Perylenediimide derivatives in new donor–acceptor dyads

Abstract

Novel donor–acceptor dyads were synthesized with tetrathiafulvalene (TTF) or perylene-3,4-mono(carboximide) (PMI) as the donor and perylene-3,4:9,10-bis(dicarboximide) (PDI) as the acceptor. These two units were covalently attached using an esterification reaction through a short and flexible linker. Thus, an original synthetic strategy for the electron-accepting dissymmetrical PDI derivative bearing an alcohol group was developed. On the other hand, donors TTF and PMI were functionalized by a carboxylic acid group. These dyads exhibited good solubilities in usual organic solvents (toluene, dichloromethane, THF…) which allowed electrochemical and spectroscopic characterizations. In particular, it was demonstrated that the TTF–PDI dyad can be assimilated as a new photo-redox switch. .