Thione-disulfide interchange of some heterocyclic tautomeric thiones and their symmetrical disulfides

Stoyanov, Stanimir; Stoyanova, Tatyana; Antonov, L.; Karagiannidis, P.; Akrivos, Pericles D.

doi:10.1007/bf00807074

Cited by 19 publications

(11 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The molar absorption coefficient of ADSDA at 232 nm was 2.02 × 10 4 M –1 cm –1 , while that at 337 nm was 5.34 × 10 3 M –1 cm –1 . The one at 232 nm was assigned as the overlapping peak of acrylate group and benzene group, while that at 337 nm was assigned as the absorption peak of the S–S bond in ADSDA. , As shown in Figure b, when the irradiation time was extended, the absorption peak of the S–S bond located at 337 nm decreased significantly and disappeared completely after irradiation for 90 s, demonstrating that the S–S bond of ADSDA had completely decomposed under UV irradiation. Moreover, the absorption peak of the acrylate group at 232 nm also decreased slightly after 90 s of the UV irradiation, suggesting the polymerization of some acrylate groups in ADSDA.…”

Section: Resultsmentioning

confidence: 96%

UV-Nanoimprinting Lithography Photoresists with No Photoinitiator and Low Polymerization Shrinkage

Zhang

Jiang

Gao

et al. 2020

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

In this work, a photopolymerizable disulfide monomer containing C(aryl)–S, disulfanediyl bis(4,1-phenylene) diacrylate (ADSDA), was designed and synthesized. UV-nanoimprinting lithography photoresists with no photoinitiator and low polymerization shrinkage were then prepared with ADSDA and benzyl methacrylate (BMA). The photoresists with ADSDA exhibited a great photopolymerization capability in the absence of any photoinitiator, and their double bond conversion reached up to 86%. With the increase of ADSDA content in the photoresists, the Young’s modulus, indentation hardness, and thermal stability of the photoresists all increased first, followed by a slight decrease. Remarkably, the photoresists with ADSDA had a very low polymerization shrinkage which dropped to as low as 0.56% because of the “breakage–recombination” reversible reaction of the S–S bond during the photopolymerization process. More significantly, the pattern of the original mold with 212 nm line width and 104 nm height could be accurately duplicated without flaws by the photoresist, which exhibited a prominent pattern transfer property.

show abstract

Section: Resultsmentioning

confidence: 96%

UV-Nanoimprinting Lithography Photoresists with No Photoinitiator and Low Polymerization Shrinkage

Zhang

Jiang

Gao

et al. 2020

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

show abstract

“…The heterocyclic compound tsacH can, in principle, exist in two, principle tautomeric forms in solution (Chart 1) that parallel the wellknown lactam ⇌ lactim equilibria established for dione-containing heterocycles. In the case of tsacH, the pertinent equilibrium involves the heterocyclic thione (thioamide) and the thiol (thioimine) forms of the molecule [12,13], with the thiol contributor favored computationally [14] and confirmed experimentally by NMR measurements [15].…”

Section: Introductionmentioning

confidence: 87%

Activation of thiosaccharin at a polynuclear osmium cluster

Pinky

Rahman

Ghosh

et al. 2019

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

The reaction of thiosaccharin (tsacH) with the triosmium cluster [Os3(CO)10(NCMe)2] furnishes the decacarbonyl isomers [HOs3(CO)10(μ-S-tsac)] (1) and [HOs3(CO)10(μ-N,S-1,3-tsac)] (2) in a 3:1 ratio at room temperature. These isomers differ by the coordination mode displayed by tsac ligand. The tsac moiety functions as an edge-bridging ligand via the sulfur atom in 1 while in 2 the bridging of adjacent osmium centers is achieved through the sulfur and nitrogen groups. The ancillary hydride in both products shares the Os-Os edge that is bridged by the heterocyclic ligand. Heating 1 at 80 °C affords 2 and demonstrates that the former cluster is the product of kinetic control. The conversion of 1  2 has been investigated by DFT and the isomerization pathway elucidated. The DFT calculations confirm cluster 2 as the thermodynamically preferred isomer in this pair of products. Thermolysis of 2 in refluxing toluene affords the hexanuclear cluster [H2Os6(CO)17(μ-C,N-1,2-C6H4CNSO2)2(μ3-S)(μ4-S)] (3) via carbon-sulfur bond scission and subsequent capture of the extruded sulfur by the cluster core. The molecular structures for the three new clusters have been determined by single-crystal X-ray diffraction analyses.

show abstract

“…It has been reported, that under ambient conditions pyridine derivatives substituted at the 2 or 4 position by potentially tautomeric groups (SH in this case) exist as the thione tautomer 3 rather than as the thiol form in polar solvents [83][84][85][86]. In the solid state, 2Mpy exists in its thione form as a hydrogen bonded dimer as shown below [80][81][82]87].…”

Section: Mpy Adsorbed From Watermentioning

confidence: 92%

“…Positions and assignments of vibrational bands of solid and adsorbed 2Mpy are summarized in Table 1. The band assignments are based on literature data [57,[68][69][70][71][72][73][74][75][76][77][78][79][80][81][82].…”

Section: Mpy Adsorbed From Watermentioning

confidence: 99%

Surface enhanced Raman spectroscopy of self-assembled monolayers of 2-mercaptopyridine on a gold electrode

Hassan

Holze

2012

Russ J Electrochem

View full text Add to dashboard Cite

Thione-disulfide interchange of some heterocyclic tautomeric thiones and their symmetrical disulfides

Cited by 19 publications

References 16 publications

UV-Nanoimprinting Lithography Photoresists with No Photoinitiator and Low Polymerization Shrinkage

UV-Nanoimprinting Lithography Photoresists with No Photoinitiator and Low Polymerization Shrinkage

Activation of thiosaccharin at a polynuclear osmium cluster

Surface enhanced Raman spectroscopy of self-assembled monolayers of 2-mercaptopyridine on a gold electrode

Contact Info

Product

Resources

About