9,10‐Diaminoanthracenes Revisited: The Influence of N‐Substituents on Their Electronic States |
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| Authors: | Masashi Uebe Prof?Dr Tatsuhisa Kato Prof?Dr Kazuyoshi Tanaka Dr Akihiro Ito |
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| Affiliation: | 1. Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan;2. Institute for Liberal Arts and Sciences, Kyoto University, Kyoto, Japan |
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| Abstract: | The electronic and molecular structures of 9,10‐diamino‐substituted anthracenes with different N‐substituents have been re‐examined. In particular, different N‐substituents influence both the electronic and molecular structures of the oxidized species of 9,10‐diaminoanthracenes. The anthrylene moiety of 9,10‐bis(N,N‐di(p‐anisyl)amino)anthracene retains its planarity during the course of two successive one‐electron oxidations, whereas 9,10‐bis(N,N‐dimethylamino)anthracene and 9,10‐bis(N‐p‐anisyl‐N‐methylamino)anthracene undergo a substantial structural change to a butterfly‐like structure through a two‐electron oxidation process. The structural changes observed for the oxidized states are ascribed to significant differences in the frontier molecular orbitals of the above‐mentioned three kinds of 9,10‐diaminoanthracenes due to different extents of mixing between the amine‐localized and anthrylene‐localized orbitals. |
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| Keywords: | acenes arylamines density functional calculations electrochemistry UV/Vis spectroscopy |
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