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Revisiting Indolo[3,2‐ b ]carbazole: Synthesis, Structures, Properties, and Applications
Author(s) -
Zhao Mengna,
Zhang Binghao,
Miao Qian
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202001803
Subject(s) - carbazole , moiety , chemistry , stacking , stereochemistry , organic semiconductor , combinatorial chemistry , organic chemistry
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.