Reaction, identification, and fluorescence of aminoperfluorophenazines

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.