137445-10-4

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 3076-56-0 p-tolyllead triacetate 
• 106-38-7 para-bromotoluene 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1443380-50-4 C₂₆H₃₅N₃O₄ 
• 118621-45-7 1-(4-methylphenyl)-1,2,3,4-tetrahydroquinoline-6-carbaldehyde 

Relevant academic research and scientific papers

A new family of bis-DCM based dopants for red OLEDs

We have synthesized a series of novel bis-DCM derivatives as candidate red dopants for use in organic light-emitting devices (OLEDs), by introducing various donor-substituted aryl rings. Compared to DCJTB (621 nm), the novel dopants (637-677 nm) showed more red-shifted emission in 1,2-dichloroethane. Using bis-DCMNEtOBu (7) as a dopant, we fabricated OLEDs with the configuration of ITO/4,4′,4″-tris(3-methylphenylammo)triphenylamine (m-MTDATA) (20 nm)/N,N′-bis(1-naphthyl)-diphenyl-1,1′-biphenyl-4,4′-diamine (NPB) (40 nm)/tris(8-quinolinolato)aluminium (Alq3) : red dopant (35 nm, x wt%)/Alq3 (35 nm) LiF/Al. The device with a doping concentration of 1.25 wt% showed pure red emission at λmax = 654 nm (chromaticity coordinate: x = 0.67, y = 0.33) and a maximum brightness of 2500 cd m-2. The chromaticity coordinates were almost independent of current density. Moreover, highly efficient red emission (x = 0.63, y = 0.36) was obtained in the 0.74 wt% doped device. The maximum external quantum efficiency was 4.46% at 7 V, the current efficiency was 3.43 cd A-1, and the power efficiency was 1.64 Im W-1. The highest brightness of 8300 cd m-2 was obtained at 19.6 V. The Royal Society of Chemistry 2005.

Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride

While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.

Copper promoted aryl/saturated heterocyclic C-N bond cross-coupling with arylboronic acid and arylstannane

Arylboronic acid/cupric acetate arylation of N-H containing saturated heterocycles has been explored and found to give good yields of the cross- coupled products. Phenyltrimethylstannane is also found to arylate N-H containing heterocycles.

Aryllead Triacetates: Regioselective Reagents for N-Arylation of Amines

Aryllead triacetates have been found to be regioselective reagents for the mono N-arylation of a range of aromatic, heterocyclic and aliphatic amines under mild and neutral conditions in a reaction catalysed by copper diacetate.The arylation of arylamines was unaffected by the steric hindrance of the arylamine but was dependent on the arylamine basicity.In addition, the position of oxidisable substituents on both the aryllead triacetate and the arylamine was found to be important due to a competing oxidation-reduction reaction.The arylation of heterocyclic amines proceeded in modest to good yields whilst aliphatic amines were arylated in poor to modest yields.The mechanism proposed for these reactions involves transfer of the aryl group onto copper forming a copper(III) intermediate which subsequently undergoes ligand coupling to give the N-arylated amine and the catalytic CuI species.