Revisiting Indolo[3,2‐<i>b</i>]carbazole: Synthesis, Structures, Properties, and Applications
Mengna Zhao, Binghao Zhang, Qian Miao
Abstract
Abstract Indolo[3,2‐ b ]carbazole presents a π‐skeleton with a remarkable electronic structure and interesting potential applications. It is, however, also associated with ambiguity and controversy. Herein, new derivatives of indolo[3,2‐ b ]carbazole are reported and they have enabled a comprehensive study on the electronic structure of indolo[3,2‐ b ]carbazole and the development of a new n‐type organic semiconductor. Experimental and computational studies show that indolo[3,2‐ b ]carbazole has a largely localized p ‐benzoquinonediimine moiety and significant antiaromaticity. When substituted with (4‐silylethynyl)phenyl groups, the indolo[3,2‐ b ]carbazole exhibits one‐dimensional π–π stacking and functions as an n‐type organic semiconductor in solution‐processed field effect transistors.