| Abstract
| - Nucleophilic substitution of N,N‘-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxydiimide (PTCDI)with an excess of corresponding alkanol in the presence of sodium hydride or anhydrous potassiumcarbonate at 85−100 °C provided both di(alkoxy)- and mono(alkoxy)-substituted PTCDI compounds,namely, N,N‘-dicyclohexyl-1,7-di(alkoxy)perylene-3,4:9,10-tetracarboxydiimide (3) and N,N‘-dicyclohexyl-1-bromo-7-alkoxyperylene-3,4:9,10-tetracarboxydiimide (2). Starting from mono(alkoxy)-substitutedPTCDI, nucleophilic substitution with thiol, thiophenol, or alkylamine led to the formation ofunsymmetrical 1,7-di(substituted) PTCDI compounds (7−10). For the purpose of comparative studies,symmetrical di(substituted) N,N‘-dicyclohexyl-1,7-di(alkylthio)perylene-3,4:9,10-tetracarboxydiimide (4),N,N‘-dicyclohexyl-1,7-di(thiophenyl)perylene-3,4:9,10-tetracarboxydiimide (5), and N,N‘-dicyclohexyl-1,7-di(alkylamine)perylene-3,4:9,10-tetracarboxydiimide (6) have also been prepared by a similarnucleophilic substitution. These newly prepared PTCDI compounds have been characterized by a widerange of spectroscopic methods in addition to elemental analysis. Electronic absorption and fluorescencestudies revealed that the absorption and emission bands as well as the fluorescence quantum yield can betuned continuously over a large range by incorporating substituents with different electron-donating abilities.
|
