Indolo[3,2-b]carbazole

5,11-Dihydroindolo[3,2-b]carbazole is a useful research chemical.

indolo[3,2-b]carbazole has a large planar and rigid conjugated structure with fused alternating three benzene and two pyrrole rings. It is a heterocyclic analogue of pentacene – one of the most used organic semiconductors – and is considered to be a nitrogen-containing electron-rich heteroacene with a ladder-type structure. It is a potent agonist of the aryl hydrocarbon receptor (AhR) and was found in Brassica family vegetables. Since its electron-donating nature, indolo[3,2-b]carbazole derivative is commonly used as hole transporting, charge injection, host, and electroluminescent materials for OLED and OFET devices with good thermal, chemical, and environmental stability[1].

Indolo[3,2-b]carbazole (ICZ) is a popular class of organic materials for various electronic applications. It has been used in a number of devices such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), solar cells, etc. ICZ is an important unit to synthesize various oligomers and polymers with interesting electrical, optical, magnetic and other features[2].

The nitrogen heteroatoms open up the possibility of functionalization and sensing capabilities, as well as lowering the HOMO energy levels, which renders them air-stable. Additionally, Indolo[3,2-b]carbazole exhibit very strong Nsingle bondHπ interactions, which can enhance charge transport by improving intermolecular interactions and thus result in an improved molecular packing motive. Because of the high glass transition temperature, ICZ compounds possess great thermal and morphological stability under ambient conditions[1].

[1] Streckaite S, et al. Fluorescence quenching of indolo[3,2-b]carbazole compounds by conformational motions of attached substituents. Dyes and Pigments, 2016; 133: 120-126.
[2] Bintinger J, et al. Synthesis, characterization and printing application of alkylated indolo[3,2-b]carbazoles. Synthetic Metals, 2017; 288: 9-17.