3,3′-Di(9H-carbazol-9-yl)biphenyl Chemical Properties

Melting point:

270℃ (chloroform ligroine )

Boiling point:

732.3±60.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

λmax

340nm(Toluene)(lit.)

InChI

InChI=1S/C36H24N2/c1-5-19-33-29(15-1)30-16-2-6-20-34(30)37(33)27-13-9-11-25(23-27)26-12-10-14-28(24-26)38-35-21-7-3-17-31(35)32-18-4-8-22-36(32)38/h1-24H

InChIKey

NSXJEEMTGWMJPY-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC(N3C4=C(C=CC=C4)C4=C3C=CC=C4)=C2)=CC=CC(N2C3=C(C=CC=C3)C3=C2C=CC=C3)=C1

Absorption

λmax 340 nm in toluene

Safety Information

HS Code 

2933998090

3,3′-Di(9H-carbazol-9-yl)biphenyl Usage And Synthesis

Description

mCBP, 3,3′-Di(9H-carbazol-9-yl)-1,1′-biphenyl, is an isomer of CBP, 4,4′-Di(9H-carbazol-9-yl)-1,1′-biphenyl. The meta-linkage in mCBP limits conjugation to the central biphenyl, preventing excimer formation and thus resulting in a higher triplet energy of 2.8?eV.

General Description

Phosphorescent host material and TADF emitter in OLEDs.

Synthesis

General procedure for the synthesis of 3,3'-bis(9H-carbazol-9-yl)-1,1'-biphenyl, compounds (CAS:1325751-60-7) and 4,4'-bis(9-carbazolyl)biphenyl from 4,4'-dichlorobiphenyl and carbazole: Potassium tert-butoxide (1.12 g, 10 mmol) and carbazole (1.67 g, 10 mmol) were added to an anhydrous toluene containing 1 mmol of appropriate dihalogenated biphenyl in a solution of anhydrous toluene (20 mL). The mixture was placed in a glass autoclave under argon protection and heated at 130-140 °C for 48 hours. Upon completion of the reaction, the resulting suspension was diluted with water to remove inorganic impurities. The organic layer was separated, concentrated to dryness and purified by silica gel column chromatography using a hexane solution of 0-10% acetone as eluent. 4,4'-Bis(9H-carbazol-9-yl)-1,1'-biphenyl (2a) was obtained in a yield of 0.43 g (90% yield) with a melting point of >250 °C. Elemental analysis measured values (%): C, 89.08; H, 4.84. theoretically calculated values (%) for C36H24N2: C, 89.23; H, 4.99. 1H NMR (DMSO-d6, δ): 8.28 (m, 4H); 8.09 (m, 4H); 7.80 (m, 4H); 7.47-7.50 (m, 8H); 7.26- 7.28 (m, 4H). esims, m/z (% relative strength): 485.20 [M+H]+ (100).

References

[1] Russian Chemical Bulletin, 2015, vol. 64, # 8, p. 1978 - 1981
[2] Izv. Akad. Nauk, Ser. Khim., 2015, # 8, p. 1978 - 1981,4

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