Polystyrenes with pendant thioether and sulfoxide functional groups: Preparation, reactivity, and coordination chemistry with platinum(II)

Davies, Julian A.; Sood, Anup

doi:10.1002/marc.1983.030041205

Cited by 25 publications

(8 citation statements)

References 11 publications

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“…Polysulfoxides are useful as polymeric oxidants and permeation membranes for isolation of SO 2 9. In this work, PVCM was oxidized to polysulfoxide and polysulfone with 4 equiv of H 2 O 2 per sulfide unit in CH 2 Cl 2 (1.0 M) for 20 h (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactions of cysteine-based telechelic polymers

Kudo¹,

Sanda²,

Endo³

2000

J. Polym. Sci. A Polym. Chem.

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The radical polyaddition of N‐4‐vinylbenzoyl‐L‐cysteine methyl ester (VCM) was carried out in the presence of 2,2′‐azobisisobutyronitrile (AIBN, 3 mol %) as an initiator in dimethyl formamide (DMF) with monomer concentrations of 0.5 and 1.0 M at 60 °C for 20 h under nitrogen atmosphere to afford the corresponding polymers [poly(VCM), PVCM] with number‐average molecular weights (Mn)'s of 5300 and 18,000 in 92 and 95% yields, respectively. The obtained polymers had a heterotelechelic structure with thiol and olefin end moieties. The radical polymerization of methyl methacrylate and trityl methacrylate was carried out in the presence of PVCM with AIBN (3 mol %) as an initiator in DMF at 60 °C for 20 h to afford the block copolymers with Mn values in the range of 13,000–26,800 in good yields. PVCM [Mn = 18,000; polydispersity (Mw/Mn) = 1.56] was treated with 4 equiv of NaOH aq. (1.0 M) to afford the polymer having carboxyl groups in the side chain with a Mn of 17,300 and Mw/Mn of 1.88 in 95% yield and was also oxidized to polysulfoxide and polysulfone with 4 equiv of H2O2 per sulfide unit in CH2Cl2 (1.0 M) for 20 h. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 23–31, 2001

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Section: Resultsmentioning

confidence: 99%

Synthesis and reactions of cysteine-based telechelic polymers

Kudo¹,

Sanda²,

Endo³

2000

J. Polym. Sci. A Polym. Chem.

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“…Polysulfoxides with sulfinyl group in the side chain can be obtained by the polymerization of monomers containing a sulfinyl group linked to the unsaturated carbon-carbon bond via aromatic or aliphatic units (107) (363, 364,366,367,373) or directly as (vinylsulfinyl)benzene (374). They can also be synthesized by a Michael-type addition of dithiols to diolefins with a double bond activated by an adjacent sulfinyl group (369,375).…”

Section: Polysulfoxidesmentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys

2010

Encyclopedia of Polymer Science and Technology

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Sulfur-containing polymers, when considering their structure, make up a complex group of macromolecular compounds of varied and often remarkable features that determine their versatile applications.The presence of sulfur atoms in polymer structure, depending on the kind of functional group, can improve some important properties, such as mechanical, electrical, and optical, and then adhesion to metals, resistance to heat, chemicals, radiation, and bacteria, biocompatibility, and so on. These are their more important functional groups: sulfide -S-, polysulfide -S n -, sulfonyl -SO 2 -, sulfinyl -SO-, sulfo -SO 3 H, as well as some organic groups containing sulfur atoms, such as thioester -Sulfur-containing polymers can be used as high performance engineering plastics, chemically stable ion-exchange membranes in electromembrane processes, proton-conducting electrolytes, as well as optical, optoelectronic, and photochemical materials. Some polymers are employed in biomedical applications, for example, sulfopolymers as biomembranes and blood-compatible materials, and polysulfates and polysulfonates as antithrombotic or antiviral agents. The presence of sulfur, particularly in the form of disulfide bridges, plays an important role in biopolymers.The purpose of this review is mainly to present recent advances in the area of sulfur-containing polymers that may not yet have commercial applications. Nevertheless, older but still significant material has been included at the beginning of the discussion of each class. Poly(monosulfide)sPolymers containing a monosulfide linkage in both the main chain and the pendent group are the subject of many detailed studies. A few reviews of the synthesis and properties of all types of polymers have been published (1-4); like the one covering polymer with sulfur in the main chain that appeared in 1992 (3). Polysulfides with controlled and well-defined structures can be easily prepared. Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)].

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“…Polysulfoxides are a catalyst for reactions conducted under phase-transfer conditions Vol. 4 (268)(269)(270). Poly(sulfinyl acrylate)s exhibit some biological activity (271,272).…”

Section: Polysulfoxidesmentioning

confidence: 99%

“…Polysulfoxides with sulfoxide group in the side chain are obtained by polymerization of monomers containing a sulfoxide group linked to the unsaturated carbon-carbon bond via aromatic or aliphatic units (107) (268,269,271,272,277). They are also synthesized by a Michael-type addition of dithiols to diolefins with a double bond activated by an adjacent sulfoxide group (274,278).…”

Section: Polysulfoxidesmentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys¹

2001

Encyclopedia of Polymer Science and Technology

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Vol. 4 SULFUR-CONTAINING POLYMERS 337Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)]. Much effort has been devoted to preparing aromatic compounds in view of their significance as reactive intermediates for the synthesis of high performance linear aromatic polymers by ring-opening polymerization (ROP) (5). In an attempt to develop a novel synthetic method for the preparation of high molecular weight poly(thioarylene)s, macrocyclic aromatic sulfides and disulfides have been intensively prepared (6-14). The coordination chemistry of macrocyclic polysulfides has also received considerable attention during the past years. The thiacrown ether polymer ligands can be used as ion-exchange resins, metal ion adsorbents, and polymeric phase-transfer catalysts (15,16). Molecular systems in which tetrathiafulvalene is incorporated into macrocycles with supplementary donor atoms are potential electroactive cation sensors (17). The π -conjugated polymers have been extensively studied because of their attractive electronic properties. SULFUR-CONTAINING POLYMERSVol. 4The novel partially crystalline polymer (3) with number-average molecular weight (M n ) of up to 5700 was prepared under various conditions by catalyzed self-condensation of 3-hydroxypropyl methoxycarbonylethyl sulfide (4) or 3-hydroxypropyl carboxyethyl sulfide (5) (22). The degree of crystallinity, melting temperature (T m ), T g , and temperature of initial decomposition (T d ) were 36-46%, 37-47 • C, −61 to −70 • C, and 164-260 • C, respectively. The monomers (4) and (5) were prepared by an addition of methyl 3-mercaptopropionate and 3-mercaptopropionic acid with allyl alcohol [107-18-6] catalyzed by AIBN [2,2 -azobis(2-methylpropionitrile), azobisisobutyronitrile, azodiisobutyrodinitrile, 2,2 -azobis(2-methylpropanenitrile), α,α -azodiisobutyronitrile, 2,2 -azobis(isobutyronitrile), 2,2 -dicyano-2,2 -azopropane, Porofor-57, 2,2 -dimethyl-2,2azodipropionitrile, 2,2(-azobis(2-methylpropionitrile))] [78-67-1].An addition of conjugate 1,4-benzenedithiol (A) to 1,4-divinylbenzene (1,4diethenylbenzene, p-divinylbenzene) (B) [105-06-6] was investigated in detail in the presence of the AIBN initiator in toluene at 75 • C (23). It was found that the polymerization proceeded without an induction period, to give a white polymer with a high molecular weight [weight-average molecular weight (M w ) = 110,000] in ∼90% yield for 2 h. In addition, it was confirmed by 1 H nmr, ir, and the sulfur contents that the polymer had an alternating structure of A and B units.The synthesis and radical addition behavior of optically active cysteinebased monomers with mercapto and olefin groups have also been studied (24). N-4-vinylbenzoyl-L-cysteine methyl ester polymerized satisfactorily to afford the corresponding polysulfide (with M n in the range of 7000-23,000) in good yields.A novel one-pot synthesis of sulfur-containing polymers incl...

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Polystyrenes with pendant thioether and sulfoxide functional groups: Preparation, reactivity, and coordination chemistry with platinum(II)

Cited by 25 publications

References 11 publications

Synthesis and reactions of cysteine-based telechelic polymers

Synthesis and reactions of cysteine-based telechelic polymers

Sulfur‐Containing Polymers

Sulfur‐Containing Polymers

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