exo-9,10,11-Trithiatetracyclo[5.5.1.02,6.08,12]tridec-3-ene

Watson, William H.; Jain, P. C.; Bartlett, Paul D.; Ghosh, Tirthankar

doi:10.1107/s0108270186096282

Cited by 11 publications

(5 citation statements)

References 7 publications

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“…In all cases, the polysulfide monomers were isolated as the exo isomers in which the two C–S bonds have a cis relationship on the same face as the bridgehead methylene group (Figure and S21). For monomer 4 , the X-ray structure was consistent with that previously reported after preparing this compound using alternative reaction conditions. , …”

Section: Resultssupporting

confidence: 87%

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Electrochemical Synthesis of Poly(trisulfides)

et al. 2023

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With increasing interest in high sulfur content polymers, there is a need to develop new methods for their synthesis that feature improved safety and control of structure. In this report, electrochemically initiated ring-opening polymerization of norbornene-based cyclic trisulfide monomers delivered well-defined, linear poly(trisulfides), which were solution processable. Electrochemistry provided a controlled initiation step that obviates the need for hazardous chemical initiators. The high temperatures required for inverse vulcanization are also avoided resulting in an improved safety profile. Density functional theory calculations revealed a reversible "self-correcting" mechanism that ensures trisulfide linkages between monomer units. This control over sulfur rank is a new benchmark for high sulfur content polymers and creates opportunities to better understand the effects of sulfur rank on polymer properties. Thermogravimetric analysis coupled with mass spectrometry revealed the ability to recycle the polymer to the cyclic trisulfide monomer by thermal depolymerization. The featured poly(trisulfide) is an effective gold sorbent, with potential applications in mining and electronic waste recycling. A water-soluble poly(trisulfide) containing a carboxylic acid group was also produced and found to be effective in the binding and recovery of copper from aqueous media.

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Section: Resultssupporting

confidence: 87%

“…For monomer 4, the X-ray structure was consistent with that previously reported after preparing this compound using alternative reaction conditions. 36,37 Monomer Redox Activity. Cyclic voltammetry was used to assess the electrochemical redox behavior of monomers 1−4 (S24−S26).…”

Section: ■ Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Poly(trisulfides)

et al. 2023

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“…This enumeration includes also systems with two independent S n units (n ) 2-8) in one ring, bridged by carbon atoms. The following are leading references: trisulfanes; 125,130,162,171,[222][223][224] bis-trisulfane; 225 tetrasulfanes; [226][227][228] bis-tetrasulfane; 229 pentasulfanes; 122,130,142,148,171,[230][231][232][233] bis-pentasulfane; 163 hexasulfanes; 148,233 heptasulfane; 47 octasulfanes; 167,175 nonasulfane; 174 undecasulfane. 157 The geometrical parameters of the S n units in cyclic organic polysulfanes may be quite different from those in chain-like compounds since the ring closure may enforce unusual valence and torsional angles and, as a consequence, the bond distances will be affected.…”

Section: Structures Of Cyclic R−s N −R Moleculesmentioning

confidence: 99%

“…This enumeration includes also systems with two independent S n units ( n = 2−8) in one ring, bridged by carbon atoms. The following are leading references: trisulfanes; ,,,,− bis-trisulfane; tetrasulfanes; − bis-tetrasulfane; pentasulfanes; ,,,,,− bis-pentasulfane; hexasulfanes; , heptasulfane; octasulfanes; , nonasulfane; undecasulfane …”

Section: Structures Of Cyclic R−s N −R Moleculesmentioning

confidence: 99%

The Chemistry of Organic Polysulfanes R−S_n−R (n > 2)

2002

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“…In agreement with the NMR analyses at ‫04מ‬ЊC, the trithiolane ring of 7 adopts an envelope conformation. The C(1)-C(2) bond length, 1.61 Å , is much longer than those of trithiolanes, 11 [10] and 12 [11], which are 1.56 and 1.57 Å , respectively ( Figure 3). The C-C bond lengthening would be the result of the angle strains originating from the …”

Section: X-ray Crystallographic Analysis Of the Trithiolanementioning

confidence: 99%