9,9'-(1,3-Phenylene)bis-9H-carbazole

Base Information

• Chemical Name: 9,9'-(1,3-Phenylene)bis-9H-carbazole
• CAS No.: 550378-78-4
• Molecular Formula: C₃₀H₂₀N₂
• Molecular Weight: 408.502
• Hs Code.: 29339900
• Mol file: 550378-78-4.mol

Synonyms:1,3-Bis(N-carbazolyl)benzene;1,3-Bis(carbazol-9-yl)benzene;1,3-Di-(9-carbazolyl)benzene;MCP(carbazole derivative);N,N'-Dicarbazolyl-3,5-benzene;

Chemical Property of 9,9'-(1,3-Phenylene)bis-9H-carbazole

Chemical Property:

• Melting Point: 176-178°C
• Boiling Point: 644.203 °C at 760 mmHg
• Flash Point: 343.402 °C
• PSA: 9.86000
• Density: 1.212 g/cm³
• LogP: 7.88080
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

1,3-Bis(carbazol-9-yl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36/37/39-41-37/38

MSDS Files:

SDS file from LookChem

Useful:

• Description: 1,3-Bis(N-carbazolyl)benzene, known as mCP, with a high triplet energy (ET ?= 2.91 eV) and a very deep highest occupied?molecular orbital (HOMO) level, is often used as host materials for efficient blue phosphorescent light-emitting diodes. Kawamura et al. demonstrated that the photoluminescence internal quantum yield of the blue emitter of FIrpic could approach nearly 100% when doped into the wide energy gap host of mCP .
• Uses: Material for use as a phosphorescent host material 9,9'-(1,3-Phenylene)bis-9H-carbazole uses as a phosphorescent host material

Technology Process of 9,9'-(1,3-Phenylene)bis-9H-carbazole

There total 8 articles about 9,9'-(1,3-Phenylene)bis-9H-carbazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

9H-carbazole (86-74-8,105184-46-1,97960-57-1) + 1,3-Dichlorobenzene (541-73-1) → 1,3-bis(9H-carbazol-9-yl)benzene (550378-78-4)

Guidance literature:

9H-carbazole; With methylmagnesium chloride; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; for 0.25h; Inert atmosphere; Schlenk technique;

1,3-Dichlorobenzene; With [2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine)](allyl-η3)palladium(II) chloride; 2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine); In 5,5-dimethyl-1,3-cyclohexadiene; at 145 ℃; for 3h; Reagent/catalyst; Temperature; Glovebox; Schlenk technique; Inert atmosphere;

Reference yield: 75.7%

1,3-Diiodobenzene (626-00-6) + 9H-carbazole (86-74-8,105184-46-1,97960-57-1) → 1,3-bis(9H-carbazol-9-yl)benzene (550378-78-4)

Guidance literature:

With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 190 ℃; for 12h; Inert atmosphere;

Reference yield: 70.0%

2-iodobiphenyl (2113-51-1) + m-phenylenediamine (108-45-2,64554-26-3,76583-20-5) → 1,3-bis(9H-carbazol-9-yl)benzene (550378-78-4)

Guidance literature:

With copper diacetate; palladium diacetate; caesium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 120 ℃; for 12h; Sealed tube;

DOI:10.1039/c9cc09493h

upstream raw materials:

1,3-Diiodobenzene

9H-carbazole

1,3-Dichlorobenzene

1,3-dibromobenzene

Refernces

• 1、 Liu, Xiaobing,Sheng, Heyun,Zhou, Yao,Song, Qiuling. "Palladium-catalyzed C-H bond activation for the assembly of: N -aryl carbazoles with aromatic amines as nitrogen sources". supporting information. p. 1665 - 1668. Retrieved 2020/02/18.
• 2、 Ageshina, Alexandra A.,Sterligov, Grigorii K.,Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Nechaev, Mikhail S.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Melnikova, Elizaveta K.. "Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions". supporting information. p. 3447 - 3452. Retrieved 2019/04/30.