Synthesis and Reactions of Perylenecarboxylic Acid Derivatives. VIII. Synthesis of N-Alkyl-3,4:9,10-Perylenetetracarboxylic Monoanhydride Monoimide

The condensations of 3,4 : 9,10-perylenetetracarboxylic dianhydride with alkylamines (isobutyl-, pentyl-, hexyl-, and octylamines) were spectroscopically determined. Under all of the reaction conditions employed, N-alkyl-3,4 : 9,10-perylenetetracarboxylic monoanhydride monoimide (2a–d) (alkyl=a; isobutyl, b; pentyl, c; hexyl, d; octyl) were obtained. As the reaction proceeded, the yield of 2a–d increased at an initial stage but decreased gradually after reaching a maximum. This maximum yield of 2a–d was: 2a; 85–88%, 2b; 85–89%, 2c; 78–84%, 2d; 79–85%. The kinetics of the reaction were also examined.