Indolo[2,3-a]carbazole

CAS Number 60511-85-5

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

Indolo[2,3-a]carbazole, Heterocyclic building blocks

Used in the synthesis of TADF-OLED host and emitting layer materials, and anticancer drugs.

Overview
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Indolo[2,3-a]carbazole (CAS number 60511-85-5), an isomer to Indolo[3,2-b]carbazole, is consisted of one fused indole and carbazole with two pyrrole cloves facing the same direction. indolo[2,3-a]carbazole derivatives are known for their favourable properties such as good planarity, high thermal stability and excellent photophysical properties.

Highly efficient green PHOLED exhibiting an impressive operational lifetime of over 10,000 h with an initial luminance of 1,000 cd m^-2 was achieved using 2-biphenyl-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (PIC-TRZ) as the host, 20 times longer than the operational lifetime while the conventional host material CBP was used.

The majority of the naturally occurring indolo[2,3-a]carbazoles bear an additional annulated pyrrole unit to the benzene ring. Indolo[2,3-a]carbazole alkaloids has shown a great range of pharmacological effects such as antifungal, antimicrobial, and anticancer activities.

General Information

CAS Number	60511-85-5
Chemical Formula	C₁₈H₁₂N₂
Molecular Weight	256.31 g/mol
Full Name	Indolo[2,3-a]carbazole
Synonyms	11,12-Dihydroindolo[2,3-a]carbazole
Classification / Family	Indocarbazole derivatives, Semiconductor synthesis intermediates, Heterocyclic building blocks, Photocatalyst

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	T_m = 371 °C
Appearance	Off-white powder/crystals

MSDS Documentation

Indolo[2,3-a]carbazole MSDS Sheet

Literature and Reviews

An Indolocarbazole-Based Thermally Activated Delayed Fluorescence Host for Solution-Processed Phosphorescent Tandem Organic Light-Emitting Devices Exhibiting Extremely Small Efficiency Roll-Off, S. Ohisa et al., Adv. Funct. Mater., 29 (16), 1808022 (2019); DOI: 10.1002/adfm.201808022.
Design of thermally activated delayed fluorescent sensitizers for high efficiency over 20% and long lifetime in yellow fluorescent organic light-emitting diodes, J. Kim et al., J. Mater. Chem. C, 8, 5265-5272 (2020); DOI: 10.1039/D0TC00178C.
Thiadiazole Fused Indolo[2,3-a]carbazole Based Oligomers and Polymer, G. Balaji et al., Org. Lett., 11 (19), 4450–4453 (2009); DOI: 10.1021/ol901806q.
Synthesis of Benzo[a]carbazoles and an Indolo[2,3-a]carbazole from 3-Aryltetramic Acids, N. Truax et al., J. Org. Chem., 81 (15), 6808–6815 (2016); DOI: 10.1021/acs.joc.6b01072.
A simple indolo[2,3-a]carbazole based colorimetric chemosensor for simultaneous detection of Cu2+ and Fe3+ ions, Z. Chen et al., Spectrochim. Acta A Mol. Biomol. Spectrosc., 234, 118326 (2020); DOI: 10.1016/j.saa.2020.118236.
Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles, H. Bi et al., Green Chem., 22, 5815-5821 (2022); DOI: 10.1039/D0GC01514H.
A New Route to the Synthesis of Indolo[2,3-a]carbazoles, B. Avijit et al., Chem. Lett., 34 (11), 1500-1501 (2005); DOI: 10.1246/cl.2005.1500.
Synthesis and characterization of novel butterfly-shaped aryl-substituted indolo[2,3-a]carbazole derivatives, S. Yang et al., Tetrahedron Lett., 56 (17), 2223-2227 (2015); DOI: 10.1016/j.tetlet.2015.03.058.
Strong Enhancement of p-Electron Donor/Acceptor Ability by Complementary DD/AA Hydrogen Bonding, C. Liu et al., Angew. Chem. Int. Ed., 58, 17312 – 17321 (2019); DOI: 10.1002/anie.201910288.

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