Iodine in Dimethyl Sulfoxide as a New General Reagent for the Preparative Oxidation of 1,2-Diarylethenes and 1,2-Diarylethynes to Aromatic 1,2-Diketones

Yusybov, M. S. O.; Филимонов, В. Д.

doi:10.1055/s-1991-26397

Cited by 63 publications

(17 citation statements)

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“…The physical properties of these materials, carrier mobilities, and OLEDs fabricated using these compounds are investigated. PdCl 2 (PPh 3 ) 2 and CuI; ii) oxidiation of the internal alkynes using iodine in dimethyl sulfoxide (3 and 4) to form the dione derivatives, in a process developed by Yusybov and Filimonov; [12] (it is worth nothing that this method is more convenient than the similar oxidation of an alkyne to dione via the use of highly toxic selenium dioxide [13] ) iii) condensation of a bisdione compound with an appropriate diamine to afford the targeted diquinoxaline or dipyrazine (5-8, Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Dibenzothiophene/Oxide and Quinoxaline/Pyrazine Derivatives Serving as Electron‐Transport Materials

Huang

Whang

Shen

et al. 2006

Adv Funct Materials

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A series of 2,8‐disubstituted dibenzothiophene and 2,8‐disubstituted dibenzothiophene‐S,S‐dioxide derivatives containing quinoxaline and pyrazine moieties are synthesized via three key steps: i) palladium‐catalyzed Sonogashira coupling reaction to form dialkynes; ii) conversion of the dialkynes to diones; and iii) condensation of the diones with diamines. Single‐crystal characterization of 2,8‐di(6,7‐dimethyl‐3‐phenyl‐2‐quinoxalinyl)‐5H‐5λ6‐dibenzo[b,d]thiophene‐5,5‐dione indicates a triclinic crystal structure with space group P1 and a non‐coplanar structure. These new materials are amorphous, with glass‐transition temperatures ranging from 132 to 194 °C. The compounds (Cpd) exhibit high electron mobilities and serve as effective electron‐transport materials for organic light‐emitting devices. Double‐layer devices are fabricated with the structure indium tin oxide (ITO)/Qn/Cpd/LiF/Al, where yellow‐emitting 2,3‐bis[4‐(N‐phenyl‐9‐ethyl‐3‐carbazolylamino)phenyl]quinoxaline (Qn) serves as the emitting layer. An external quantum efficiency of 1.41 %, a power efficiency of 4.94 lm W–1, and a current efficiency of 1.62 cd A–1 are achieved at a current density of 100 mA cm–2.

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Section: Introductionmentioning

confidence: 99%

Dibenzothiophene/Oxide and Quinoxaline/Pyrazine Derivatives Serving as Electron‐Transport Materials

Huang

Whang

Shen

et al. 2006

Adv Funct Materials

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“…Compound 6 was obtained by the oxidation of the corresponding diphenylacetylene derivatives 5 . In case of 5a , oxidation was accomplished by usage of iodine in DMSO at 155 °C, while these drastic conditions were not suitable for the oxidation of 5b and 5c , possibly due to the partial decomposition of the neopentyl ester. Thus a Wacker‐type oxidation was suitable for 5b and 5c under oxygen atmosphere at milder condition to afford 6b and 6c in high yields.…”

Section: Resultsmentioning

confidence: 99%

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

Stangenberg

Saeed

Kuan

et al. 2013

Macromol. Rapid Commun.

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In the ideal case, a precise synthesis yields molecules with a constitutional as well as a conformational perfectness. Such a case of precision is demonstrated by the synthesis of semi-rigid amphiphilic polyphenylene dendrimers (PPDs). Polar sulfonate groups are precisely placed on their periphery in such a manner that patches of polar and non-polar regions are created. Key structural features are the semi-rigid framework and shape-persistent nature of PPDs since the limited flexibility introduces a nano-phase-separated amphiphilic rim of the dendrimer. This results in both attractive and repulsive interactions with a given solvent. Frustrated solvent structures then lead to a remarkable solubility in solvents of different polarity such as toluene, methanol, and water or their mixtures. Water solubility combined with defined surface structuring and variable hydrophobicity of PPDs that resemble the delicate surface textures of proteins are important prerequisites for their biological and medical applications based upon cellular internalization.

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“…In order to increase hole transport efficiency of TBP, we have synthesized the arylamine tribenzo[ fj,ij,rst ]pentaphene derivative 1 with two nitrogen‐containing groups attached at the opposite ends of the aromatic core. Scheme summarizes the few reaction steps towards the target aryl amine pentaphene derivatives; 4,4′‐didodecylbenzil was prepared from the oxidation of 4,4′‐didodecyltolane in presence of iodine and dimethyl sulfoxide (DMSO) (see Supporting Information for synthetic details) . The double Knoevenagel condensation reaction between the benzil and 1,3‐bis(4‐bromophenyl)acetone in refluxing diphenyl ether affords the tetraarylcyclopentadienone moiety 2 in 55 % yield.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Arylamine Tribenzopentaphenes and Investigation of their Hole Mobility

et al. 2015

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We report the versatile synthesis of two tribenzo[fj,ij,rst]pentaphene (TBP) derivatives bearing two diarylamine substituents attached at the opposite ends of the aromatic core. Field effect transistor (FET) devices of the bis-diarylamine-TBP compounds were fabricated using spin coating under different concentrations, spin speed, and solvent conditions. Emission spectra and surface investigation by atomic force microscopy (AFM) reveal the formation of aggregates induced by the strong π–π stacking of the aromatic core leading to island features, and thus, unexpected low hole mobilities. The synthetic strategy we show herein, however, offers the possibility to decorate the TBP core structure with various charge-carrier peripheral groups and optimized alkyl chains, which should improve the crystalline property of their thin films upon deposition, leading consequently to a better hole transport mobility.

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Iodine in Dimethyl Sulfoxide as a New General Reagent for the Preparative Oxidation of 1,2-Diarylethenes and 1,2-Diarylethynes to Aromatic 1,2-Diketones

Abstract: 1,2-Diarylethenes and 1,2-diarylethynes are readily converted to the corresponding 1,2-diketones in high yield using the reagent iodine in dimethyl sulfoxide. Alkynes in these reactions are more reactive than alkenes.

Cited by 63 publications

References 0 publications

Dibenzothiophene/Oxide and Quinoxaline/Pyrazine Derivatives Serving as Electron‐Transport Materials

Dibenzothiophene/Oxide and Quinoxaline/Pyrazine Derivatives Serving as Electron‐Transport Materials

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

Synthesis of Arylamine Tribenzopentaphenes and Investigation of their Hole Mobility

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