Supramolecular control of oligothienylenevinylene-fullerene interactions: evidence for a ground-state EDA complex.

Complementary hydrogen-bonding interactions between a barbituric acid-substituted fullerene derivative (1) and corresponding receptor (2) bearing thienylenevinylene units are used to assemble a 1:1 supramolecular complex (K = 5500 M(-1)). Due to the close proximity of the redox-active moieties within the assembly, strong ground-state electron-donor-acceptor interactions are observed. Photoinduced electron transfer from electron-rich thienylenevinylene subunits to the fullerene is very fast (k(et) = 5.5 x 10(12) s(-1)), as determined by fs-time-resolved transient absorption spectroscopy. [reaction: see text]