Indolo[3,2-b]carbazole

CAS Number 6336-32-9

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

Indolo[3,2-b]carbazole, used for the preparation of semiconducting molecules and polymers

High-quality and high-purity monomer available to purchase online.

Specifications | MSDS | Literature and Reviews

Found in Brassica family vegetables, indolo[3,2-b]carbazole (CAS number 6336-32-9) is a potent agonist of the aryl hydrocarbon receptor (AhR). With good thermal, chemical and environmental stability, Indolo[3,2-b]carbazole structure is highly desired in OLED and OFET devices.

Indolo[3,2-b]carbazole (ICz) has a large planar and rigid conjugated structure with fused alternating three benzene and two pyrrole rings. It can be considered as a structure of fused indole and carbazole, or two indoles fused at the opposite positions of a benzene ring.

Indolo[3,2-b]carbazole has been a useful building block for the preparation of various semiconducting small molecules and polymers. By introducing various functional groups into the 2,8,3,6-, or especially 5,11- positions of ICZ main structure, tuneable outstanding photophysical properties, great morphological stability and thermal stability can be achieved. Due to their electron donating nature, Indolo[3,2-b]carbazole derivatives have been used as hole transporting, charge injection, host and electroluminescent materials for OLED and OFET devices.

Semiconducting Indolo[3,2-b]carbazole derivatives are relatively bearing low HOMO levels and large band gaps. Exhibiting p-type FET behaviour with hole mobilities as high as 0.2 cm² V^-1 s^-1 and an on/off current ratio higher than 10⁶, 5,11-bis(4-octylphenyl)indolo[3,2-b]carbazole allows efficient overlap between the oligomeric molecules due to its planar and rigid structure, promoting self-organized readily into highly crystalline layered structures in solid films.

Indolocarbazole building block

For the synthesis of OFET, OPV, and OLED materials

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Planar and rigid

Promoting self-assemble layered structure

High purity

>98% Purity

General Information

CAS Number	6336-32-9
Chemical Formula	C₁₈H₁₂N₂
Full Name	Indolo[3,2-b]carbazole
Molecular Weight	256.31 g/mol
Synonyms	5,11-Dihydroindolo[3,2-b]carbazole, ICz
Classification / Family	Indolo-carbazoles, semiconductor synthesis intermediates, Electron donor unit, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	460 °C
Appearance	White to yellowish green powder/crystals

MSDS Documentation

Indolo[3,2-b]carbazole MSDS Sheet

Literature and Reviews

Synthesis, Characterization, and Application of Indolo[3,2-b]carbazole Semiconductors, P. Boudreault et al., J. Am. Chem. Soc., 129, 29, 9125–9136 (2007); DOI: 10.1021/ja071923y.
Indolo[3,2-b]carbazole-Based Thin-Film Transistors with High Mobility and Stability, Y. Wu et al., J. Am. Chem. Soc., 127, 2, 614–618 (2005); DOI: 10.1021/ja0456149.
Four new bipolar Indolo[3,2-b]carbazole derivatives for blue OLEDs, H. Yang et al., Dyes Pigm., 187, 109096 (2021); DOI: 10.1016/j.dyepig.2020.109096.

A Simple and Efficient Method for the Synthesis of Indolo[3,2-b]carbazoles, M. Deb et al., Synthesis, 6, 929-932 (2010); DOI: 10.1055/s-0029-1218644.
Two novel indolo[3,2-b]carbazole derivatives containing dimesitylboron moieties: synthesis, photoluminescent and electroluminescent properties, H. Shi et al., New J. Chem., 38, 2368-2378 (2014); DOI: 10.1039/C4NJ00140K.
Molecular order of air-stable p-type Organic Thin-Film Transistors by tuning the extension of the π-conjugated core: the cases of Indolo[3,2-b]carbazole and Triindole semiconductors, M. Reig et al., J. Mater. Chem. C, 3, 506-513 (2015); DOI: 10.1039/C4TC01692K..