3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole

CAS Number 173063-52-0

Chemistry Building Blocks, Dibromo Monomers, Materials, Monomers

3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole MSDS

3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole CAS 173063-52-0

A dibromo-substituted 2-ethylhexyl-carbazole building block

serves as a monomer in the preparation of organic semiconducting materials for use in solar cells and OLEDs

Overview
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3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole (CAS number 173063-52-0) is a carbazole derivative bearing two bromide groups at 3 and 6-positions as well as a 2-ethylhexyl group at the 9-position. The bromo-substituents enable 3,6-dbromo-9-(2-ethylhexyl)-9H-carbazole to undergo facile reactions, including Suzuki coupling reactions and Kumada polymerisation. A carbazole copolymer, linked at the position 2,7 and 3,6, is synthesised by combining 3,6-dibromo-9-(2-ethylhexyl)-9H-carbazole with 2,7-dipinacol-(2-ethylhexyl)-9H-carbazole. The resulting carbazole copolymer possesses a wide band gap of 3.2 eV and displays a narrow emission band at 400 nm (with a full width half maximum of 56 nm).

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Versatile building block

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Synthetic monomer

Synthetic monomer for HTL materials (in OPVs and OLEDs)

A novel copolymer of fluorene and carbazole, known as PF8Cz (poly[(9,9-dioctylfluorenyl-2,7-diyl)-alt-(9-(2-ethylhexyl)-carbazole-3,6-diyl)]) can be prepared from 3,6-dibromo-9-(2-ethylhexyl)-9H-carbazole and 2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane). PF8Cz has an optical bandgap of 3.06 eV, widely used as a hole-transport layer (HTL) material in OLEDs.

General Information

CAS Number	173063-52-0
Chemical Formula	C₂₀H₂₃Br₂N
Full Name	3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole
Molecular Weight	437.22 g/mol
Synonyms	3,6-Dibromo-N-(2-ethylhexyl)carbazole, 9-(2’-Ethylhexyl)-3,6-dibromo carbazole
Classification / Family	Carbazole building blocks, Bromide ligands, Organic photovoltaics, Polymer solar cells, Perovskite solar cells, Polycarbazoles, OLEDs, Hole-transport layers, Organic semiconducting materials

Chemical Structure

Product Details

Purity	98%
Melting Point	N/A
Appearance	Colourless to pale yellow liquid

MSDS Documentation

3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole MSDS Sheet

Literature and Reviews

Alternating 2,7- and 3,6-linked carbazole copolymers as wide band gap energy transfer donors, D. Pickup et al., The Solid Films, 517(9), 2840–2844(2009); DOI: 10.1016/j.tsf.2008.10.044.
Carbazole-functionalized polyfluorenes: synthesis and conformational properties in chloroform solution and β-phase formation in copolyfluorene films, M. Simonova et al., Mater. Today Chem., 22, 100553(2021); DOI: 10.1016/j.mtchem.2021.100553.
Efficient synthesis of well-defined polycarbazoles via catalyst-transfer Kumada coupling polymerization, H. Wen et al., Eur. Polym. J., 49(11), 3740–3743(2013); DOI: 10.1016/j.eurpolymj.2013.08.016.
3,6-Linked 9-alkyl-9H-carbazole main-chain polymers: preparation and properties, A. Iraqi et al., J. Polym. Sci., Part A: Polym. Chem., 42, 6041–6051(2004); DOI: 10.1002/pola.20420.
Highly efficient light-emitting diodes based on self-assembled colloidal quantum wells, Y. Zhu et al., Adv. Mater., 2305382(2023). DOI: 10.1002/adma.202305382.
Solution-processed green and blue quantum-dot light-emitting diodes with eliminated charge leakage, Y. Deng et al., Nat. Photonics, 16, 505–511(2022); DOI: 10.1038/s41566-022-00999-9.

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