Orthogonal self-assembly of perylenebisimide derivatives with p-type oligo (p-phenylene vinylene)s.

A series of perylene bisimide mols. contg. aliph., arom. or ethyleneoxide side chains were synthesized and fully characterized. They form supramol. stacks in apolar methylcyclohexane (MCH) soln. as demonstrated by concn. and temp. dependent absorption, CD and fluorescence studies. Among the four perylene bisimides, P4 was chosen to be investigated in more detail in the solid state. It was found to orthogonal self assembly with p-type OPV derivs. into sep. nano-sized p-and n-type stacks in MCH. In contrast, in toluene only molecularly dissolved species were present. In films deposited from MCH as well as from toluene photo-induced electron transfer takes place from the p-type material to the n-type material. As a result of the orthogonal self-assembly process, in films from MCH an ordered network of fibers was formed whereas in films from toluene no ordering was obsd.