Issue 3, 2023

Diazazethrene bisimide: a strongly electron-accepting π-system synthesized via the incorporation of both imide substituents and imine-type nitrogen atoms into zethrene

Abstract

The development of highly electron-accepting π-systems is a fundamentally challenging issue despite their potential applications as high-performance n-type organic semiconductors, organic rechargeable batteries, and stable redox-active organocatalysts. Herein, we demonstrate that the incorporation of both imide substituents and imine-type nitrogen atoms into zethrene affords the strongly electron-accepting π-system diazazethrene bisimide (DAZBI). DAZBI has a low-lying LUMO (−4.3 eV vs. vacuum) and is readily reduced by the weak reductant L-ascorbic acid to afford the corresponding dihydro species. The injection of two electrons into DAZBI provides the corresponding dianion. These reduced species display remarkable stability, even under ambient conditions, and an intense red fluorescence. A DAZBI dimer, which was also synthesized, effectively accommodated four electrons upon electron injection.

Graphical abstract: Diazazethrene bisimide: a strongly electron-accepting π-system synthesized via the incorporation of both imide substituents and imine-type nitrogen atoms into zethrene

Supplementary files

Article information

Article type
Edge Article
Submitted
28 Oct 2022
Accepted
03 Dec 2022
First published
06 Dec 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 635-642

Diazazethrene bisimide: a strongly electron-accepting π-system synthesized via the incorporation of both imide substituents and imine-type nitrogen atoms into zethrene

K. Tajima, K. Matsuo, H. Yamada, N. Fukui and H. Shinokubo, Chem. Sci., 2023, 14, 635 DOI: 10.1039/D2SC05992D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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