Studies in the Sulfone Series. I. The Preparation of 2,8-Diaminodibenzothiophene-5-dioxide

Neumoyer, C. R.; Amstutz, E. D.

doi:10.1021/ja01200a023

Cited by 24 publications

(10 citation statements)

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“…[12] Scheme 1 illustrates the synthesis of the new compounds 1-4 in this study. Compounds 1 and 4 were synthesized from 2,8-dibromo-dibenzothiophene-S,S-dioxide [13] and diarylamines by the palladium-catalyzed C-N coupling strategy developed by Hartwig et al [14] Stille's cross-coupling reaction [15] of triarylaminostannyl reagents and 2,8-dibromo-dibenzothiophene-S,S-dioxide led to the compounds 2 and 3. These compounds were isolated in moderate to good yields (1, 53 %; 2, 32 %; 3, 71 %; 4, 60 %).…”

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confidence: 99%

Dipolar Dibenzothiophene S,S‐Dioxide Derivatives Containing Diarylamine: Materials for Single‐Layer Organic Light‐Emitting Devices

Huang¹,

Lin²,

Chen³

et al. 2006

Advanced Materials

199

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Dipolar compounds for use in simplified, single‐layer organic light‐emitting devices (OLEDs) containing a dibenzothiophene S,S‐dioxide core and two peripheral diarylamines are synthesized. These materials exhibit bipolar carrier‐transport properties, and efficient single‐layer electroluminescent devices (see Figure; ITO: indium tin oxide) using these materials are demonstrated. These compounds may lead to devices with performances comparable to multilayer ones at lower costs.

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confidence: 99%

Dipolar Dibenzothiophene S,S‐Dioxide Derivatives Containing Diarylamine: Materials for Single‐Layer Organic Light‐Emitting Devices

Huang¹,

Lin²,

Chen³

et al. 2006

Advanced Materials

199

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“…The first step in the preparation of compound 3 (Figure 2) is the bromination of the commercially available dibenzothiophene molecule. 20 The larger scale reaction occurs overnight with a yield of 83%. The resulting dibrominated compound 2 can be further oxidized with a solution of hydrogen peroxide in glacial acetic acid, yielding 19.3 g of a white powder after filtration and washing.…”

Section: Discussionmentioning

confidence: 99%

“…Synthesis of compound 2 (2,8-dibromodibenzothiophene) 20 Using a 500 mL three-neck round-bottom flask, dissolve dibenzothiophene (15.0 g, 81.3 mmol) in chloroform (100 mL) under nitrogen atmosphere. Next, add dropwise bromine (9.3 mL, 180 mmol) at 0 °C under vigorous stirring.…”

Section: Protocolmentioning

confidence: 99%

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Vybornyi

Findlay

Skabara

2017

JoVE

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We report a procedure to linearly scale-up the synthesis of 2,8-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzothiophene-S,S-dioxide (compound 4) and 2,8-bis(10H-phenothiazin-10-yl)dibenzothiophene-S,S-dioxide (compound 5) using Buchwald-Hartwig cross-coupling reaction conditions. In addition, we demonstrate a scaled-up synthesis of all non-commercially available starting materials that are required for the amination cross-coupling reaction. In the present article, we provide the detailed synthetic procedures for all of the described compounds, alongside their spectral characterization. This work shows the possibility to produce organic molecules for optoelectronic applications on a large scale, which facilitates their implementation into real world devices.

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“…The 2,s-dibromo derivative of dibenzothiophene was obtained by direct bromination of the parent compound in glacial acetic acid, following the method of Neymoyer and Amstutz (6). The product melted at 225-226 "C (lit.…”

Section: Methodsmentioning

confidence: 99%

A Paramagnetic Resonance Study of Unhindered Biphenyl Anion Radicals (III)

Adam¹,

Kepford²

1971

Can. J. Chem.

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The radical anions of biphenyl and some of its bridged derivatives have been studied by e.s.r. It is found that the proton hyperfine coupling constants change monotonically through the series of radical anions derived from biphenyl, 9,lO-dihydrophenanthrene, fluorene, dibenzothiophene, and dibenzofuran. Deuterations have been carried out for the latter two compounds and the hyperline coupling constants are assigned to specific positions in these anions. The data are displayed in the form of a correlation diagram from which assignments for other bridged biphenyl anions can be made.Les anions radicalaires du biphCny1 et des dCrivCs pontes ont Ct C Ctudits par r.p.e. I1 a Ct C trouve que les Ccarts hyperfins de protons changent graduellement dans la sCrie des anions radicalaires derives du biphenyl, 9,lO-dihydrophenanthrene, fluortne, dibenzothiophene et du dibenzofuranne. Des deutkrations ont ete effectukes pour les deux derniers composCs et les Ccarts hyperfins ont ete assignes a des positions specifiques pour ces anions.Les resultats sont reprCsentCs sous forme de diagramme de corrClation au moyen duquel des valeurs de couplages d'autres anions hyperfins pontts peuvent &re obtenues.Canadian Journal of Chemistry, 49, 3529 (1971) IntroductionIn previous papers in this series (1,2) the spectra of hindered diarylmethyl radicals were obtained and some insight was gained into the internal configuration of such molecules from a study of the proton hyperfine structure. The ideas behind this work have been extended to the biphenyl series of compounds. It has been suggested that biphenyl itself is not planar, and that steric interactions between the ortho protons prevent the two rings from assuming a perfectly coplanar arrangement. The results of gas phase electron diffraction studies suggest the rings are oriented at an angle of 42" to each other (3) while X-ray studies on the crystal suggest the rings are coplanar, but are connected by a rather long bond (for an aromatic)

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Studies in the Sulfone Series. I. The Preparation of 2,8-Diaminodibenzothiophene-5-dioxide

Cited by 24 publications

References 0 publications

Dipolar Dibenzothiophene S,S‐Dioxide Derivatives Containing Diarylamine: Materials for Single‐Layer Organic Light‐Emitting Devices

Dipolar Dibenzothiophene S,S‐Dioxide Derivatives Containing Diarylamine: Materials for Single‐Layer Organic Light‐Emitting Devices

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

A Paramagnetic Resonance Study of Unhindered Biphenyl Anion Radicals (III)

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