2065-66-9Relevant articles and documents
Synthesis and properties of novel polyimide fibers containing phosphorus groups in the main chain
Zhao, Yong,Feng, Tao,Li, Guomin,Liu, Fangfang,Dai, Xuemin,Dong, Zhixin,Qiu, Xuepeng
, p. 42482 - 42494 (2016)
A series of polyamic acid copolymers (co-PAAs) containing phosphorous groups in the main chain were synthesized using different ratios of two diamines, i.e., bis(3-aminophenyl)methyl phosphine oxide (DAMPO) and 4,4′-oxydianiline (ODA), with 3,3′,4,4′-biphenyltetracarboxylic dianhydride (s-BPDA) by polycondensation in N,N′-dimethyacetamide (DMAc). The co-PAA solutions were spun into fibers by a dry-jet wet spinning process, and then polyimide copolymer (co-PI) fibers were obtained by thermal imidization. ATR-FTIR spectra and elemental analysis confirmed the chemical structure of PAA and PI fibers. The as-prepared PI fibers have smooth and dense surface as well as uniform diameter. Compared with the blank PI-0, the Tg values of co-PI fibers increased considerably with the increase in DAMPO content. TGA results indicated that the co-PI fibers possessed good thermal stability up to 510 °C and a residual char yield of up to 61% at 850 °C. All co-PI fibers exhibited excellent elongation, and their tensile strength and modulus can reach 0.9 GPa and 14.97 GPa when the molar ratio of DAMPO/ODA was 6/4 and the draw ratio was 3.0. The relationship between microstructure and mechanical property is also discussed.
Quaternary Phosphorus-Induced Iodocuprate(I)-Based Hybrids: Water Stabilities, Tunable Luminescence and Photocurrent Responses
Zhang, Wen-Ting,Liu, Jian-Zhi,Liu, Jing-Bo,Song, Kai-Yue,Li, Yi,Chen, Zhi-Rong,Li, Hao-Hong,Jiang, Rong
, p. 4234 - 4244 (2018)
Four (triphenyl)phosphonium-based quaternary phosphorus salts with different substituents (varying from methyl to n-butyl) were selected to be structural directed agents (SDAs) to construct four iodocuprate(I) hybrids via solution method, i.e., [(PPh3Me)(Cu3I4)]n (1), [(PPh3Et)(Cu3I4)]n (2), (PPh3iPr)2(Cu2I4) (3), [(PPh3nBu)(Cu3I4)]n (4). The inorganic iodocuprates in 1, 2 and 4 are 1-D (Cu3I4)nn– chains constructed from Cu5I11 units, but (Cu2I4)2– in 3 is a di-nuclear cluster. Interestingly, the strength of Cu···Cu and π–π stacking interactions are weakened with the lengthening of alkyl groups on P-atom. The best water stability of 4 can be ascribed to the better hydrophobicity of n-butyl group, which deters the dispersing of organic and inorganic moieties and as a result, inhibit hydrolysis reaction. Furthermore, all compounds exhibit typical reversible luminescent thermochromic behaviors, among which 4 exhibits blue emission and the quenching of higher energy (HE) zone in 1 and 2 are led by strong π–π stacking interactions. Besides, effective and repeatable photocurrent responses can be detected in these compounds. In all, by systematically introducing alkyl groups into (triphenyl)phosphonium as SDAs to prepare hybrid iodocuprates, we can find that the longer alkyl groups can achieve stronger tunable PL materials with enhanced water stabilities.
Electrospray Mass Spectrometric Studies of Some Phosphonium Cations
Colton, Ray,Traeger, John C.,Harvey, Justin
, p. 1030 - 1033 (1992)
A series of methylphosphonium cations derived from mono- and polyphosphines were generated by interaction of the phosphine with methyl iodide.Electrospray mass spectra of the cations were obtained directly from dichloromethane-methanol solutions.In all cases the intact phosphonium cations were observed, often as the base peak, emphasizing the 'soft' nature of this type of ionization.Some of the polyphosphines showed additional peaks at m/z 16 and 32 units higher than the molecular ions due to oxidation of the non-methylated phosphine groups.Collisionally activated dissociation mass spectra show a consistent mode of fragmentation with the formation of alkene ions being dominant.Where comparisons are possible, there is a close correlation with the electron impact mass spectra of the neutral phosphines.
Unexpected oxidative dimerisations of a cyclopentadienyl-phosphane formation of unprecedented, structurally remarkable phosphacyclic compounds
Lichtenberg, Crispin,Elfferding, Michael,Sundermeyer, Joerg
, p. 3117 - 3124 (2010)
The reactions of Me2PCp# (1) (Cp# = C 5HMe4) with Ph3PCH2X+ X-(X = Cl, Br, I) and diiodomethane as potential electrophiles have been investigated. Unexpectedly, in all four cases unprecedented oxidative dimerisations of the cyclopentadienylphosphane 1 have been observed. In the reactions with the phosphonium salts, an ionic group 15 analogue of octamethyl-tetrahydro-s-indacene with different: counterions X- has been obtained (5-7) as a result of X+ transfer and H+ elimination. In the reaction of 1 with dilodomethane a fourfold anellated, partially unsaturated, heterocyclic compound 9 exhibiting two spiro carbon centres, which are directly linked, was formed, presumably as a result of iodine radical transfer. Both of the novel phosphorus heterocycles have been characterised by means of single crystal XRD analysis.
Solvent-dependent changes in the ene reaction of RTAD with alkenes: The cyclopropyl group as a mechanistic probe
Roubelakis, Manolis M.,Vougioukalakis, Georgios C.,Angelis, Yiannis S.,Orfanopoulos, Michael
, p. 39 - 42 (2006)
(Chemical Equation Presented) The vinylcyclopropyl moiety was used as an efficient probe to test mechanistic possibilities of the triazolinedione-alkene ene reaction. In non-hydroxylic solvents, this reaction afforded only the ene adducts via a closed three-membered aziridinium imide (Al) intermediate, whereas in hydroxylic solvents a dipolar intermediate is favored and trapped by the cyclopropyl moiety to form the corresponding cyclopropyl-rearranged solvent-trapped adducts.
Stereoselective synthesis of (6Z,8E)-undeca-6,8,10-trien-3-one (yuzunone) for its characterization in yuzu and various citrus essential oils
Uehara, Ayaka,Baldovini, Nicolas
, (2020/10/02)
(6Z,8E)-Undeca-6,8,10-trien-3-one (yuzunone) is reported to be one of the main olfactory contributors of the specific fruity-green-balsamic odor of yuzu peel oil. Using an original stereoselective synthesis, we prepared a pure sample of yuzunone, which was used as a reference compound to check its presence by GC–MS and GC–O in 5 commercial samples of yuzu and citrus essential oils. Surprisingly, we could not detect yuzunone by GC–MS in any of our samples. However, it could be detected by a small part of the panelists involved in GC–O/AEDA experiments in a yuzu commercial oil, but its olfactory contribution proved to be very limited.
Structure-Activity-Relationship-Aided Design and Synthesis of xCT Antiporter Inhibitors
Cirillo, Davide,Sarowar, Shahin,?yvind Enger, Per,Bj?rsvik, Hans-René
, p. 2650 - 2668 (2021/06/01)
The xCT antiporter is a cell membrane protein involved in active counter-transportation of glutamate (outflux) with cystine (influx) over the human cell membrane. This feature makes the xCT antiporter a crucial element of the biosynthesis of the vital free radical scavenger glutathione. The prodrug sulfasalazine, a medication for the treatment of ulcerative colitis, was previously proven to inhibit the xCT antiporter. Starting from sulfasalazine, a molecular scaffold jumping followed by SAR-assisted design and synthesis provided a series of styryl hydroxy-benzoic acid analogues that were biologically tested in vitro for their ability to decrease intracellular glutathione levels using four different cancer cell lines: A172 (glioma), A375 (melanoma), U87 (glioma) and MCF7 (breast carcinoma). Depletion of glutathione levels varied among the compounds as well as among the cell lines. Flow cytometry using propidium iodide and the annexin V marker demonstrated minimal toxicity in normal human astrocytes for a promising candidate molecule (E)-5-(2-([1,1′-biphenyl]-4-yl)vinyl)-2-hydroxybenzoic acid.
Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle
Woof, Callum R.,Durand, Derek J.,Fey, Natalie,Richards, Emma,Webster, Ruth L.
supporting information, p. 5972 - 5977 (2021/03/17)
Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.
Highly Efficient and Convenient Access to Phosphinates via CHCl3-Assisted Direct Phosphorylation between R2P(O)H and ROH by Phosphonium Salt Catalysis
Jiang, Zhiyu,Wang, Tianli,Yu, Xiaojun,Zhang, Hong-Su,Zhang, Song
supporting information, (2020/05/25)
A mild, efficient, convenient and scalable method to synthesize phosphinates via direct phosphorylation between R2P(O)H and ROH was developed. All aromatic substrates completed this transformation with excellent yields (up to 98 %), and preliminary mechanistic studies suggest that a carbene-involving process from CHCl3 to CH2Cl2 facilitates the phosphorylation.
Practical synthesis of phosphonium salts with orthoformates and their application as flame retardants in polycarbonate
Jiang, Pingkai,Li, Tao,Xu, Chencong,Zhang, Yong Jian
, (2020/03/23)
An efficient and practical approach to phosphonium salts has been developed. By the reaction of phosphines and different acid sources with orthoformates in one-step operation, the process allowed rapid access to phosphonium salts with diverse counterions in high yield after the purification by recrystallization. The flame retardant performance in PC has also been examined by blending several phosphonium salts to PC respectively. Phosphonium phosphates showed excellent flame retardancy in PC with only 2 phr blending.
