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Synthesis and Properties of Diazapentacene Diimides
Author(s) -
Li Cheng,
Jiang Wei,
Zhu Xiaozhang,
Wang Zhaohui
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300195
Subject(s) - diimide , chemistry , homo/lumo , aromatization , band gap , photochemistry , semiconductor , absorption (acoustics) , organic semiconductor , organic chemistry , perylene , optoelectronics , molecule , catalysis , materials science , composite material
Abstract Diazapentacene diimides were prepared by the double cross‐coupling of zirconacyclopentadienes with unilateral dibromonaphthalene diimide derivatives, and subsequent dehydrogenative aromatization of the resulting dihydrodiazapentacene diimides. The optical and electrical properties of this series of diazapentacene diimides have high electron affinity (up to 4.39 eV) and significantly smaller HOMO–LUMO gaps (as small as 1.26 eV). Those diimides with wide absorption bands and small band‐gaps are promising candidates for n‐type semiconductors and NIR dyes.