Revisiting Indolo[3, 2‐b]carbazole: Synthesis, Structures, Properties, and Applications. Issue 24 (1st April 2020)

• Record Type: Journal Article
• Authors: Zhao, Mengna; Zhang, Binghao; Miao, Qian
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 24(2020)
• Page Start: 9678
• Page End: 9683
• Publication Date: 2020-04-01
• Subjects: antiaromaticity -- fused-ring systems -- heterocycles -- organic semiconductors -- polycycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202001803
• Languages: English
• ISSNs: 1433-7851

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. Abstract : The syntheses of new derivatives of indolo[3, 2‐ b ]carbazole have enabled a comprehensive study on the remarkable electronic structure of indolo[3, 2‐ b ]carbazole. This work has also led to the development of a new n‐type organic semiconductor for solution‐processed organic field effect transistors.