) copolymers, poly[9,10-bis(4-(dodecyloxy)phenyl)-2,6-anthracene-alt-5,5-(4',7'-bis(2-thienyl)-2',1',3'-benzothiadiazole-N-5,6-(3,7-dimethyloctyl)dicarboxylic imide)] (PPADTBTDI-DMO) and poly[9,10-bis(4-(dodecyloxy)phenyl)-2,6-anthracene-alt-5,5-(4',7'-bis(2-thienyl)-2',1',3'-benzothiadiazole-5,6-N-octyl-dicarboxylic imide)] (PPADTBTDI-8) were synthesized in the present work by copolymerising the bis-boronate ester of 9,10-phenylsubstituted anthracene flanked by thienyl groups as electron-donor units with benzothiadiazole dicarboxylic imide (BTDI) as electron-acceptor units. Both polymers were synthesized in good yields via Suzuki polymerisation. Two different solubilizing alkyl chains were anchored to the BTDI units in order to investigate the impact upon their solubilities, molecular weights, optical and electrochemical properties, structural properties and thermal stability of the resulting polymers. Both polymers have comparable molecular weights and have a low optical band gap (Eg) of 1.66 eV. The polymers have low-lying highest occupied molecular orbital (HOMO) levels of about -5.5 eV as well as the similar lowest unoccupied molecular orbital (LUMO) energy levels of -3.56 eV. Thermogravimetric analyses (TGA) of PPADTBTDI-DMO and PPADTBTDI-8 did not prove instability with decomposition temperatures at 354 and 313 °C, respectively. Powder X-ray diffraction (XRD) studies have shown that both polymers have an amorphous nature in the solid state, which could be used as electrolytes in optoelectronic devices.

Characteristics of Low Band Gap Copolymers Containing Anthracene-Benzothiadiazole Dicarboxylic Imide: Synthesis, Optical, Electrochemical, Thermal and Structural Studies.

Four pyrene-vinyl-tetraphenylethylene based conjugated materials were synthesized and characterized by FT-IR, NMR, and mass spectroscopy. The photophysical (including absorption, fluorescence, and fluorescence lifetime) and aggregation properties in tetrahydrofuran were investigated. The photophysical and aggregation behavior depends on the spacer, substituent, and also the architecture (mono or tetra-branched) of the molecule. The vinyl spacer mono-branched compound is aggregation induced emission (AIE) active (αAIE = ∼6). Vinyl spacer tetra-branched compounds are AIE inactive, but their emitting efficiency is good in both solution (Φfl = 63%) phase and in the aggregated state (Φfl = 43%). Phenylvinyl spacer tetra-branched compounds emit light strongly in solution (Φfl = 92%), but not in the aggregated state (Φfl = 8%). They are shown to be thermally stable and emit light in the green region (500-550 nm). The results of cyclic voltammetry measurements of these materials showed irreversible oxidation waves, and have high HOMO energy levels (-5.66 to -5.53 eV).

Planar-rotor architecture based pyrene-vinyl-tetraphenylethylene conjugated systems: photophysical properties and aggregation behavior.

The nucleosides zidovudine (AZT), stavudine (d4T), and telbivudine (LdT) are approved for use in the treatment of human immunodeficiency virus (HIV) and hepatitis B virus (HBV) infections. To promote positron emission tomography (PET) imaging studies on their pharmacokinetics, pharmacodynamics, and applications in cancer diagnosis, a convenient one-pot method for Pd(0)-Cu(I) co-mediated rapid C-C coupling of [(11)C]methyl iodide with stannyl precursor was successfully established and applied to synthesize the PET tracers [(11)C]zidovudine, [(11)C]stavudine, and [(11)C]telbivudine. After HPLC purification and radiopharmaceutical formulation, the desired PET tracers were obtained with high radioactivity (6.4-7.0 GBq) and specific radioactivity (74-147 GBq/µmol) and with high chemical (>99%) and radiochemical (>99.5%) purities. This one-pot Pd(0)-Cu(I) co-mediated rapid C-[(11)C]methylation also worked well for syntheses of [methyl-(11)C]thymidine and [methyl-(11)C]4'-thiothymidine, resulting twice the radioactivity of those prepared by a previous two-pot method. The mechanism of one-pot Pd(0)-Cu(I) co-mediated rapid C-[(11)C]methylation was also discussed.

Tri(o-tolyl)phosphine

97%

Properties

Quality Level

assay

reaction suitability

mp

functional group

SMILES string

InChI

InChI key

Related Categories

Description

Packaging

Application

Safety Information

Storage Class Code

WGK

Flash Point(F)

Flash Point(C)

Personal Protective Equipment

Documentation

Certificate of Analysis

Certificate of Origin

Data Sheets

More Documents

Quotes and Ordering

Peer Reviewed Papers

Technical Service