Reactions of 3, 4: 9, 10-Perylenetetracarboxylic with Alkylaminest

Abstract

The condensation products of 3, 4: 9, 10-perylenetetracarboxylic dianhydride [1] with amines [4 a-e ](a; ammonia, b; methylamine, c; ethylamine, d; propylamine, e; butylamine) were spectroscopically determined. Under all reaction conditions, N-substituted 3, 4: 9, 10-perylenetetracarboxylic monoanhydride monoimides [2 a-e] (R=H, CH3, CH₂CF1₃, CH₂CH₂CH₃, CH₂, - CH₂, CH₂, CH₃, ) were obtained. As the reactions proceed, the yield of [2 a, -e] increased at an initial stage but decreased after reaching a maximum. This maximum yield of[2] was: [2 e]; 50-60%, [2 b]; 40-50%, [2 c]; 60-70%, [2 d]; 65-75%, [2e];80 85%. A long alkyl chain in amines appeared to be favorable for the increased formation of[2]
The kinetics of this reaction were also examined and discussed.