78049-20-4Relevant academic research and scientific papers
Synthesis of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices
Thanh, Nguyen Chung,Ikai, Masamichi,Kajioka, Takanori,Fujikawa, Hisayoshi,Taga, Yasunori,Zhang, Yanmei,Ogawa, Satoshi,Shimada, Hiroko,Miyahara, Yosuke,Kuroda, Shigeyasu,Oda, Mitsunori
, p. 11227 - 11239 (2006)
After a preliminary search of the reaction conditions for the Suzuki-Miyaura cross-coupling of haloazulenes with arylboronic acids, the title compounds were synthesized either by the direct coupling reaction between 1,3-dihaloazulene and the corresponding N,N-disubstituted 4-aminophenylboronic acids or by a two-step sequence involving the cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Application of the title diamines to a hole-injecting material in organic electroluminescent devices was carried out to provide their prominent characteristics as a novel durable, non-cyanine and non-polyamine substance without color fade. The diamine derivatives, extended by an ethynyl unit between the azulenyl core and the 4-aminophenyl moiety, were also synthesized and found, unfortunately, unsuitable for vacuum deposition in preparing a multilayer composite.
OXIDATIVE SUBSTITUTION XIV. SUBSTITUTION OF HALOGEN IN AROMATIC RING. NEW THEORIES ABOUT THE MECHANISM OF THE ACTION OF CuX2
Nefedov, V.A.,Tarygina, L.K.,Kryuchkova, L.V.,Ryabokobylko, Yu.S.
, p. 487 - 499 (2007/10/02)
The stoichiometry, the comparative reactivity of halogens and hydrogen, the effect of substituents, and the action of an additional oxidizing agent were determined for the reactions of halogenoazulenes with CuX2., leading to substitution of the halogen by the group X (X = Cl, Br, SCN, SeCN, NO2, SO2, Ph).According to model experiments, the equilibrium CuX2 + CuX+ X+ + 2CuX is possible.The reaction of Cu(SO2Ph)2 with Cu(BF4)2 leads to the formation of two equivalents of a copper(I) salt; short-lived particles which substitute the hydrogen and halogen in the substrate are generated during the reaction.It is suggested that the electron generated during oxidation or autooxidation of CuX2 is capable of combining with the substrate.New methods were found for the synthesis of azulene derivatives, and known methods were improved.
