19287-68-4Relevant academic research and scientific papers
Synthesis and functional properties of star-burst dendrimers that contain carbazole as peripheral edges and triazine as a central core
Xiong, Mo Jun,Li, Zhong Hui,Wong, Man Shing
, p. 603 - 607 (2007)
With the aim of combining the electron and hole-transporting moieties into one molecule and to continue our investigation into the structure?property correlations of dendrimers, two novel star-burst dendrimers 1 and 2 constructed with carbazoles as the peripheral hole-transporting moieties and one triazine moiety as an electron-transporting central core, have been synthesized. The convergent synthetic approach uses palladium-catalyzed Suzuki cross-coupling as a key reaction. Their functional properties have also been investigated. CSIRO 2007.
Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
Kerner, Luká?,Gmucová, Katarína,Ko?í?ek, Jozef,Pet?í?ek, Václav,Putala, Martin
, p. 7081 - 7092 (2016/10/14)
We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurements supported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores. The diphenylamine derivative gets oxidized more readily when compared to its carbazole analogs. Expanding the core to binaphthalene did not alter electronic properties, but influenced the physical characteristics significantly.
An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride
Nakayama, Yuji,Yokoyama, Naota,Nara, Hideki,Kobayashi, Tohru,Fujiwhara, Mitsuhiko
supporting information, p. 2322 - 2330 (2015/07/27)
An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.
