Rearrangement with 4-Iododibenzothiophene in Amination by Sodamide

Gilman, Henry; Nobis, John F.

doi:10.1021/ja01225a020

Cited by 21 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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. 21 Compound 3 was used in the cross-coupling reaction without any further purification.…”

Section: Discussionmentioning

confidence: 99%

“…Synthesis of compound 3 (2,8-dibromodibenzothiophene-5-dioxide) 21 Load a 500 mL one-neck round bottom flask with a suspension of 2,8-dibromodibenzothiophene (21.3 g, 60 mmol) and hydrogen peroxide solution (30 mL of 30% (w/w) in H 2 O) in glacial acetic acid (250 mL) and reflux for 2 h under a nitrogen atmosphere. Cool the resulting mixture to room temperature, and filter off a white precipitate.…”

Section: Protocolmentioning

confidence: 99%

See 1 more Smart Citation

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

Vybornyi

Findlay

Skabara

2017

JoVE

View full text Add to dashboard Cite

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.

show abstract

Section: Discussionmentioning

confidence: 99%

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

View full text Add to dashboard Cite

show abstract

“…This compound was prepared by the oxidation of 3 by means of H 2 O 2 in glacial acetic acid according to a reported method 45…”

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared by the oxidation of 2 by means of H 2 O 2 in glacial acetic acid according to a reported method. 45 2,8-Dibromodibenzothiophene-5,5-dioxide (5) This compound was prepared by the oxidation of 3 by means of H 2 O 2 in glacial acetic acid according to a reported method. 45…”

Section: -Bromodibenzothiophene-55-dioxide (4)mentioning

confidence: 99%

Novel blue‐greenish electroluminescent poly(fluorenevinylene‐alt‐dibenzothiophenevinylene)s and their model compounds

Mikroyannidis

Moshopoulou

Anastasopoulos

et al. 2006

J. Polym. Sci. A Polym. Chem.

View full text Add to dashboard Cite

Poly(9,9‐dihexylfluorene‐2,7‐vinylene‐alt‐dibenzothiophene‐2,8‐vinylene) (PS) and poly(9,9‐dihexylfluorene‐2,7‐vinylene‐alt‐dibenzothiophene‐5,5‐dioxide‐2,8‐ vinylene) (PSO) as well as corresponding model compounds were synthesized by Heck coupling. Both the polymers and model compounds were readily soluble in common organic solvents such as tetrahydrofuran, dichloromethane, chloroform, and toluene. The polymers showed a decomposition temperature at ∼430 °C and a char yield of about 65% at 800 °C in N2. The glass‐transition temperatures of the polymers were almost identical (75–77 °C) and higher than those of the model compounds (26–45 °C). All samples absorbed around 390 nm, and their optical band gaps were 2.69–2.85 eV. They behaved as blue‐greenish light emitting materials in both solutions and thin films, with photoluminescence emission maxima at 450–483 nm and photoluminescence quantum yields of 0.52–0.72 in solution. Organic light‐emitting diodes with an indium tin oxide/poly(ethylene dioxythiophene):poly(styrene sulfonic acid)/polymer/Mg:Ag/Ag configuration with polymers PS and PSO as emitting layers showed green electroluminescence with maxima at 530 and 540 nm, respectively. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 6790–6800, 2006

show abstract

“…3. Synthesis of compound 3 (2,8-dibromodibenzothiophene-5-dioxide) 21 1. Load a 500 mL one-neck round bottom flask with a suspension of 2,8-dibromodibenzothiophene (21.3 g, 60 mmol) and hydrogen peroxide solution (30 mL of 30% (w/w) in H 2 O) in glacial acetic acid (250 mL) and reflux for 2 h under a nitrogen atmosphere.…”

Section: Synthesis Of the Reported Compoundsmentioning

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

View full text Add to dashboard Cite

Rearrangement with 4-Iododibenzothiophene in Amination by Sodamide

Cited by 21 publications

References 0 publications

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

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

Novel blue‐greenish electroluminescent poly(fluorenevinylene‐alt‐dibenzothiophenevinylene)s and their model compounds

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

Contact Info

Product

Resources

About