Dye-functionalized head-to-tail coupled oligo(3-hexylthiophenes) -: perylene-oligothiophene dyads for photovoltaic applications

A series of novel donor - acceptor systems, consisting of head- to-tail coupled oligo(3- hexylthiophene) s covalently linked to perylenemonoimide, is described. These hybrid molecules, which differ by the length of the oligothiophene units from a monothiophene up to an octathiophene, were created via effective palladium- catalyzed Negishi and Suzuki cross-coupling reactions in good to excellent yields. The optical and electrochemical properties of these compounds were determined and based on this series structure - property relationships have been established which give vital information for the fabrication of photovoltaic devices. Because the synthesized perylenyl-oligothiophenes distinguish themselves by a high absorption between 300 and 550 nm and an almost complete fluorescence quenching of the perylene acceptor, they meet the requirements for organic solar cells.