49658-22-2Relevant academic research and scientific papers
Experimental evidence for carbonyl-π electron cloud interactions
Gautrot, Julien E.,Hodge, Philip,Cupertino, Domenico,Helliwell, Madeleine
, p. 1801 - 1807 (2006)
In this work we present some experimental evidence of the existence of carbonyl-π electron cloud interactions. Such interactions are analogous to anion-π interactions, which have been predicted to be energetically favourable in the case of electron deficient aromatic rings. UV-Visible spectroscopy and cyclic voltammetry results obtained for 9,10-anthraquinone, 1,1′-bis-9,10-anthraquinone, poly(9,10-anthraquinone-1,4-diyl) and other 1,4-diaryl substituted anthraquinone derivatives are described. It was found that the steric hindrance occurring between the carbonyl groups and the adjacent aromatic substituent forces the plane of the anthraquinone moiety and that of the aromatic substituent to adopt a nearly orthogonal conformation, resulting in relatively strong carbonyl-π interactions that affect both the UV-Vis absorption spectrum and the reduction potential of the compound. Moreover, in the case of thiophene substituted derivatives, the torsion angle between the anthraquinone moiety and its aromatic substituent is smaller and therefore carbonyl-π interaction effects are not observed in these compounds. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Paragraph 0187-0190; 0223-0226, (2021/02/09)
The present invention relates to a compound represented by chemical formula 1 and to an organic light emitting device comprising the same. The compound is capable of improving efficiency, having low driving voltage, and/or improving service life properties in the organic light emitting device.
The electrochemistry of arylated anthraquinones in room temperature ionic liquids
Gomis-Berenguer, Alicia,Gomez-Mingot, Maria,Garcia-Cruz, Leticia,Thiemann, Thies,Banks, Craig E.,Montiel, Vicente,Iniesta, Jesus
, p. 367 - 375 (2013/05/21)
Arylated anthraquinone derivatives of different sizes and different π-basicities have been prepared, and the electrochemical behaviour of these substances has been studied on screen printed graphite electrodes in the three room temperature ionic liquids (RTILs), 1-butyl-3-methylimidazolium hexafluorophosphate ([C4MIM][PF6]), 1-hexyl-3- methylimidazolium hexafluorophosphate ([C6MIM][PF6]) and 1-octyl-3-methylimidazolium hexafluorophosphate ([C8MIM][PF 6]). Half redox potentials for the first and second one electron reduction waves were identified, and the diffusion coefficient values were estimated from cyclic voltammetry measurements. The influence of the nature of the RTIL and of the substitution pattern of the anthraquinone on the solvodynamic radii were studied. A correlation of the reductive potentials with the corresponding Hammett constants of the substituents was tested. Copyright
Arylation of chloroanthraquinones by surprisingly facile Suzuki-Miyaura cross-coupling reactions
Thiemann, Thies,Tanaka, Yasuko,Iniesta, Jesus,Varghese, H. Tresa,Pannicker, C. Yohannan
experimental part, p. 732 - 736 (2010/03/24)
Chloroanthraquinones were found to undergo facile Suzuki-cross coupling with substituted phenyl boronic acids using a commercial catalyst Pd(PPh 3)4 and with Pd(PPh3)4 prepared in situ from Pd(PPh3)2Cl2 and PPh3.
Brominated thiophenes as precursors in the preparation of brominated and arylated anthraquinones
Thiemann, Thies,Tanaka, Yasuko,Iniesta, Jesus
experimental part, p. 1013 - 1031 (2009/10/10)
Brominated anthraquinones can be synthesized directly from bromothiophenes when these are reacted with 1,4-naphthoquinones in the presence of meta-chloroperoxybenzoic acid. The bromoanthraquinones are versatile building blocks in the preparation of arylated anthraquinones and of extended π-systems with interspersed anthraquinone units.
