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CAS Number 37500-95-1

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

Product Code B1131-10g
Price $132 ex. VAT

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An electron donating intermediate for the synthesis of semiconducting molecules

For applications in highly efficient OLEDs and DSSCs.

3,6-Di-tert-butylcarbazole (DtBuCz) is an electron-donating 9H-carbazole derivative with tert-butyl groups at 3,6-positions. The bulky tert-butyl groups can disrupt aggregates that otherwise form dimers or excimers through π–π interactions by enlarging the distance between carbazole rings, leading to loose molecular packing in films.

Carbazoles are typically electrochemically active due to dimerization and polymerization of the corresponding radical cations at their 3,6-positions. The substitutions with tert-butyl groups at 3,6-positions can also suppress such reactions. 3,6-Di-tert-butylcarbazole has also been incorporated in the semiconducting small molecules for OLED applications to gain higher glass-transition temperatures. The introduction of the tert-butyl units can also effectively separate molecules thus reduce the chance of triplet-polaron annihilation to greatly improve the device efficiency and stability.

3,6-Di-tert-butylcarbazole is prepared by Friedel–Crafts alkylation of carbazole with tert-butyl chloride in the presence of aluminium trichloride (AlCl3).

General Information

CAS Number 37500-95-1
Chemical Formula C20H25N
Full Name 3,6-Di-tert-butylcarbazole
Molecular Weight 279.42 g/mol
Synonyms 3,6-Di-tert-butyl-9H-carbazole, Cz-tBu, DtBuCz
Classification / Family Carbazoles, semiconductor synthesis intermediates, Electron donor unit, OLED, OFETs, organic photovoltaics

Chemical Structure

3,6-Di-tert-butylcarbazole, 37500-95-1
3,6-Di-tert-butylcarbazole  (DtBuCz) chemical structure, CAS 37500-95-1

Product Details

Purity >98% (1H NMR)
Melting Point 232 °C
Appearance White to off-white powder/crystals

MSDS Documentation

3,6-Di-tert-butylcarbazole3,6-Di-tert-butylcarbazole MSDS Sheet

Literature and Reviews

  1. Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence, B. Kaafarani et al., J. Mater. Chem. C, 1, 1638-1650 (2013); DOI: 10.1039/C2TC00474G.
  2. Steric Effect on Dimer Radical Cation Formation of Poly(3,6-di-tert-butyl-9-vinylcarbazole) and Its Dimeric Model Compounds Studied by Laser Photolysis, Y. Tsujii et al., Polym. J., 22, 319–325 (1990); DOI: 10.1295/polymj.22.319.
  3. Synthesis and Characterization of 2D-D-π-A-Type Organic Dyes Bearing Bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline as Donor Moiety for Dye-Sensitized Solar Cells, T. Khanasa et al., Eur. J. Org. Chem., 13, 2608-2620 (2013); DOI: 10.1002/ejoc.201201479.
  4. Novel D–A chromophores with condensed 1,2,4-triazine system simultaneously display thermally activated delayed fluorescence and crystallization-induced phosphorescence, A. Maggiore et al., Phys. Chem. Chem. Phys., 24, 17770-17781 (2022); DOI: 10.1039/D2CP00777K.
  5. Color tuning of dibenzo[a,c]phenazine-2,7-dicarbonitrile-derived thermally activated delayed fluorescence emitters from yellow to deep-red, S. Kothavale et al., J. Mater. Chem. C, 8, 7059-7066 (2020); DOI: 10.1039/d0tc00960a.
  6. Elucidating the Electronic Structure of a Delayed Fluorescence Emitter via Orbital Interactions, Excitation Energy Components, Charge-Transfer Numbers, and Vibrational Reorganization Energies, Z. Pei et al., J Phys Chem Lett., 12(11): 2712–2720 (2021); DOI: 10.1021/acs.jpclett.1c00094.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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