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Reaction, identification, and fluorescence of aminoperfluorophenazines |
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| Authors: | Masaki Matsui Masayuki Suzuki Yasuhiro Kubota Motoo Shiro Hisayoshi Shiozaki |
| Institution: | a Department of Materials Science and Technology, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan b X-ray Research Laboratory, Rigaku Corporation, 3-9-12 Matubara-cho, Akishima, Tokyo 196-8666, Japan c Department of Environmental Sciences, Faculty of Education and Human Sciences, Yokohama National University, 79-2 Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan d Leather Testing Center, Technology Research Institute of Osaka Prefecture, 1-18-13 Kishibe-naka, Suita, Osaka 564-0002, Japan |
| Abstract: | Perfluorophenazine regiospecifically reacted with monoalkyl-, dialkyl-, and arylamines to afford the corresponding 2-amino-substituted derivatives. 2-(Ethylamino)- and 2-(diethylamino)perfluorophenazine reacted with another molar amount of ethylamine and diethylamine to preferentially provide the 2,7-disubstituted derivatives, respectively. Perfluoro(2,7-dimethylphenazine) was allowed to react with ethylamine to give the 1-ethylamino derivative. These regiospecific reactions were explained by the density functional theory (DFT) calculations. Perfluorophenazine reacted with ethylenediamine to afford the 2,3-cyclized and N,N′-bis(2-perfluorophenazinyl) derivatives. These amino-substituted products showed UV-vis absorption (λmax) and fluorescence maxima (Fmax) in the range of 439-536 and 524-613 nm in hexane, respectively. Some of them exhibit intense fluorescence. |
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