| Identification | Back Directory | [Name]
3,6-BIS(TERT-BUTYL)CARBAZOLE | [CAS]
37500-95-1 | [Synonyms]
DBUC
3,6-Di-tert-butyL
3,6-di terbutyl carbazole
3,6-Di-tert-butylcarbazole
3,6-BIS(TERT-BUTYL)CARBAZOLE
3,6-Ditert-butyl-9H-carbazole
3,6-Di-tert-butyl-9H-carbazole
3,6-Di-tert-butylcarbazole >
3,6-Bis(tert-butyl)-9H-carbazole
3,6-Di-tert-butylcarbazole≥ 99% (GC)
9H-Carbazole, 3,6-bis(1,1-diMethylethyl)- | [Molecular Formula]
C20H25N | [MDL Number]
MFCD03425849 | [MOL File]
37500-95-1.mol | [Molecular Weight]
279.42 |
| Chemical Properties | Back Directory | [Melting point ]
233-235℃ | [Boiling point ]
424.2±14.0 °C(Predicted) | [density ]
1.037 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder | [pka]
17.70±0.30(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C20H25N/c1-19(2,3)13-7-9-17-15(11-13)16-12-14(20(4,5)6)8-10-18(16)21-17/h7-12,21H,1-6H3 | [InChIKey]
OYFFSPILVQLRQA-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(C(C)(C)C)C=C2)C2=C1C=CC(C(C)(C)C)=C2 |
| Hazard Information | Back Directory | [Chemical Properties]
gray powder | [Uses]
3,6-Di-tert-butylcarbazole is mainly used as a monomeric precursor in the syntheses of new carbazole based materials which consist of ethynylphenyl. These materials include 9-(4-bromophenyl)-3,6-di-tert-butylcarbazol and 2-(4-(2-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)benzylidene)malononitrile (PBM) which can be further be used in organic light emitting diodes (OLEDs) and optical switching devices. | [General Description]
3,6-Di-tert-butylcarbazole is a carbazole based material with hole transporting characteristics. The 3,6-Di-tert-butyl component of the carbazole results in an increase in the glass transition temperature (Tg) of the compound. It can be used in combination with another carbazole to form novel electroluminescent materials. | [Synthesis]
9H-carbazole (1) (5.00 g, 29.9 mmol) was dissolved in dichloromethane and tert-butyl chloride (6.6 ml, 59.8 mmol) and anhydrous aluminum chloride (4.00 g, 29.9 mmol) were added sequentially. The reaction mixture was stirred at 25°C for 24 hours. Upon completion of the reaction, the mixture was poured into ice water (100 mL) to quench the reaction. The organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate and filtered to remove the desiccant. The filtrate was concentrated under reduced pressure at room temperature to give the crude product. The crude product was recrystallized by petroleum ether to give 6.30 g of 3,6-di-tert-butyl-9H-carbazole (2a) as a white solid in 75% yield. | [References]
[1] New Journal of Chemistry, 2016, vol. 40, # 11, p. 9160 - 9169
[2] Journal of the American Chemical Society, 2006, vol. 128, # 17, p. 5592 - 5593
[3] Chemical Communications, 2012, vol. 48, # 28, p. 3382 - 3384
[4] Chemistry Letters, 2008, vol. 37, # 9, p. 986 - 987
[5] Organic Electronics: physics, materials, applications, 2012, vol. 13, # 1, p. 43 - 52 |
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