3,6-Di-tert-butylcarbazole
- Product Name
- 3,6-Di-tert-butylcarbazole
- CAS No.
- 37500-95-1
- Chemical Name
- 3,6-Di-tert-butylcarbazole
- Synonyms
- 3,6-Di-tert-butyl-9H-carbazole;3,6-Di-tert-butylcarbazole;DBUC;3,6-Di-tert-butyL;3,6-di terbutyl carbazole;3,6-BIS(TERT-BUTYL)CARBAZOLE;3,6-Ditert-butyl-9H-carbazole;3,6-Di-tert-butylcarbazole >3,6-Bis(tert-butyl)-9H-carbazole;3,6-Di-tert-butylcarbazole
- CBNumber
- CB5166721
- Molecular Formula
- C20H25N
- Formula Weight
- 279.42
- MOL File
- 37500-95-1.mol
3,6-Di-tert-butylcarbazole Property
- Melting point:
- 233-235℃
- Boiling point:
- 424.2±14.0 °C(Predicted)
- Density
- 1.037
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 17.70±0.30(Predicted)
- form
- powder
- 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
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26
- WGK Germany
- 3
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 757322
- Product name
- 3,6-Di-tert-butylcarbazole
- Purity
- 97%
- Packaging
- 5g
- Price
- $248.06
- Updated
- 2025/07/31
- Product number
- D3952
- Product name
- 3,6-Di-tert-butylcarbazole
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $79
- Updated
- 2025/07/31
- Product number
- D3952
- Product name
- 3,6-Di-tert-butylcarbazole
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $225
- Updated
- 2025/07/31
- Product number
- FD62357
- Product name
- 3,6-Di-tert-butylcarbazole
- Packaging
- 10g
- Price
- $800
- Updated
- 2021/12/16
- Product number
- CHM0010114
- Product name
- 3,6-BIS(TERT-BUTYL)CARBAZOLE
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $947.1
- Updated
- 2021/12/16
3,6-Di-tert-butylcarbazole Chemical Properties,Usage,Production
Description
3,6-Di-tert-butylcarbazole (DtBuCz) is an electron-donating 9h-carbazole derivative with tert-butyl groups at the 3,6 positions. The bulky tert-butyl group can disrupt the aggregation of dimers or excimers that would otherwise form through π-π interactions by increasing the distance between the carbazole rings, leading to loose molecular stacking in thin films. Carbazoles are generally electrochemically active due to the dimerization and polymerization of the corresponding radical cations at their 3,6 positions. Substitution with tert-butyl groups at the 3,6 positions can also inhibit this reaction. 3,6-Di-tert-butylcarbazole has also been incorporated into semiconducting small molecules for OLED applications to achieve higher glass transition temperatures. The introduction of the tert-butyl unit also effectively separates the molecules, reducing the chance of triplet polaron annihilation and significantly improving device efficiency and stability.
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.
Application
3,6-Di-tert-butylcarbazole (DtBuCz) is an electron-donating optoelectronic material, mostly used as a semiconductor intermediate for the preparation of high-performance OLED materials. Specific applications are as follows:
(1) Preparation of complexes by chelation with metal ions. The chelating ligand contains a derivative of 3,6-di-tert-butylcarbazole as a color developer. The resulting complexes have high stability above 200°C. In solvents such as acetone, benzene, and dichloromethane, the complexes exhibit strong π-π*, n-π*, and charge transfer (CT) bands in the range of 200 to 400 nm, while the ligands only exhibit strong π-π* and n-π* bands. In the transition from non-polar solvents to polar solvents, a strong red shift (21-31 nm) in the maximum emission band of the complexes is observed[6].
(2) Preparation of derivatives of trifluorobiphenyl and 3,6-di-tert-butylcarbazole as potential components of the OLED light-emitting layer. In the solid state, the ionization energy of the compound is between 5.98 and 6.17 eV[7].
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
507-20-0
86-74-8
37500-95-1
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
[6] MATVEY S. GRUZDEV. Schiff base complexes with different metals incorporating derivatives of 3,6-di-tert-butylcarbazole[J]. Applied Organometallic Chemistry, 2021, 35 4. DOI:10.1002/aoc.6145.
[7] KERUCKIENE R, GUZAUSKAS M, LAPIENYTE L, et al. An experimental and theoretical study of exciplex-forming compounds containing trifluorobiphenyl and 3,6-di-tert-butylcarbazole units and their performance in OLEDs†[J]. Journal of Materials Chemistry C, 2020, 40: 14186-14195. DOI:10.1039/D0TC02777D.
3,6-Di-tert-butylcarbazole Preparation Products And Raw materials
Raw materials
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View Lastest Price from 3,6-Di-tert-butylcarbazole manufacturers
- Product
- 3,6-Di-tert-butylcarbazole 37500-95-1
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1Kg
- Purity
- 98％
- Supply Ability
- 100kg
- Release date
- 2024-07-26
- Product
- 3,6-BIS(TERT-BUTYL)CARBAZOLE 37500-95-1
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-10
- Product
- 3,6-BIS(TERT-BUTYL)CARBAZOLE 37500-95-1
- Price
- US $50.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-22