The Preparation and Polymerization of Monomeric Cyclic Disulfides

Davis, Frank; Fettes, E. M.

doi:10.1021/ja01187a524

Cited by 29 publications

(20 citation statements)

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“…Thermal curing of glass slides silanized with MPTS takes place at 100 • C in air. It is well established that under these conditions, both formation of disulfides [20] and polymerization of cyclic disulfides [21] are promoted. In the case of glass-grafted propanethiol fragments, it has also to be stressed that local concentration of -SH groups is increased (as it is indicated also by the significant π -stacking interactions after functionalization with Rh-M), so that reactivity toward S-S formation is promoted.…”

Section: Discussionmentioning

confidence: 99%

Spectroscopic evaluation of surface functionalization efficiency in the preparation of mercaptopropyltrimethoxysilane self-assembled monolayers on glass

Pallavicini

Dacarro

Galli

et al. 2009

Journal of Colloid and Interface Science

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Section: Discussionmentioning

confidence: 99%

Spectroscopic evaluation of surface functionalization efficiency in the preparation of mercaptopropyltrimethoxysilane self-assembled monolayers on glass

Pallavicini

Dacarro

Galli

et al. 2009

Journal of Colloid and Interface Science

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“…[39][40][41][42][43][44][45][46] Ringopening polymerization of cyclic disulfide compounds is one method for synthesizing such polymers. Although many studies on the polymerizations of cyclic disulfides were reported since the second half of the 1940s, 39,40 the detailed structural analyses and characterizations of the resulting polymers have not been investigated for a long time. Recently, we reported the thermal polymerization of 1,2-dithiane (DT) and detailed structural analyses and characterizations of the resulting polymers.…”

mentioning

confidence: 99%

Ring-Opening Polymerization of Aromatic 6-Membered Cyclic Disulfide and Characterization of the Polymer

Ishida¹,

Kisanuki²,

Endo³

2009

Polym. J.

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Synthesis and characterization of polymers obtained from polymerization of 1,4-dihydro-2,3-benzodithine (XDS) were investigated. The polymerization of XDS proceeded at reaction temperatures above the melting points of XDS to give polymers, and the molecular weight, which determined by GPC was high. From the structural analysis of poly(XDS), the polymer was found to have cyclic structure, in contrast to their linear polymer (poly(XDS-XDT) obtained from the polymerization of XDS in the presence of chain transfer thiol compounds such as , 0 -mercapto-o-xylene (XDT). From TGA and DSC measurements, poly(XDS) with benzene rings in the main chain is more thermal stable than the polymer obtained from the polymerization of 1,2-dithiane (DT). From dynamic viscoelastic measurements, poly(XDS) showed a rubbery plateau under the molten state even though poly(XDS) has no crosslinking system. The difference in solubility between poly(XDS) and poly(XDS-XDT) was also observed. On the basis of the polymer characterizations, it may be concluded that the poly(XDS) obtained from thermal ring-opening polymerization of XDS includes a polycatenane structure.KEY WORDS: Ring-Opening Polymerization / 1,4-Dihydro-2,3-Benzodithine / Cyclic Polymer / Polycatenane Structure / Cyclic Disulfides / Thermal Decomposition / Recently, much attention has been paid to topologically unique macromolecules containing a single cyclic and multicyclic polymer unit from the viewpoints of not only their distinctive properties that is different from linear polymers, but also elements of architecturally complex polymers and interlocked macromolecules such as polyrotaxanes and polycatenanes.1-11 Many studies on synthesis of cyclic polymers in the polymerizations have been also reported.12-26 Although efficient synthesis of rotaxanes and catenanes have been achieved, 27-37 a high molecular weight polycatenane which consists of only ring components has not been synthesized. Recently, Takata et al. reported that the Diels-Alder polymerization of [2]catenane bearing diene and dienophile moieties on each ring afforded a ''bridged polycatenane'' with a poly[2]catenane skeleton. 38 Many approaches have been reported to prepare polymers containing disulfide linkages in the main chain. [39][40][41][42][43][44][45][46] Ringopening polymerization of cyclic disulfide compounds is one method for synthesizing such polymers. Although many studies on the polymerizations of cyclic disulfides were reported since the second half of the 1940s, 39,40 the detailed structural analyses and characterizations of the resulting polymers have not been investigated for a long time. Recently, we reported the thermal polymerization of 1,2-dithiane (DT) and detailed structural analyses and characterizations of the resulting polymers. From analyses of the polymer, the cyclic structure was formed mainly by a backbiting reaction of propagating species. [44][45][46] We also reported that a polycatenane structure composed of interlocking system by entanglements with cyclic polymers was formed durin...

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“…118 » 119 They found phosphorus pentoxide to be an effective catalyst for the etherification reaction 118 and also prepared copolymers from thiodiglycol and dithiodiglycol. 55 From cyclic disulfides An extremely interesting although not especially useful method for the preparation of polymeric disulfides is the self-polymerization of a cyclic disulfide.…”

Section: /°\mentioning

confidence: 99%

Progress in Polysulfide Polymers

Fettes¹

1961

Organic Sulfur Compounds

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The Preparation and Polymerization of Monomeric Cyclic Disulfides

Cited by 29 publications

References 0 publications

Spectroscopic evaluation of surface functionalization efficiency in the preparation of mercaptopropyltrimethoxysilane self-assembled monolayers on glass

Spectroscopic evaluation of surface functionalization efficiency in the preparation of mercaptopropyltrimethoxysilane self-assembled monolayers on glass

Ring-Opening Polymerization of Aromatic 6-Membered Cyclic Disulfide and Characterization of the Polymer

Progress in Polysulfide Polymers

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