2020
DOI: 10.1038/s41598-020-76907-4
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Formation of intramolecular dimer radical ions of diphenyl sulfones

Abstract: Dimer radical ions of aromatic molecules in which excess charge is localized in a pair of rings have been extensively investigated. While dimer radical cations of aromatics have been previously produced in the condensed phase, the number of molecules that form dimer anions is very limited. In this study, we report the formation of intramolecular dimer radical ions (cations and anions) of diphenyl sulfone derivatives (DPs) by electron beam pulse radiolysis in the liquid phase at room temperature. The density fu… Show more

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Cited by 4 publications
(5 citation statements)
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“…It is unclear whether the dimer itself or the free arene undergoes oxidation. Arene cation radical dimers have previously been observed in solution using time-resolved laser spectroscopy as an association between one neutral and one oxidized form of the relevant arene. We were unable to observe cation radical dimer formation in solution; however, we believe this may serve to stabilize the oxidized intermediate and extend its lifetime by preventing premature back electron transfer with the reduced form of the photoredox catalyst. Ultimately, nucleophilic addition to the dissociated arene cation radical would lead to product formation.…”
Section: Resultsmentioning
confidence: 78%
“…It is unclear whether the dimer itself or the free arene undergoes oxidation. Arene cation radical dimers have previously been observed in solution using time-resolved laser spectroscopy as an association between one neutral and one oxidized form of the relevant arene. We were unable to observe cation radical dimer formation in solution; however, we believe this may serve to stabilize the oxidized intermediate and extend its lifetime by preventing premature back electron transfer with the reduced form of the photoredox catalyst. Ultimately, nucleophilic addition to the dissociated arene cation radical would lead to product formation.…”
Section: Resultsmentioning
confidence: 78%
“…Details have been provided elsewhere. 28,33) Polymers 1-4 (100 mM/unit conc.) in 1,2dichloroethane (DCE) solutions were used as the samples.…”
Section: Methodsmentioning
confidence: 99%
“…In this study, trioctylamine was used as a model for quencher. Table II shows the degree of polymerization of each polymer 36) The optimized structures of DTS 28) and PAG 41) were obtained from previous reports. The radial distribution function (RDF) was calculated from the MD results using GROMACS.…”
Section: Calculationsmentioning
confidence: 99%
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“…We propose that diphenyl sulfone derivatives show promise as an AGP. Although diphenyl sulfones capture electrons to form radical anions, 31) the acid yield is not reduced by electron transfer from the radical anion to the PAG. 29) Moreover, in ArF lithography, the addition of di-p-tolyl sulfone (DTS) as an AGP to methacrylate polymers has been found to increase the initial acid yield.…”
Section: Introductionmentioning
confidence: 99%