795-43-7Relevant articles and documents
PHENYLPHOSPHINE OXIDE AND OXYGEN STABLE EPOXY POLYMERS AND METHODS OF SYNTHESIS
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, (2022/03/07)
A polymer formed of at least one phenylphosphine oxide functional epoxide crosslinked with at least one phenylphosphine oxide amine such that the polymer has phosphorous concentrations of at least about 8 percent by weight, at least about 8.5 percent by weight, or any value or range of values therebetween.
A Track-Based Molecular Synthesizer that Builds a Single-Sequence Oligomer through Iterative Carbon-Carbon Bond Formation
McTernan, Charlie T.,De Bo, Guillaume,Leigh, David A.
supporting information, p. 2964 - 2973 (2020/11/02)
We report an artificial molecular machine that moves along a track, iteratively joining building blocks to form an oligomer of single sequence with a continuous backbone of carbon-carbon bonds. The rotaxane features a macrocycle bearing an aldehyde-terminated chain and an axle containing different phosphonium ylides separated by rigid spacers. Each ylide is large enough to block the passage of the macrocycle, trapping the ring between the stopper at the terminus of original threading and the next ylide along the track. Once a building block is reachable, it is removed from the track through a Wittig reaction that adds it to the terminus of the growing chain. Operation on a four-barrier tetra(phosphonium salt) track produces a tetra(diphenylpropane) of single sequence linked through alkene bonds. The prototype extends the principle for molecular machines that build polymers by moving along tracks to the synthesis of sequence-encoded chains with continuous carbon backbones. Sequence is crucial in the molecular world. Proteins are built from a common set of 20 amino acids, but different sequences afford materials as diverse as snake venom, muscle, and spider silk. However, the synthesis of artificial sequence polymers remains challenging. Biology uses molecular machines (e.g., ribosomes) for such tasks, inspiring the invention of artificial systems that move along tracks, picking off and joining building blocks in sequence. To date, such small-molecule machines have used amide formation to join building blocks, the same bonds the ribosome uses to make peptides. Here, we report on the design, synthesis, and operation of a track-based molecular machine that assembles a single-sequence oligomer with a continuous backbone of carbon-carbon bonds. This new class of de novo molecular synthesizer utilizes chemistry and reactivity patterns unavailable to biological machines. The long-term goal is for such molecular assemblers to ultimately be able to play significant roles in molecular construction. Molecular machines, such as ribosomes, are ubiquitous in biology. These natural systems are inspiring artificial systems that move along tracks, picking off and joining building blocks in sequence. To date, such small-molecule machines have used amide formation to connect building blocks, much like the ribosome. Here, the design, synthesis, and operation of a track-based molecular machine that iteratively forms a continuous backbone of carbon-carbon bonds is described. This new class of de novo molecular synthesizer utilizes chemistry and reactivity patterns unavailable to biological machines.
Flame retardant polycyanurate thermosets from the cyanate esters of triphenylphosphine oxide
Davis, Matthew C.,Garrison, Michael D.,Ghiassi, Kamran B.,Groshens, Thomas J.,Redeker, Neil D.
, p. 1100 - 1110 (2018/03/21)
Three cyanate esters containing phosphorus are synthesized in good overall yields starting from bromoanisoles. Di- and tricyanates with meta configuration are most stable while para is less so. The para dicyanate ester isomer is particularly affected by water from the atmosphere. The meta dicyanate ester 2 has good thermal properties with glass transition at 268 °C and char yield of 65% in air at 600 °C. All three phosphorus-containing cyanate esters are low flammability in an open flame. They make highly combustible cyanate esters resins less flammable simply by blending. Mixing 10 wt% dicyanate ester 2 into bisphenol A or E dicyanate esters makes them rate V-0. Published 2018.? J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1100–1110.
Synthesis method of carbonate modified fluoride-free organic phosphine ligand
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Paragraph 0030; 0031; 0038; 0039, (2017/08/28)
The invention relates to the field of organic synthesis and provides a synthesis method of a carbonate modified fluoride-free organic phosphine ligand. The synthesis method comprises the following steps: preparing a Grignard reagent from the raw material p-bromoanisole or derivative thereof; enabling the Grignard reagent to react with a phosphorus source to generate a skeleton structure molecule with triphenylphosphine; and performing oxidation, demethylation, nucleophilic substitution and reduction to obtain a target molecular structure. The synthesis method has the following effects and benefits: a novel carbon dioxide-philic organic phosphine ligand is synthesized, the solubility of the phosphine ligand in supercritical CO2 is increased, and application of a fluoride-free phosphine ligand organic metal catalyst in supercritical CO2 is realized. Moreover, the organic carbonate compound is insoluble in a weakly (non-) polar organic solvent (such as alkane compounds), the property enables a phase splitting function of the carbonate modified fluoride-free organic phosphine ligand in the reaction system, and the recycling and reusing of the catalyst are realized.
Phosphine oxide hydroxyaryl mixtures with novolac resins for co-curing epoxy resins
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, (2008/06/13)
A mixture of hydroxyarylphosphine oxides comprising (a) a mono(hydroxyaryl)phosphine oxide, (b) a bis(hydroxyaryl)phosphine oxide, (c) a tris((hydroxyaryl)phosphine oxide, and, optionally (d) a tri- aryl, alkyl, or aralkyl-substituted phosphine oxide combined with a phenolic co-crosslinking composition is useful as a polyhtdroxy mixture for co-crosslinking an epoxy resin which also imparts flame resistance.
Synthesis of a family of triarylphosphanes with fluorous phase affinity
Sinou, Denis,Maillard, David,Pozzi, Gianluca
, p. 269 - 275 (2007/10/03)
A very efficient synthesis of new perfluoro-functionalized triarylphosphanes using an oxygen substituent as the branching point for the introduction of the perfluoro chain has been developed. This approach enabled the introduction of the perfluoro tail at the para, meta, and oitho position, giving highly perfluorinated analogues of triphenylphosphane con-taining between 54 and 59 wt% fluorine. This methodology has been extended to the synthesis of a perfluoro analogue of l,2-bis(diphenylphosphanyl)ethane. Fluorous/organic partition coefficients of some of the perfluorophosphanes have been measured, as well as their rates of oxidation. WILEY-VCH Verlag GmbH, 2002.
synthesis and Solid-State Structure of Substituted Arylphosphine Oxides
Whitaker, Craig M.,Kott, Kevin L.,McMahon, Robert J.
, p. 3499 - 3508 (2007/10/02)
We described the preparation and characterization of several new arylphosphine oxides, which are of interest as second-order nonlinear optical materials. (4-Aminophenyl)diphenylphosphine oxide (1a), bis(4-aminophenyl)phenylphosphine oxide (2a), and (4-aminophenyl)bisphosphine oxide (5) were prepared by addition of aryl Grignard and organolithium reagents containing protected amines to phosphorus oxyhalides.Alternatively, 1a was prepared by treatment of (4-bromophenyl)diphenylphosphine oxide with azidomethyl phenyl sulfide, followed by hydrolysis. (4-Aminophenyl)(4'-nitrophenyl)phenylphosphine oxide (6) was prepared by nucleophilic aromatic substitution of bis(4-fluorophenyl)phenylphosphine oxide to give the corresponding dinitro compound, followed by selective mono-reduction.The X-ray crystal structure of (4-aminophenyl)diphenylphosphine oxide (1a), along with those of mono-, di-, and trihydroxy triphenylphosphine oxides 1b, 2b, and 3b, exhibit extensive intermolecular hydrogen bonding.The hydrogen bonding in 1a and 1b produces chains of arylphosphine oxide molecules with a head-to-tail alignment; the chains pack in an antiparallel manner to produce solid-state structures that display only slight deviations from centrosymmetry.
