Aromatic pentafluoro-λ6-sulfanyl (SF5) surfactants: m-SF5(CF2)nC6H4SO3K

Winner, Scott W.; Winter, R.; Smith, Jeremy A.; Gard, Gary L.; Hannah, Nicole A.; Rananavare, Shankar B.; Piknová, Barbora; Hall, Stephen B.

doi:10.1070/mc2006v016n03abeh002315

Cited by 3 publications

(1 citation statement)

References 16 publications

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“…Sandmayer-type chemistry was then used to functionalise the scaffold with a number of different functionalities including halogens, hydroxyl and acyloxy functions, SO 2 Cl, vinyl and azide groups (Scheme 90) [98,99].The corresponding sulfonic acids were also obtained by treatment of the same substrate with chlorosulfonic acid [100].…”

Section: Scheme 84mentioning

confidence: 99%

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

198

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The pentafluorosulfanyl group (SF5) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF5-compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF5-group into organic molecules. However, recent synthetic progress, the availability of some SF5-building blocks from commercial suppliers and the discovery of interesting properties of SF5-substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF5-substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000. Object *Cover Letter or Page containing Author DetailsAll of the referees' suggestions have been accepted, with the only exception of Referee's 2 point 5 "Reactions of ArylSF5 systems should be divided into sections …electrophilc substitutions, nucleophilic substitutions, reactions of diazo systems,…" because in that section the chemistry is inherently heterogeneous and we feel that such a subclassification would be very challenging to achieve and would make less homogeneous the discussion of the topic. Molecolare, via Mancinelli 7, 20131 Milano, Italy Synthesis, reactivity and biological properties of SF 5 -substituted organic molecules are reviewed in this article, with an emphasis on the work published in the last decade. *Graphical Abstract -Synopsis Highlights We review the synthesis of SF 5 -compounds, with an emphasis on work published after year 2000.  We review the reactivity of SF 5 -substituted organic molecules.  We review the biological properties of SF 5 -substituted drug candidates. Aberdeen, Foresterhill, Aberdeen AB25 2ZD, Scotland, UK; e-mail: m.zanda@abdn.ac.uk b C.N.R.-Istituto di Chimica del Riconoscimento Molecolare, via Mancinelli 7, 20131 Milano, Italy AbstractThe pentafluorosulfanyl group (SF 5 ) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF 5 -compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF 5 -group into organic molecules. However, recent synthetic progress, the availability of some SF 5 -building blocks from commercial suppliers and the discovery of interesting properties of SF 5 -substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF 5 -substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000.

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Section: Scheme 84mentioning

confidence: 99%

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

198

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Aromatic Pentafluoro‐λ⁶‐sulfanyl (SF₅) Surfactants: m‐SF₅ (CF₂)_nC₆H₄SO₃K

et al. 2006

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Green Phosphorescence and Electroluminescence of Sulfur Pentafluoride-Functionalized Cationic Iridium(III) Complexes

et al. 2015

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We report on four cationic iridium(III) complexes [Ir(C^N)2(dtBubpy)](PF6) that have sulfur pentafluoride-modified 1-phenylpyrazole and 2-phenylpyridine cyclometalating (C^N) ligands (dtBubpy = 4,4'-di-tert-butyl-2,2'-bipyridyl). Three of the complexes were characterized by single-crystal X-ray structure analysis. In cyclic voltammetry, the complexes undergo reversible oxidation of iridium(III) and irreversible reduction of the SF5 group. They emit bright green phosphorescence in acetonitrile solution and in thin films at room temperature, with emission maxima in the range of 482-519 nm and photoluminescence quantum yields of up to 79%. The electron-withdrawing sulfur pentafluoride group on the cyclometalating ligands increases the oxidation potential and the redox gap and blue-shifts the phosphorescence of the iridium complexes more so than the commonly employed fluoro and trifluoromethyl groups. The irreversible reduction of the SF5 group may be a problem in organic electronics; for example, the complexes do not exhibit electroluminescence in light-emitting electrochemical cells (LEECs). Nevertheless, the complexes exhibit green to yellow-green electroluminescence in doped multilayer organic light-emitting diodes (OLEDs) with emission maxima ranging from 501 nm to 520 nm and with an external quantum efficiency (EQE) of up to 1.7% in solution-processed devices.

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Aromatic pentafluoro-λ6-sulfanyl (SF5) surfactants: m-SF5(CF2)nC6H4SO3K

Cited by 3 publications

References 16 publications

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Aromatic Pentafluoro‐λ⁶‐sulfanyl (SF₅) Surfactants: m‐SF₅ (CF₂)_nC₆H₄SO₃K

Green Phosphorescence and Electroluminescence of Sulfur Pentafluoride-Functionalized Cationic Iridium(III) Complexes

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Aromatic pentafluoro-λ6-sulfanyl (SF5) surfactants: m-SF5(CF2)nC6H4SO3K

Cited by 3 publications

References 16 publications

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules