77308-67-9Relevant academic research and scientific papers
Blue-light-emitting multifunctional triphenylamine-centered starburst quinolines: Synthesis, electrochemical and photophysical properties
Jiang, Peng,Zhao, Dong-Dong,Yang, Xiao-Li,Zhu, Xiao-Lin,Chang, Jin,Zhu, Hong-Jun
, p. 4704 - 4711 (2012/08/08)
A series of triphenylamine-centered starburst quinolines (1a-1g) have been synthesized by Friedlaender condensation of the 4,4′,4′′- triacetyltriphenylamine (2) and 2-aminophenyl ketones (3a-3g) in the presence of catalytic sulfuric acid and characterized well. They are thermally robust with high glass transition temperatures (above 176.4 °C) and decomposition temperatures (above 406 °C). These compounds emit blue fluorescence with λEmmax ranging from 433 to 446 nm in dilute toluene solution and 461 to 502 nm in the solid-state and have a relatively high efficiency (Φu = 0.98-0.57). 1a-1g have estimated ionization potentials (IP) of 4.54 to 6.45 eV which are significantly near or higher than those of well-known electron transport materials (ETMs), including tris(8- hydroxyquinoline)aluminium (Alq3) (IP = 5.7-5.9 eV), and previously reported oligoquinolines (IP = 5.53-5.81 eV). Quantum chemical calculations using DFT B3LYP/6-31G* showed the highest occupied molecular orbital (HOMO) of -5.05 to -4.81 eV, which is close to the work function of indium tin oxide (ITO). These results demonstrate the potential of 1a-1g as hole-transporting/light-emitting/electron-transport materials and the host-materials of a dopant for hole-injecting for applications in organic light-emitting devices.
Fonctionnalisation d'hydrocarbures aromatiques polycycliques. Introduction de fonctions alcool, acide ou amine sur le biphenyle, le fluorene ou le phenanthrene
Guilhemat, Robert,Pereyre, Michel,Petraud, Michel
, p. 334 - 344 (2007/10/02)
With aluminium chloride as a catalyst, 3-methyl-1,3-butanediol, a primary-tertiary diol, yielded Friedel-Crafts primary alcohols with fluorene and biphenyl.The monosubstituted derivatives have been characterized mainly by 13C nmr and polysubstituted products have been obtained with excess diol.With the same substrates and in the same conditions a tertiary-tertiary diol such as 2,5-dimethyl-2,5-hexanediol gave only mono or bicycloalkylated hydrocarbons.The reactions of phtalic anhydride with fluorene, biphenyl and phenanthrene have been studied and the monosubstituted products characterized mainly by 13C nmr by means of a relaxation reagent.Bifunctionalized derivatives were also obtained and identified in the case of fluorene and biphenyl.On the other hand, amino functional groups were introduced on fluorene either by transformation of acid functions or by more direct routes such as reaction with isatoic anhydride or p-toluenesulfonylanthranilic acid.Some results have been used for the functionalization of an industrial residue containing polycyclic aromatic hydrocarbons.
